smiles zinc_id inchikey mwt logp reactive purchasable tranche_name features COc1cc(OC)c2c(=O)cc(C3(OC)C=CC(=O)C=C3)oc2c1 28710336 ZVLDZKFNBIXDHH-UHFFFAOYSA-N 328.320 2.347 30 1 EEEF O=C(O)/C=C1\CN([C@H](C(=O)O)c2ccccc2Cl)CC[C@H]1S 53229815 GZZDPOCSWMTUJU-ODAKQPGBSA-N 341.816 2.481 30 1 EEEF C=C(C)C(=O)O[C@@H]1CC(=C)[C@@H]2C[C@H](O)[C@H](C)[C@@H]2[C@@H]2OC(=O)C(=C)[C@H]21 2356664662 FQKDBWKMFCRELP-DAVMEFKJSA-N 332.396 2.165 30 1 EEEF C[C@H]1Cc2cc(Br)c(F)cc2[C@@](CCC=O)(C(=O)O)N1 587828370 OZXIIBKYYJVMTP-RTHLEPHNSA-N 344.180 2.381 30 1 EEEF COC(=O)/C=C/c1cccc(CNC2=CC(=O)c3cccnc3C2=O)c1 1857636149 WGQYBENCVBLGKU-BQYQJAHWSA-N 348.358 2.321 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@H]2C(=C)C[C@H](O)[C@@H]3[C@H](C)C(=O)O[C@@H]3[C@@H]2C1=C 2356488761 ZNXKZMIVEDDWGE-MCKAYZRLSA-N 332.396 2.165 30 1 EEEF C#C[C@]1(O)[C@H](O)C[C@@H]2[C@@H]3CCc4cc(O)ccc4[C@@H]3[C@@H](OC)C[C@]21C 2356485658 OOMBHDXDTAYDBF-LQDXZBFHSA-N 342.435 2.208 30 1 EEEF N#Cc1c2n(c(=O)n(-c3ccccc3)c1=N)CCCC[C@H]2N1CCCC1 53295978 ADVWRHQQTDKLMY-QGZVFWFLSA-N 349.438 2.311 30 1 EEEF COC(=O)[C@@]1(c2cccc(OCc3ccccc3)c2)C[C@@H]1C(=O)NO 29134806 GVBYOUWYVHIZCE-VQIMIIECSA-N 341.363 2.202 30 1 EEEF CCCCCCCCCNCC(P(=O)(O)O)P(=O)(O)O 71315827 DXTYOSQHSRZDRD-UHFFFAOYSA-N 331.286 2.008 30 1 EEEF COc1cc2c(cc1OC)[C@]13C[C@@H](OC)C(=O)C=C1CCN3CC2 15204026 GFSAAWPDCQHEAN-MOPGFXCFSA-N 329.396 2.075 30 1 EEEF biogenic N#Cc1nc(Cl)cc2nc(CCNC(=O)Cc3ccccc3)[nH]c12 587228215 JDXLICCKPKNMKL-UHFFFAOYSA-N 339.786 2.384 30 1 EEEF CO/N=C1/C(=O)N(CCCCCCC(=O)NO)c2ccc(C)cc21 103294335 JRGZEGIUJRUFDD-KNTRCKAVSA-N 333.388 2.148 30 1 EEEF CNC(=O)/C(=N/OC)c1ccccc1Oc1ccc([N+](=O)[O-])cc1 90161354 GJDKWLQRFNTTKF-OBGWFSINSA-N 329.312 2.484 30 1 EEEF C[C@H]1C/C=C/[C@H](O)C/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 14614737 DRRQOEPQLQGLLP-ABBKGTABSA-N 332.352 2.022 30 1 EEEF CCC1=C/C(=C2/NC(N)=NC=C2c2csc(C)n2)C(=O)C=C1OC 103917593 CTLCZTQISSSQOC-WJDWOHSUSA-N 342.424 2.414 30 3 EEEF CC1=C/C(=N\Nc2ccc(S(=O)(=O)N3CCCC3)cc2)C(=O)C=C1 104009555 FINIQRSVULLKEP-KNTRCKAVSA-N 345.424 2.324 30 3 EEEF CCCCCCCCCCCCNC(=O)[C@@H](N)CCCN=C(N)N 43335148 QRXYOLQBNNYWCJ-INIZCTEOSA-N 341.544 2.404 30 1 EEEF C=C(C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)C(=C)[C@@H]2[C@H]2OC(=O)[C@@H](C)[C@H]12 238742745 IXOAQFFFKPCXLB-OGEQHFGCSA-N 332.396 2.165 30 1 EEEF C/N=C1/N/C(=C/c2c[nH]c3c(Br)cccc23)C(=O)N1C 96937894 BRWAMNLZPYODKK-IZZDOVSWSA-N 333.189 2.319 30 1 EEEF COC1=C(OC)C(=O)c2cc(SC)c(=O)c(SC)cc2C1=O 1634945 SPLAJGDLMTVLAC-UHFFFAOYSA-N 338.406 2.374 30 1 EEEF C[C@@H]1CC(=O)C2=C(CC[C@@]34O[C@@]23C(=O)c2cccc(O)c2[C@@H]4O)C1 36378650 NNMGLXNJGVNRCH-KUAJCHEXSA-N 326.348 2.219 30 1 EEEF COc1c2c(c(OC)c3c1C(=O)C1=C(C3=O)[C@H](C)O[C@@H](C)C1)OCO2 14827941 FRYKBCAHLYVUDQ-YUMQZZPRSA-N 346.335 2.305 30 1 EEEF biogenic C[C@@H]1Cc2cc(Br)c(F)cc2[C@]2(CCNC[C@@H]2C#N)N1 587794324 MGFDYUSZRRNEOF-BPYAMOTFSA-N 338.224 2.451 30 1 EEEF Cc1nc(NS(C)(=O)=O)sc1-c1nc2ccc(C#N)cc2[nH]1 586951613 RHGWJNSNLGYSSV-UHFFFAOYSA-N 333.398 2.238 30 1 EEEF C=C(CO)[C@@]12C=C3C(=O)C[C@H](C(C)C)[C@@]3(C)C[C@@H](O)[C@]1(C)CC(=O)O2 169674824 LAUXGJSHPLNZHD-GQJWIHHCSA-N 348.439 2.169 30 1 EEEF C=C1CC[C@H]2CCC3=C(C(=O)[C@@H](C(C)=C[C@H](O)[C@H]1O)[C@H]3O)C2(C)C 2356571486 SMYOLHGQHZBFAQ-ADBDHWBDSA-N 332.440 2.297 30 1 EEEF O=C(C=C[C@@H](O)Cc1ccc(O)c(O)c1)CCc1ccc(O)c(O)c1 2356632590 PAUUCJGSDZNVOR-OAHLLOKOSA-N 344.363 2.171 30 1 EEEF N#Cc1c(NC(=O)c2cccs2)[n+](=O)c2cc(F)c(F)cc2n1O 377819827 SKLOVVNDDDUGDO-UHFFFAOYSA-O 349.298 2.257 30 1 EEEF CNCC#Cc1cc(Oc2cnc(N)nc2N)c(C(C)C)cc1OC 168083142 JNMRNGMETLCYPW-UHFFFAOYSA-N 341.415 2.136 30 1 EEEF CNC[C@H](O)CN1CCc2c(cccc2Oc2ccc(C#N)cc2)C1 1857574758 ZSZHFVBJHDAIQK-KRWDZBQOSA-N 337.423 2.289 30 1 EEEF CC(C)C1=C[C@H]2C[C@@]3(C=O)[C@@H]4CC[C@@](C)(O)[C@@H]4C[C@@]2(CO)[C@@]13C(=O)O 2356465763 GEHSSDSUIBHHAH-XXZNDTCPSA-N 348.439 2.018 30 1 EEEF CCC[C@@H]1O[C@H](CC(=O)O)C[C@]23O[C@@]12C(=O)c1ccccc1C3=O 2356561275 WVRWIGGCJAKRAH-MZCYAGRSSA-N 330.336 2.006 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]1(C)[C@@H]2[C@@H](OC(=O)[C@]2(C)CC[C@H]1O)[C@@H]3O 238762942 KKNCULVZVJJLMP-OQWPZIHVSA-N 332.440 2.432 30 1 EEEF C=C1C[C@]23C[C@H]1[C@@H](O)C[C@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@@H]2[C@@H]3C(=O)O 238771606 ZCRLGANQNRMURE-PTAFSMAPSA-N 346.423 2.384 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 257447094 IPHNMKITOREFLW-JJFQCNDFSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C=C[C@H](C)N1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5 169341394 VFYJSHIQOIHURC-XKNMSPGRSA-N 325.408 2.143 30 1 EEEF O=C(O)[C@H]1CNC[C@@H](CCN/N=C/c2sccc2-n2cccc2)C1 1857593260 QDDJCBGVFHJCJL-NNUFEUBYSA-N 346.456 2.163 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@@](C2)(C(=O)O[C@@H]2CCC(C)(C)[C@@H]4[C@H](O)OC[C@]432)[C@@H]1O 2356410495 MSSXZZIDIPKYEB-BGZJFMLSSA-N 348.439 2.016 30 1 EEEF Cn1c([N+](=O)[O-])cnc1-c1nnc(N/N=C/c2ccccc2)s1 28457341 QTCYXLKKMRJOGS-VIZOYTHASA-N 329.345 2.293 30 1 EEEF C/C=C/C(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)C(=O)C[C@]3(C)[C@]1(C)[C@]21CO1 85564212 LJWZOKOFCBPNAG-WSAWODHZSA-N 332.396 2.346 30 1 EEEF CC(C)C[C@H](NC(=O)O[C@H]1CCOc2ccccc21)C(=O)NCC#N 82065210 KIZVLCBYIBQTSN-HOCLYGCPSA-N 345.399 2.291 30 1 EEEF CC1=C[C@]2(O)C(=C[C@](C)(O)CC[C@@H]3[C@H](C[C@@H](C)[C@H]2O)C3(C)C)C1=O 2356515848 CZUBZNDQQZRXMB-JOUGVQFBSA-N 334.456 2.377 30 1 EEEF O=C(/C=C/c1cc(C(=O)c2ccc(F)cc2)c[nH]1)CC(=O)C(=O)O 95920732 YJVBLWPFNPJKMT-AATRIKPKSA-N 329.283 2.011 30 1 EEEF Cc1cc(-c2n[nH]c(=S)n2/N=C\c2ccccc2[N+](=O)[O-])n[nH]1 13136355 DTSPVZZJWPPQKQ-AUWJEWJLSA-N 329.345 2.430 30 1 EEEF C=CCn1c(=O)c2ccccc2[n+]2c(C)c(C(=O)OCC)sc12 1636467 PEHOYMFACWVTSH-UHFFFAOYSA-N 329.401 2.473 30 1 EEEF C[C@@H]1C[C@H]2O[C@H]2/C=C\C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 104958834 XTUZVEOWUSGCSV-DEBGRNBRSA-N 330.336 2.038 30 1 EEEF Cc1ccc2n(c1)cc(/C=C/c1ccc(/C=N/NC(=N)N)cc1)[n+]2C 26825451 DLKXCMRWVOFFAR-PREBZYBQSA-N 333.419 2.060 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@H](C(=O)OC)[C@H]1[C@@]2(C)CCC[C@@]31OC2=O 2356636507 KVXQCEAWXGANQC-XEENTPLFSA-N 346.423 2.225 30 1 EEEF CCCCC(=O)O[C@H]1CCn2c1nc1c2C(=O)C(C)=C(N2CC2)C1=O 38792490 SSAUGKDFJRHWJM-NSHDSACASA-N 343.383 2.030 30 1 EEEF C[P@@](=O)(c1ccccc1)N(CCc1ccccc1)CC(=O)NO 13782646 LMQSRMOBSSJUST-HSZRJFAPSA-N 332.340 2.270 30 1 EEEF N#Cc1cncc(N2CC[C@H](S(=O)(=O)c3ccccc3Cl)C2)n1 168419630 RWGKNIMCLPBXOA-LBPRGKRZSA-N 348.815 2.054 30 1 EEEF COC1=C(O)C(=O)c2c(OC)c3c(c(O)c2C1=O)[C@H](C)O[C@@H](C)C3 2356408893 RVZCNHHDKHVNPP-BQBZGAKWSA-N 334.324 2.218 30 1 EEEF C=C1C[C@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100783024 BSBICXIQCTXPMN-AMWDFQDTSA-N 330.380 2.056 30 1 EEEF endogenous,in-man N#Cc1cccc(S(=O)(=O)n2c(=O)[nH]c3ccc(Cl)cc32)c1 43073362 XWLKTUZBARSUCP-UHFFFAOYSA-N 333.756 2.092 30 1 EEEF CCCn1c(=O)c(C#N)nn(-c2cccc(-c3ccccc3)c2)c1=O 49125090 KXWBYNBRTXJLMG-UHFFFAOYSA-N 332.363 2.343 30 1 EEEF C#C[C@]1(O)[C@H](O)C[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3[C@@H](OC)C[C@@]21C 13651862 OOMBHDXDTAYDBF-WYLBFHJUSA-N 342.435 2.208 30 1 EEEF CN1CCN(c2ccc(NC3=CC(=O)c4cccnc4C3=O)cc2)CC1 1857749936 OHGBLPNOIBVHQS-UHFFFAOYSA-N 348.406 2.208 30 1 EEEF COC(=O)N1CCC2(CC1)C[C@](O)(C#Cc1cccc(C)c1)CO2 103273454 SCOTVKYJDVTBLI-GOSISDBHSA-N 329.396 2.099 30 1 EEEF CC1=CC(=O)[C@]2(CN1)N[C@@H](C)Cc1ccc(F)c(Br)c12 587799466 XHIZTKJYJVNHTR-VFZGTOFNSA-N 339.208 2.394 30 1 EEEF CN(Cc1nc2cccc(C#N)c2[nH]1)S(=O)(=O)c1ccc(F)cc1 587170811 SYLYFFONSKMKOM-UHFFFAOYSA-N 344.371 2.394 30 1 EEEF C[C@@H](Sc1nc(N)cc(O)n1)c1nc2cc(C#N)c(C#N)cc2[nH]1 586961559 KEDQBTHXTBJRLN-SSDOTTSWSA-N 337.368 2.237 30 1 EEEF CN[C@](C)(C#N)Cn1cc(C#Cc2cc(Cl)ccc2OC)cn1 587909107 JNMJLVCTLGPDPC-QGZVFWFLSA-N 328.803 2.447 30 1 EEEF C#C[C@]1(O)C[C@H](O)[C@@H]2[C@@H]3CCc4cc(O)ccc4[C@@H]3[C@@H](OC)C[C@@]21C 2356613659 TYTYJGWQMLLBDD-MQWPULPWSA-N 342.435 2.208 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@]4(C2)[C@H]1OC(=O)[C@H]4[C@@H]1[C@@]3(C)CC[C@H](O)[C@]1(C)C(=O)O 2356691278 CXVXNQFWGOEIMV-HYRWVMOISA-N 346.423 2.382 30 1 EEEF N/C(=N\O)c1cccc(COc2ccc(/C(N)=N/O)cc2Cl)c1 96910520 DTXKVAGKJVDYCS-UHFFFAOYSA-N 334.763 2.108 30 1 EEEF COC(=O)[C@H](C#N)c1ncc(C#Cc2cc(Cl)ccc2OC)cn1 587908121 LWKQOGNDMWRIMP-CQSZACIVSA-N 341.754 2.319 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(NCCO)c([N+](=O)[O-])c1 587909317 OUJRYNQDYBGPGL-UHFFFAOYSA-N 347.758 2.456 30 1 EEEF Cc1cc(C)nc(N2C[C@H]3CN(C(=O)c4ccccc4C#N)C[C@H]3C2)n1 116825025 FEMHBRHDPBAADC-CALCHBBNSA-N 347.422 2.174 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]3C(COC(C)=O)=CC[C@@H](OC(C)=O)[C@@]3(C)CC[C@H]12 2356430897 VHZJGEKNJYFJNY-VYIWNADRSA-N 348.395 2.325 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@]2(C)C[C@@H]2C(=O)C=C(C)[C@H](O)C1=O 2356671142 PCTOPLUNRDRIQE-IPLAQRPESA-N 344.407 2.296 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)[C@]12CCCC(C)(C)[C@H]1C[C@@]3(O)OC2 1911584979 XWOHTSDVCYONEG-UPGGTKCWSA-N 332.440 2.434 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)[C@]1(C)CC[C@@H](O)C(C)(C)[C@H]1C[C@H]3O 84588785 BAXVJERFBZODKZ-IMZDMEOWSA-N 334.456 2.067 30 1 EEEF biogenic,in-vitro COc1cc(O)c2c(c1O)OC/C(=C\c1ccc(O)c(O)c1)C2=O 13481948 ZCFXRZACTOEVGD-RUDMXATFSA-N 330.292 2.176 30 1 EEEF C=C1[C@H]2CC(=O)[C@@H]3[C@]4(C)CCCC(C)(C)[C@@H]4[C@H](O)[C@H](O)[C@@]3(C2)[C@@H]1O 2356643670 AUVGEKXCVIHEPI-XBMVRRMNSA-N 334.456 2.067 30 1 EEEF C=CC(C)(C)c1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@@H](C)NC1=O 1560626 LVPZJIGICMPWFH-ABAIWWIYSA-N 325.412 2.177 30 1 EEEF biogenic O=C(NO)c1ccc(CNCc2nc(-c3ccc(F)cc3)no2)cc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endogenous,in-man C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@H](O)[C@@H]1C(=C)[C@H](C)CC[C@@]21C 2356574598 GCVDFMXIDUYWBG-HIEVZYGTSA-N 344.407 2.167 30 1 EEEF CCCCCC[C@H](O)[C@@H]1C[C@H](OC(C)=O)C2=C(O1)[C@H](O)CCC2=O 2356620152 GXYWRLQZWPUUNP-UKMLZYKCSA-N 340.416 2.016 30 1 EEEF CN(O)C(=O)C[C@@H](CCCc1cccc(F)c1)CP(=O)(O)O 584905589 HGIGLZBKPPPKTL-GFCCVEGCSA-N 333.296 2.180 30 1 EEEF in-vitro Cc1c(O)ccc2c1[C@@](CCC#N)(c1ccco1)N[C@H](C(=O)O)C2 963474534 VUGOXCALCJYIMD-SCLBCKFNSA-N 326.352 2.440 30 1 EEEF CC1([C@@H]2CC(=O)N(CCOc3ccc(F)c(C#N)c3)C2)CCNCC1 1772574431 JNLBXUGTFLPZTB-OAHLLOKOSA-N 345.418 2.314 30 1 EEEF C[C@H]1CO[C@H]2C(=O)C3=C4OC(=O)C5=C4[C@@](C)(CCC5=O)CC[C@]3(C)[C@@H]12 169657271 NYXWRIOSIQNJKH-DDHNXKPLSA-N 342.391 2.497 30 1 EEEF CC1=CCC[C@@]2(C)O[C@@H]2[C@H]2OC(=O)[C@@H](CN3CCCCC3)[C@@H]2C[C@@H]1O 1857537925 RHKZDVNMLMFSCO-DWGVPJFMSA-N 349.471 2.279 30 1 EEEF COC(=O)c1ccc(-c2c(C#N)n(O)c3cc(F)ccc3[n+]2=O)cc1 139328273 CRKFOROIVURCTD-UHFFFAOYSA-N 340.290 2.257 30 1 EEEF C=CCNC(=S)Nc1ccc(OCc2nnc(S)n2C)cc1 40430402 AYDAIAYVMFZQRN-UHFFFAOYSA-N 335.458 2.155 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)C3=CC(=O)[C@@](C)(C[C@@H](OC(=O)/C=C/C)[C@@H]12)O3 238778834 ZUSPJLQZGBITEG-VZVCFNRMSA-N 346.379 2.244 30 1 EEEF C=C1C[C@]23C[C@@]1(O)CC[C@@H]2C1=C[C@@H]2C[C@@](C)(C(=O)O2)[C@@H]1[C@@H]3C(=O)O 238761768 VLTQADXREMVNJX-YJZHVKNOSA-N 330.380 2.056 30 1 EEEF C#CCNC(=O)c1ccc(NC(=O)c2cc(OC)ccc2OC)cc1 473115516 UBGZUBLUZGSTDC-UHFFFAOYSA-N 338.363 2.319 30 1 EEEF C#CCNC(=O)C1CC2(CC(=O)c3ccc(O)c(CCC)c3O2)C1 587472212 ZEFHUBYTGRYPIU-UHFFFAOYSA-N 327.380 2.208 30 1 EEEF O=C1CCCC2=C1[C@H](c1cc3ccccc3[nH]c1=O)NC(=S)N2 103285164 LILXRXMAYLRMKZ-HNNXBMFYSA-N 325.393 2.054 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@H]1CC[C@H]2[C@@]12CCC[C@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100781426 MJFVMFNFTCKAEV-XASFKZBDSA-N 346.423 2.384 30 1 EEEF endogenous,in-man C=CCNC[C@H](O)COc1cccc2c(=O)c3ccccc3oc12 40936195 RNEPUWOVSZUZJP-ZDUSSCGKSA-N 325.364 2.462 30 1 EEEF CC(C)C[C@@H](C(=O)NCC#N)n1cnc2c(Cl)nc(Cl)nc21 82061650 XUYTXMWETIBUJD-QMMMGPOBSA-N 341.202 2.360 30 1 EEEF CS(=O)(=O)c1ccc(C#CC(=O)c2ccc([N+](=O)[O-])cc2)cc1 13683396 YPQKUKYNIHNDRK-UHFFFAOYSA-N 329.333 2.233 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)CCC=C(C)C[C@@H](C(=O)/C(=C/CO)CO)[C@@H]12 1857535810 WHIGIQOLZJSTRO-MSOHYXHXSA-N 346.423 2.257 30 1 EEEF O=C1C=Cc2cc(S(=O)(=O)O)ccc2/C1=N\Nc1ccccc1 100821967 RWZPEBJPWGVNIQ-FBMGVBCBSA-N 328.349 2.345 30 1 EEEF endogenous,in-man C[C@@]1(C=O)[C@H]2CCC3=C[C@H]4C[C@]3(CC[C@]4(O)CO)[C@]2(C)CC[C@H]1O 2356324654 KZRJAXKCOWVRTH-JXUVHZKSSA-N 334.456 2.213 30 1 EEEF COC1=C[C@]2(C=CC1=O)C[C@H]1c3c(cc(OC)c(O)c32)CCN1C 14618487 RICRDZJWIPYDGM-BUXKBTBVSA-N 327.380 2.241 30 1 EEEF biogenic C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)OC1)[C@H]2[C@H]3C(=O)O 257527888 QYXZQZMPZUEEML-VMOJUYBOSA-N 346.423 2.384 30 1 EEEF endogenous,in-man S=C(NN=C(c1ccccn1)c1ccccn1)N1CCSCC1 1857557085 WMNWUHRWOODFCN-UHFFFAOYSA-N 343.481 2.152 30 1 EEEF C=C[C@@H]1[C@](C)(CO)C(=O)[C@H]2C[C@@]1(C)[C@@H]1[C@@H]3OC(=O)C(=CC)[C@@H]3O[C@]21C 2356677554 UAVHCHBOMMAUHU-LQTMORERSA-N 346.423 2.042 30 1 EEEF C=C1C(=O)[C@@]23[C@H](O)C[C@H](C(C)(C)CCCO)C(=C)[C@H]2CC[C@H]1[C@H]3O 2356737577 FBXNWXLXYGRNOE-NMHNBYPJSA-N 334.456 2.235 30 1 EEEF COc1ccc(C(=O)C#Cc2ccc(S(C)(=O)=O)cc2)cc1O 13683388 WJSBSGFLLJDNNO-UHFFFAOYSA-N 330.361 2.039 30 1 EEEF C[C@H](O)[C@@H]1C(=O)C(=C(O)[C@H]2[C@H]3CCCC[C@H]3C=C[C@H]2C)C(=O)N1C 2356417409 ACUUAFHILDALFB-UBKONASUSA-N 333.428 2.218 30 1 EEEF C[C@@H]1C(=O)[C@@]23C[C@H]1CC[C@H]2[C@@]12CO[C@@H](CC1=O)C(C)(C)C2=C(O)C3=O 2356509591 UZPIZMWEFRPQNY-PZBOPDROSA-N 344.407 2.387 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@]2(C)C[C@H]2C(=O)C=C(C)[C@@H](O)C1=O 2356671141 PCTOPLUNRDRIQE-CZQHIENXSA-N 344.407 2.296 30 1 EEEF C=C1CC[C@H]2[C@@H](/C=C(\C)C(=O)[C@@]3(O)C[C@@H](C)[C@@H](O)[C@@H]3[C@H]1O)C2(C)C 238782616 SDBITTRHSROXCY-DWWRPMESSA-N 334.456 2.233 30 1 EEEF COC1=CC(=O)[C@@]2(O)C[C@H]3[C@H](c4ccccc4C3(C)C)[C@@H](O)C2=C1 15122218 VZQCDBNQPVXLLR-TXJVSEOTSA-N 326.392 2.213 30 1 EEEF CCC#C[C@](O)(C(=O)O[C@H]1C2CCN(CC2)[C@@H]1C)c1ccccc1 17250310 VOCRJOMVKAJZBC-XFQXTVEOSA-N 327.424 2.314 30 1 EEEF Oc1nc2ccc(C3=NNC(=NCc4cccnc4)SC3)cc2[nH]1 1857652776 ZIIDWBKLLHBQQG-UHFFFAOYSA-N 338.396 2.260 30 1 EEEF N#Cc1ccc2nc(CO[C@H]3CN(C4CCOCC4)C[C@@H]3F)[nH]c2c1 2356299175 ANHAAGFWRVPBII-YOEHRIQHSA-N 344.390 2.152 30 1 EEEF C=C[C@]1(C)C(=O)C=C2C(=CC[C@H]3C(C)(C)[C@@H](O)[C@@H](O)C[C@]23C)[C@@H]1O 2356432456 AZNDIKGKUJHYJB-QCIVWXMUSA-N 332.440 2.153 30 1 EEEF C=C1C[C@@]23C[C@@]1(O)CC=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)OC 2356473033 QQZHQZNECSBZML-LJIVFDACSA-N 344.407 2.289 30 1 EEEF C=C1C[C@@]23C[C@H]1CC(=O)[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1[C@@H](O)[C@@H]3O 2356684938 ZAPSETLSDTWUQE-NEEHOPHOSA-N 348.439 2.161 30 1 EEEF C=CC(C)(C)n1cc(C[C@@H]2NC(=O)[C@@H](C)NC2=O)c2ccccc21 2356800933 RGJOYRGQGOLRLW-DOMZBBRYSA-N 325.412 2.108 30 1 EEEF CC(C)C1=C[C@]23O[C@H]2C[C@H]2C4=C(CC[C@]2(C)[C@@]32O[C@H]2C1=O)C(=O)OC4 40556768 XRDMUFFSKAWRFY-BVJMBNRTSA-N 342.391 2.100 30 1 EEEF C=C(CC[C@@H]1C(=C)CC[C@@H]2[C@@](C)(CO)[C@@H](O)CC[C@]21C)[C@H](O)CO 238784238 GLRQCZGXPULESM-XVMXLUHGSA-N 338.488 2.418 30 1 EEEF C[C@H](C(=O)N(C)O)c1ccc2c(c1O)C(=O)c1c(O)cccc1C2 13606219 FMWKENZICXRFGI-VIFPVBQESA-N 327.336 2.184 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)[C@@H]3C=CC(=O)[C@]3(C)[C@H](OC(=O)C(C)C)[C@H]12 2356636027 SKAOENNHESXSCC-OMNUSTLDSA-N 332.396 2.453 30 1 EEEF C[C@H]1O[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)OCc1ccccc1 28530219 XRLMLBLLFRZQEE-FHLIZLRMSA-N 339.391 2.245 30 1 EEEF CN(C)C(=O)c1ccc(-c2cc(C3=CC(=O)C=CC3=O)no2)s1 653827949 VOXGYLXTPDIRLR-UHFFFAOYSA-N 328.349 2.196 30 1 EEEF N#Cc1cccnc1N1CCN(CC/C(=N/O)c2ccccc2)CC1 38147638 UQKXNFUEBSXDBC-PYCFMQQDSA-N 335.411 2.344 30 1 EEEF C=C(C[C@H]1C=C(C)C(=O)O1)[C@@H](O)COc1ccc2ccc(=O)oc2c1 15212313 BJAAKPBQJCDTGE-HOTGVXAUSA-N 342.347 2.351 30 1 EEEF biogenic C=C1C[C@@]23C[C@]1(O)CC[C@@H]2[C@@]12C=CC[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 103836617 UXLXLQYIDWLPKX-ICBSXVHVSA-N 330.380 2.056 30 1 EEEF in-man C[C@@]12CCC[C@]3(OC1=O)[C@H]1CC[C@@H]4C[C@]1(C[C@]41CO1)[C@@H](C(=O)O)[C@H]23 2356849789 PXYCXLNQKAEBRB-HVVFNJCKSA-N 332.396 2.378 30 1 EEEF CC[C@H]1C=NN(/C(=N/S(=O)(=O)c2cccc(Cl)c2)N(C)C)C1 72122931 DBUZGONQGQCYAT-QRAHRUOTSA-N 342.852 2.274 30 1 EEEF CS(=O)(=O)Nc1ccc(NC(=O)c2ccc(C#N)cc2)cc1F 1857601176 AHJDVHCRLFJVAR-UHFFFAOYSA-N 333.344 2.321 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(=O)n(CCC(=O)O)c1 587912844 PVJOLXCLNYXICJ-UHFFFAOYSA-N 331.755 2.385 30 1 EEEF C[C@@](Cc1ccccc1)(C(=O)NO)C(=O)N1CCc2ccccc2C1 13780633 BZDNZMAIXJGVGF-HXUWFJFHSA-N 338.407 2.326 30 1 EEEF C#CCNC(=O)c1cn(C)nc1OCc1cccc(C(F)(F)F)c1 103277729 SAQIHDDKUZOECO-UHFFFAOYSA-N 337.301 2.381 30 1 EEEF COC(=O)c1ccc(CNC(=O)c2ccc(/C=C/C(C)=O)[nH]2)cc1 40875774 XWZJACYAEOYOKR-FPYGCLRLSA-N 326.352 2.334 30 1 EEEF C=C1[C@@H]2CC[C@H]3[C@]4(C)CCC(=O)C(C)(C)[C@H]4C[C@@H](O)[C@@]3([C@@H]1O)[C@@H]2O 95914762 NTFFIALEDUMPAM-ZUZPKDNOSA-N 334.456 2.067 30 1 EEEF biogenic,in-vitro COc1ccc(NC(=O)C2=CC(=C3C=CC(=O)C=C3)ON2)cc1OC 13119876 FZWIJBFMFQCXCO-UHFFFAOYSA-N 340.335 2.010 30 3 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCC[C@]2(CO)C(=O)O[C@@H]([C@H]3O)[C@@H]21 14812350 RDUNXXWNAKBVER-VOYHXECJSA-N 332.440 2.434 30 1 EEEF endogenous,in-man C=C(CO)[C@@H]1CC2=CC[C@H]3[C@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@H]2[C@H](O)C1 2356443946 FISRUIAPOPDKNG-JLPZLSSXSA-N 336.472 2.028 30 1 EEEF C=C1CO[C@@H]2C(=O)N(Cc3ccccc3)[C@@H]1C(=O)N2Cc1ccccc1 100975748 PMMTVBPXYUFOBA-GHTZIAJQSA-N 348.402 2.339 30 1 EEEF C=C1C[C@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 231170533 CSOGGDRRRLWUTQ-MCDHERAVSA-N 344.407 2.145 30 1 EEEF CC(C)(C)C(=O)N[C@H](C(=O)NO)c1ccc(Br)cc1 653805815 QSMFBPVNXFNEGF-JTQLQIEISA-N 329.194 2.158 30 1 EEEF C=CCn1c(=S)sc2c(-n3ncc(C#N)c3N)nc(C)nc21 958560934 KEWUKKRLSMEODW-UHFFFAOYSA-N 329.414 2.356 30 1 EEEF COc1ccc(CCNC2=CC3=NCCc4cn(C)c(c43)C2=O)cc1 29131783 YMVQBESPQGVOOA-UHFFFAOYSA-N 335.407 2.291 30 1 EEEF C[C@]12CC[C@H]3[C@@H](CC[C@]45O[C@@H]4C(O)=C(C(N)=O)C[C@]35C)[C@@H]1CC[C@@H]2O 118933287 RSGSNGFUKZTCGU-XVYWUUJHSA-N 347.455 2.429 30 1 EEEF C=C1[C@@H]2C[C@@H](O)C(C)(C)[C@]2(O)[C@@H](O)C[C@@]23CC(=O)[C@@](C)(CC[C@@H]12)C3 2356593378 IRZVFDISJFITJT-YYVWGASFSA-N 334.456 2.211 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@]1(C)CCC[C@]2(CO)C(=O)O[C@@H]([C@@H]21)[C@@H]3O 85932794 RDUNXXWNAKBVER-NFWHWKORSA-N 332.440 2.434 30 1 EEEF in-man O=C1C(NCCc2ccc3c(c2)OCO3)=CC2=NCCc3c[nH]c1c32 29124219 IOKQNUTWBDBIMT-UHFFFAOYSA-N 335.363 2.001 30 1 EEEF CCc1nc2n(c(=O)c1C(N)=O)[C@H](C)CC/C2=N\Nc1ccccc1 40465621 ROUYGSNPBKRWQM-JALQTOONSA-N 339.399 2.076 30 1 EEEF N#Cc1cccc(C(=O)N[C@@H]2CCC[C@@H](NC(=O)c3ccccn3)C2)c1 95587695 WSQGEPYGCDINHA-IAGOWNOFSA-N 348.406 2.424 30 1 EEEF COc1cc2c3c(c1)O[C@H](c1cnc4c(C#N)cnn4c1)[C@@H](C2)C3=O 587436834 URKGANQYUYYHCN-SUMWQHHRSA-N 332.319 2.098 30 1 EEEF Cc1cc2c(cc1O)[C@@]1(Cc3ccccc3[C@@H]1C#N)N[C@H](C(=O)O)C2 963553098 RLECXGGYOMJNLF-ABSDTBQOSA-N 334.375 2.358 30 1 EEEF COC1=C[C@]23CCc4ccc(O)c(OC)c4[C@]2(CCN3C)CC1=O 2356394474 AQJBMLRXZGTSTA-RBUKOAKNSA-N 329.396 2.162 30 1 EEEF Cn1c(Nc2ccc(-c3cccc(C#N)c3)cc2)cc(=O)n(O)c1=O 1857542562 LSCQADWRWOEQGM-UHFFFAOYSA-N 334.335 2.067 30 1 EEEF O=[N+]([O-])/N=C1\NCCN1Cc1cnc(Cl)c(-c2ccccc2)c1 103200064 MUPHCSPQJDQVNT-UHFFFAOYSA-N 331.763 2.355 30 1 EEEF CC1=C2OCCCCN3C(=O)[C@@](O)(c4ccccc43)[C@]2(C)SC1=O 102830950 KFSYAIIGWGRHHI-MSOLQXFVSA-N 345.420 2.337 30 1 EEEF C[C@H](CO)C1=C(O)C(=O)C2=C(C[C@H](O)[C@H]3C(C)(C)CCC[C@@]23C)C1=O 504703448 KSXQZHNLPHBARZ-WSLYCFHRSA-N 348.439 2.473 30 1 EEEF biogenic C/N=C1/N/C(=C/c2c[nH]c3cc(Br)ccc23)C(=O)N1C 96937893 WIJJEZADZQGDSE-LFYBBSHMSA-N 333.189 2.319 30 1 EEEF C#CCNC(=O)N1CCC(c2nc(-c3ccc(F)cc3)no2)CC1 299830157 NITFQRSMPYETEB-UHFFFAOYSA-N 328.347 2.398 30 1 EEEF C[C@@H]1CC(=O)[C@H](Cc2nc3cc(Cl)nc(C#N)c3[nH]2)[C@@H]1C[N+](=O)[O-] 587266132 YQSUHXZFPMTARU-IWSPIJDZSA-N 347.762 2.143 30 1 EEEF C#CCN1CCC[C@@H](CNS(=O)(=O)c2ccc3ccccc3c2)C1 1772640105 UWQSVNKQBCCLCY-INIZCTEOSA-N 342.464 2.463 30 1 EEEF N#Cc1cccc(CN2CCC(=O)N([C@H](CO)c3ccccc3)CC2)c1 12474367 LRYGOSLHXMDDBW-HXUWFJFHSA-N 349.434 2.326 30 3 EEEF CCC#C[C@@](O)(C(=O)O[C@@H]1C2CCN(CC2)[C@@H]1C)c1ccccc1 17250315 VOCRJOMVKAJZBC-BPAFIMBUSA-N 327.424 2.314 30 1 EEEF COc1ccc([C@@H](O)C#C[C@H](O)c2ccccc2)c(OC)c1OC 1857760846 DDKCKMHUTOSATP-HOTGVXAUSA-N 328.364 2.483 30 1 EEEF C/C1=C/[C@]23O[C@H]2[C@H](C)C=C3C(=O)[C@@](C)(O)C(=O)CC(C)(C)/C=C/C1=O 103146605 FIRDPUAWQIZLCV-YGZJLGPDSA-N 344.407 2.091 30 1 EEEF COc1cc(/C=C/C(O)=C2/C(=O)C=C(C)OC2=O)cc(OC)c1O 198679422 ANTDONGDPORXMP-WEPZFIBGSA-N 332.308 2.264 30 3 EEEF Cc1nc(Br)sc1-c1nc2nc(C#N)c(C#N)nc2[nH]1 587011182 LUTREAFLEXIGFC-UHFFFAOYSA-N 346.173 2.291 30 1 EEEF N#C[C@H](C(=O)Nc1ccc(C(F)(F)F)cc1)C(=O)[C@@H]1CCOC1 13760258 QRECZZCVBQCIIJ-SKDRFNHKSA-N 326.274 2.389 30 1 EEEF CCC/C=C/[C@@H]1C(=O)[C@@H]2O[C@@H]2C2(OCC(CC)(CC)CO2)[C@@H]1CO 169305746 TWGDZVIUZPIUAD-QFUHKWRQSA-N 338.444 2.467 30 1 EEEF COc1cc2c(cc1OCCO)Cc1c(-c3ccc(C#N)nc3)n[nH]c1-2 28951600 GLRHTPRKKRRYPC-UHFFFAOYSA-N 348.362 2.294 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@@H]3C=C(C)[C@H](C[C@@H]3C(C)C)[C@H]2C1=O 253677986 PBDZFTMSQJXALQ-KHMAMNHCSA-N 347.484 2.021 30 1 EEEF CCCC/C(=N/CCO)C1=C(O)[C@@H](C(=O)OC)C(C)(C)CC1=O 101865097 WUMJQCTZODTZAB-DZBQEORWSA-N 325.405 2.210 30 1 EEEF C#C[C@]12O[C@]1(C=O)[C@H]1[C@H](CC2=O)[C@@]2(C)CCCC(C)(C)[C@H]2C[C@H]1O 2356471218 RLCVKAJQPCOLQK-OZGBQCQWSA-N 330.424 2.129 30 1 EEEF CCN(Cc1ccccc1)C(=O)N[C@@H](CC(C)C)C(=O)NCC#N 82065399 KSGKBXBJCOPUGX-INIZCTEOSA-N 330.432 2.273 30 1 EEEF C[C@H]1C[C@]23C(=O)[C@H](C)C[C@H]4C(C)(C)[C@]45O[C@](C)(C=C2C1=O)[C@H](O)[C@@H]53 45289357 XKHKWWYWWNXZDZ-NOBMYEPTSA-N 330.424 2.291 30 1 EEEF Cc1ccc2ncccc2c1-n1ncc(C(=O)N=C(N)N)c1C1CC1 149422430 JVXZUAAAJOCBAD-UHFFFAOYSA-N 334.383 2.020 30 1 EEEF O=C(NCCCc1ccccc1)N[C@H](C(=O)NO)c1ccccc1 95559762 LZIXHKSGMXOUMQ-INIZCTEOSA-N 327.384 2.165 30 1 EEEF COc1ccc(S(=O)(=O)Cc2nc3ccc(C#N)cc3[nH]2)cc1 586921115 YFRADBPOFYLFNX-UHFFFAOYSA-N 327.365 2.417 30 1 EEEF COc1ccc2nc(-c3nc4nc(C#N)c(C#N)nc4[nH]3)sc2c1 587034533 HAWUWAFWXFCJKC-UHFFFAOYSA-N 333.336 2.382 30 1 EEEF C=C[C@@H](C)N1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5 169341393 VFYJSHIQOIHURC-QHOWBERBSA-N 325.408 2.143 30 1 EEEF CCCCC/C=C/C1=C(CO)C(=O)[C@H]2O[C@@]2(C/C=C(\C)C(=O)O)C1=O 1857549744 UJNVMSXVUCFBMB-SLHMXGKOSA-N 348.395 2.122 30 1 EEEF CCCCN[C@@H]1C2=C(OC(C)(C)[C@@H]1O)C(=O)c1ccccc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c3ccc(C#Cc4cccnc4)cc3[C@@H]21 95878789 ZFWVHLMUMICASE-DUXKGJEZSA-N 347.418 2.177 30 1 EEEF O=C(CCCCCONC(=O)Nc1cccc2cccnc12)NO 1772623490 BVNOFHWBVSJDDT-UHFFFAOYSA-N 332.360 2.354 30 1 EEEF C=CC1=CC(=O)[C@@H]2[C@@H](CC[C@@H]3C(C)(C)[C@@H](O)[C@@H](O)[C@@H](O)[C@@]23C)[C@@H]1C 14777605 XFRCVLKGZMPUFQ-YFHFLRFXSA-N 334.456 2.089 30 1 EEEF endogenous,in-man CC1=C(O)C(=O)C[C@]2(C)[C@@H]3CCc4cocc4[C@]3(CO)CC[C@]12O 2356337345 YJYCGDAWLMWZRS-AITUJVMLSA-N 332.396 2.408 30 1 EEEF O=C(CCCCCCCNC(=O)c1ccc2c(c1)CCC(=O)N2)NO 222861961 HOSCTMSEDXIJLQ-UHFFFAOYSA-N 347.415 2.147 30 1 EEEF C[C@@H]([C@@H](NC(=O)OCc1ccccc1)C(=O)NCC#N)C(F)(F)F 82064907 DQUMJPBSYXBJLB-CMPLNLGQSA-N 343.305 2.120 30 1 EEEF Cc1c(O)ccc2c1[C@](CCC#N)(c1ccco1)N[C@H](C(=O)O)C2 963474535 VUGOXCALCJYIMD-UGSOOPFHSA-N 326.352 2.440 30 1 EEEF CC(=O)O[C@H]1[C@H](N2CCCC2=O)c2cc(C#N)ccc2OC1(C)C 26283942 MUCIVWGGWJZCBJ-SJORKVTESA-N 328.368 2.324 30 1 EEEF CC#CC#CC=C1O[C@]2(CCCCO2)[C@H](O)[C@@H]1OC(=O)CC(C)C 2356472881 LEOZNWWIPMVKHH-GUDVDZBRSA-N 332.396 2.143 30 1 EEEF C=C1C[C@@]23C[C@@]1(O)CC=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)OC 2356473035 QQZHQZNECSBZML-TULYMBKGSA-N 344.407 2.289 30 1 EEEF CCOC(=O)c1c(N/C(O)=N/S(C)(=O)=O)sc2c1CCCC2 28567758 SQOQKRHOECNUPD-UHFFFAOYSA-N 346.430 2.089 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)[C@@H]3C=CC(=O)[C@]3(C)[C@@H](OC(=O)C(C)C)[C@H]12 2356636026 SKAOENNHESXSCC-GPQGTUGBSA-N 332.396 2.453 30 1 EEEF C=C1CC[C@H]2[C@@](C)(CC[C@@H](O)[C@@]2(C)CO)[C@H]1CC(=O)C1=CCOC1=O 2356711149 KPJIGLLMDBHXEB-NGMIUWCPSA-N 348.439 2.171 30 1 EEEF C=C[C@]1(C)C=C2CC[C@H]3C(CO)(CO)[C@@H](O)[C@H](O)C[C@]3(C)[C@H]2CC1 238766897 QGUUHNNGZFMSRY-ZOVJDJALSA-N 336.472 2.028 30 1 EEEF CN(C)c1nonc1C(=NO)Nc1ccc(F)c(Br)c1 1772588728 KYIHGCYWLVORRZ-UHFFFAOYSA-N 344.144 2.285 30 1 EEEF CC1=C[C@]23O[C@H]2[C@H](C)C=C3C(=O)[C@@](C)(O)C(=O)CC(C)(C)C=CC1=O 1857626506 FIRDPUAWQIZLCV-GZZLFNETSA-N 344.407 2.091 30 1 EEEF C=C[C@]1(C)CCC2=C([C@H](O)C(=O)[C@@H]3C(C)(C)CC[C@H](O)[C@]23C)[C@@H]1O 2356734934 KKWFUTJLCATXQH-JJWNMWMSSA-N 334.456 2.377 30 1 EEEF CC#Cc1nc(C(=O)Nc2ccccc2N2CCNCC2)cs1 84710386 OOPCIBFGSURVOQ-UHFFFAOYSA-N 326.425 2.176 30 1 EEEF O=C(/C=C/c1ccc([N+](=O)[O-])o1)c1ccc(N2CCNCC2)cc1 1772618065 ZZXWVWNECFVHBY-FNORWQNLSA-N 327.340 2.494 30 1 EEEF C[C@@](Cc1ccccc1)(C(=O)NO)C(=O)NCCc1ccccc1 13528314 AZWBRVJQJIHTAP-IBGZPJMESA-N 326.396 2.100 30 1 EEEF N#CC1(C#N)N[C@@H](c2ccccc2)C(C#N)(C#N)N[C@H]1c1ccccc1 19365560 QVPFDGMLHNLKDK-ROUUACIJSA-N 338.374 2.234 30 1 EEEF CC#CC#CC=C1O[C@]2(CCCCO2)[C@H](O)[C@H]1OC(=O)CC(C)C 2356472882 LEOZNWWIPMVKHH-IPMKNSEASA-N 332.396 2.143 30 1 EEEF Cc1[nH]nc(N)c1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587880226 HTTUNALIVOATNI-UHFFFAOYSA-N 337.210 2.318 30 1 EEEF COc1ccc(CCC[C@H](CC(=O)N(C)O)CP(=O)(O)O)cc1 584904818 QEUMCKOMQCGMBO-CYBMUJFWSA-N 345.332 2.050 30 1 EEEF in-vitro C=CC(=O)N[C@@H]1Cn2c(c(-c3ccc(O)cc3)c3c(N)ncnc32)C1=C 1857763913 QFWUHKIRFIGAEO-CYBMUJFWSA-N 347.378 2.084 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)[C@@H]4O[C@@H]4[C@@]3(C)[C@@]1(C)[C@]21CO1 2356419981 LAQCZBYXNRANFU-DLUMUDRGSA-N 332.396 2.154 30 1 EEEF C=C(C)C(=O)O[C@@H]1CCC(=C)[C@@H]2[C@@H]3OC(=O)[C@H](C)[C@@H]3[C@@H](O)C[C@@]21C 2356480134 QHTWVJOMDDBORA-BGIXRKOTSA-N 334.412 2.389 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(=O)C(C)=CC)CC(=C)[C@@H]1[C@@H](O)C=C(C)[C@H]21 2356530235 JEAWGNYMYMHNGM-IZPLOLCNSA-N 344.407 2.475 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@@H](C(=C)C)C(=O)C=C(C)C(=O)[C@H]1O 2356843914 NQSGQBPUUPHFQJ-RUENVJTFSA-N 344.407 2.462 30 1 EEEF CC1=C2OCCCCN3C(=O)[C@](O)(c4ccccc43)[C@@]2(C)SC1=O 71329177 KFSYAIIGWGRHHI-ZWKOTPCHSA-N 345.420 2.337 30 1 EEEF CN(C)/C=N/N1C(=O)[C@@H]2C3c4ccccc4C(c4ccccc43)[C@H]2C1=O 49053335 HDPDOFWCHBSNSP-OYJMSAJPSA-N 345.402 2.384 30 1 EEEF O=C(/C=C/c1ccc2c(=O)n(CCc3ccccc3)cnc2c1)NO 96934290 VAAWIYIVFTYJRI-VQHVLOKHSA-N 335.363 2.158 30 1 EEEF Nc1c(C(=O)c2cccc(C#CCO)c2)cnn1-c1ccc(F)cc1 13683032 ABLHKLIEDOTYMC-UHFFFAOYSA-N 335.338 2.168 30 1 EEEF N#CCCCn1c(Cn2c(=O)[nH]c3ccncc32)nc2ccccc21 28821616 KZKLCCKSOWPENQ-UHFFFAOYSA-N 332.367 2.426 30 1 EEEF C=C1C(=O)[C@]23[C@@H](O)[C@@H]1CC[C@H]2[C@@]1(C(=O)O)CCCC(C)(C)[C@H]1C[C@H]3O 2356455477 VBQWGSKSQFBYOX-FMAVKDFTSA-N 348.439 2.161 30 1 EEEF C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@H](O)[C@@H]1C(C)(C)CCC[C@@]21C 2356480242 UXBITRKCDARMSM-BOLBYERCSA-N 346.423 2.391 30 1 EEEF COC(=O)/C(=C/c1ccccc1)CS/C(=N\C(C)=O)NC(C)=O 95558323 CPKFMIGIHMPWIK-NTEUORMPSA-N 334.397 2.015 30 1 EEEF C=C1C[C@@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@H](O)CO)[C@@H]2C[C@H]1CC3 299813639 FYKIZBPSTADBEK-BUSATUKNSA-N 348.439 2.171 30 1 EEEF CC1=C(O)C(=O)C[C@]2(C)[C@H]3CCc4cocc4[C@]3(CO)CC[C@@]12O 299827333 YJYCGDAWLMWZRS-NXWXRZEISA-N 332.396 2.408 30 1 EEEF Cc1ccc(Nc2c(N[C@@H](C)CCCCC(=O)NO)c(=O)c2=O)cc1 1857766678 ZPCDSQXLCVDHBZ-LBPRGKRZSA-N 345.399 2.201 30 1 EEEF CCOc1ccc(C#Cc2ccc(C[C@@H](C)NC(=O)CN)cc2)cc1 113410789 SKPGZSWOVIGHGF-MRXNPFEDSA-N 336.435 2.491 30 1 EEEF COc1ccc(NC(=O)C2=C/C(=C3/C=CC=CC3=O)NN2)cc1Cl 103917327 PLTZZZXQGYAWFO-ACCUITESSA-N 343.770 2.228 30 3 EEEF CC(C)[C@@H](C=O)c1c(O[C@H](O)C(C)(C)O)ccc2ccc(=O)oc12 2356496199 FOMXOHFJUKCTAU-PXAZEXFGSA-N 334.368 2.200 30 1 EEEF C=C1[C@H]2CC[C@@]3([C@H]1O)[C@@H](C2)[C@]12C=N[C@H](O)[C@](C)(CCC1)[C@H]2C[C@H]3O 14861194 DTWRNBPLILRYBH-KDRUZJHHSA-N 331.456 2.280 30 1 EEEF biogenic N#CCCn1c(SCC(=O)NC[C@H]2CCCO2)nc2ccccc21 3504286 HYEGCIFIULAWCR-CYBMUJFWSA-N 344.440 2.337 30 3 EEEF CNC(=O)/C(=N/OC)c1ccccc1COc1cccnc1Cl 103180003 QMSDYQZJKWUYHW-XSFVSMFZSA-N 333.775 2.411 30 1 EEEF O=C1O/C(=C\c2ccc(O)c(O)c2)C(O)=C(c2ccc(O)cc2)C1=O 34582427 OLZRNPOBVWGCKN-ZSOIEALJSA-N 340.287 2.240 30 1 EEEF CCOC(=O)c1cc2c(n1CC)C(=O)C(Br)=CC2=O 299825163 DAIDRHNIKRAVLU-UHFFFAOYSA-N 326.146 2.343 30 1 EEEF CCN(CC)[C@H]1CN(C(=O)c2ccc(C#N)cc2)[C@H]2CCCO[C@@H]12 299842802 ZPSYDGPWHCTPNE-OKZBNKHCSA-N 327.428 2.272 30 1 EEEF Cn1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)ccc1=O 587891060 LUASZHFLDZCPBG-UHFFFAOYSA-N 349.217 2.403 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C=C3[C@](C)(C(=O)O)CC[C@H](O)[C@]3(C)[C@@]2(O)CC1 2356436782 ZQZVXOUQMKWMED-LFAQGZIKSA-N 346.423 2.391 30 1 EEEF CC(=O)OC[C@@H]1O[C@H](C#Cc2ccc(C)cc2C)C=C[C@H]1OC(C)=O 7992538 FLENGSMTXSLATM-AQNXPRMDSA-N 342.391 2.473 30 1 EEEF CCOC(=O)C1=CNC2=C(/C=N/c3ccccc3)C[C@H](C)N2C1=O 28255405 IQZJQFGQBJJQQE-NJDFMEINSA-N 325.368 2.272 30 1 EEEF CC1=C[C@H](O)CC(CO)=CC[C@H]2CCC3=C(C(=O)[C@H]1[C@@H]3O)C2(C)C 2356536673 PLSLPANFUZMMNZ-KJGCVMFHSA-N 332.440 2.299 30 1 EEEF Cc1ccc2n(c1)cc(-c1ccc(/C=N/Nc3nc[nH]n3)cc1)[n+]2C 26828688 CIPBSCMIAQIOHV-AWQFTUOYSA-N 332.391 2.303 30 1 EEEF C#CCN1C(=O)[C@]2(Oc3cc(OC)cc4c3C(=O)[C@H]2C4)c2ccccc21 587436633 SNXCODTWZHXKHU-VFNWGFHPSA-N 345.354 2.318 30 1 EEEF COC(=O)c1ccnc2[nH]c(C#Cc3ccc([N+](=O)[O-])c(C)c3)nc12 587262090 MULKKPMSBPMTCI-UHFFFAOYSA-N 336.307 2.361 30 1 EEEF COc1cc([C@@H](C)C#Cc2c(C)nc(N)nc2N)cc(OC)c1OC 14968139 RUQVXLIOJPKNCM-JTQLQIEISA-N 342.399 2.130 30 1 EEEF C=C(CSC1=CC(=O)C(NC[C@H](C)O)=CC1=O)c1ccccc1 1857646180 FHDTYBNNTDWHFG-ZDUSSCGKSA-N 329.421 2.323 30 1 EEEF C=C1[C@H](O)[C@@]23C(=O)C[C@H]4[C@@](C)(CO)CCC[C@@]4(C)[C@H]2CC[C@H]1[C@H]3O 2356407506 DBVNQUBNOIPPEM-OYCNVIAQSA-N 334.456 2.068 30 1 EEEF COc1ccccc1N1C(=O)[C@@H]2[C@H]3C[C@H]([C@H](S)[C@H]3S)[C@@H]2C1=O 4030501 LUMFAWHJRRAZQX-OSTXOMKTSA-N 335.450 2.047 30 1 EEEF CC=C(C)C(=O)O[C@@H]1CCN2C[C@H]3C[C@@H](CN4C=CC(=O)C[C@@H]34)[C@@H]2C1 2356436104 ANLPQANGWMODSI-PHAGKYIGSA-N 344.455 2.136 30 1 EEEF N#CCN1CCN(Cc2cccc(Oc3ccccc3)c2)S1(=O)=O 72127578 AAAJXNMGEPTLAG-UHFFFAOYSA-N 343.408 2.365 30 1 EEEF CC(C)C[C@@H](C(=O)NCC#N)c1cccc(N2CCN(C)CC2)c1 82061725 GCMRYWPWBAOWRM-GOSISDBHSA-N 328.460 2.208 30 1 EEEF CCN1C(=O)CC[C@H]1C(=O)NCc1cccc(C(F)(F)F)c1C#N 95565435 ARZOBCVPNCJJCR-ZDUSSCGKSA-N 339.317 2.204 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@@H](c2ccccc2-c2ccccc2)[C@H]1CO 95668338 RRMULCFNGGBUJN-QWFCFKBJSA-N 336.391 2.179 30 1 EEEF NC(=S)NN=C1c2cc([N+](=O)[O-])ccc2-c2ccc([N+](=O)[O-])cc21 96908461 XKISVBSLGZJQBZ-UHFFFAOYSA-N 343.324 2.069 30 1 EEEF COc1cc(O)c2c(c1)CC(=O)/C=C\C=C\[C@H]1O[C@@H]1C[C@@H](C)OC2=O 169293680 BXYHHINRBKIWCZ-XBFGLOEPSA-N 344.363 2.341 30 1 EEEF N#Cc1cn(-c2ccc(C(=O)O)c(O)c2)c2ccc(OCCO)cc12 202394496 VAXTUMSFWPNUEG-UHFFFAOYSA-N 338.319 2.277 30 1 EEEF Cn1c(Oc2cccc(-c3ccc(C#N)cc3)c2)cc(=O)n(O)c1=O 1857575202 RFHPPBLTFNJLSQ-UHFFFAOYSA-N 335.319 2.115 30 1 EEEF CCOC(=O)Cc1cc(O)cc(O)c1C(=O)C=CC=CCCCO 2356499457 DOCDDNYMBXDQJE-UHFFFAOYSA-N 334.368 2.271 30 1 EEEF Cc1csc2c1c(=O)n(CCc1ccccc1)c(=O)n2CC#N 1857592788 LVCNJYPNQZLFFM-UHFFFAOYSA-N 325.393 2.299 30 1 EEEF C[C@]1(C=O)[C@@H]2CC[C@@]3(C)O[C@@]14C(=O)c1ccc(O)cc1C(=O)C4=C[C@@H]23 102958917 NMLFNFAGOHGLMD-QPDGGIQXSA-N 338.359 2.470 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)OC 504672482 PVIQXTWXWOHHFV-PYAKXWGRSA-N 344.407 2.001 30 1 EEEF biogenic COc1cccc(C(=O)N[C@@H](CC2CCCCC2)C(=O)NCC#N)c1 82064591 NKKXATKPFSFCFT-KRWDZBQOSA-N 343.427 2.404 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@H](c2ccccc2C2=CCCCC2)[C@H]1CO 95866654 XJOIDJIXTAYCGR-GGPKGHCWSA-N 340.423 2.469 30 1 EEEF C=C1C[C@@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@@H](O)CO)[C@@H]2C[C@H]1CC3 299813638 FYKIZBPSTADBEK-BROHORATSA-N 348.439 2.171 30 1 EEEF N#C[C@@H](C(=O)Nc1ccc([S@](=O)C(F)(F)F)cc1)C(=O)C1CC1 169714953 HWZMCOGRZDFBES-BGJPBQGDSA-N 344.314 2.371 30 1 EEEF COc1ccc2c(CCN/C(N)=N\c3nc(C)cc(C)n3)c[nH]c2c1 53246714 MBTYAIBNXXIOCM-UHFFFAOYSA-N 338.415 2.362 30 1 EEEF C=C1C[C@@H]2[C@@H](O)[C@@H](C)C[C@]2(O)C(=O)/C(C)=C\[C@@H]2[C@H](C[C@H]1O)C2(C)C 59779255 XYXDIXJADPYNOO-WJVFRGTLSA-N 334.456 2.233 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N2CC[C@@H](O)C2)nc1 587908486 XSCCSLJVBQUGGU-OAHLLOKOSA-N 329.787 2.109 30 1 EEEF N#Cc1cccc(-c2cc(NC(=O)[C@]3(F)CCCN(C#N)C3)on2)c1 1857540550 AXIFCCZGQFOIJY-KRWDZBQOSA-N 339.330 2.437 30 1 EEEF O=C(C[N+]1(C[C@H](O)c2ccccc2)CCOCC1)c1ccccc1 38142118 KIODMQGFGSAVJP-IBGZPJMESA-N 326.416 2.450 30 1 EEEF O=C1C=Cc2ccccc2/C1=C/NN1C(=O)[C@H]2[C@H]3C=C[C@@H](CC3)[C@H]2C1=O 136965839 CXENGHZKMYPUDO-BNNJERAJSA-N 346.386 2.325 30 3 EEEF COC1=CC(=O)c2c(c(COc3ccc([N+](=O)[O-])cc3)cn2C)C1=O 13558518 GCOUWLHOXJEPCS-UHFFFAOYSA-N 342.307 2.422 30 1 EEEF Cc1ccc(/C(=N\O)c2cccc(NS(=O)(=O)N(C)C)c2)cc1 27420347 GUBVLQFQNXYMOY-WUKNDPDISA-N 333.413 2.440 30 1 EEEF CC(=O)O[C@@H]1O[C@H](OC(C)=O)[C@@H]2CC[C@@H]3C(C)(C)[C@H]4C[C@@]23C1=CC4=O 2356696888 YUEBDHFRUOFFJT-OKDCYFEHSA-N 348.395 2.363 30 1 EEEF O=C1C=C2O[C@@]3(O)CC(=O)c4c(O)cccc4C3=C2c2cccc(O)c21 13368992 OEPGXEJLGRYQSA-FQEVSTJZSA-N 348.310 2.394 30 1 EEEF biogenic C[C@H](CS)C(=O)N[C@@H](CSCc1ccc(F)cc1)C(=O)O 40875518 AWXMUVBCGJJEFI-SKDRFNHKSA-N 331.434 2.194 30 1 EEEF Cc1cc2c(cc1C)[n+](=O)c(NC(=O)c1ccco1)c(C#N)n2O 377845790 BLGGVVFYQXABSJ-UHFFFAOYSA-O 325.304 2.127 30 1 EEEF CCOC(=O)CCOCCCOCCc1nc2ccc(C#N)cc2[nH]1 587568025 JWYKJTLMLIVDLJ-UHFFFAOYSA-N 345.399 2.354 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)C2=CC3=C(CO)C(=O)CC[C@@]3(C)CC[C@@]21C 2356514867 OTUPIQJUQWGDQX-SLHNCBLASA-N 334.456 2.379 30 1 EEEF C=C1CC[C@H]2CCC3=C(C(=O)[C@@H](C(C)=C[C@H](O)[C@@H]1O)[C@H]3O)C2(C)C 2356571487 SMYOLHGQHZBFAQ-AHMROAQXSA-N 332.440 2.297 30 1 EEEF C[C@@](COc1ccc(-c2ccccc2)cc1)(C(=O)NO)S(C)(=O)=O 73310067 PBUOBWNMBHSRIY-QGZVFWFLSA-N 349.408 2.041 30 1 EEEF C=C(C)C(=O)O[C@H]1CCC(=C)[C@@H]2[C@H]3OC(=O)[C@@H](C)[C@@H]3[C@@H](O)C[C@@]12C 238747975 QHTWVJOMDDBORA-WXJIJOBPSA-N 334.412 2.389 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@H]2[C@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100826196 IPHNMKITOREFLW-VIJSRRTDSA-N 332.396 2.136 30 1 EEEF endogenous,in-man O=C(CCCc1ccc(NS(=O)(=O)c2ccccc2)cc1)NO 26718736 KJRQLODJJCERFP-UHFFFAOYSA-N 334.397 2.316 30 1 EEEF C[C@H]([C@H](NC(=O)OCc1ccccc1)C(=O)NCC#N)C(F)(F)F 82064906 DQUMJPBSYXBJLB-PWSUYJOCSA-N 343.305 2.120 30 1 EEEF N#CC1(n2cc([C@@H](NC(=O)c3cnco3)C3CCCCC3)nn2)CC1 95563609 AQPUHBYNYPLGKU-HNNXBMFYSA-N 340.387 2.330 30 1 EEEF O=C1Nc2ccccc2[C@]12/C(=N/CC1CC1)NC(=S)N2CC1CC1 146450706 SNWJRLBOESACRE-SFHVURJKSA-N 340.452 2.243 30 1 EEEF COc1cc2c3c(c1)O[C@]1(CCCC(=O)/C1=C\N(C)C)[C@@H](C2)C3=O 587427256 CTRDIESGJSGEEB-VTFRSSIHSA-N 327.380 2.380 30 1 EEEF C[C@H]1Cc2cc(Br)c(F)cc2[C@](CCC=O)(C(=O)O)N1 587828369 OZXIIBKYYJVMTP-RMLUDKJBSA-N 344.180 2.381 30 1 EEEF O=S(=O)([C@@H]1O[C@@H]1c1ccccc1)N1CCN(c2ccccc2)CC1 26291955 UPZFQDXXSQSJFN-MSOLQXFVSA-N 344.436 2.236 30 1 EEEF CNC(=O)[C@H](Cc1ccccc1)NC(=O)C1(CS)CCCCC1 26151533 OPPRSMACRJLYDL-HNNXBMFYSA-N 334.485 2.340 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@]3(C)C[C@@H](OCC(C)C)[C@@H]12 2356671228 RDYCVUNQBCWGOT-WRPWXNSMSA-N 336.428 2.384 30 1 EEEF Cn1c(Nc2cccc(-c3ccc(C#N)cc3)c2)cc(=O)n(O)c1=O 1857540899 ZTELEPNLOCMRSV-UHFFFAOYSA-N 334.335 2.067 30 1 EEEF C=C1C[C@@H]2OC(=O)C(=C)[C@@H]2[C@@H](OC(=O)C(C)C)C[C@@]2(C)OC1=CC2=O 2356428325 HKQSOGUZSSFJSM-IWKLRQMXSA-N 346.379 2.244 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1C[C@@H]1O[C@@]1(CO)CCC=C(C)CCC=C(C)[C@H]2O 2356381445 MULWDJOXRRXULO-HBWRTXEVSA-N 348.439 2.432 30 1 EEEF N#C[C@@H]1C(N)=NC(=S)[C@@H](C(N)=O)[C@@H]1c1ccc(Cl)cc1Cl 55545300 LCFKVZGBMDLSCI-FXBDTBDDSA-N 341.223 2.016 30 1 EEEF CCO/N=C(\N)Nc1nc(-c2cccc(CNC(C)=O)c2)cs1 26983140 GFMPXDFEXZSMAY-UHFFFAOYSA-N 333.417 2.124 30 1 EEEF C[C@@H]1CC/C(=N\Nc2ccccc2)c2ncc(CC(=O)O)c(=O)n21 40791237 LBQDBYOUOYUTAL-OHARDZCESA-N 326.356 2.041 30 1 EEEF C=C(C)C(=O)O[C@H]1[C@@H]2C(=C)C(=O)O[C@@H]2C[C@H](C)[C@@H]2C=CC(=O)[C@@]12C 238763688 USRAFFQOAADTTD-QTPIOQLMSA-N 330.380 2.373 30 1 EEEF COc1cc2c3c(c1)O[C@]1(C(=O)Nc4cc(C#N)ccc41)[C@@H](C2)C3=O 587438232 DEYIJIKOHGYTCK-DJJJIMSYSA-N 332.315 2.162 30 1 EEEF C[C@@H]1Cn2c(N=C(N)N)nc3cc(Cl)cc(c32)CN1CC1CC1 5890359 CJHRVDIZIMGJJA-SECBINFHSA-N 332.839 2.209 30 1 EEEF C=C1[C@@H]2C[C@H](O)C(C)(C)[C@]23O[C@]12CC[C@@H]1C[C@@]2(C[C@H]3O)C[C@@]1(C)O 169649806 DQSRNQKRJJISCO-HTWSAMNKSA-N 334.456 2.163 30 1 EEEF C[C@@H]1CC/C(=N\Nc2ccccc2F)c2ncc(C(=O)O)c(=O)n21 38153678 PFTZFJAHLMEEKS-FLNUOUKISA-N 330.319 2.252 30 1 EEEF COC(=O)[C@H](C=O)[C@H]1N[C@H](C)Cc2ccc(F)c(Br)c21 587803865 CCYWOEOSTLKZON-HUQFOHBGSA-N 344.180 2.152 30 1 EEEF CC(=O)OC[C@H]1O[C@@H](C#CCCc2ccccc2)C=C[C@@H]1OC(C)=O 7991925 PEMFRHXMDHFDFC-SLFFLAALSA-N 342.391 2.441 30 1 EEEF COC1=C(Br)C[C@@](O)(CC#N)C(O)=C1Br 238764920 QJGRBPFVRFQRMW-VIFPVBQESA-N 338.983 2.452 30 1 EEEF Cn1cncc1C#Cc1ccc2nnc(-c3ccc4c(c3)OCO4)n2c1 653684770 OAQRNZPFZCTIDT-UHFFFAOYSA-N 343.346 2.258 30 1 EEEF C=C1C[C@@]23C[C@]1(O)CC[C@@H]2[C@]12C=CC[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 5249428 UXLXLQYIDWLPKX-SZGLFONZSA-N 330.380 2.056 30 1 EEEF in-man CCOC(=O)/C(C#N)=N/Nc1sc2c(c1C(=O)OCC)CCC2 1857643788 MMXKNBXLHSCHSZ-LICLKQGHSA-N 335.385 2.268 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@@H](C(=O)O)[C@@H]1[C@]2(C)CCC[C@@]31OC2=O 104365806 MBNDVMTZEKAWKP-LPTQGDSLSA-N 332.396 2.136 30 1 EEEF in-man C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 62235276 QYXZQZMPZUEEML-HVFZVJTISA-N 346.423 2.384 30 1 EEEF in-man O=C1C2=CCCC3(Oc4cccc5cccc(c45)O3)[C@@H]2[C@H](O)[C@H]2O[C@H]12 2356793058 GZNZGNSOLGAMAJ-GDAAHCPNSA-N 336.343 2.355 30 1 EEEF C[C@@H]1CC2=C(C1=O)[C@H](O)[C@]1(C)CC[C@@H]3[C@H]([C@H](O)[C@]1(C)C2=O)C3(C)C 2356876551 ZLWDXUVVPOSFGG-NRNQFRROSA-N 332.440 2.275 30 1 EEEF COc1cc(C(=O)O)c(Cl)cc1NC(=O)Nc1cnc(C#N)cn1 63298427 YBQVRQQJXBGPTB-UHFFFAOYSA-N 347.718 2.352 30 1 EEEF N#C[C@@H](c1cccnc1)N1CCN(C(=O)CCc2ccccc2)CC1 13728964 JPGLHQCUFYGSDQ-IBGZPJMESA-N 334.423 2.423 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 104374179 IPHNMKITOREFLW-VCWPGAKESA-N 332.396 2.136 30 1 EEEF in-man C=C[C@](C)(CO)c1cc(CC(=O)c2ccc(O)cc2O)c(O)cc1O 210537653 NBHSGRBQPPWKAV-LJQANCHMSA-N 344.363 2.370 30 1 EEEF C[C@@]12CC[C@H](O)[C@@H]3COC(=C31)C(=O)c1cc3c(cc12)C(=O)CC[C@H]3O 40918707 LDBFCXDBDKSROL-OZONBXFNSA-N 340.375 2.206 30 1 EEEF C[C@H](C=O)NC(=O)[C@H](Cc1ccccc1)NC(=O)Nc1ccccc1 82061190 IOBSHJKFMZWHDJ-PBHICJAKSA-N 339.395 2.123 30 1 EEEF COC1=C(OC)C(=O)C2=C(CCc3ccc(OC)c(OC)c32)C1=O 238778535 WFZYDHQWLRHFNX-UHFFFAOYSA-N 330.336 2.060 30 1 EEEF N#Cc1c(NCCCn2ccnc2)[n+](=O)c2ccc(Cl)cc2n1O 377576690 VYKSWYHONRVGMR-UHFFFAOYSA-N 345.770 2.017 30 1 EEEF O=C(C1CC1)[C@H](c1ccccc1F)N1CC[C@H]2C(=CC(=O)[S@]2=O)C1 299851200 BGWGSGYBPUVHJJ-IIOOSLMMSA-N 347.411 2.136 30 1 EEEF CC(C)CC(=O)N[C@H](CC(N)=O)c1nc2cc(C#N)cc(Cl)c2[nH]1 587203535 KVRCDJQKEPWOJQ-GFCCVEGCSA-N 347.806 2.167 30 1 EEEF Cc1ccc(CNCCCCNC(=O)CCCCC(=O)NO)cc1 13674138 AXICHWHVLCIHOM-UHFFFAOYSA-N 335.448 2.047 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(CO)CCC[C@](C)(CO)[C@H]1C[C@H]3O 169313033 NLKCAXRWGIRDDQ-WTPAFRAOSA-N 334.456 2.070 30 1 EEEF C=C(C)[C@@H]1CC[C@@]23O[C@@H]2[C@@H](C/C(C)=C/[C@]2(O)C=C(C)C(=O)[C@@H]12)OC3=O 238760418 XCSMOAULMOLHGO-ZNXQIONCSA-N 344.407 2.248 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@@]2(COC[C@H]2C#N)N1 587744417 ZUMGHCAWUGYXMG-PWZJLYFZSA-N 325.181 2.488 30 1 EEEF CCC1=C(C)N[C@@H](OC)C(C(=O)CN2C(=O)c3ccccc3C2=O)=C1 27206959 FLROWEGEBWIQIO-KRWDZBQOSA-N 340.379 2.038 30 1 EEEF Cc1ccc(C(=O)/C=C/c2nc(O)[nH]c(=O)c2Br)cc1 26500801 VAPOIYLFUBZXHV-VOTSOKGWSA-N 335.157 2.443 30 1 EEEF COc1ccc(Cl)cc1C#CC1=C(Br)C(=O)O[C@H]1O 587911987 AVHHOCJXRILQNR-GFCCVEGCSA-N 343.560 2.224 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2/C=C\C=C\C(=O)Cc2cc(O)cc(O)c2C(=O)O1 14614732 XTUZVEOWUSGCSV-HLZLSLRQSA-N 330.336 2.038 30 3 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)C3=CC(=O)[C@@](C)(C[C@@H](OC(=O)C=CC)[C@@H]12)O3 2356443078 ZUSPJLQZGBITEG-CNWJYLPWSA-N 346.379 2.244 30 1 EEEF Cc1cccnc1CNC(=O)c1cc(-c2ccccc2C#N)nc(N)n1 45348183 HRZQUYPTNWLNOJ-UHFFFAOYSA-N 344.378 2.231 30 1 EEEF C=CC[C@@](C)(N)c1nc2ccc(S(=O)(=O)NCCCC)cc2[nH]1 587258060 WWMYXNFMWKHGAQ-MRXNPFEDSA-N 336.461 2.391 30 1 EEEF C#CCCCn1c(Sc2ccccc2CO)nc2c(N)ncnc21 13642736 UHLGRKPZDRDVNY-UHFFFAOYSA-N 339.424 2.465 30 1 EEEF CN1CCc2c(c(=O)oc3c(/C=N/N4CCCCC4)c(O)ccc23)C1 1857606351 YGICDYCZLIGPBI-RGVLZGJSSA-N 341.411 2.306 30 1 EEEF C[C@@H]1C[C@@H]2O[C@H]2CC/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 105564230 XFALPAMSDFFXGY-ULNSOIEHSA-N 332.352 2.262 30 1 EEEF O=C(O)/C=C1\CN([C@H](C(=O)O)c2ccccc2Cl)CC[C@@H]1S 53229813 GZZDPOCSWMTUJU-VWZQRQAESA-N 341.816 2.481 30 1 EEEF C[C@]1(O)CC[C@@H]2[C@@H]3CCC4=CC(=O)C(CO)=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C 2356867882 WXBPWNNGZDXSDG-ZYJDFEQASA-N 346.467 2.379 30 1 EEEF COc1cccc2c1[C@H](O)[C@]1(O)CCC3=C(C(=O)C[C@H](C)C3)[C@@H]1[C@@H]2O 13366633 GOUAMPBBOSYLQB-AOXQZDLESA-N 344.407 2.212 30 1 EEEF biogenic C[C@@H]1CCN(C(=O)C(C)(C)C#N)C[C@@H]1N(C)c1ncnc2[nH]ccc12 66252348 VWSCLEOQSBFMNS-OCCSQVGLSA-N 340.431 2.181 30 1 EEEF C=C[C@@]1(C)C(=O)C=C2C(=CC[C@@H]3C(C)(C)[C@H](O)C(=O)C[C@@]23C)[C@@H]1O 95619547 WNHOOXVMGONUHL-XUMBOQAASA-N 330.424 2.361 30 1 EEEF endogenous,in-man O=CC(C=O)c1ccc(-c2nc3cccc(O)c3[nH]2)cc1[N+](=O)[O-] 587262625 ZBEKIYNWVLVBRU-UHFFFAOYSA-N 325.280 2.325 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N)c(C(=O)O)c1OC 587909601 VXKLSNCITLDACD-UHFFFAOYSA-N 332.743 2.432 30 1 EEEF C[C@H](O)CNC1=CC(=O)C(SC/C=C/c2ccccc2)=CC1=O 1857645795 URXSALGSXCHPPY-LJLILKBBSA-N 329.421 2.323 30 1 EEEF C=C(C#CC1=C[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O)CC/C=C(\C)CCC=C(C)C 1857746508 CADYTUXNRNXAES-NYJGJKORSA-N 346.467 2.403 30 1 EEEF Cc1ccc(C(=O)/C=C/c2nc3cccc(S(N)(=O)=O)c3[nH]2)cc1 587965181 HXGQNVVWFMSKFJ-MDZDMXLPSA-N 341.392 2.415 30 1 EEEF Cc1ccc(S(=O)(=O)N/N=C2\CCCC[C@@]23CCC(=O)NC3)cc1 5809815 XYCWNNPFZKUTNG-BYFYWULKSA-N 349.456 2.100 30 1 EEEF COC(=O)c1cccc(Oc2cccc(NC(=O)[C@@H](N)CS)c2)c1 28765069 RTZQMPXZUXFCAU-HNNXBMFYSA-N 346.408 2.461 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)OC 504672483 PVIQXTWXWOHHFV-RUZHRRLVSA-N 344.407 2.001 30 1 EEEF biogenic N#C[C@H]1CCCCN1C(=O)[C@@H](N)CCNCc1ccc(Cl)cc1 26732970 BVDDYIAHKIERDK-CVEARBPZSA-N 334.851 2.052 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]12CC[C@@H](O)[C@@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 62235273 QYXZQZMPZUEEML-JIDAHXIUSA-N 346.423 2.384 30 1 EEEF in-man CO[C@](C)(C(=O)O)C1=C[C@]2(C)C(=CC1=O)CC[C@@H](OC(C)=O)[C@H]2C 2356656320 RDRVOBNXHXPXJL-OKGDGOIHSA-N 336.384 2.280 30 1 EEEF COC(=O)C1=C2[C@](C)(C[C@@H]3O[C@@H]3[C@]2(C)C(=O)OC)c2ccccc21 2356695941 CCCHYPOECSYCKC-LAKGBWAGSA-N 328.364 2.235 30 1 EEEF O=C(CCC1=CCN(CCc2ccc(C(F)(F)F)cc2)C1=O)NO 84759419 YXWVAKWMZGFXHZ-UHFFFAOYSA-N 342.317 2.302 30 1 EEEF C=C1C[C@H]2OC(=O)C(=C)[C@@H]2[C@H](OC(=O)C(C)C)C[C@@]2(C)OC1=CC2=O 96269578 HKQSOGUZSSFJSM-GTACMHHNSA-N 346.379 2.244 30 1 EEEF Cn1c(O)c(C=Nc2ccccc2-c2ccccc2)c(=O)n(C)c1=O 1779623368 XYXHBFAKCYKEII-UHFFFAOYSA-N 335.363 2.207 30 1 EEEF CCN/C(=N\S(=O)(=O)c1ccccc1Cl)N1C[C@H](CC)C=N1 72126897 MVMXJZAAQMLRNG-LLVKDONJSA-N 342.852 2.322 30 1 EEEF C=C1CC[C@@H]2C[C@@H](O)C3=C(C(=O)[C@@H](/C(C)=C/[C@@H](O)C1)[C@H]3O)C2(C)C 238737541 YZCJZJQRTRSJHJ-MAIPUDKPSA-N 332.440 2.297 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1cc[n+]([O-])cc1 587886382 OOXAFPFFPGEZTE-UHFFFAOYSA-N 335.190 2.337 30 1 EEEF Nc1cnc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cn1 587889748 XBRRVPPGSPYWBP-UHFFFAOYSA-N 335.194 2.076 30 1 EEEF C=C(C)[C@@H]1CCC(=C)[C@@H]2C3=C(C[C@H](C)C3=O)C(=O)[C@](C)(O)[C@@H](O)[C@@H]12 2356500236 RLNWZRIDRKCQGX-QRQSVIADSA-N 330.424 2.361 30 1 EEEF O=C(/C=C/c1cn(S(=O)(=O)c2ccccc2)c2ccccc12)NO 84670756 GIIVJOFGKGBXAS-ZHACJKMWSA-N 342.376 2.397 30 1 EEEF O=C(/C=C\c1cc(C(=O)c2cccc(F)c2)c[nH]1)/C=C(\O)C(=O)O 103521899 WQEAOCAOIXLGFY-YAWWFHRPSA-N 329.283 2.494 30 1 EEEF in-vitro CCOC(=O)c1noc([C@H](CCCc2ccccc2)CC(=O)NO)n1 28701994 ZPTQFUMRMHOLBG-CYBMUJFWSA-N 347.371 2.248 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@]12CCC[C@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 85799968 ZCRLGANQNRMURE-XSUTVMHDSA-N 346.423 2.384 30 1 EEEF in-man COc1cc2c(cc1OC)[C@@]13C[C@@H](OC)C=C[C@]14O[C@@H]4CN3CCC2 95911275 JCKPCZAYDZJZIL-WEFJBSGNSA-N 343.423 2.273 30 1 EEEF biogenic,in-vitro N#CC1(C#N)N[C@H](c2ccccc2)C(C#N)(C#N)N[C@@H]1c1ccccc1 19365561 QVPFDGMLHNLKDK-QZTJIDSGSA-N 338.374 2.234 30 1 EEEF N#Cc1ccc2nc(CO[C@@H]3CN(C4CCOCC4)C[C@H]3F)[nH]c2c1 2356299173 ANHAAGFWRVPBII-RHSMWYFYSA-N 344.390 2.152 30 1 EEEF C=C[C@@H]1CN2[C@H]3C[C@@]45c6ccccc6N[C@@]4(O3)[C@H]2C[C@H]1[C@H]5C(=O)OC 2356762800 VQQRVBOFQXPEAN-ABJPWUGKSA-N 338.407 2.102 30 1 EEEF N#Cc1cccc(/C(CCN2CCN(c3ccccn3)CC2)=N/O)c1 36476172 GPRBXEJIWUKAOW-RELWKKBWSA-N 335.411 2.344 30 1 EEEF C[C@]12C(=O)C[C@@H]3[C@@H](C=CC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2[C@H](O)CO 255242904 NCBLKWGLSQARQJ-ZDPVWBBSSA-N 344.451 2.443 30 1 EEEF COC(=O)[C@H](C=O)[C@H]1N[C@H](C)Cc2cc(Br)c(F)cc21 587804283 DKWOWZAXZYXXJE-OHILOLKFSA-N 344.180 2.152 30 1 EEEF CS(=O)(=O)OCCCOc1ccccc1OCC(F)(F)F 72187408 FAXMDTIMSRJDNO-UHFFFAOYSA-N 328.308 2.373 30 1 EEEF CNC(=O)c1ccc(-c2ccnc(C)c2C#Cc2ccc(N)nc2)cn1 202387726 GEDSADFOSJJXJF-UHFFFAOYSA-N 343.390 2.189 30 1 EEEF N#C[C@@H]1C[C@@H]2CN3CCc4cc5c(cc4[C@@H]3C[C@@H]2C[C@@H]1O)OCO5 28766718 QHGNBFHROQKCSX-VUBIOHBQSA-N 326.396 2.245 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)([C@@H](O)CC[C@@]4(C)CO)[C@H]2CC[C@H]1[C@H]3O 2356695481 IOLAXGYDTVZNNV-RLJQHAHTSA-N 334.456 2.068 30 1 EEEF CCC#CCOC(=O)CNC(=O)c1csc(-c2ccccc2)n1 82072224 PDVVMOFBAFRNLV-UHFFFAOYSA-N 328.393 2.497 30 1 EEEF N#Cc1ccc2c(c1)CC[C@H]2N1C[C@H](N)[C@H](C(=O)[C@H]2CCC[C@H]2C#N)C1 261190764 ZAWGLJVNJZBVID-MVBLQPKNSA-N 348.450 2.314 30 1 EEEF CCCCCOc1cc(CN2CCN/C2=N\[N+](=O)[O-])cnc1Cl 103186172 FFZKQYGSOGXMIE-UHFFFAOYSA-N 341.799 2.257 30 1 EEEF CC1(C)C=Cc2c(ccc3c2O[C@@H]2[C@@H]3COC3=CC(=O)C=C[C@]32O)O1 14502675 XBSGPVUHRGTYRA-DJKXOVBDSA-N 338.359 2.500 30 1 EEEF biogenic Cc1ccc(/C(N)=N/O)c(Oc2cccc(N3CCOCC3)c2)n1 72180512 JRNUNZMKGNIQRK-UHFFFAOYSA-N 328.372 2.113 30 1 EEEF COc1ccc(C(=O)O[C@@H]2c3cocc3[C@@H](CC=O)[C@@H]2O)cc1OC 238783085 SFCCTINUDYTREN-ZTFRIQLXSA-N 346.335 2.242 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 257434379 HHDWSDSMWJQURA-JJFQCNDFSA-N 332.396 2.136 30 1 EEEF endogenous,in-man Cn1cccc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)c1=O 587891269 WAPWBCVKHMQNMY-UHFFFAOYSA-N 349.217 2.403 30 1 EEEF CC(=O)OC[C@@H]1O[C@@H](C#Cc2ccc(C)cc2C)C=C[C@H]1OC(C)=O 7992539 FLENGSMTXSLATM-ZCNNSNEGSA-N 342.391 2.473 30 1 EEEF O=C([C@@H]1CSC(c2ncccc2O)=N1)N(O)Cc1ccccc1 26736431 ICFWJGZOILOKNF-LBPRGKRZSA-N 329.381 2.067 30 1 EEEF C=C[C@]12CNCC[C@@H]1[C@](C(=O)OC)(c1cc3ccccc3[nH]1)CO2 14693447 KZLFAYYOKRWYDO-SNRMKQJTSA-N 326.396 2.143 30 1 EEEF biogenic C[C@H](N[C@@H]1c2cc(C#N)ccc2OC(C)(C)[C@@H]1O)C(=O)OC(C)(C)C 96941746 HTQRBOPBRPMVKW-IUIKQTSFSA-N 346.427 2.451 30 1 EEEF Oc1ccc(O)c(C=NNC(=S)N[C@@H]2C[C@H]3C[C@H]2[C@H]2C=CC[C@@H]32)c1 254047244 OFXIRPMFRVBDKI-RLPSOPLKSA-N 343.452 2.497 30 1 EEEF CN(C)S(=O)(=O)c1ccc2nc(C#Cc3ccccc3)[nH]c2c1 587953675 PYDYOUCVKVJTBE-UHFFFAOYSA-N 325.393 2.213 30 1 EEEF CC(C)[C@H]1[C@@H](O)[C@@H](O)C2=CC3=C(CO)C(=O)CC[C@@]3(C)CC[C@@]21C 202800958 OTUPIQJUQWGDQX-KNJMJIDISA-N 334.456 2.379 30 1 EEEF CC(N)=C1C(=O)[C@@H]2[C@H]3c4c[nH]c5cccc(c45)C[C@H]3C(C)(C)N2C1=O 2356386930 AFOUSJMOYMLOPA-DQYPLSBCSA-N 335.407 2.229 30 1 EEEF C[C@]1(C=O)[C@@H]2CC[C@@]3(C)O[C@@]14C(=O)c1ccc(O)cc1C(=O)C4=C[C@H]23 102958919 NMLFNFAGOHGLMD-HROFAYACSA-N 338.359 2.470 30 1 EEEF CC=CC=CC1=CC2=CC(=O)[C@](C)(OC(=O)C[C@@H](C)O)C(=O)C2=CO1 2356859859 TZCZFKHZYAXVCK-BLVKFPJESA-N 344.363 2.068 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)[C@H](C)C[C@@H]2OC(=O)C(=C)[C@@H]21 5662889 KYTKEOOPALLADL-OPEXITSUSA-N 346.379 2.244 30 1 EEEF biogenic COc1ccc(N/N=C2\C(O)=NN=C2c2cnccc2OC)cc1 49021495 SVYQHTDGUMYYKA-UHFFFAOYSA-N 325.328 2.241 30 1 EEEF N#Cc1cccc(-n2nnc([C@@H]3CCCCN3C(=O)C3CCC3)n2)c1 49045475 RDVZDMOJYYFVOJ-INIZCTEOSA-N 336.399 2.388 30 1 EEEF CC(=O)OCC[C@@H](/C=C/C=C/C#CC#C/C=C/CO)OC(=O)C(C)C 238784970 RLOXIGRNKNTVJQ-DMYSCGTASA-N 344.407 2.175 30 1 EEEF Oc1ccc(/C=N/N2CCN(CCc3ccccc3)CC2)c(O)c1 299852139 NYNJCGUDQXDRET-HMMYKYKNSA-N 325.412 2.292 30 1 EEEF Cc1ccnc2c(C(=O)NC3[C@H]4CC5C[C@H]3CC(C#N)(C5)C4)cnn12 653795342 HFPWXYWWVQHMJI-QABYGRRUSA-N 335.411 2.486 30 1 EEEF C[C@H]1CCN(C(=O)CC#N)[C@]12CCCN(c1ncnc3[nH]ccc13)C2 169699011 FDSLGXNJYBLDDV-UGSOOPFHSA-N 338.415 2.079 30 1 EEEF C=C1C[C@@]23C[C@]1(O)CC[C@@H]2[C@]12C=CC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 103836622 UXLXLQYIDWLPKX-BNFRVXKXSA-N 330.380 2.056 30 1 EEEF in-man C=C1C[C@@]23C[C@H]1[C@H](O)C[C@H]2[C@]12CCC[C@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100776680 ZCRLGANQNRMURE-JJDQNSNLSA-N 346.423 2.384 30 1 EEEF endogenous,in-man N#C[C@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)C1(N)CCOCC1 113496381 YEOQUBBPBNJOAA-IBGZPJMESA-N 349.434 2.412 30 1 EEEF N[C@@H](CS)C(=O)Nc1ccc(Oc2ccc(C(=O)O)cc2)cc1 28766010 ZVUYERCVYDMSPI-AWEZNQCLSA-N 332.381 2.373 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](COC(C)=O)CCC=C(C(=O)OC)CC[C@@H]12 2356493722 DRSUBRLQXQEHHE-VNQPRFMTSA-N 336.384 2.327 30 1 EEEF CCN1C(=O)N(CC)[C@H]2NC(=O)N(/N=C/C=C/c3ccccc3)[C@@H]21 1857754172 NRUADQHKBGCFCV-RNDHMKDESA-N 327.388 2.140 30 1 EEEF C[C@H]1CC/C(=N/N(C)c2ccccc2)c2ncc(C(=O)O)c(=O)n21 40641083 DXCAOAFKYKPQRQ-UXNQKTKSSA-N 326.356 2.137 30 1 EEEF CC(C)[C@H]1[C@@H](O)[C@@H](O)C2=CC3=C(CO)C(=O)C=C[C@@]3(C)CC[C@@]21C 238786216 IQSIJJOWDAYBIC-KNJMJIDISA-N 332.440 2.155 30 1 EEEF Cc1ncnc2c1/C(=N/N=C(N)N)C[C@@H](c1ccccc1Cl)C2 13474684 SJVDKRAFRLTANA-ADUAYUHLSA-N 328.807 2.146 30 1 EEEF COC1CCC2(CC1)Cc1ccc(C#N)cc1[C@@]21N=C(N)N(C)O1 169700447 AOZVUBOFLFKDDG-UYJHFMRCSA-N 326.400 2.034 30 1 EEEF C/C(=N\N=C1C(=C\N(C)C)/C(=O)NC(=O)N/1C)c1ccc(Cl)cc1 106439955 PKIXMBJLCHTOJY-FOMBHFDKSA-N 347.806 2.090 30 1 EEEF CC(=O)Oc1cc(O)cc2c1C(=O)/C(=C/c1ccc(O)c(O)c1)CO2 211226168 DBQSMZBWTHHICO-NYYWCZLTSA-N 342.303 2.387 30 1 EEEF C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@H]2[C@@H](O)CO 2356431752 DCMCEXCRUWBAFV-LWYCANNGSA-N 348.483 2.459 30 1 EEEF CCOC(=O)C1=CNC2=C(/C=N/c3ccccc3)C[C@@H](C)N2C1=O 28255399 IQZJQFGQBJJQQE-AINDZBIGSA-N 325.368 2.272 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@H](n2ncc3ccccc3c2=O)[C@@H]1O 27557298 UMDKMLKKBGABSS-ROUUACIJSA-N 347.374 2.389 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 2356675175 JTSAEZNOAXDDOQ-JFUOKHFQSA-N 346.423 2.225 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)([C@@H](O)CC[C@@]4(C)CO)[C@@H]2CC[C@H]1[C@H]3O 2356695480 IOLAXGYDTVZNNV-DQAPRGMSSA-N 334.456 2.068 30 1 EEEF C[C@H]1CC(=O)C2=C(CC[C@@]3(O)[C@@H]2C(=O)c2cccc(O)c2[C@H]3O)C1 238752883 CRULJZWXPCYLAC-BXXNDXQRSA-N 328.364 2.059 30 1 EEEF CC(C)(C)C(=O)Nc1ccc(-c2nc3nc(C#N)c(C#N)nc3[nH]2)cn1 587244851 MBAAYBNRDKMRDE-UHFFFAOYSA-N 346.354 2.143 30 1 EEEF CO[C@@]1(C#C[C@](O)(c2ccccc2)c2ccccn2)CN2CCC1CC2 28563815 LLHFDYRCKMNGML-VXKWHMMOSA-N 348.446 2.432 30 1 EEEF C=C(C)[C@@H]1C[C@@H]2[C@H](CC[C@]2(O)CCNC(=N)NC)[C@@]2(O)CC=C[C@H]1C2 2356676438 SYAVXIORAFJRNU-WDYSCTGBSA-N 347.503 2.171 30 1 EEEF C=C1[C@H]2OC(=O)C=C(C)[C@H]2C[C@H]2/C(=C/C=C/C(C)(C)O)C(=O)OC[C@H]12 38858322 LUHDPMVWXCNPMF-KVNRGGCFSA-N 344.407 2.477 30 1 EEEF Cc1nc(C(=O)Nc2ccc([C@H]3CNCCO3)c(F)c2)ccc1C#N 149890471 IOLQKVXFTBCMAU-QGZVFWFLSA-N 340.358 2.314 30 1 EEEF CC(C)[C@]12O[C@H]1C=C1[C@@]3(C)CCC4=C(COC4=O)[C@H]3C[C@@H]3O[C@]13C2=O 64503817 NDBFYINIVHOHLP-GSBAHSKOSA-N 342.391 2.100 30 1 EEEF C=C1C(=O)[C@]23CC[C@H]4[C@@](C)(C(=O)O)CC[C@@H](O)[C@]4(C)C2=C[C@H](O)[C@H]1C3 238748240 ILHYJJMPRBZUJC-MOPYFOGVSA-N 346.423 2.081 30 1 EEEF N=C(N)NN=Cc1cc([N+](=O)[O-])ccc1Sc1ccccc1CO 299809573 YXMQLRAQBWUKBW-UHFFFAOYSA-N 345.384 2.055 30 1 EEEF O=C(O)[C@@H]1Cc2cccc(F)c2[C@@H](c2cccc(OC[C@H]3CO3)c2)N1 962903171 VSHFMNJQRIDHIY-QILLFSRXSA-N 343.354 2.292 30 1 EEEF COc1ccc2[nH]c(C(=O)NCCCCCCC(=O)NO)cc2c1 13490061 CHCZVVGBFOJTEK-UHFFFAOYSA-N 333.388 2.362 30 1 EEEF O=C(/C=C/c1cccn1Cc1cccc(F)c1F)CC(=O)C(=O)O 103295926 CVPAUOMIWMWRTR-VOTSOKGWSA-N 333.290 2.441 30 1 EEEF N#Cc1ccc2c(c1)CC[C@H]2N1C[C@H](N)[C@H](C(=O)[C@@H]2CCC[C@H]2C#N)C1 28955123 ZAWGLJVNJZBVID-FAJAVTLNSA-N 348.450 2.314 30 1 EEEF C=CCCC(=O)NCCOc1ccc(C[C@H]2SC(=O)NC2=O)cc1 26502604 WHPJZXYAGCQXGA-CQSZACIVSA-N 348.424 2.042 30 1 EEEF C=C1[C@H](O)C[C@@H]2[C@](C)(CO)C[C@H](O)C[C@@]2(C)[C@H]1CCC(C)=CCO 2356639997 LCWHTWNKEOSQBZ-GTYQWKCWSA-N 338.488 2.418 30 1 EEEF COC1=CC2=C3C[C@@H]4C[C@H](OC)[C@H](OC)C[C@H]4CN3CCC2=CC1=O 2356847090 OTLSHWIHWKUYQL-BBNYVJOESA-N 345.439 2.446 30 1 EEEF Cn1cc(C#N)c2ncnc(N3CCN(CCc4ccccc4)CC3)c21 38934485 GTTMZNJRBZJIOK-UHFFFAOYSA-N 346.438 2.205 30 1 EEEF C=C1C[C@H](OC(=O)C(C)C)[C@H]2[C@H](C)C(=O)O[C@@H]2[C@@H]2[C@H]1C[C@H]1O[C@@]21C 238750760 ZEIPBAWKAWZVOR-AUTBAJHYSA-N 334.412 2.485 30 1 EEEF C[C@]12COC(=O)N1C(=O)N(c1ccc(C#N)c(C(F)(F)F)c1)C2=O 40752891 WQKXGQFGVRREAS-CYBMUJFWSA-N 339.229 2.255 30 1 EEEF CN(O)C(=O)CO[C@@H](c1ccc(Cl)c(Cl)c1)P(=O)(O)O 95553956 BNXJAJGNFMLKQG-SNVBAGLBSA-N 344.087 2.034 30 1 EEEF COc1nccc2nc(-c3ccc(C(C=O)C=O)c([N+](=O)[O-])c3)[nH]c12 587261416 BCISFQHBQWSDHF-UHFFFAOYSA-N 340.295 2.023 30 1 EEEF C[C@](CCc1ccccc1)(C(=O)NO)S(=O)(=O)c1ccccc1 1772576619 JNNBFIBVHIDVHP-KRWDZBQOSA-N 333.409 2.357 30 1 EEEF CCc1nc2n(c(=O)c1C(N)=O)[C@H](C)CCC2=NNc1ccccc1 253634366 ROUYGSNPBKRWQM-LLVKDONJSA-N 339.399 2.076 30 1 EEEF O=C1C=Cc2cc(S(=O)(=O)O)ccc2C1=NNc1ccccc1 2356856092 RWZPEBJPWGVNIQ-UHFFFAOYSA-N 328.349 2.345 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)c2ccc(C#N)cc2)[C@@H]1O 40503869 FZBBUIVMCCYQOP-MSOLQXFVSA-N 347.374 2.433 30 1 EEEF Cc1nc2n(c(=O)c1C(=O)O)[C@H](C)CC/C2=N\Nc1ccccc1 40631433 PTMLSROVUJDKCJ-MDSXTQFQSA-N 326.356 2.421 30 1 EEEF COC(=O)[C@H](C=O)[C@@H]1N[C@H](C)Cc2cc(Br)c(F)cc21 587804284 DKWOWZAXZYXXJE-XBURVNOZSA-N 344.180 2.152 30 1 EEEF C=C(C)C[C@@H]1N(c2ccccc2)C(=O)[C@@H]2[C@H](C(=O)O)[C@@H]3C=C[C@]12O3 169620170 IDZVBZRLNMBRMS-NAHJCDBISA-N 325.364 2.392 30 1 EEEF N#CCNC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)c1ccccc1 82064478 FQOUDTRXHGQUIW-SFHVURJKSA-N 346.390 2.149 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc2c([nH]1)C(=O)NCCC2=O 587912375 MZRDWFVCVBPODQ-UHFFFAOYSA-N 328.755 2.393 30 1 EEEF CC#CC#COC1=C[C@]2(CC[C@H](OC(=O)CC(C)C)CO2)[C@@H]2O[C@H]12 5158076 RYAXKMRZPSXCFZ-JEDBISTDSA-N 330.380 2.159 30 1 EEEF biogenic CC1(C)Oc2ccc(C#N)cc2[C@@H](Oc2cc[nH]c(=O)c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c2[nH]c(-c3cc(OC)no3)nc21 72108904 ODQVSYSJORWZAV-VIFPVBQESA-N 342.359 2.040 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O[C@@H]([C@H]3O)[C@@H]21 257506481 OSYJLXUUZYSFTC-LVVMLOCMSA-N 332.440 2.432 30 1 EEEF endogenous,in-man C[C@H](Oc1ccc(C#N)cc1)c1nc2ccc(S(N)(=O)=O)cc2[nH]1 587191706 VTKSHOFMVXXKOB-JTQLQIEISA-N 342.380 2.222 30 1 EEEF CNS(=O)(=O)c1ccc(/N=C/[C@@H]2C(=O)Nc3ccccc32)cc1 169685173 XTPZAFMBWDNWIW-XKYMITNMSA-N 329.381 2.033 30 1 EEEF COc1ccc(C2(Nc3ncc(C(=O)NO)cn3)CCCC2)cc1 166641374 IXISPUSZLURAQL-UHFFFAOYSA-N 328.372 2.486 30 1 EEEF COc1cccc2c1O[C@H]1C=C(OC[C@@]3(C)CO3)C=C(O)[C@H]1C2=O 64475221 GLCNXGRTIKCJRG-DAYGRLMNSA-N 330.336 2.400 30 1 EEEF C=C(C)C(=O)O[C@@H]1[C@@H]2C(=C)C(=O)O[C@@H]2CC(=C)[C@@H]2C[C@@H](O)C(=C)[C@H]12 2356627896 ZQBZOPWDBPOXPR-URRYWWILSA-N 330.380 2.085 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@]12OC(=O)[C@](C)(CC[C@@H]1O)[C@H]2[C@@H]3C(=O)O 85800211 JKQCGVABHHQYKQ-VCWPGAKESA-N 332.396 2.136 30 1 EEEF in-man N#C[C@@H]1[C@@H](c2ccc(-c3cccnc3)cc2)[C@H](CO)N1C(=O)C1CC1 95896227 FYALJDMLJJPLTL-CEXWTWQISA-N 333.391 2.337 30 1 EEEF C=C1C[C@@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 257389676 BSBICXIQCTXPMN-MVUGAQQQSA-N 330.380 2.056 30 1 EEEF endogenous,in-man CC(C)(C#Cc1ccc(-c2nc3ncnc(N)c3[nH]2)cc1)CC(=O)O 1857637383 OZSQUWLXXGMAMF-UHFFFAOYSA-N 335.367 2.455 30 1 EEEF CC(C)NC[C@@H](O)CO/N=C1/c2ccccc2[C@H]2CCCC[C@]12O 26944095 RTKLMTIRQZCKHN-DJYWVDBBSA-N 332.444 2.169 30 1 EEEF C=C1C[C@@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@@H](O)CO)[C@H]2C[C@H]1CC3 299813641 FYKIZBPSTADBEK-VQEGESQYSA-N 348.439 2.171 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc(S(=O)(=O)O)cnc1O 587919846 YURVMDIIWDREEM-UHFFFAOYSA-N 339.756 2.096 30 1 EEEF C[C@H](CO)C1=C2CC[C@H](CO)C3=C(C[C@]2(C)CC1)[C@@H](C)[C@@H](O)C3=O 2356325645 QNDHAMGPYFFBHA-QOMVIXHLSA-N 334.456 2.380 30 1 EEEF CCCC[C@@H]1CC(=O)N(OS(=O)(=O)/C=C/c2ccccc2)C1=O 101166139 UNVFZNKIAUTQBV-PLSXKVAHSA-N 337.397 2.484 30 1 EEEF CC=CC(=O)O[C@@H]1[C@H](O)[C@H]2O[C@@H]3C=C(C)CC[C@@]3(C)[C@@]1(C)[C@@]21CO1 2356487414 AGQQMRNEWSVYSU-MNSRNUEESA-N 334.412 2.138 30 1 EEEF COCCc1ncc(-c2c(C#N)c(N)nc3c2CCc2[nH]ccc2-3)cn1 71613767 USOGSRSFKQYAPY-UHFFFAOYSA-N 346.394 2.275 30 1 EEEF C[C@](Cc1ccccc1)(C(=O)NO)S(=O)(=O)c1cccs1 13520940 UQRFKNRXERPSMG-AWEZNQCLSA-N 325.411 2.029 30 1 EEEF COC(=O)[C@H](CCSC)/N=C1/C(=O)c2ccccc2C(O)=C1O 28529658 WNMKVDOQTGURMS-TUCQUAOGSA-N 335.381 2.403 30 1 EEEF C[C@H](O)[C@@H]1C(O)=C(C(=O)[C@H]2[C@H]3CCCC[C@H]3C=C[C@H]2C)C(=O)N1C 2356723590 NOYBJWXGAYWITN-UBKONASUSA-N 333.428 2.218 30 1 EEEF C[C@H]1CC/C(=N\Nc2ccccc2F)c2ncc(C(=O)O)c(=O)n21 38153679 PFTZFJAHLMEEKS-PQHMUEMWSA-N 330.319 2.252 30 1 EEEF C=CC/N=C1\N[C@@H](c2ccccc2)C(C(=O)OC)=C(C)N1CCOC 15935434 IEVFHLVLBVQGHO-KRWDZBQOSA-N 343.427 2.268 30 3 EEEF C=CCc1cc(NC(=O)NCC)ccc1OC[C@@H](O)CNC1CC1 169317309 IBRIYEJEZDJIDG-INIZCTEOSA-N 333.432 2.048 30 1 EEEF C[C@H]1CCN(C(=O)CC#N)[C@@]12CCCN(c1ncnc3[nH]ccc13)C2 169699009 FDSLGXNJYBLDDV-SCLBCKFNSA-N 338.415 2.079 30 1 EEEF C/C(=N\NC(N)=S)c1ccc(-c2ccc(OCC(=O)O)cc2)cc1 1857746479 SLVKUSIGJRJBBG-YBFXNURJSA-N 343.408 2.374 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(C)(C)C)[C@H]1[C@](C)([C@H]3CC[C@@]1(C)O3)[C@H]2O 2356544660 XVJNAEOCXFSHRU-NUWRFZTQSA-N 336.428 2.216 30 1 EEEF CC[C@@H]1O[C@]1(C)[C@H](OCOC)[C@H](C)C(=O)N1C(=O)OC[C@@H]1C(C)C 2356700666 DMBYGHSIWBDJGS-TVRNETQVSA-N 343.420 2.183 30 1 EEEF O=C(CCCCCNC(=O)NC(=O)c1ccc2ccccc2c1)NO 49046259 HPXNIWNVCNUTRT-UHFFFAOYSA-N 343.383 2.345 30 1 EEEF O=C(C[C@@H](S)C(F)(F)F)N[C@H](Cc1ccc(F)cc1)C(=O)O 43066222 PGJZLTNQRTXDPB-NXEZZACHSA-N 339.310 2.188 30 1 EEEF COc1ccc(Cl)cc1C1(Nc2ncc(C(=O)NO)cn2)CC1 166665372 LWSBXNJSHGFJCT-UHFFFAOYSA-N 334.763 2.359 30 1 EEEF CCOC(=O)c1cn(C[C@H]2CO2)c2cc(Cl)c(F)cc2c1=O 207914468 DTISBMDFRLIPKN-QMMMGPOBSA-N 325.723 2.370 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@@H]2OC[C@]23O[C@@H]2C=C(C)C(=O)C[C@@]2(C)[C@@]13C 2356397105 GUTBYIDIQSFHLV-BQIOYJHESA-N 332.396 2.346 30 1 EEEF CC[C@H](O)c1c(C/C=C/CO)cc2c(c1OC)C(=O)C=C(OC)C2=O 28366697 RUMPUGDOZMKASN-GFUIURDCSA-N 346.379 2.139 30 1 EEEF CCCC[C@H](O)C#C[C@H](O)C=CCCCCC[C@H](O)CC(=O)O 2356516004 IRDUBXGVWQSMKQ-BBWFWOEESA-N 326.433 2.244 30 1 EEEF C=C1C(=O)[C@]23CC[C@H]4[C@@](C)(C(=O)O)CC[C@@H](O)[C@]4(C)C2=CC[C@@]1(O)C3 238783598 FQLVUGQOFVEUJQ-MTZQICQISA-N 346.423 2.225 30 1 EEEF N#Cc1cc(F)ccc1-c1cnc(N)c(C(=O)NC2CCCC2)n1 473106415 XENZNUXTSZZFEG-UHFFFAOYSA-N 325.347 2.409 30 1 EEEF C=C1C[C@@H]2OC(=O)C(=C)[C@@H]2[C@H](OC(=O)C(C)C)C[C@@]2(C)OC1=CC2=O 2356428326 HKQSOGUZSSFJSM-QMYADUOMSA-N 346.379 2.244 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)CC[C@H](O)[C@]2(C)C[C@@H]2OC(=O)C(=C)[C@H]21 2356509316 LJFQOYCUYZGFOE-MABMQTIPSA-N 332.396 2.453 30 1 EEEF CCCCCCCCC[C@@H]1OC(=O)C[C@@H](O)C[C@H](O)/C=C\[C@@H]1O 138792698 HFGOXJHLMBNOHC-YCCSFSNZSA-N 328.449 2.472 30 1 EEEF CCCCCCCCCC(=O)CC(=O)N[C@@H](CCO)C(=O)OC 43628114 ONNAFMARUDXNPQ-HNNXBMFYSA-N 329.437 2.127 30 1 EEEF C=C1C[C@@H](O)[C@@H]2O[C@]2(C)CC[C@@H]2/C(=C/C=C/C(C)(C)O)C(=O)OC[C@@H]12 40956110 DHTWVKTXQLZELP-MALFFHSUSA-N 348.439 2.288 30 1 EEEF O=C(NO)c1ccc(N[C@H]2CCN(Cc3ccccc3)C2=O)cc1 143726836 ALXBWSHZBQTFJJ-INIZCTEOSA-N 325.368 2.019 30 1 EEEF Cc1cc(C#Cc2nc3ccc(-n4cnnn4)cc3[nH]2)ccc1[N+](=O)[O-] 587262167 PFUWHWGUAFACDF-UHFFFAOYSA-N 345.322 2.155 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCC[C@@]2(CO)C(=O)O[C@@H]([C@H]3O)[C@H]12 14812353 RDUNXXWNAKBVER-XUYWJHTBSA-N 332.440 2.434 30 1 EEEF endogenous,in-man COC(=O)/C=C/c1ccc(CNC2=CC(=O)c3ncccc3C2=O)cc1 1857749367 JKHNNZZBXFYAGL-CMDGGOBGSA-N 348.358 2.321 30 1 EEEF CC(C)[C@]1(O)C=C2C(=O)C[C@H]3[C@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@@H]2CC1 2356337244 TVHWXCUVXSEILO-ZIDVSRPDSA-N 336.472 2.459 30 1 EEEF CC1=C2C=C3C(=O)C(O)=C([C@H](C)CO)[C@]3(C)CC[C@@]2(C)C[C@@H](O)C1=O 2356521437 XUINLCMVOIWOKB-SFZFCKMESA-N 346.423 2.393 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OCC(C)C)C[C@]1(C)[C@H](O)CC(=O)[C@@H](C)[C@@H]21 2356702919 BQKSKQIZKSAQEI-XWWAYRIXSA-N 336.428 2.121 30 1 EEEF C[C@@H]1[C@@H](CO)C[C@@H]2CC3=C(CCCCN=C(N)N)C(=O)C[C@@]31C2(C)C 85549642 JACXVAGUXWETDD-AVUKIGBWSA-N 347.503 2.380 30 1 EEEF biogenic,in-vitro O=C(/C=C/c1cc(C(=O)c2ccccc2F)c[nH]1)CC(=O)C(=O)O 96285896 AQGGDCGFYLXOER-AATRIKPKSA-N 329.283 2.011 30 1 EEEF N#Cc1nc2nc(-c3ccc(F)c(Br)n3)[nH]c2nc1C#N 587154971 HKWMYKFBOCLERE-UHFFFAOYSA-N 344.107 2.060 30 1 EEEF NC(N)=N/N=C1\c2ccccc2C[C@H]1Sc1nc2ccccc2[nH]1 101277711 OLXDFULPBKAYAM-CVZTXRPJSA-N 336.424 2.257 30 1 EEEF COC1=CC(=O)c2c(COc3ccc(N)cc3)c(C)n(C)c2C1=O 28864293 KUKWXOPJLRICKN-UHFFFAOYSA-N 326.352 2.404 30 1 EEEF COc1cccc(CCCn2cccc(/C=C/C(=O)NO)c2=O)c1 143989701 MSWKVZRQRACREJ-MDZDMXLPSA-N 328.368 2.008 30 1 EEEF COc1ccc2c3c1O[C@H]1C=C(C(C)=O)C[C@@H]4[C@@H](C2)N(C)CC[C@]314 27711482 FKNWJBZMTKZQMB-RNKNFESXSA-N 325.408 2.490 30 1 EEEF CN(C)CCCO/N=C1\c2ccccc2-n2c1nc1ccccc1c2=O 26378245 RFAZEUVPHGJZFE-RELWKKBWSA-N 348.406 2.420 30 1 EEEF CCO/N=C(\CCN1CCN(c2ncccn2)CC1)c1ccccc1 36476227 LQDOOQAUHRWSAG-RELWKKBWSA-N 339.443 2.430 30 1 EEEF CS(=O)(=O)Nc1ccc(-c2nc3cc(C#N)c(C#N)cc3[nH]2)cc1 586950167 BNZFNCZGIZSRDK-UHFFFAOYSA-N 337.364 2.345 30 1 EEEF CC1=C2C=C3C(=O)C(O)=C([C@H](C)CO)[C@@]3(C)CC[C@]2(C)C[C@@H](O)C1=O 169309054 XUINLCMVOIWOKB-WQILTUSXSA-N 346.423 2.393 30 1 EEEF O=C(/C=C/c1cccn1Cc1c(F)cccc1F)CC(=O)C(=O)O 103295939 FNQPIRNAHZGGGE-VOTSOKGWSA-N 333.290 2.441 30 1 EEEF C/C(=N\N=C1C(=C/N(C)C)\C(=O)NC(=O)N\1C)c1ccc(Cl)cc1 102933714 PKIXMBJLCHTOJY-QOHLMHBPSA-N 347.806 2.090 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@](C)(CO)CCC[C@]4(C=O)[C@@H]2CC[C@H]1[C@H]3O 2356462313 NGMHJAMTHJNIJX-GSFMDEFVSA-N 332.440 2.277 30 1 EEEF CCCC[C@H](O)C#C[C@H](O)C=CCCCCC[C@@H](O)CC(=O)O 2356516005 IRDUBXGVWQSMKQ-GVDBMIGSSA-N 326.433 2.244 30 1 EEEF C=CC[C@@]12C[C@H](OC)[C@H](O)[C@@H]([C@H](c3ccc4c(c3)OCO4)[C@@H]1C)[C@H]2O 2356606166 GGFOVZYLYBVWDX-FLSJBGELSA-N 346.423 2.468 30 1 EEEF CC=CC=CC1=CC2=CC(=O)[C@@](C)(OC(=O)C[C@@H](C)O)C(=O)C2=CO1 2356859861 TZCZFKHZYAXVCK-CWTRNNRKSA-N 344.363 2.068 30 1 EEEF CCc1nc2n(c(=O)c1C(N)=O)[C@@H](C)CC/C2=N\Nc1ccccc1 40465616 ROUYGSNPBKRWQM-MAMUZICDSA-N 339.399 2.076 30 1 EEEF C/N=C1/N/C(=C/c2c[nH]c3cccc(Br)c23)C(=O)N1C 96937891 IPEDGFQBWJGPBU-IZZDOVSWSA-N 333.189 2.319 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 257754422 ZCRLGANQNRMURE-JZDDWXORSA-N 346.423 2.384 30 1 EEEF endogenous,in-man O=C(CCCc1ccc2c(c1O)C(=O)c1c(O)cccc1C2)NO 13606196 ITBWRPKQCXCWRI-UHFFFAOYSA-N 327.336 2.061 30 1 EEEF C=CCNC(=O)Nc1ccc(OC[C@H](O)CNC(C)C)c(Cl)c1 169317378 XCZZSQOOQIILSK-CYBMUJFWSA-N 341.839 2.385 30 1 EEEF Cc1nc2n(c(=O)c1C(=O)O)[C@H](C)CC/C2=N/Nc1ccccc1 101165696 PTMLSROVUJDKCJ-JPYHIROTSA-N 326.356 2.421 30 1 EEEF C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@@H]12 2356435470 DHTWVKTXQLZELP-GINSCSNVSA-N 348.439 2.288 30 1 EEEF C=C1CC[C@H]2[C@@](C)(CCC(=O)[C@@]2(C)C=O)[C@@H]1C/C=C1/C(=O)OC[C@H]1O 96935357 YZKJGBDSKBLPHO-IZRDHSPGSA-N 346.423 2.377 30 1 EEEF N#Cc1c(O)nc(SC[C@H]2CO2)nc1-c1ccc([N+](=O)[O-])cc1 96910367 HSBFNWSCFJVKJN-SNVBAGLBSA-N 330.325 2.120 30 1 EEEF C=C(CN(C)C)c1nc2cc(I)cnc2[nH]1 587190571 LIKQBOLBVQZGJY-UHFFFAOYSA-N 328.157 2.137 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@@H]3C[C@@H](OCC(C)=CC)[C@H]12 2356499441 DMVINTHATJOGFW-HVKXIDHRSA-N 334.412 2.304 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@H]2C(=C)C[C@H](O)[C@@H]3C(=C)C(=O)O[C@H]3[C@@H]2C1=C 2356532147 RWWQHQZKBAELGL-NEMWNAMBSA-N 330.380 2.085 30 1 EEEF CCC#C[C@@](O)(C(=O)OC1C[C@@H]2CC[C@H](C1)N2C)c1ccccc1 5458408 CPSOCUUSNHHZOV-WMWLNJEOSA-N 327.424 2.456 30 1 EEEF COC1=C[C@]23CCc4ccc(O)c(OC)c4[C@@]2(CCN3C)CC1=O 2356394475 AQJBMLRXZGTSTA-RTBURBONSA-N 329.396 2.162 30 1 EEEF C#C[C@@H]1CN2CC[C@H]1C[C@@H]2CNC(=S)Nc1ccc(N(C)C)cc1 2356315203 DTTJJVZOCATUDS-RVKKMQEKSA-N 342.512 2.383 30 1 EEEF CN(C)CCO/N=C1\c2ccccc2-n2c1nc1ccccc1c2=O 26383641 YGEJILOJMUUPQY-HEHNFIMWSA-N 334.379 2.030 30 1 EEEF C[C@]12C3=C(C(=O)c4occ(c41)[C@H](O)[C@@H]1O[C@H]12)[C@@H]1CC[C@@H](O)[C@@]1(C)CC3 2356449776 XPAHMBAVRBKIJS-UBCVAJMYSA-N 342.391 2.416 30 1 EEEF CCN/C(=N\S(=O)(=O)c1ccc(Cl)s1)N1C[C@H](CC)C=N1 72124408 SBCKDJZRMMRMDJ-SECBINFHSA-N 348.881 2.383 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]12CO[C@H](CC1=O)C(C)(C)C2=C(O)C3=O 40395473 PTXBJCCXMBZGPW-ZUIFNPILSA-N 342.391 2.307 30 1 EEEF biogenic,in-vitro C=C1C[C@]23C[C@H]1CC(=O)[C@H]2[C@]1(C)CCC[C@@](C)(C(=O)O)[C@H]1[C@H](O)[C@@H]3O 238780348 ZAPSETLSDTWUQE-VAEMSJHRSA-N 348.439 2.161 30 1 EEEF Cn1ncc(C#N)c1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587889995 JRJZVMSTNJAUIQ-UHFFFAOYSA-N 347.205 2.309 30 1 EEEF N#Cc1ccc2nc(CS(=O)(=O)c3ccc([N+](=O)[O-])cc3)[nH]c2c1 586919577 BNRIGXQNAHUIBP-UHFFFAOYSA-N 342.336 2.317 30 1 EEEF Nc1ccc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)c(N)n1 587881633 USOYOUXWGBBQAJ-UHFFFAOYSA-N 349.221 2.263 30 1 EEEF C=C(CN(C)C)c1nc2ccc(S(=O)(=O)C(F)(F)F)cc2[nH]1 587190214 ISMVLWNAGFJVFC-UHFFFAOYSA-N 333.335 2.431 30 1 EEEF C/C(=N\NC(=N)N)c1ccc(NC(=O)Cc2ccc(F)cc2)cc1 1772640542 IUVSCKHCZPUURB-SSDVNMTOSA-N 327.363 2.214 30 1 EEEF Oc1ccc(/C=N/NC(=S)NCCc2c[nH]c3ccccc23)nc1 1857546568 QLJGHFINXDSDTC-UFFVCSGVSA-N 339.424 2.309 30 1 EEEF Cc1nc2ccc(C#C[C@@](C)(O)CC3CC3)cc2n1-c1ncnc(N)n1 103249634 QLGJIHXONUCKCU-LJQANCHMSA-N 348.410 2.004 30 1 EEEF C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@H](O)[C@@H]1C(=C)[C@@H](C)CC[C@@]21C 2356574596 GCVDFMXIDUYWBG-CXXVVEIQSA-N 344.407 2.167 30 1 EEEF N#Cc1ccc2c(c1)CN(S(=O)(=O)c1cccc(C(=O)O)c1)CC2 95555246 ZCKJLTOWUDOHDJ-UHFFFAOYSA-N 342.376 2.003 30 1 EEEF C=C1C(=O)[C@@]23C[C@@H]1CC[C@H]2[C@@]12CO[C@@H]4OC[C@](C)(CC[C@@H]1OC3=O)[C@H]42 95884398 QRZAIOQXVJRCBS-KLNRZHFJSA-N 344.407 2.243 30 1 EEEF CC(=O)OC[C@@H]1O[C@H](C#CCCc2ccccc2)C=C[C@H]1OC(C)=O 253981736 PEMFRHXMDHFDFC-AQNXPRMDSA-N 342.391 2.441 30 1 EEEF C=C(CO)[C@@H]1CC[C@@H]2C(=CC[C@H]3[C@@]2(C)CC[C@@H](O)[C@@]3(C)CO)[C@@H]1O 35028863 OCSPOCDQHVVGDZ-ZWYOZPBWSA-N 336.472 2.028 30 1 EEEF biogenic COc1ccc(N2C(=S)[C@H](C#N)C(=O)N[C@H]2c2ccco2)cc1 169688086 PSLDKXQWVTXHEX-TZMCWYRMSA-N 327.365 2.390 30 1 EEEF O=C1C=C(NCCc2cc(F)c(O)c(F)c2)C(=O)c2ncccc21 103235106 RAGIRKJMOHDHRU-UHFFFAOYSA-N 330.290 2.161 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@](C)(O)CC[C@@H]2C3=C[C@H]([C@@H]4OC4(C)C)O[C@H]3OC[C@@H]12 2356515461 PVAIAJLEMKCLCA-CNGKGLGCSA-N 348.439 2.336 30 1 EEEF N#C[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H](N)Cc1cccs1 49032922 UAAFPZGRKJCEOD-BBRMVZONSA-N 338.436 2.350 30 1 EEEF C=C(C)C(=O)O[C@@H]1[C@H]2C(=C)CC[C@@H](O)[C@]2(C)C[C@@H]2OC(=O)C(=C)[C@H]21 238735504 QLVFBEGPYMTPBV-QHJVRGJGSA-N 332.396 2.309 30 1 EEEF O=C(/C=C/c1ccc(O)cc1)[C@@]1(CCN2CCCC2)CCOC1=O 299833140 OKYXTSIQTZMHBL-MTCRFPMVSA-N 329.396 2.394 30 1 EEEF CCOC(=O)CCCOc1ccc(C/C(C)=N/NC(N)=S)cc1 299854626 AECYZNZNNMPZLK-LDADJPATSA-N 337.445 2.160 30 1 EEEF CN1C(=O)[C@@H](NC(=O)c2cc3cc(C#N)ccc3[nH]2)Cc2ccccc21 13587903 VDFAECYBULQGGS-KRWDZBQOSA-N 344.374 2.357 30 1 EEEF O=C(NO)[C@H]1C[C@H](c2ccc(Oc3ccc(F)cc3)cc2)C(=O)N1 13808795 TUIHSDQRXNNCLL-HUUCEWRRSA-N 330.315 2.096 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C(O)=C3C(C)(C)[C@H](O)CC[C@]3(C)[C@@]2(O)[C@H](O)C1 2356460942 PYMRQNNIAHSRKU-DWPFRNKMSA-N 348.439 2.183 30 1 EEEF CC=C(C)C(=O)O[C@@H]1C[C@H](O)C2=CC(=O)C(C(C)(C)O)=C[C@]2(C)[C@@H]1C 2356594906 LHZKEPWOCHFOLY-RXDRHKEWSA-N 348.439 2.478 30 1 EEEF C=C1C(=O)[C@]23[C@@H](O)[C@@H]1CC[C@H]2[C@]1(C)O[C@@H]3CC2=C1C(=O)CC2(C)C 2356621035 MJXXHOYVYOQSOU-SBDWWIJDSA-N 328.408 2.356 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)([C@@H](O)CC[C@@]4(C)CO)[C@H]2CC[C@H]1[C@@H]3O 2356695482 IOLAXGYDTVZNNV-VUKVDKESSA-N 334.456 2.068 30 1 EEEF C=C1C[C@@]23C=CC(=O)[C@](C)(CCC(=O)OC[C@@H](O)CO)[C@@H]2C[C@H]1CC3 2356712543 FYKIZBPSTADBEK-OPOMMLRYSA-N 348.439 2.171 30 1 EEEF NC(N)=N/N=C\c1c(-c2cc(F)c(F)cc2F)nc2sccn12 73139391 TUHHHQNHRGUXPV-IPKBDRFQSA-N 338.318 2.087 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2CC/C=C\[C@H](O)Cc2cc(O)cc(O)c2C(=O)O1 169298051 LTYXUGJWWVZNBY-OSMWJZBMSA-N 334.368 2.054 30 1 EEEF C=C1C(=O)O[C@@H]2C3=C(COC(C)=O)CC[C@H](OC(C)=O)[C@@]3(C)CC[C@H]12 2356410448 LLUIAKNHFIRVHK-WXSAJPJJSA-N 348.395 2.470 30 1 EEEF C=CC[C@]12CC(=O)[C@H](O)[C@H]([C@@H]1O)[C@H](c1ccc(OC)c(OC)c1)[C@@H]2C 2356602597 FWKAJIVKMLFWPD-QKMMFRNJSA-N 346.423 2.310 30 1 EEEF O=C1C[C@H](O)[C@@H](O)[C@H]2C1=CCCC21Oc2cccc3cccc(c23)O1 2356649600 QZXGWZACFKTEPU-GDIGMMSISA-N 338.359 2.338 30 1 EEEF C=C1C[C@@]23C=CC(=O)[C@](C)(CCC(=O)OC[C@H](O)CO)[C@H]2C[C@H]1CC3 2356712544 FYKIZBPSTADBEK-SQOWSMRPSA-N 348.439 2.171 30 1 EEEF Cc1noc(C)c1COc1ccc(C(=O)N2CCOC[C@@H]2C#N)cc1 76042349 VWDYGRPFQCZWMD-HNNXBMFYSA-N 341.367 2.235 30 1 EEEF COc1cc(C)c(-c2nc(=O)o[nH]2)cc1-c1ccc(C#CCO)s1 653812759 VWSIWYIZDSBMJF-UHFFFAOYSA-N 342.376 2.419 30 1 EEEF N#C[C@@H]1CNCC[C@]12Oc1ccccc1C(=O)[C@H]2C(=O)c1ccco1 587593376 IXOYQXXDJKBETN-GFJSAUFNSA-N 336.347 2.226 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@@](C)(CO)[C@H](O)CC[C@@]4(C)[C@@H]2C[C@H](O)[C@@H]1C3 169313026 YYNFNCPHITUVRP-OBUMVCGPSA-N 334.456 2.068 30 1 EEEF COc1cc([C@@H]2c3c(n[nH]c3C)OC(=N)[C@@H]2C#N)cc2c1OCO2 169690885 UXHONJABCASPMN-RNCFNFMXSA-N 326.312 2.097 30 1 EEEF CCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O 101065822 NXNYZMCJEATBKA-XHDPSFHLSA-N 330.377 2.284 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4C(C)(C)[C@H](O)CC[C@@]4(C)[C@@H]2[C@@H](O)C[C@]1(O)C3 33831988 JBQRSXZPXBXNGX-JEAKYOOPSA-N 334.456 2.211 30 1 EEEF biogenic,in-vitro COc1ccc(CCC(=O)Nc2ccc(C(=O)NO)cc2)cc1OC 45256816 NKWHVVGYBKPFSR-UHFFFAOYSA-N 344.367 2.394 30 1 EEEF N#C[C@@H]1CC(F)(F)CN1C(=O)CNC(=O)c1cccc2ccccc12 84615945 YJNMDFARAFJSEZ-ZDUSSCGKSA-N 343.333 2.329 30 1 EEEF N#CCNC(=O)[C@@H](NC(=O)c1ccccc1)SC1CCCCC1 82064735 HLAIIAJZJGMXPW-KRWDZBQOSA-N 331.441 2.448 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@@H]3C=C(C)[C@H](C[C@H]3C(C)C)[C@H]2C1=O 253677981 PBDZFTMSQJXALQ-AHDPXTMNSA-N 347.484 2.021 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 257527887 QYXZQZMPZUEEML-NZRFLNHFSA-N 346.423 2.384 30 1 EEEF endogenous,in-man CC[S@@](=O)C[C@@](C)(O)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1 28015240 XXMKUOWGHUBGCA-ZLOXQWCVSA-N 348.346 2.035 30 1 EEEF N#CCNC(=O)[C@@H]1CCCC[C@H]1C(=O)N1CCc2ccccc2C1 95554016 QOUJDAITQNPNTN-IAGOWNOFSA-N 325.412 2.017 30 1 EEEF N#C[C@H](C(=O)Nc1ccc(C(F)(F)F)cc1)C(=O)[C@H]1CCOC1 13760259 QRECZZCVBQCIIJ-CABZTGNLSA-N 326.274 2.389 30 1 EEEF CN1CCc2cn(C)c3c2C1=CC(=NCCc1ccc(O)cc1)C3=O 1857584451 OLEMIURMTKKFSE-UHFFFAOYSA-N 335.407 2.440 30 1 EEEF CC[S@@](=O)C[C@](C)(O)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1 28015249 XXMKUOWGHUBGCA-NPMABZOXSA-N 348.346 2.035 30 1 EEEF COC1=C(O)C(=O)c2c(OC)c3c(c(O)c2C1=O)[C@H](C)O[C@H](C)C3 2356408895 RVZCNHHDKHVNPP-RQJHMYQMSA-N 334.324 2.218 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1CC[C@]1(C)[C@H](OC(C)=O)CC=C(COC(C)=O)[C@@H]21 2356430896 VHZJGEKNJYFJNY-OGJJZOIMSA-N 348.395 2.325 30 1 EEEF C=C(CO)[C@@H]1CC2=CC[C@H]3[C@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@H]2[C@@H](O)C1 2356443947 FISRUIAPOPDKNG-SCDLFQHWSA-N 336.472 2.028 30 1 EEEF C=C(C)C(=O)O[C@@H]1C=C(C)C2=CC(=O)[C@@](C)(C[C@H]3OC(=O)C(=C)[C@H]13)O2 2356686319 AERIPQYYSNTIDA-NPNMTCQASA-N 344.363 2.164 30 1 EEEF C[C@@]12CC[C@H](O)[C@@H]3COC(=C31)C(=O)c1cc3c(cc12)[C@H](O)CC[C@H]3O 140521755 VWJHLPXIBLZUOE-WFWNNMHGSA-N 342.391 2.056 30 1 EEEF CCOC1=CC(=O)/C(=C2\NC(N)=NC=C2c2ccc(OC)cc2)C=C1 104003694 BXVXFKHCGJBFEG-SDXDJHTJSA-N 337.379 2.267 30 3 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@@]1(C)[C@H](C[C@H]3O)[C@@](C)(C(=O)O)CC[C@H]1O 2356410453 LRECIABFFPIQSO-ZREPZQCESA-N 348.439 2.161 30 1 EEEF C=C([C@H](O)C=C[C@](C)(O)CO)[C@@H]1CC(=O)[C@@]2(C)[C@H]1[C@H]1[C@@H](C)CC[C@H]12 2356727542 PIQKTPMDCOQYRT-DVXYUZEMSA-N 334.456 2.090 30 1 EEEF C=C1CC[C@H](OC(=O)C(C)C)[C@]2(C)C[C@H](O)[C@H]3C(=C)C(=O)O[C@@H]3[C@@H]12 238764085 KUOBBZCXVSNVQG-GTPBXFKWSA-N 334.412 2.389 30 1 EEEF biogenic CCCCN1C(=O)/C(=C/NN2CCOCC2)C(=O)c2cccc(C)c21 473090848 AWKQEJXJGULNMP-DTQAZKPQSA-N 343.427 2.045 30 1 EEEF COCCNC(=O)[C@H]1CCCC[C@H]1c1nc2cccc(C#N)c2[nH]1 587230107 FJLCJTIIYPNMKU-KGLIPLIRSA-N 326.400 2.471 30 1 EEEF N#Cc1c(-c2ccc3ccn(Cc4cccnc4O)c3c2)[nH][nH]c1=N 1857570086 RTLAMMYDMUSFRK-UHFFFAOYSA-N 330.351 2.465 30 1 EEEF C=C1C[C@@H]2OC(=O)C(=C)[C@H]2[C@@H](OC(=O)C(C)C)C[C@@]2(C)OC1=CC2=O 2356428327 HKQSOGUZSSFJSM-QRCPMIHRSA-N 346.379 2.244 30 1 EEEF O=C(CCCCC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1)NO 73164061 LXERZPUZQYCSEP-UHFFFAOYSA-N 338.345 2.209 30 1 EEEF CC1=C(C)C(=O)c2c(nc(CS(=O)(=O)c3ccccc3)n2C)C1=O 40845113 PMDZJRKHFSYADV-UHFFFAOYSA-N 344.392 2.109 30 1 EEEF Cc1c(/C=N/Nc2ccc(C(=O)O)cc2)[n+](=O)c2ccccc2n1O 1772657536 RWHCGYZLOMDCMP-VCHYOVAHSA-O 339.331 2.246 30 1 EEEF O=C(O)[C@H]1CCCN(CCO/N=C/c2ccccc2-n2cccn2)C1 1857544652 HIELEYYSSNZACD-UOEVCUDDSA-N 342.399 2.019 30 1 EEEF CC(=O)OC[C@@H]1O[C@@H](C#Cc2ccc(C)cc2C)C=C[C@@H]1OC(C)=O 7992537 FLENGSMTXSLATM-UFYCRDLUSA-N 342.391 2.473 30 1 EEEF CC(C)C[C@H](NC(=O)c1ccc(OC(F)F)cc1)C(=O)NCC#N 82065132 RSYYDTOOQKXSDW-ZDUSSCGKSA-N 339.342 2.072 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@@](C2)([C@@H](C(=O)O)[C@H]2[C@@]4(C)CCC[C@@]32OC4=O)[C@@H]1O 257480366 MBNDVMTZEKAWKP-NWISTXJASA-N 332.396 2.136 30 1 EEEF endogenous,in-man N#Cc1nc2nc(C[C@H](N)c3cccc4ccccc34)[nH]c2nc1C#N 587258328 HHPDBPYETYXVJC-AWEZNQCLSA-N 339.362 2.492 30 1 EEEF C[C@H](O)CNC1=CC(=O)C(SC/C=C/c2ccc(F)cc2)=CC1=O 1857644658 WLWPMOHLSSYRSE-JDGPPOGSSA-N 347.411 2.462 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]12C[C@@H](O)C[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 104365792 HHDWSDSMWJQURA-AAPDSVFJSA-N 332.396 2.136 30 1 EEEF in-man CC(C)NC[C@H](O)CO/N=C1/c2ccccc2[C@@H]2CCCC[C@]12O 26944089 RTKLMTIRQZCKHN-MHOKHWTASA-N 332.444 2.169 30 1 EEEF C=C(C)[C@@H]1CCC(=C)[C@@H]2C3=C(C[C@H](C)C3=O)C(=O)[C@](C)(O)[C@H](O)[C@@H]12 2356500239 RLNWZRIDRKCQGX-SSLKNUKPSA-N 330.424 2.361 30 1 EEEF C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@H]2C(=CC=CC(C)(C)O)COC(=O)[C@H]12 2356613192 CHWOLNBRUULGCY-SAGLZJIZSA-N 348.439 2.288 30 1 EEEF Cc1nc(N)ncc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587881617 SXDSQVACTSTMGD-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF N=c1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)[nH]cc1N 587889744 WTQZCRVKOOYQID-UHFFFAOYSA-N 349.221 2.094 30 1 EEEF C=CC1=CC(=O)[C@@H]2[C@H](CC[C@@H]3C(C)(C)[C@H](O)[C@H](O)[C@H](O)[C@]23C)[C@H]1C 104382316 XFRCVLKGZMPUFQ-DJYICQIISA-N 334.456 2.089 30 1 EEEF endogenous,in-man CCSC1(SCC)C[C@@H](C(=O)O)N(C(=O)[C@H](C)CS)C1 27991987 KQXPOBZTCGQQQT-ZJUUUORDSA-N 337.532 2.440 30 1 EEEF CCCC(=O)/C=C/C1=C(O)C(=O)c2cc(OC)c(O)c(O)c2C1=O 85997163 NERSELQTDRDIKE-AATRIKPKSA-N 332.308 2.223 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@@](C)(CO)CCC[C@@]4(C)[C@@H]2C[C@H](O)[C@@H]1[C@H]3O 95914746 QOCQIGXDJNSEGM-DTMCMCHMSA-N 334.456 2.068 30 1 EEEF biogenic,in-vitro C=C1C[C@]23C[C@H]1C[C@@H](O)[C@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O[C@H]([C@@H]12)[C@@H]3O 238738366 BSUSNTHCECKPSS-OWAQTHFISA-N 332.440 2.432 30 1 EEEF C=C(C)C(=O)O[C@H]1C=C(C)C2=CC(=O)[C@](C)(C[C@H]3OC(=O)C(=C)[C@@H]13)O2 685935512 AERIPQYYSNTIDA-MVWRLGRASA-N 344.363 2.164 30 1 EEEF biogenic,in-vitro O=C(CCCCCONC(=O)c1c(Cl)cncc1Cl)NO 1911576065 HKGUNQCCAGITDN-UHFFFAOYSA-N 336.175 2.116 30 1 EEEF Cc1ccn2cc(-c3ccc(/C=N/NC4=NCCCN4)cc3)[n+](C)c2c1 26830250 CDFLYVBMPYARQF-YDZHTSKRSA-N 347.446 2.012 30 1 EEEF C=C1C[C@H](O)[C@@H]2O[C@@]2(C)CC[C@H]2/C(=C\C=C\C(C)(C)O)COC(=O)[C@H]12 140245895 CHWOLNBRUULGCY-RETLCUPJSA-N 348.439 2.288 30 1 EEEF CN(CCO)c1ccc(/C=N/N2CCN(c3ccccc3)CC2)cc1 299852682 WDMQGIHIYMGARR-HEHNFIMWSA-N 338.455 2.271 30 1 EEEF CC(C)NS(=O)(=O)c1c[nH]c(-c2nc3cc(C#N)ccc3[nH]2)c1 586936610 SKZMIHZHVFAQEC-UHFFFAOYSA-N 329.385 2.116 30 1 EEEF N#Cc1nc2nc([C@@H]3CS[C@@H](Cc4ccccc4)N3)[nH]c2nc1C#N 587040598 IHUXBNSHRYAUJR-KBPBESRZSA-N 347.407 2.043 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1conc1O 587880516 PEQQNGTXTLVNOZ-UHFFFAOYSA-N 325.151 2.397 30 1 EEEF CC(N)=C1C(=O)[C@@H]2[C@@H]3c4c[nH]c5cccc(c45)C[C@H]3C(C)(C)N2C1=O 2356386931 AFOUSJMOYMLOPA-JLZZUVOBSA-N 335.407 2.229 30 1 EEEF CCOC(=O)Cc1cc(O)cc(O)c1C(=O)C=CC=CC[C@H](C)O 2356505085 QVACWFLAVQMDNR-LBPRGKRZSA-N 334.368 2.269 30 1 EEEF CC(C)[C@H]1OC(=O)C=C2[C@@]3(C)CC=C[C@]4(C)C(=O)O[C@@H]([C@H]43)[C@H]3O[C@]213 69481937 NGMZHPQMBVXJMC-KPHWFTJISA-N 330.380 2.160 30 1 EEEF biogenic,in-vitro C[C@](O)(C#Cc1ccc2c(c1)-c1nc(C(N)=O)cn1C1CC2C1)CF 219438171 MNRGQBJVTUSAFH-RMTLACHYSA-N 339.370 2.153 30 1 EEEF Cc1ccc(/C(=N/O)NC[C@@H]2CCCO2)c(OCc2ccccn2)n1 72181663 WRGFVTZPPBOUEI-HNNXBMFYSA-N 342.399 2.268 30 1 EEEF O=C(/C=C/c1cccc2cccnc12)NCCCCCC(=O)NO 40939225 ILXXPCVHANACCG-ZHACJKMWSA-N 327.384 2.430 30 1 EEEF CCC/C=C/[C@H]1C(=O)[C@H]2O[C@H]2C2(OCC(CC)(CC)CO2)[C@@H]1CO 13783069 TWGDZVIUZPIUAD-JLXXONCMSA-N 338.444 2.467 30 1 EEEF CC(C)C1=C[C@@H]2O[C@@]23[C@@]2(C)CCC4=C(COC4=O)[C@@H]2C[C@@H]2O[C@@]23C1=O 1857759625 AAQGJDXQUVCTKP-MXZSYGRSSA-N 342.391 2.100 30 1 EEEF C=C1C[C@@]23C[C@@]4(O)CN5C[C@@]6(C)CCC[C@@]7([C@@H]5[C@H]2C[C@H]1C(=O)[C@@H]37)[C@H]64 2356506556 MGEDPNBPAMLIHW-VJTIWJPHSA-N 325.452 2.393 30 1 EEEF C=C[C@](C)(O)C=C[C@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2[C@@H](O)[C@@H](O)[C@@]1(C)O 2356783859 MHBIPUOMMSRZKQ-DYAQGPOSSA-N 338.488 2.415 30 1 EEEF CC(=O)C1=C(C)N=C(SCCC(=O)O)N[C@@H]1c1cccc(O)c1 98084776 LFVCHCWJLBIVBU-OAHLLOKOSA-N 334.397 2.463 30 1 EEEF C=C[C@@]12CNCC[C@@H]1[C@](C(=O)OC)(c1cc3ccccc3[nH]1)CO2 14693450 KZLFAYYOKRWYDO-IPELMVKDSA-N 326.396 2.143 30 1 EEEF C=CC(=C)[C@H](O)C[C@H]1[C@](C)(O)[C@@H](O)[C@H](O)[C@H]2C(C)(C)CCC[C@@]21C 1857579297 IBGMRNOLPKLLRL-SKHRHGRFSA-N 338.488 2.415 30 1 EEEF C=C(CO)[C@H]1C=C2[C@@H](O)C[C@H]3[C@@](C)(CC[C@@H](O)[C@]3(C)CO)[C@@H]2CC1 136907421 YKSOUKMSKAWWQG-SBSFFHCLSA-N 336.472 2.028 30 1 EEEF C(#Cc1ccccc1)CSc1nsnc1C12CN3C[C@H]1[C@H]2C3 58496617 YRHXYFPBQSSIPM-VMZNBEPHSA-N 325.462 2.495 30 1 EEEF C=C(Cc1c(OC)ccc(C(=O)O)c1O)[C@H]1CC[C@](C)(O)[C@@H](O)C1 27559300 JNPNGXWCEMBWHW-GYOIFBIXSA-N 336.384 2.110 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc(C(N)=O)cc2nc(N)oc12 587911743 PLFCNSPQRUJYDJ-UHFFFAOYSA-N 341.754 2.571 30 1 EEEF COc1cc2c3c(c1)O[C@@H](c1cnc4c(C#N)cnn4c1)[C@@H](C2)C3=O 587436832 URKGANQYUYYHCN-GUYCJALGSA-N 332.319 2.098 30 1 EEEF C=CCOC(=O)N1CCc2c(c(=O)oc3c(C(C)=O)c(O)ccc23)C1 169347643 NPQCSLDFJZDGTC-UHFFFAOYSA-N 343.335 2.382 30 1 EEEF C[C@H](O)[C@@H]1C(O)=C(C(=O)[C@H]2[C@H]3CCCC[C@@H]3C=C[C@H]2C)C(=O)N1C 2356723589 NOYBJWXGAYWITN-QLBXMJNRSA-N 333.428 2.218 30 1 EEEF COC1=CC2=C3C[C@@H]4CC[C@H](OC)[C@@H](OC)[C@@H]4CN3CCC2=CC1=O 2356845134 OBXUDMPYADNLEQ-NSUZUWQXSA-N 345.439 2.446 30 1 EEEF CCSCC[C@@H](NC(=O)OCc1ccccc1)C(=O)NCC#N 82064870 ZGKHJIRHVYSKEM-CQSZACIVSA-N 335.429 2.064 30 1 EEEF CCC#CCOC(=O)CN(C)C(=O)c1coc(-c2cccs2)n1 82085815 YPKBTAXAWJIJPI-UHFFFAOYSA-N 332.381 2.432 30 1 EEEF C[C@@H](Cn1cc([N+](=O)[O-])cn1)c1nc2cc(Cl)nc(C#N)c2[nH]1 587276030 IAZWKBSKYADPDT-ZETCQYMHSA-N 331.723 2.391 30 1 EEEF COC(=O)[C@H](C=O)[C@H]1N[C@@H](C)Cc2cc(Br)c(F)cc21 587804282 DKWOWZAXZYXXJE-NYNLCMDTSA-N 344.180 2.152 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@H]([C@@H](C=O)[N+](=O)[O-])N1 587747103 PCGJRFLRAQYEJS-JSTDYGSISA-N 331.141 2.008 30 1 EEEF CC1=C[C@@H]2[C@H](C[C@H](O)C(C)=C[C@@H]3C(=O)[C@H](C)C[C@]3(O)C1=O)C2(C)C 2356453084 NHOIUGORUWWMAP-HDWZNDTQSA-N 332.440 2.441 30 1 EEEF C[C@@]1(CO)C(=O)CC[C@@]2(C)[C@H](CCC3=CCOC3=O)[C@@]3(CC[C@H]12)CO3 73277315 SRXQZIJOJMMIIN-WOCWYEKDSA-N 348.439 2.413 30 1 EEEF C=C(CO)[C@@H]1CC[C@@H]2C(=CC[C@H]3[C@@]2(C)CC[C@@H](O)[C@]3(C)CO)[C@@H]1O 138360689 OCSPOCDQHVVGDZ-UFANPLCHSA-N 336.472 2.028 30 1 EEEF COCC(=O)N1[C@H](CO)[C@H](c2ccccc2C2=CCCCC2)[C@@H]1C#N 95866652 XJOIDJIXTAYCGR-NLWGTHIKSA-N 340.423 2.469 30 1 EEEF N#Cc1nc2nc(-c3ncc(Br)cc3F)[nH]c2nc1C#N 587157473 MXBLJCXYIZSCEY-UHFFFAOYSA-N 344.107 2.060 30 1 EEEF CC(C)[C@@H]1CC[C@]23C[C@@H]4[C@H](C)C(=O)[C@@H]5O[C@@]54[C@]2(C)C(=O)[C@H](O)[C@]13C 2356871567 YCAWNFYZBRTGCT-HWRAYMHJSA-N 332.440 2.371 30 1 EEEF Cc1ccc2c(c1)[C@@]1(C(=O)N2)C2=C(CN1C)C(=O)c1ccccc1C2=O 73298489 XNYBKQLDFJSITF-NRFANRHFSA-N 344.370 2.464 30 1 EEEF C=C1[C@@H]2CC[C@@H]3[C@](C2)(C(=O)O[C@H]2O[C@@H](O)[C@@H]4C(C)(C)CCC[C@]324)[C@@H]1O 95913417 CXNYLUJFZZXBEK-OXXYCVLBSA-N 348.439 2.364 30 1 EEEF biogenic,in-vitro C=C[C@H]1CC(=O)[C@H]2Oc3c(OC)ccc4c3[C@@]23CCN(C)[C@@H](C4)[C@@H]13 101209432 NTWGNEUJRLFCNI-ZKOBIFCHSA-N 325.408 2.345 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@H]1CC[C@H]2[C@]12CCC[C@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100781428 MJFVMFNFTCKAEV-ZFUCNUEDSA-N 346.423 2.384 30 1 EEEF endogenous,in-man C[C@@H](OS(=O)(=O)c1ccc([N+](=O)[O-])cc1)[C@@H]1CC(C)(C)OC1=O 64634100 ADFXPKPWYXFXBX-SKDRFNHKSA-N 343.357 2.030 30 1 EEEF in-vitro CO[C@@]1(C#C[C@@](O)(c2ccccc2)c2cccnc2)CN2CCC1CC2 28563566 ZGBSEJYQXDWFRF-FCHUYYIVSA-N 348.446 2.432 30 1 EEEF C=C1C[C@]23CC(=O)[C@@H]4[C@@]5(C)CC(=O)C[C@]46[C@@H]([C@H]2C(=O)[C@H]1C[C@H]36)N(C)C5 38877020 MAYJMKOWBZXVIJ-DPFMCKMCSA-N 339.435 2.026 30 1 EEEF C#Cc1cccc(-c2nc3cccc(S(=O)(=O)N(C)C)c3[nH]2)c1 586878952 BWDOEOKGIGHWPQ-UHFFFAOYSA-N 325.393 2.462 30 1 EEEF C=CC[C@@]1(OCc2ccccc2)C(=O)C(=O)O[C@H]1[C@H]1COC(C)(C)O1 17259963 QUSJNYTVFAJGCT-SIXWZSSISA-N 346.379 2.164 30 1 EEEF Cc1ccc(S(=O)(=O)NCC/N=C\c2ccc(N(C)C)cc2)cc1 17778642 SBLATKKEZPWZDE-RGEXLXHISA-N 345.468 2.458 30 3 EEEF C=CCNC1=C(NCCCN(CC)CC)C(=O)c2ccccc2C1=O 169340154 FIWSWDYMUYNQOL-UHFFFAOYSA-N 341.455 2.374 30 1 EEEF C[C@@H]1CC(=O)C2=C(CC[C@@]34O[C@]23C(=O)c2cccc(O)c2[C@@H]4O)C1 100266985 NNMGLXNJGVNRCH-SUPOCEJMSA-N 326.348 2.219 30 1 EEEF C[n+]1ccc(COc2ccc(/C=N/NC(=N)N3CCCC3)cc2)cc1 26831557 NPNOXGGLPHKYST-KGENOOAVSA-N 338.435 2.044 30 1 EEEF CC(C)(C)C(=O)CN1C(=O)[C@@H](CC(=O)NO)Sc2ccccc21 29247234 UKQILYFNJNVXDG-GFCCVEGCSA-N 336.413 2.005 30 1 EEEF C=C(C)[C@@H]1CC(=O)[C@@H]2[C@H]3C(=O)C[C@@H](C=C3C(C)=O)[C@@H](C(=O)O)[C@@H]2C1 2356807586 XWUMXWKSQYTAOG-DYWLJHAKSA-N 330.380 2.209 30 1 EEEF CCCCCCC[C@@H](O)[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12 89469602 ZNDOHEBDAFJMEG-NRWUCQMLSA-N 329.462 2.471 30 1 EEEF COc1ccc(Cl)cc1C#Cc1c(C(=O)O)nn2cccnc12 587911233 AWHQLWUHJIOCBF-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF COC(=O)c1cc2c([nH]1)C(=O)C=C1N(C(=O)OC(C)(C)C)C[C@@H]3C[C@@]123 26831858 JVWWPRHIXMFAED-YYSFKGJASA-N 344.367 2.390 30 1 EEEF CC1=C[C@H](CC#N)[C@@H](C(C)C)C[C@H]1CC(=O)N1CCN(CCO)CC1 2356318005 ITEREEYPHAIAQL-GBESFXJTSA-N 347.503 2.281 30 1 EEEF CC(=O)N[C@H](C)Cc1ccc(C#Cc2cnc(OCCF)nc2)cc1 113412337 LGXUCECBFQADPO-CQSZACIVSA-N 341.386 2.292 30 1 EEEF C[C@H](CO)C1=C2CC[C@H](CO)C3=C(C[C@]2(C)CC1)[C@@H](C)[C@H](O)C3=O 2356325640 QNDHAMGPYFFBHA-HVDZYKQDSA-N 334.456 2.380 30 1 EEEF Cc1nc2c3cc(N4CCOCC4)ccc3nc(SCC#N)n2n1 71333205 UBUNOVOWKVYMLU-UHFFFAOYSA-N 340.412 2.038 30 1 EEEF C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@@H](O)[C@H]1C(C)(C)CCC[C@]21C 238734957 UXBITRKCDARMSM-ZNWBIBPKSA-N 346.423 2.391 30 1 EEEF C=C1[C@@H]2CC[C@H]3[C@]4(C)CCC[C@](C)(CO)[C@H]4CC(=O)[C@@]3([C@@H]1O)[C@@H]2O 238785099 DBVNQUBNOIPPEM-AOIGJGNCSA-N 334.456 2.068 30 1 EEEF CC1=C(O)C(=O)C[C@]2(C)[C@@H]3CCc4cocc4[C@@]3(CO)CC[C@@]12O 2356337383 YJYCGDAWLMWZRS-WZGPROSRSA-N 332.396 2.408 30 1 EEEF N#C[C@@]1(NC(=O)[C@H](N)Cc2sccc2F)C[C@@H]1c1ccccc1 40402909 UUKJIEBFYVGYRF-MRRJBJDNSA-N 329.400 2.323 30 1 EEEF CCc1ncnc(N2CCC(OC)CC2)c1C#Cc1ccc(N)nc1 149222357 RKRNEPOVPHARMC-UHFFFAOYSA-N 337.427 2.031 30 1 EEEF C=C1C(=O)[C@@]23CC(=O)[C@@H]4C(C)(C)CCC[C@@]4(C)[C@@H]2[C@@H](O)C[C@@H]1[C@H]3O 169313028 JLKBHAAAVQFJPZ-FHALXRMRSA-N 332.440 2.275 30 1 EEEF O=C1C=CC2(Oc3cccc4cccc(c34)O2)[C@H]2[C@H]1[C@@H](O)CC[C@H]2O 13433770 GNGBJYHHQABICI-JUUKFZBDSA-N 338.359 2.194 30 1 EEEF biogenic O=C1/C(=C\c2ccco2)[C@@H](CO)[n+]2cc(O)c(Cc3ccco3)cc21 1642676565 NCBGWRSEHNWMNA-BAPRJRNISA-O 338.339 2.270 30 1 EEEF CCO[P@@](=O)(N[C@H](CC(C)C)C(=O)NO)c1ccc(OC)cc1 13490335 KTCRMROJXXSPQJ-QKFKETGDSA-N 344.348 2.060 30 1 EEEF C=C1C[C@@]23C[C@H]1C(=O)C[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1[C@@H](O)[C@H]3O 2356378092 VYSJMJOARWDSIN-LYKAYCHNSA-N 348.439 2.161 30 1 EEEF Cc1ccc(S(=O)(=O)OC[C@]2(O)O[C@H](C)[C@@H](C)C[C@H]2C)cc1 27647978 CZHHLUDJWWROTN-NHIYQJMISA-N 328.430 2.470 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](C[C@H](O)[C@@H]1[C@H]2O)[C@]1(C)CCCC(C)(C)[C@H]1C[C@H]3O 59046362 UWJKFPFMTSZKRY-ANQHUWQMSA-N 334.456 2.067 30 1 EEEF C=CCCO[C@H]1C=C2CCN3Cc4cc5c(cc4[C@H]([C@@H]1O)[C@@H]23)OCO5 103269016 PGVLINOSQFPUMG-VNTMZGSJSA-N 341.407 2.349 30 1 EEEF C#CC=C[C@@H]1[C@@H]2[C@H]3C[C@@H]4O[C@](OC)([C@H]2[C@H]4O3)[C@]1(Br)CC 2356795171 IKEWAOKGFUGNOH-DXVJDFSHSA-N 339.229 2.494 30 1 EEEF CCCCCCCCc1ccc(NC(=O)[C@H]2NC[C@@H](O)[C@@H]2O)cc1 49695546 IHMKXPTZEFZPAS-SQNIBIBYSA-N 334.460 2.222 30 1 EEEF N#Cc1cncc(Nc2nn([C@H]3CCCC[C@@H]3C#N)cc2C(N)=O)c1 221150600 SNUFUKMCJHYONS-DOMZBBRYSA-N 335.371 2.247 30 1 EEEF COc1ccc(Cl)cc1C#Cc1c(C(=O)O)nn2c1OCCC2 587911469 IMXSRGHGLPJPQP-UHFFFAOYSA-N 332.743 2.426 30 1 EEEF CCOc1ccc(N(CC(=O)O)C(=O)[C@@H](C)CS)cc1OCC 28259906 SFPRIWLQFPMFOE-NSHDSACASA-N 341.429 2.468 30 1 EEEF C=C[C@H]1CC(=O)[C@@H]2Oc3c(OC)ccc4c3[C@@]23CCN(C)[C@H](C4)[C@H]13 29463136 NTWGNEUJRLFCNI-CVXZJHOASA-N 325.408 2.345 30 1 EEEF C[C@H]1CC(=O)C2=C(CC[C@@]34O[C@@]23C(=O)c2cccc(O)c2[C@@H]4O)C1 36378649 NNMGLXNJGVNRCH-MXJPBCORSA-N 326.348 2.219 30 1 EEEF C=C1[C@@H]2CC[C@H]3[C@](C2)(C(=O)O[C@H]2CC[C@@]4(C)CO[C@@H]5OC[C@]23[C@H]54)[C@@H]1O 70450909 QALWKTNRDDDECH-XHSWRCIISA-N 346.423 2.034 30 1 EEEF biogenic,in-vitro C=C(C)C(=O)O[C@H]1[C@@H]2C(=C)C(=O)O[C@H]2CC(=C)[C@@H]2C[C@H](O)C(=C)[C@@H]21 136710623 ZQBZOPWDBPOXPR-NQLMQOPMSA-N 330.380 2.085 30 1 EEEF CC(C)N1CC(=O)N=C1N/C(N)=N/c1ccc(Cl)c(Cl)c1 72114310 YOBMLFXWMMTJRV-UHFFFAOYSA-N 328.203 2.136 30 1 EEEF CN1C(=O)[C@H](CN2CCCCC2)C[C@@H]1C#Cc1ccc2c(c1)CCO2 96248475 BSAYMXGAHRLDCA-OALUTQOASA-N 338.451 2.306 30 1 EEEF CC1=C[C@H](C)[C@H](c2cc(O)cc(O)c2)OC(=O)[C@H](C)[C@@H](O)[C@H](C)C1=O 2356733729 RFQJAVYYIHIQAI-ZOTCYRDBSA-N 348.395 2.480 30 1 EEEF COC(=O)/C=C\C(C#N)(C#N)/N=C/c1cc(Br)cs1 31900395 JOZKWGGTNATEHW-UCFLSTRGSA-N 338.186 2.445 30 1 EEEF C=C1[C@H](O)[C@H]2O[C@@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@@]1(C)[C@@H](O)C(=O)[C@]32C 198332475 ILPXHKMIZLTLAS-HZUZVOAWSA-N 332.440 2.083 30 1 EEEF C#CCN1C[C@@H](COCCCC)Oc2cccc(F)c2S1(=O)=O 96021258 DNNYIMBJLOXRDM-ZDUSSCGKSA-N 341.404 2.027 30 3 EEEF CC(=O)Nc1ccc(Cl)c(-c2nc3nc(C#N)c(C#N)nc3[nH]2)c1 587051323 VSUHIOIKPFGEPE-UHFFFAOYSA-N 337.730 2.375 30 1 EEEF COC(=O)[C@]1(C)CCC(=O)C(C)=C1C=CC(C)=C[C@@H](O)C[C@@H](C)O 2356377843 NGPTWMZMECMCMC-ZXYWRSMDSA-N 336.428 2.479 30 1 EEEF CC(C)[C@H]1O[S@](=O)O[C@]1(Cn1cncn1)c1ccc(Cl)cc1 26010835 NPFKMHWOXVEEPD-XDEPDNQISA-N 341.820 2.477 30 1 EEEF COc1ccc(N(C(=O)[C@@H](C)CS)[C@@H](C)C(=O)O)cc1OC 28263305 QMKCAFICSCUPEE-UWVGGRQHSA-N 327.402 2.076 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)C(=O)C=C[C@](C)(O)C[C@@H](OCC(C)C)[C@@H]12 2356653595 LUEQCEAVADXVIC-VXNCWWDNSA-N 334.412 2.352 30 1 EEEF COc1ccc(S(=O)(=O)Cc2nc3cccc(C#N)c3[nH]2)cc1 586920716 PNUCCBVBAQRIEZ-UHFFFAOYSA-N 327.365 2.417 30 1 EEEF C[C@H](N/N=C(\S)N1CCN(c2ccccn2)CC1)c1ccccn1 6571115 MWYOSZXOEFQZRY-AWEZNQCLSA-N 342.472 2.150 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@H]2C(=C)C[C@H](O)[C@@H]3C(=C)C(=O)O[C@@H]3[C@@H]2C1=C 2356532145 RWWQHQZKBAELGL-IZKTWJBDSA-N 330.380 2.085 30 1 EEEF COC1=C[C@@]23CCN(C)[C@@H](Cc4cc(OC)c(OC)cc42)[C@@H]3CC1=O 14636217 LTXOYPDADNTKER-AVYPCKFXSA-N 343.423 2.321 30 1 EEEF biogenic COc1ccc(CCCn2cccc(/C=C/C(=O)NO)c2=O)cc1 143989918 ANIKOPXKPXWXSB-DHZHZOJOSA-N 328.368 2.008 30 1 EEEF Cc1oc(CNS(C)(=O)=O)cc1-c1nc2ccc(C#N)cc2[nH]1 586946510 ZFXZMHXXOFHINB-UHFFFAOYSA-N 330.369 2.052 30 1 EEEF COc1ccc2c3c1O[C@H]1C=C(C(C)=O)C[C@@H]4[C@@H](C2)N(C)CC[C@@]314 169295579 FKNWJBZMTKZQMB-UOSKARGWSA-N 325.408 2.490 30 1 EEEF O=C(O)/C(O)=C/C(=O)c1cccc(NC(=O)c2ccc(O)cc2)c1 100751978 VASYKLFKKQPIGD-DHDCSXOGSA-N 327.292 2.354 30 1 EEEF C=C1C[C@H](OC(C)=O)[C@H](OC(C)=O)[C@]2(C)C[C@H]3OC(=O)C(=C)[C@H]3C[C@@H]12 238754044 PWJVYBVQKWFKNT-IYUJOENBSA-N 348.395 2.324 30 1 EEEF O=CC(C=O)c1ccc(-c2nc3c(Cl)ncnc3[nH]2)cc1[N+](=O)[O-] 587261770 INZHREJCESRMLP-UHFFFAOYSA-N 345.702 2.063 30 1 EEEF CO[C@H](C)[C@@]1(CC#N)N[C@@H](C(=O)C(F)(F)F)Cc2ccccc21 962728256 DHTCGHMJWKFPMC-WDBKCZKBSA-N 326.318 2.476 30 1 EEEF COc1ccc(C(=O)NO)cc1OCc1noc(-c2ccccc2)n1 1857584102 CSAUSOMVIPDWNC-UHFFFAOYSA-N 341.323 2.443 30 1 EEEF N#Cc1c(-c2ccccc2)cn(-c2ccc(S(N)(=O)=O)cc2)c1N 29132282 CYOZWDBFBDPNOS-UHFFFAOYSA-N 338.392 2.246 30 1 EEEF Cc1ccc(NS(=O)(=O)c2cccc(/C=C/C(=O)NO)c2)cc1 29132906 UHFLTFWSPYVZHA-JXMROGBWSA-N 332.381 2.314 30 1 EEEF C=C(C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)[C@@H](C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 238759708 FQKDBWKMFCRELP-PDGWKQKYSA-N 332.396 2.165 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@@H](c2ccccc2C2=CCCC2)[C@@H]1CO 95868000 OERKOXUAKKWALJ-ZIFCJYIRSA-N 326.396 2.079 30 1 EEEF N#Cc1cccc(C(=O)N=c2nc3nc(-c4ccccc4)ccn3[nH]2)c1 1857559752 OGYJJUKUZRHLHS-UHFFFAOYSA-N 340.346 2.337 30 1 EEEF O=C(NC1(C(=O)NO)CCC1)c1ccc(C#Cc2ccccc2)cc1 96909802 ORCDATBMTSTADG-UHFFFAOYSA-N 334.375 2.244 30 1 EEEF CN1C(=O)C[C@@](C#N)(C(=O)NCCc2ccccc2)[C@H]1c1ccccc1 203470015 WJHCFTLSGASIOS-CTNGQTDRSA-N 347.418 2.459 30 3 EEEF C=C(C)[C@@H]1C(=O)C=C(C)C(=O)[C@H](O)[C@H](C(=C)C)CCC2=C[C@H]1OC2=O 2356843912 NQSGQBPUUPHFQJ-KNIMUDFMSA-N 344.407 2.462 30 1 EEEF COC(=O)c1cnc(O)c(C#Cc2cc(Cl)ccc2OC)c1O 587902878 DEGJXKUSTKORNP-UHFFFAOYSA-N 333.727 2.341 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccccc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n2ccccc2=O)c2cc(C#N)ccc2OC1(C)C 27558140 FICJOKLQZVRDSJ-MSOLQXFVSA-N 338.363 2.412 30 1 EEEF C=C[C@@]1(C)C=C2C(=O)C=C3[C@@](C)([C@H](O)CC[C@@]3(C)C(=O)O)[C@]2(O)CC1 198844732 ZQZVXOUQMKWMED-XLSIIYIISA-N 346.423 2.391 30 1 EEEF CC(C)NC(=O)N1[C@H](C#N)[C@@H](c2ccc(C#CC3CC3)cc2)[C@@H]1CO 95897424 FGRJVUDIIQYRHF-CEXWTWQISA-N 337.423 2.218 30 1 EEEF C=CCC(C)(C)c1nc2ccc(S(=O)(=O)N3CCOCC3)cc2[nH]1 587954060 AEUUPVSCVFVUKV-UHFFFAOYSA-N 349.456 2.438 30 1 EEEF CC(C)(C)OC(=O)N1CC[C@@]2(NCCc3ccc(O)cc32)[C@@H](C=O)C1 963351241 FUNVDCFOCWPYPX-AUUYWEPGSA-N 346.427 2.189 30 1 EEEF CC[C@@H](O)c1cc(C#Cc2cc(C(N)=O)c(NC(N)=O)s2)cs1 28524066 YFEAUXQZZQNVTD-LLVKDONJSA-N 349.437 2.242 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@@H]3C[C@H](OC[C@H](C)CC)[C@@H]12 2356673966 WULWDKXUHKIGSZ-CYRRODMKSA-N 336.428 2.384 30 1 EEEF COCC#Cc1nccnc1OC1CN(c2ccc3ccccc3n2)C1 96168885 CDHXEELWPVSGLR-UHFFFAOYSA-N 346.390 2.290 30 1 EEEF C=C1C(=O)O[C@H]2C=C(COC(C)=O)CCC=C(C(=O)OC)CC[C@@H]12 2356738317 FELNAJVVBXSDQN-HOTGVXAUSA-N 334.368 2.247 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@]2(CC[C@H]3C(=CC=CC(C)(C)O)C(=O)OC[C@H]13)CO2 2356803325 WZDCQTZIRFGNEC-GWKKSSCLSA-N 346.423 2.306 30 1 EEEF N#C[C@@H]1C[C@@H](N=[N+]=[N-])CN1C(=O)CNC(=O)c1cccc2ccccc12 84616478 IPKHAZSRZNIQAI-KGLIPLIRSA-N 348.366 2.373 30 1 EEEF C[C@H]1C[C@H]2O[C@@H]2CC/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 137657299 XFALPAMSDFFXGY-VNEQQNAQSA-N 332.352 2.262 30 1 EEEF CCOc1ccccc1CCCn1cccc(/C=C/C(=O)NO)c1=O 143878939 KLNPMERKLHISFS-VAWYXSNFSA-N 342.395 2.398 30 1 EEEF C[C@@H](Oc1ccc(C#N)cc1)c1nc2ccc(S(N)(=O)=O)cc2[nH]1 587191707 VTKSHOFMVXXKOB-SNVBAGLBSA-N 342.380 2.222 30 1 EEEF COc1nonc1C(=NO)Nc1ccc(F)c(Br)c1 1857596916 NQMOGZYWWBZMGC-UHFFFAOYSA-N 331.101 2.228 30 1 EEEF C=C(C)[C@@H]1CC[C@]2(CO)OC(=O)C3=C(CC(C)=O)C(=O)C(C)=C[C@H]1[C@H]32 2356411333 MMENEXZIHVFHNM-AADOQKPJSA-N 344.407 2.298 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@H](c2ccccc2C2=CCCC2)[C@H]1CO 95867991 OERKOXUAKKWALJ-LMMKCTJWSA-N 326.396 2.079 30 1 EEEF C[n+]1c2ccccc2c(CN[C@H](CS)C(=O)O)c2ccccc21 5614363 MIWGSRCJYBHQTP-OAHLLOKOSA-O 327.429 2.290 30 1 EEEF C=C1C[C@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@H](O)CO)[C@@H]2C[C@@H]1CC3 102830919 FYKIZBPSTADBEK-MHZKCTCGSA-N 348.439 2.171 30 1 EEEF C[C@@H](OS(=O)(=O)c1ccc([N+](=O)[O-])cc1)[C@H]1CC(C)(C)OC1=O 64634102 ADFXPKPWYXFXBX-BXKDBHETSA-N 343.357 2.030 30 1 EEEF in-vitro C=CCCN1CCN(CC(=O)[C@@](O)(c2ccccc2)C2CCC2)CC1 22940353 XYJZEMYDBLYKMK-OAQYLSRUSA-N 342.483 2.437 30 1 EEEF CCCC[C@H]1CC(=O)N(OS(=O)(=O)/C=C/c2ccccc2)C1=O 40632362 UNVFZNKIAUTQBV-VNDWYCCKSA-N 337.397 2.484 30 1 EEEF CCc1cc(=O)n2[nH]c(=NCc3ccc(Cl)cc3)c(C#N)c2[nH]1 473247946 KCVHOGJCAOLLBX-UHFFFAOYSA-N 327.775 2.144 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@]2(COC=CC2=O)N1 587836679 XGVUTVUEYPXGQD-CLAHSXSESA-N 326.165 2.431 30 1 EEEF NCCCNCCCCNCCC/N=C1/CCc2ccccc2N1 13678633 OZTTZJAWBGJXTN-UHFFFAOYSA-N 331.508 2.142 30 1 EEEF C=CCN(CC(=C)F)C(=O)[C@@]1(c2ccc3c(c2)OCCO3)C[C@H]1CN 29046886 OYNDMWYYCBLSSM-HNAYVOBHSA-N 346.402 2.172 30 1 EEEF CN1C[C@]23C[C@H](O)[C@H]4[C@@H](CCC5=CC(=O)C=C[C@@]54C)[C@H]2CC[C@@H]3C1=O 2356501571 GDWBXDLUQZIGKG-HNDBUWPCSA-N 341.451 2.333 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@@H]1CC(=O)[C@@H]2[C@]1(C)CCCC(C)(C)[C@@H]1[C@H](O)[C@@H]3O 2356643669 AUVGEKXCVIHEPI-WWURTVCNSA-N 334.456 2.067 30 1 EEEF C#CC(=O)Nc1ccc2c(c1)/C(=C/c1[nH]c(CC)nc1C)C(=O)N2C 72139710 UBEWSNYQULDEAG-UVTDQMKNSA-N 334.379 2.369 30 1 EEEF [CH2-]c1c2c(C)nc(OC)c(C#N)c2nc[n+]1Cc1ccc(OC)cc1 72125723 FZEUYQYHDUZRPF-UHFFFAOYSA-N 334.379 2.345 30 1 EEEF CCC#CCOC(=O)[C@@H](C)NC(=O)c1coc(-c2cccs2)n1 82083889 QXQRDTYLBWEAHR-LLVKDONJSA-N 332.381 2.478 30 1 EEEF C[C@@H]1C(=O)Nc2ccc(F)cc2N1S(=O)(=O)c1cccc(C#N)c1 40977513 LJCCMWZWWXOJQN-SNVBAGLBSA-N 345.355 2.233 30 1 EEEF C=C(C)[C@@H]1CCC(=C)[C@@H]2C3=C(C[C@H](C)C3=O)C(=O)[C@@](C)(O)[C@@H](O)[C@@H]12 238776202 RLNWZRIDRKCQGX-XGXVBPICSA-N 330.424 2.361 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@@]2(N1)C(=O)C=CN[C@@H]2C 587799526 XROGJGIIBPMHKL-XWRVAKJBSA-N 339.208 2.392 30 1 EEEF N#Cc1ncn(-c2ccc(O)cc2)c1/N=C/c1cc(O)c(O)c(O)c1 169350306 PAXWCMRYQVZHSA-UFWORHAWSA-N 336.307 2.317 30 1 EEEF COc1ccc2c3c1O[C@H]1C[C@@H](O)C=C[C@@]31CCN(CCC#N)C2 39293252 PISDITDWFFETGF-QOKNQOGYSA-N 326.396 2.134 30 1 EEEF C=C(CO)[C@]1(O)C=C2C(=O)C[C@H](C(C)C)[C@]2(C)C[C@@H]2OC(=O)C[C@]21C 2356423707 CMFMNGXFTLTMOH-QIYYAMEXSA-N 348.439 2.169 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@@](C2)([C@@H](C(=O)OC)[C@H]2[C@@]4(C)CCC[C@@]32OC4=O)[C@@H]1O 2356636506 KVXQCEAWXGANQC-WMFPHPQOSA-N 346.423 2.225 30 1 EEEF Cc1cnc2c(C(=O)NC3[C@H]4CC5C[C@H]3CC(C#N)(C5)C4)cnn2c1 653795385 VPQDQBKFNNLJTM-QABYGRRUSA-N 335.411 2.486 30 1 EEEF C[n+]1c(-c2ccc(/C=N/NC(=N)N3CCCC3)cc2)cn2ccccc21 6072357 OAMCFDRHMBXRKG-HYARGMPZSA-N 347.446 2.385 30 1 EEEF CCCOC[C@H](O)COc1ccc(NC(=O)CC[S+](C)C)cc1 26994363 VYCPJZZIISAKJX-HNNXBMFYSA-O 342.481 2.059 30 1 EEEF N#CCNC(=O)[C@@H]1CCCC[C@@H]1CS(=O)(=O)c1ccc(F)cc1 82064382 XESRYDKCSDPZPR-IUODEOHRSA-N 338.404 2.046 30 1 EEEF C[C@@H]1CC/C(=N/N(C)c2ccccc2)c2ncc(C(=O)O)c(=O)n21 40641077 DXCAOAFKYKPQRQ-PFMFLNCGSA-N 326.356 2.137 30 1 EEEF Cc1cccc(S(=O)(=O)Nc2ccc(/C=C/C(=O)NO)cc2)c1 26719967 ULRPDWFEDWSIRY-JXMROGBWSA-N 332.381 2.314 30 1 EEEF Cc1nnsc1C1=NNC(=O)/C1=C\c1cn(C)c2ccc(C#N)cc12 28954959 QZAGARZFFJBVAX-MLPAPPSSSA-N 348.391 2.127 30 1 EEEF CC[C@H](C)[C@H](NC(=O)C[C@@H]1CCC(=O)[C@H]1CC=CCC=O)C(=O)O 2356812772 BLZRWMJJRGXFHK-WSMBLCCSSA-N 337.416 2.123 30 1 EEEF Cc1ccc(N/N=C2\CC[C@@H](C)n3c2ncc(C(=O)O)c3=O)cc1 38153701 CGEJHGRKXOOFHL-OHARDZCESA-N 326.356 2.421 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@](C)(O)[C@@H]2CC=C(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 238741636 UPDPHQRQFSASPS-NCMUWALVSA-N 332.396 2.309 30 1 EEEF CCOC(=O)c1cccc(/N=C2\NC(NC)=NC3(CCCCC3)N2)c1 95617482 HEOXYJVVVNWPBB-UHFFFAOYSA-N 343.431 2.279 30 1 EEEF C=C1C[C@H](OC(=O)/C(C)=C/C)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@@H](O)C[C@@H]12 13326337 SDRJABGPZHYDOV-FPEITNRTSA-N 344.407 2.475 30 1 EEEF O=C(O)[C@H]1CNC[C@H](CCN/N=C/c2sccc2-n2cccc2)C1 1857596177 QDDJCBGVFHJCJL-JRABBWDTSA-N 346.456 2.163 30 1 EEEF C=CCOc1ccc(/C(O)=C2\C(=O)CN(C(C)C)C2=O)c(OC)c1 103154546 IEGLVURDGCAHAX-MSUUIHNZSA-N 331.368 2.349 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cc4c(cc3[nH]2)OCO4)C1=O 587038156 CYWIIYYFQAENMI-LBPRGKRZSA-N 331.353 2.084 30 1 EEEF O=C(O)COc1ccccc1/C=C1/Oc2c(ccc(O)c2O)C1=O 27421909 IBLKBNQJQUCCMG-NTUHNPAUSA-N 328.276 2.177 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(CO)CC[C@@]3(C)[C@@]1(C)[C@@]21CO1 2356551313 ZJTUORWHCGIUBM-OUPALVCYSA-N 334.412 2.140 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@@]1(C)CCC[C@@]2(C)C(=O)O[C@H]([C@@H]3O)[C@@H]21 33698785 OSYJLXUUZYSFTC-GIBNJYBESA-N 332.440 2.432 30 1 EEEF in-man C=CCCC(=O)N1C[C@@H]([C@@H](C)OC(=O)COCc2ccccc2)C1=O 95597943 UNRCRMYCUUSWML-ZBFHGGJFSA-N 345.395 2.086 30 1 EEEF C#Cc1cccc(-c2nc3ccc(S(=O)(=O)N(C)C)cc3[nH]2)c1 586881567 YBWQBRLRZAIZJB-UHFFFAOYSA-N 325.393 2.462 30 1 EEEF CC1=CC(=O)CC(C)(C)[C@@]12N[C@H](C(=O)O)Cc1ccc(O)c(C)c12 963475069 ZWHPICJKNPIVQY-IFXJQAMLSA-N 329.396 2.440 30 1 EEEF Cn1c([N+](=O)[O-])cnc1-c1nnc(N/N=C/c2ccc(F)cc2)s1 28462945 KKIFMPFVPVZXSI-OMCISZLKSA-N 347.335 2.432 30 1 EEEF C=C(C)[C@@H]1CC[C@@]23O[C@@H]2[C@@H](CC(C)=C[C@@]2(O)C=C(C)C(=O)[C@H]12)OC3=O 2356529178 XCSMOAULMOLHGO-HQWWHFISSA-N 344.407 2.248 30 1 EEEF C=C[C@@H]1C(=C)CC[C@@H]2[C@@H]1CC(=O)[C@@]1(O)[C@](C)(C(=O)O)[C@@H](O)CC[C@]21C 2356720507 BSSPIUBSZQCUDG-MGOAHOADSA-N 348.439 2.327 30 1 EEEF C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)C(CO)=C[C@@]43C)[C@@H]1CC[C@@]2(C)O 2356867880 WXBPWNNGZDXSDG-HFTOWYAQSA-N 346.467 2.379 30 1 EEEF COC(=O)C1CCN(/C(=N\O)c2cccnc2OCC(C)C)CC1 72180629 BYSKSIGKYINFFD-CYVLTUHYSA-N 335.404 2.137 30 1 EEEF COc1ccc(-c2cnnc(N/N=C\c3ccc([N+](=O)[O-])o3)n2)cc1 36066984 HZOAUTKXMRDKAU-PXNMLYILSA-N 340.299 2.494 30 1 EEEF C/C=C(/C)C(=O)O[C@@H]1[C@@H](O)[C@@H](O)[C@@]2(C)[C@@H]3C(=O)C=C(C)[C@H]2[C@@H]3C1(C)C 238741332 HOXNGFVTRBWUMU-HGZQAUSGSA-N 348.439 2.024 30 1 EEEF CN1C(=O)[C@@H](CN2CCCCC2)C[C@@H]1C#Cc1ccc2c(c1)CCO2 96248473 BSAYMXGAHRLDCA-MOPGFXCFSA-N 338.451 2.306 30 1 EEEF N#Cc1ncc(-c2nc3ccc(CN4CCOCC4)cc3[nH]2)s1 587022131 NWINQEHHVZMOJQ-UHFFFAOYSA-N 325.397 2.390 30 1 EEEF Cn1ccc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cc1=O 587890797 DDPBLVLTTQTWKI-UHFFFAOYSA-N 349.217 2.403 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cc4c(cc3[nH]2)OCCO4)C1=O 587038644 KGVYMNGWHUTTAD-ZDUSSCGKSA-N 345.380 2.127 30 1 EEEF COC(=O)[C@H]1C(=O)C2=C(C[C@@H]1C)NC(=O)C[C@@H]2c1cccc(C)c1 13147441 MQFJELARWFGEHX-NORZTCDRSA-N 327.380 2.251 30 1 EEEF COc1cccc2c1O[C@H]1C=C(OC[C@@]3(C)CO3)C=C(O)[C@@H]1C2=O 169368026 GLCNXGRTIKCJRG-MPGHIAIKSA-N 330.336 2.400 30 1 EEEF C#CCOc1ccc2cc(Cn3cc(O)c(=O)cc3C)c(=O)oc2c1 1857606330 TXABDNQFJAOQTE-UHFFFAOYSA-N 337.331 2.029 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@H](C)[C@@]2(O)C=C(C)[C@@H](C[C@@H]3OC(=O)C(=C)[C@@H]31)O2 2356287790 PWWKARNXEFCPJO-CZCDKJNOSA-N 348.395 2.036 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(C)=O)C[C@]1(C)[C@@H](OC(C)=O)CCC(=C)[C@@H]21 2356431877 IDVKLEJKBPWDKI-CLCAGADWSA-N 348.395 2.324 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1[C@@H](OC(=O)C(C)C)C[C@@](C)(O)[C@@H]1CC=C(C)[C@H]21 238764645 SLWRMDVPXSTKON-NCMUWALVSA-N 334.412 2.389 30 1 EEEF COc1cccc2c1[C@@H]1O[C@H]2[C@@]23O[C@@]12C=CC1=C3C(=O)C[C@@](C)(O)C1 238760813 BOYWLALFDCIWJG-JAZQRGJZSA-N 338.359 2.309 30 1 EEEF COC1=CC(=O)C[C@@H](C)[C@]12Oc1c(F)c(OC)cc(OC)c1C2=O 1772627649 DQILFTAGYIWGAI-RBHXEPJQSA-N 336.315 2.296 30 1 EEEF COc1ccc(C2=NO[C@H](C(=O)N(C)O)C2)cc1OC1CCCC1 20040 RMTPBROFMJKTND-INIZCTEOSA-N 334.372 2.357 30 1 EEEF C=C[C@@H]1CC[C@@H]2[C@@H]3CC(=O)[C@@]4(O)C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C 2356429460 VQFKUKMXFNCVKK-HOFAOMGYSA-N 348.483 2.457 30 1 EEEF O=C1/C(=C\c2ccc(OCCCO)cc2O)Oc2c1ccc(O)c2O 27419194 CPCNRLDUQBRBRW-OVCLIPMQSA-N 344.319 2.181 30 1 EEEF C[C@@H]1CC2=C(C1=O)[C@H](O)[C@]1(C)CC[C@@H]3[C@H]([C@H](O)[C@@]1(C)C2=O)C3(C)C 2356876552 ZLWDXUVVPOSFGG-XCYFISRBSA-N 332.440 2.275 30 1 EEEF Cc1ccc(/N=C/C2=C3NC=C(C(=O)O)C(=O)N3[C@@H](C)CC2)cc1 100770904 OAXWUPGGPFTBDN-BFNDQCEFSA-N 325.368 2.492 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)[C@@H]3C=CC(=O)[C@]3(C)[C@H](OC(=O)C(C)C)[C@@H]12 2356636024 SKAOENNHESXSCC-BUEVGNNTSA-N 332.396 2.453 30 1 EEEF O=C(NO)[C@H](Cc1ccccc1)C(=O)NCCCCc1ccccc1 35270453 WBIXUIDQAJRMSZ-GOSISDBHSA-N 340.423 2.490 30 1 EEEF in-vivo CCC[C@H]1O[C@@H]2CC(=O)O[C@@H]2C2=C1C(=O)c1c(OC)cccc1C2=O 40913909 PICJQLJNOPUUBL-CLUVUEOHSA-N 342.347 2.254 30 1 EEEF COc1ccc2c(c1)[C@@H]1CN/C(=C\C(=O)c3ccccc3)C(=O)N1CC2 96934351 YUWRQMRQVKNYSG-OVCORXIESA-N 348.402 2.491 30 1 EEEF N#Cc1ccccc1SCc1nc2ccc(S(N)(=O)=O)cc2[nH]1 586964563 HCWXNKSBOIDTGD-UHFFFAOYSA-N 344.421 2.374 30 1 EEEF Cc1nn(C)c(Oc2ccccc2)c1/C=N/OCCN1CCOCC1 28470127 COVUFFYGOBSEGP-XMHGGMMESA-N 344.415 2.204 30 1 EEEF CC[C@@H]1O[C@]1(C)[C@H](OCOC)[C@@H](C)C(=O)N1C(=O)OC[C@@H]1C(C)C 2356700665 DMBYGHSIWBDJGS-MPZWGZMNSA-N 343.420 2.183 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@@H](c2ccc(C3=CCCCC3)cc2)[C@@H]1CO 95896164 NSZKTJJQZYFHQH-WSTZPKSXSA-N 340.423 2.469 30 1 EEEF C=CCc1cccc2nc([C@H](C)NS(=O)(=O)c3cnn(C)c3)[nH]c12 586937468 FCPZVHZOUQTAAZ-NSHDSACASA-N 345.428 2.064 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc2nnc(C(=O)O)n2c1 587913023 UHQVKRQANFHLGS-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF Cn1nc(-c2nc3cc(C#N)cc(Br)c3[nH]2)c(F)c1O 587154237 AKWJFSDXYZFTLK-UHFFFAOYSA-N 336.124 2.442 30 1 EEEF COc1cccc(-c2c(C#N)c(N)nc(SCCO)c2C#N)c1 13612602 BMXPJVHSWPNGIF-UHFFFAOYSA-N 326.381 2.167 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)C3=CC(=O)[C@@](C)(C[C@H](OC(=O)C=CC)[C@H]12)O3 2356443080 ZUSPJLQZGBITEG-FJUFYYFPSA-N 346.379 2.244 30 1 EEEF C[n+]1cccc(COc2ccc(/C=N/NC(=N)N3CCCC3)cc2)c1 26826885 BMAWRWIFEHASAB-FYJGNVAPSA-N 338.435 2.044 30 1 EEEF CC1=C(c2ccc3nc(-c4cnc(C#N)s4)[nH]c3c2)NNC(=O)C1 587021818 LJMAAHOVUNNLAQ-UHFFFAOYSA-N 336.380 2.314 30 1 EEEF COc1ccc(Cn2cccc2/C=C/C(=O)CC(=O)C(=O)O)cc1 13674096 WTMMMHOYGFOJHB-VOTSOKGWSA-N 327.336 2.171 30 1 EEEF C=C1C[C@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)O 100783029 BSBICXIQCTXPMN-LYUQRIDMSA-N 330.380 2.056 30 1 EEEF endogenous,in-man COc1cc(/C=N/c2ccc(S(N)(=O)=O)cc2)ccc1C(C)=O 49066620 RLUUBTYKYZLMNY-VCHYOVAHSA-N 332.381 2.296 30 1 EEEF C=CCn1c(=O)c(NCC2CC2)c2n(c1=O)[C@@H](c1ccccc1)CN2 82209188 LYGRWWDVQGTXPY-OAHLLOKOSA-N 338.411 2.033 30 1 EEEF C[C@H]1Cc2ccc(F)c(Br)c2[C@]2(COC=CC2=O)N1 587835166 NUURRDCZWYFTPT-RMLUDKJBSA-N 326.165 2.431 30 1 EEEF N#C[C@H](C(=O)Nc1ccc([S@](=O)C(F)(F)F)cc1)C(=O)C1CC1 22221 HWZMCOGRZDFBES-BSNNYGBQSA-N 344.314 2.371 30 1 EEEF C[C@@]1(C=O)[C@H]2CCC3=C[C@H]4C[C@]3(CC[C@@]4(O)CO)[C@]2(C)CC[C@H]1O 2356324660 KZRJAXKCOWVRTH-YGJNQFLQSA-N 334.456 2.213 30 1 EEEF C=C(C)C(=O)O[C@H]1[C@@H]2[C@H](C)C(=O)O[C@@H]2C[C@@H](C)[C@@H]2C=CC(=O)[C@]12C 103885170 NZESEVTYUVXOTC-WMHULLHSSA-N 332.396 2.453 30 1 EEEF CC(C)[C@H]1O[S@@](=O)O[C@@]1(Cn1cncn1)c1ccc(Cl)cc1 84711454 NPFKMHWOXVEEPD-QLEMLULZSA-N 341.820 2.477 30 1 EEEF C=C[C@]1(C)C=C2[C@H](O)[C@H](O)[C@@H]3C(C)(C)C(=O)C=C[C@]3(C)[C@@]2(O)CC1 2356325940 RNZJQFGWISERJP-JFVPRCSHSA-N 332.440 2.153 30 1 EEEF Cc1cc(CN2C[C@H](N)[C@H](C(=O)[C@H]3CCC[C@H]3C#N)C2)ccc1C#N 28955148 FWKUWRLCCHFYDK-OKYOBFRVSA-N 336.439 2.135 30 1 EEEF C=C(CO)[C@@H]1CC2=CC[C@@H]3[C@](C)(CO)[C@H](O)CC[C@]3(C)[C@H]2C[C@H]1O 2356464953 VJVZOSZFDKSLNA-JHQBWLJPSA-N 336.472 2.028 30 1 EEEF C=CC(C)(C)n1cc(C[C@H]2NC(=O)[C@@H](C)NC2=O)c2ccccc21 2356800934 RGJOYRGQGOLRLW-IUODEOHRSA-N 325.412 2.108 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@@H]2[C@@H]3C[C@H](C(C)C)[C@@H](C=C3C)[C@H]2C1=O 195181092 PBDZFTMSQJXALQ-KJWHEZOQSA-N 347.484 2.021 30 1 EEEF C=C[C@H]1CC(=O)[C@H]2Oc3c(OC)ccc4c3[C@@]23CCN(C)[C@H](C4)[C@@H]13 169368478 NTWGNEUJRLFCNI-CWGXPGDPSA-N 325.408 2.345 30 1 EEEF C[C@]1(Nc2ccc(C(=O)NO)cc2)CCN(c2ccccc2)C1=O 200964321 LNFNYVNCDUDQFX-SFHVURJKSA-N 325.368 2.413 30 1 EEEF C=C(C)C(=O)O[C@@H]1CC(=C)[C@@H]2C[C@H](O)[C@H](C)[C@@H]2[C@@H]2OC(=O)C(=C)[C@@H]21 2356664661 FQKDBWKMFCRELP-BATVILNXSA-N 332.396 2.165 30 1 EEEF C=C1C[C@@H](O)[C@H]2O[C@@]2(C)CC[C@@H]2/C(=C/C=C/C(C)(C)O)C(=O)OC[C@@H]12 40956119 DHTWVKTXQLZELP-VZDDEZTBSA-N 348.439 2.288 30 1 EEEF COCCNC(=O)[C@@H]1CCCC[C@@H]1c1nc2ccc(C#N)cc2[nH]1 587230248 GVQINTUAKQBKOC-UONOGXRCSA-N 326.400 2.471 30 1 EEEF Oc1c(/C=N/N2CCOCC2)c(C(F)(F)F)nn1-c1ccccc1 13597597 ADLMIYZFTZANCP-VXLYETTFSA-N 340.305 2.263 30 1 EEEF CCN1C(=O)N(CC)[C@@H]2[C@H]1NC(=S)N2/N=C/C=C/c1ccccc1 1857645993 ZKFBHJXHPXBJBI-QKJONGJWSA-N 343.456 2.305 30 1 EEEF CC1=C[C@H](O)CC(CO)=CC[C@H]2CCC3=C(C(=O)[C@H]1[C@H]3O)C2(C)C 2356536674 PLSLPANFUZMMNZ-KMCQBPLKSA-N 332.440 2.299 30 1 EEEF C=C1C(=O)[C@]23C[C@@H](O)[C@H]1C[C@H]2[C@]1(C)CCC[C@](C)(CO)[C@H]1C[C@H]3O 28651474 WHNRXVKFGPGHAF-HSVPHDSMSA-N 334.456 2.068 30 1 EEEF CC(C)=CCCc1ccc2c(c1)C(=O)C1=C(C2=O)S(=O)(=O)CCN1 13406852 BGLUXTSGFQZINB-UHFFFAOYSA-N 345.420 2.194 30 1 EEEF biogenic C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@]12OC(=O)[C@](C)(CC[C@H]1O)[C@H]2[C@@H]3C(=O)O 85800212 JKQCGVABHHQYKQ-VKROUOPBSA-N 332.396 2.136 30 1 EEEF in-man Cn1c(Oc2cccc(-c3cccc(C#N)c3)c2)cc(=O)n(O)c1=O 1857600366 IBTREUBVKMVHEN-UHFFFAOYSA-N 335.319 2.115 30 1 EEEF CCCSC1=C(N2CC2)C(=O)C(SCCC)=C(N2CC2)C1=O 1746215 WPULXUKTRPOSFH-UHFFFAOYSA-N 338.498 2.479 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@@H]2OC[C@]23O[C@@H]2C=C(C)C(=O)C[C@]2(C)[C@@]13C 2356397107 GUTBYIDIQSFHLV-OMEKBDSISA-N 332.396 2.346 30 1 EEEF C=C1C[C@@]23C[C@@]1(C)CC[C@@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)O 2356832913 JXHBGFBFCVSITH-NOQZAJSJSA-N 344.407 2.302 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)[C@]1(C)CCC[C@](C)(C=O)[C@H]1C[C@H]3O 35824705 ZXYPBEZVRIDTAX-YNDYFHGHSA-N 332.440 2.275 30 1 EEEF NC(=NO)c1ccc(NC(=O)CCCNCCc2ccccc2)cc1 1772649133 VIBOHOCRMUTOFJ-UHFFFAOYSA-N 340.427 2.332 30 1 EEEF COc1c(O)cc2c(c1O)C(=O)/C(=C\c1ccc(O)c(O)c1)CO2 13481945 KUIRIGZNHOTLPQ-WTKPLQERSA-N 330.292 2.176 30 1 EEEF CC(C)(O)C#Cc1cc2c(cc1F)C1CC(C1)c1[nH]c(C(N)=O)nc1-2 215771998 SWZJMNUERBKOGJ-UHFFFAOYSA-N 339.370 2.412 30 1 EEEF N#Cc1nccnc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587889603 OWMMAFBYYLYKAI-UHFFFAOYSA-N 345.189 2.365 30 1 EEEF O=C(CCCCC1CCN(S(=O)(=O)c2ccccc2)CC1)NO 71296819 OBZPRAVUYOBSFM-UHFFFAOYSA-N 340.445 2.153 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@H](NC(=O)c2ccc(O)cc2)[C@@H]1O 40812377 GBKMQCYVHBYTGQ-IRXDYDNUSA-N 338.363 2.267 30 1 EEEF CC(=O)OC[C@H]1O[C@H](C#CCCc2ccccc2)C=C[C@@H]1OC(C)=O 13782949 PEMFRHXMDHFDFC-HSALFYBXSA-N 342.391 2.441 30 1 EEEF CC1(C)C(=O)c2ccc(C#N)cc2[C@@H](NC(=O)c2ccncc2)[C@@H]1O 13832180 SRXFVGITHMAJKQ-WBVHZDCISA-N 335.363 2.008 30 1 EEEF N#CCC1(n2cc(C(N)=O)c(Nc3ccccc3)n2)CCOCC1 204980429 HFZUMJDTVZIGGE-UHFFFAOYSA-N 325.372 2.145 30 1 EEEF COc1ccc(Cl)cc1C#Cc1[nH][nH]c2nc(=N)nc(Cl)c1-2 587912307 LFMOJTCXNOWFTP-UHFFFAOYSA-N 334.166 2.432 30 1 EEEF C#CCN(C)C[C@H]1CN2CC[C@H]1C[C@H]2CNC(=O)Nc1ccsc1 2356298903 IYIDYUMTPGQBJD-ZOBUZTSGSA-N 346.500 2.145 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@](C)(O)CC[C@@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@@H]12 2356677097 GUGYUSGXSKYCJD-FHXVVSRQSA-N 348.439 2.288 30 1 EEEF C=CCn1c(=O)c(NCC(C)C)c2n(c1=O)[C@@H](c1ccccc1)CN2 82209180 KOJAAMGLIXQWFF-OAHLLOKOSA-N 340.427 2.279 30 1 EEEF N#Cc1c(-c2ccc(Br)cc2)nc(S)n2c(=O)[nH]nc12 96932751 NMIGLQQMERGKFN-UHFFFAOYSA-N 348.185 2.007 30 1 EEEF C[C@@H]1CC(=O)[C@@H](Cc2nc3cc(Cl)nc(C#N)c3[nH]2)[C@@H]1C[N+](=O)[O-] 587266013 YQSUHXZFPMTARU-HRDYMLBCSA-N 347.762 2.143 30 1 EEEF CC(=O)C(C(C)=O)c1ccccc1-c1nc2nc(C#N)c(C#N)nc2[nH]1 586880871 CMCVJCJJAGKKQW-UHFFFAOYSA-N 344.334 2.025 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cccc(C(=O)OC)c3[nH]2)C1=O 587039454 RWYIFQLPOLNNSW-LLVKDONJSA-N 345.380 2.142 30 1 EEEF CS(=O)(=O)ON1C(=O)/C(=C/c2ccccc2)N=C1c1ccccc1 3633137 TZVCPFZKUIWIAD-QINSGFPZSA-N 342.376 2.208 30 1 EEEF CC#CC#CC=C1O[C@]2(CC[C@H](OC(=O)CC(C)C)CO2)[C@H]2O[C@@H]12 2356508580 IZOBIZVXEKNCNN-UDTPNQRGSA-N 330.380 2.159 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H](O)/C(C)=C/CC/C(C)=C/CC[C@@]3(CO)O[C@@H]3C[C@H]12 34578037 MULWDJOXRRXULO-XJFSRSTNSA-N 348.439 2.432 30 1 EEEF N#C/N=C(/NCCCCc1c[nH]cn1)NCCc1c[nH]c2ccccc12 49020450 BMCMMMRTWLCMFW-UHFFFAOYSA-N 349.442 2.473 30 1 EEEF COc1cc(/C=C/C(=O)[C@]2(CCCN(C)C)CCOC2=O)ccc1O 299833549 PWQKWWJWZRTZJC-FNQPIQQGSA-N 347.411 2.258 30 1 EEEF CC(C)(C)OC(=O)[C@H](N)CCc1nc2cc(Cl)nc(C#N)c2[nH]1 587256694 NMRPRTWKLLNNND-MRVPVSSYSA-N 335.795 2.085 30 1 EEEF COC(=O)c1[nH]nc([N+](=O)[O-])c1C#Cc1cc(Cl)ccc1OC 587903779 PPSUQXSKPHUQOW-UHFFFAOYSA-N 335.703 2.166 30 1 EEEF COC(=O)Cc1n[nH]c2c1[C@@H](c1c[nH]c3ccccc13)[C@@H](C#N)C(=N)O2 169690875 REGVENFQJHUBDE-MEBBXXQBSA-N 349.350 2.248 30 1 EEEF C=C1[C@H]2OC(=O)C=C(C)[C@H]2C[C@H]2/C(=C\C=C\C(C)(C)O)C(=O)OC[C@H]12 154116081 LUHDPMVWXCNPMF-IFUVXTCWSA-N 344.407 2.477 30 1 EEEF C=C(C)[C@@H]1C[C@@H]2[C@@H](CC[C@@]2(O)CCNC(=N)NC)[C@@]2(O)CC=C[C@H]1C2 2356676440 SYAVXIORAFJRNU-YSFZOSMKSA-N 347.503 2.171 30 1 EEEF CC(C)[C@H](C(=O)NO)c1ccc2c(c1O)C(=O)c1c(O)cccc1C2 13606205 BOQGERWXXRKMKH-AWEZNQCLSA-N 341.363 2.478 30 1 EEEF C=CCO/C(O)=C1\C(C)=Nc2nnnn2[C@@H]1c1cccc(OC)c1 103539581 TWODDRDYPSFNRP-SXWSKBOKSA-N 327.344 2.349 30 1 EEEF C=C1CC[C@H]2[C@@H]([C@@H]3[C@H]1[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@]3(C)O)C2(C)C 238755324 LLWAIJLNXRKXTQ-JSTLXOBDSA-N 336.428 2.469 30 1 EEEF N#C[C@H]1[C@@H](c2ccc(-c3cccnc3)cc2)[C@@H](CO)N1C(=O)C1CC1 95896230 FYALJDMLJJPLTL-IPMKNSEASA-N 333.391 2.337 30 1 EEEF O=CCC[C@@]1(C(=O)O)Oc2ccccc2C(=O)[C@H]1C(=O)c1ccco1 587603580 NTVWIXHUYWRWHD-KBXCAEBGSA-N 342.303 2.156 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cc(C(=O)O)c(F)cc3[nH]2)C1=O 587038109 CWGARMMSGGNKLW-NSHDSACASA-N 349.343 2.193 30 1 EEEF N#Cc1nc2nc(CCc3cc(F)c(F)c(F)c3)[nH]c2nc1C#N 587138810 RBJOETZYCSNKBW-UHFFFAOYSA-N 328.257 2.299 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]1(C)CCC[C@@]2(CO)C(=O)O[C@@H]([C@H]3O)[C@@H]21 14812355 RDUNXXWNAKBVER-ACOPLKQNSA-N 332.440 2.434 30 1 EEEF endogenous,in-man Cc1nc(CCCN/C(=N\C#N)NCCSc2ccccc2)c[nH]1 169327569 GXMHMYPDQCEMKW-UHFFFAOYSA-N 342.472 2.459 30 1 EEEF C=C1C[C@]23CC[C@H]1C[C@H]2[C@]12CCC[C@@](C)(CO)[C@H]1[C@@H](OC2=O)[C@@H]3O 169654470 OMDPLJPNOXTENE-BGSZKXRRSA-N 332.440 2.434 30 1 EEEF N#Cc1ccc(N2C(=O)[C@@H]3[C@@H]4CC[C@@H](O4)[C@@H]3C2=O)cc1C(F)(F)F 29126975 QZRQLVZGQQVBIK-FNFFVJSTSA-N 336.269 2.244 30 1 EEEF N=c1[nH]cc2nc(CCCCCC#CCO[C@@H]3CCCCO3)nc-2[nH]1 586909974 LDKJPNOJZAEHMT-INIZCTEOSA-N 343.431 2.367 30 1 EEEF O=S(=O)(O)c1ccc2[nH]c(C=NOCc3ccccc3)nc2c1 587189288 BAIMBXKYPWRLNA-UHFFFAOYSA-N 331.353 2.360 30 1 EEEF CN(/N=C\c1ccc(N(C)C)cc1)C1=NS(=O)(=O)c2ccccc21 13132583 TZEJUXVSLJJQGJ-PDGQHHTCSA-N 342.424 2.167 30 1 EEEF O=C(O)/C(O)=C/C(=O)c1cccc(NC(=O)c2ccccc2O)c1 101628596 ZZIQWIGKZWJIBJ-DHDCSXOGSA-N 327.292 2.354 30 1 EEEF C=C1CC[C@H]2C[C@H](O)C3=C(C(=O)[C@@H](C(C)=C[C@H](O)C1)[C@H]3O)C2(C)C 2356605256 YZCJZJQRTRSJHJ-SFUJAXRZSA-N 332.440 2.297 30 1 EEEF O=C(NO)c1ccc2c(c1)nc(CCc1ccccc1)n2CCCO 40866740 GVDINOVHHJJJDD-UHFFFAOYSA-N 339.395 2.323 30 1 EEEF CC1=C[C@]2(O)C(=O)/C(C)=C/[C@@H]3[C@H](C[C@@H](O)/C(C)=C/[C@H]2C1=O)C3(C)C 238732398 QSTBGARAGIHHBB-UIJPAUIQSA-N 330.424 2.361 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc(C[C@H](N)C(=O)O)ccc1O 587899628 DSGGYUCUKIIJJY-HNNXBMFYSA-N 345.782 2.408 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(COC(C)=O)CCC=CC[C@@H](OC(C)=O)[C@@H]12 2356401885 RTCARLYNKKVHJD-BRWVUGGUSA-N 334.368 2.246 30 1 EEEF Cn1c(NCC(=O)c2cccc(C#N)c2)nc(-c2ccncc2)cc1=O 103245670 ZQDSZRQZASMIJD-UHFFFAOYSA-N 345.362 2.009 30 1 EEEF COc1ccc(/N=C/C2=C3NC=C(C(=O)O)C(=O)N3[C@H](C)CC2)cc1 102199455 MYYOXKVMGJMRFT-YXZFXQPTSA-N 341.367 2.192 30 1 EEEF C[C@]1(C=O)[C@H](O)CC[C@]2(C)[C@H]1CCC1=C[C@H]3C[C@@]12CC[C@@]3(O)CO 2356324656 KZRJAXKCOWVRTH-SLLBGGHUSA-N 334.456 2.213 30 1 EEEF N#C[C@@H]1C[C@H](F)CN1C(=O)C[C@H](N)Cc1ccc(C(F)(F)F)cc1 299832831 WNCLMLGRMWYEPC-MJBXVCDLSA-N 343.324 2.428 30 1 EEEF O=C(NO)c1ccc(Cn2nnc(-c3ccc4ccccc4n3)n2)cc1 1857584893 BSSLAUBSRPDZRV-UHFFFAOYSA-N 346.350 2.056 30 1 EEEF COC(=O)[C@@H](CCSC)/N=C1/C(=O)c2ccccc2C(O)=C1O 28529657 WNMKVDOQTGURMS-NVGQTZGUSA-N 335.381 2.403 30 1 EEEF N#Cc1cccc(-c2ccc(-c3ccccc3)n2CC(=O)N=C(N)N)c1 29039770 BPSSSXZPLIFAFY-UHFFFAOYSA-N 343.390 2.494 30 1 EEEF COCCNC(=O)[C@H]1CCCC[C@@H]1c1nc2ccc(C#N)cc2[nH]1 587230245 GVQINTUAKQBKOC-KBPBESRZSA-N 326.400 2.471 30 1 EEEF N#Cc1cccc([C@H](O)C2=C3C=C[C@@H]4C[C@@]3(OC2=O)[C@H]2CCCCN42)c1 1772654688 JGRCTRMFLQFCCH-DOSUHQCWSA-N 348.402 2.380 30 1 EEEF COc1cccc2c1O[C@H]1C=C(OC[C@]3(C)CO3)C=C(O)[C@@H]1C2=O 169368028 GLCNXGRTIKCJRG-RLFYNMQTSA-N 330.336 2.400 30 1 EEEF O=C(/C=C/c1cccn1Cc1cc(F)cc(F)c1)CC(=O)C(=O)O 103290200 QPNMZFJFCSWVAS-ONEGZZNKSA-N 333.290 2.441 30 1 EEEF O=S(=O)([C@H]1O[C@@H]1c1ccccc1)N1CCN(c2ccccc2)CC1 26291960 UPZFQDXXSQSJFN-QZTJIDSGSA-N 344.436 2.236 30 1 EEEF CCOC(=O)Cc1cc(O)cc(O)c1C(=O)C=CC=CC[C@@H](C)O 2356505084 QVACWFLAVQMDNR-GFCCVEGCSA-N 334.368 2.269 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@@](C2)(C(=O)O[C@@H]2O[C@H](O)[C@@H]4C(C)(C)CC=C[C@@]234)[C@@H]1O 2356678694 PMIAIQKUXKRZIR-VXCHZHJLSA-N 346.423 2.140 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@H]2C(=C)C[C@H](O)[C@@H]3[C@H](C)C(=O)O[C@H]3[C@H]2C1=C 2356488760 ZNXKZMIVEDDWGE-JUTUNNCASA-N 332.396 2.165 30 1 EEEF C=C1[C@@H]2CC[C@@H]3[C@@]45CCC[C@@](C)(C(=O)O4)[C@H]5[C@H](C(=O)O)[C@]3(C2)[C@@H]1O 238736371 MBNDVMTZEKAWKP-XFEHBKOQSA-N 332.396 2.136 30 1 EEEF COCC(=O)N1[C@@H](C#N)[C@H](c2ccccc2-c2ccccc2)[C@@H]1CO 95668348 RRMULCFNGGBUJN-BJLQDIEVSA-N 336.391 2.179 30 1 EEEF O=C1C[C@H](O)[C@@H](O)[C@@H]2C1=CCCC21Oc2cccc3cccc(c23)O1 299832750 QZXGWZACFKTEPU-ZOCIIQOWSA-N 338.359 2.338 30 1 EEEF O=C(OCC1=CS(=O)(=O)c2ccccc2C1=O)c1ccccc1 27901355 CLQRAXWTAALGPM-UHFFFAOYSA-N 328.345 2.398 30 1 EEEF COc1ccc(/C=C2\N=C(Cc3ccccc3)C(=O)N(O)C2=O)cc1 34074886 JMJSGGYOFKXGRZ-ATVHPVEESA-N 336.347 2.478 30 1 EEEF C[C@H]1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]12CO[C@H](CC1=O)C(C)(C)C2=C(O)C3=O 238773694 UZPIZMWEFRPQNY-ZQBIZSCKSA-N 344.407 2.387 30 1 EEEF CCCOC(=O)c1cccc(/N=C2\N=C(N)NC3(CCCCC3)N2)c1 95617477 QFWZEIFNBMFODA-UHFFFAOYSA-N 343.431 2.409 30 1 EEEF O=C1C2=CCCC3(Oc4cccc5cccc(c45)O3)[C@@H]2[C@H](O)[C@@H]2O[C@H]12 1772619185 GZNZGNSOLGAMAJ-KANFNMMFSA-N 336.343 2.355 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(COC3=O)[C@H]2CC[C@@]3(C)CO[C@@H](O2)[C@@H]13 2356350124 VGHUWBCJSRMGIQ-RGMKMCSVSA-N 344.407 2.243 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](COC(C)=O)CCC=C(C(=O)OC)CC[C@H]12 2356493720 DRSUBRLQXQEHHE-FVQBIDKESA-N 336.384 2.327 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12OC(=O)[C@@](C)(CC[C@@H]1O)[C@H]2[C@@H]3C(=O)OC 2356559839 NZAMXUVSJOQDKJ-QPEPJFPRSA-N 346.423 2.225 30 1 EEEF N#CCCCCN1COc2cc3c(cc2C1=O)O[C@H]1CCCN1C3=O 72173105 UWBONOROIYFKGA-INIZCTEOSA-N 341.367 2.127 30 1 EEEF CC(C)[C@@H](c1nc2ccccc2o1)n1cc(/C=C/C(=O)NO)nn1 84723338 IOAXCKZMCHPECI-KIUWMYQTSA-N 327.344 2.183 30 1 EEEF C=C1[C@@H]2CC[C@@H]3[C@](C2)(C(=O)O[C@H]2O[C@@H](O)[C@H]4C(C)(C)CC=C[C@]432)[C@@H]1O 238746127 PMIAIQKUXKRZIR-TZKJZBJJSA-N 346.423 2.140 30 1 EEEF COc1ccccc1C(=O)/C=C1\NC[C@@H]2c3ccccc3CCN2C1=O 96934350 PBSPRMMNFZKZHW-XUDLPTGHSA-N 348.402 2.491 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1[C@@H](O)CC(=C)[C@@H]1[C@@H](OC(=O)C(C)C)CC(=C)[C@@H]12 13326110 JCWQENUEJOVTIV-YHPRMOQLSA-N 332.396 2.165 30 1 EEEF C=C(C)C(=O)O[C@@H]1/C=C(/C)C2=CC(=O)[C@@](C)(C[C@@H]3OC(=O)C(=C)[C@H]31)O2 238784594 AERIPQYYSNTIDA-MFRWKCHVSA-N 344.363 2.164 30 1 EEEF CCOc1ccc(C(=O)Nc2cc(C(=O)NO)ccc2OC)cc1 653851547 KZDIIWXOZJOZET-UHFFFAOYSA-N 330.340 2.465 30 1 EEEF COc1ccc(C[C@@H](C)c2nc3nc(C#N)c(C#N)nc3[nH]2)cc1OC 587926092 HZGRUUAMXABAPA-SNVBAGLBSA-N 348.366 2.460 30 1 EEEF C[C@]1(CCC(=CCO)CO)[C@H](C=O)CC[C@@]23COC(=O)C2=CCC[C@@H]31 2356379734 GUKSFBJMSDUTIA-MFHCWRBVSA-N 348.439 2.172 30 1 EEEF C=C1CC/C=C(\C)CC[C@@H]2/C(=C\C=C\C(O)(CO)CO)COC(=O)[C@@H]12 145211989 WVMYRDBAJSJKGW-VIZLUMSNSA-N 348.439 2.050 30 1 EEEF C=C1CC(=O)[C@@H](O)CC(=O)C[C@H](C(=C)C)CCC2=C[C@@H](C1)OC2=O 238754540 LRZNKDYERIHNCD-QBIMZIAESA-N 332.396 2.440 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@@]1(CCC[C@]2(C)[C@H]1CO[C@H]2O)COC3=O 95913313 COKCKHYUZSETSY-BRUMOIPRSA-N 346.423 2.226 30 1 EEEF biogenic,in-vitro CC#CC#CC=C1O[C@]2(CCCCO2)[C@@H](O)[C@H]1OC(=O)CC(C)C 2356472880 LEOZNWWIPMVKHH-GBESFXJTSA-N 332.396 2.143 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@@H](C(=O)O)[C@@H]1[C@@]2(C)CCC[C@]13COC2=O 85799973 MJFVMFNFTCKAEV-YIKNXGDOSA-N 346.423 2.384 30 1 EEEF in-man CC1=C(O)C(=O)C[C@]2(C)[C@H]3CCc4cocc4[C@]3(CO)CC[C@]12O 299827335 YJYCGDAWLMWZRS-OWYHZJEWSA-N 332.396 2.408 30 1 EEEF COc1ccccc1NCCNCc1ccc(/C=C/C(=O)NO)cc1 13528188 NHVFHHKXUUGRHH-ZHACJKMWSA-N 341.411 2.416 30 1 EEEF C=C1CCC=C(C)CC[C@@H]2C(=CC=CC(O)(CO)CO)COC(=O)[C@@H]12 2356427344 WVMYRDBAJSJKGW-MSOLQXFVSA-N 348.439 2.050 30 1 EEEF O=C1C=C[C@]2(O[C@@H]3c4c2ccc(O)c4C(=O)[C@@H]2O[C@H]23)c2cccc(O)c21 2356482041 GLLQRSNTBBQHPX-FYQPLNBISA-N 348.310 2.129 30 1 EEEF COc1c(O)c(O)c(O)c2c1OCC(=Cc1ccc(O)cc1)C2=O 2356595837 VBEHRZIHLNLYBT-UHFFFAOYSA-N 330.292 2.176 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@](C)(O)C(=O)CC/C(C)=C\[C@H]2OC(=O)C(=C)[C@@H]21 13337916 AYLHAROHTWZRTO-CLTPXQQRSA-N 348.395 2.022 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1CC[C@]1(C)[C@@H](OC(C)=O)CC=C(COC(C)=O)[C@@H]21 2356430894 VHZJGEKNJYFJNY-DIKXUDHVSA-N 348.395 2.325 30 1 EEEF CC(=O)OCC[C@H](C=CC=CC#CC#CC=CCO)OC(=O)C(C)C 2356397875 RLOXIGRNKNTVJQ-IBGZPJMESA-N 344.407 2.175 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@@]12CCC[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 104374175 IPHNMKITOREFLW-AAPDSVFJSA-N 332.396 2.136 30 1 EEEF in-man C=C1CC[C@H]2CCC3=C(C(=O)[C@@H](C(C)=C[C@H](O)[C@H]1O)[C@@H]3O)C2(C)C 2356571488 SMYOLHGQHZBFAQ-GIVGJKMXSA-N 332.440 2.297 30 1 EEEF C=C1[C@@H]2C(=C(COC(C)=O)CC[C@@H]3C(=C)C(=O)O[C@@H]23)C[C@H]1OC(C)=O 2356674995 BRBKGYDAQMCZSA-VDHUWJSZSA-N 346.379 2.246 30 1 EEEF N#C[C@@]1(NC(=O)[C@@H](N)Cc2sccc2F)C[C@@H]1c1ccccc1 40402912 UUKJIEBFYVGYRF-IFIJOSMWSA-N 329.400 2.323 30 1 EEEF CCC#CCOC(=O)[C@H](C)NC(=O)c1coc(-c2cccs2)n1 82083891 QXQRDTYLBWEAHR-NSHDSACASA-N 332.381 2.478 30 1 EEEF O=C(CCc1nnc2sc(CS)nn12)c1nc2ccccc2[nH]1 95589696 ZKIBAWAFXGWWBE-UHFFFAOYSA-N 344.425 2.307 30 1 EEEF COC1=C[C@@]23CCN(C)[C@@H](Cc4cc5c(cc42)OCO5)[C@@H]3CC1=O 14587535 CQOIKQRNRZTGLJ-NJSLBKSFSA-N 327.380 2.033 30 1 EEEF biogenic,in-vitro C=C1C(=O)O[C@@H]2C3=C(COC(C)=O)CC[C@H](OC(C)=O)[C@]3(C)CC[C@@H]12 2356410446 LLUIAKNHFIRVHK-MRHSLFKSSA-N 348.395 2.470 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)CC[C@@](C)(C(=O)O)[C@@H]1C[C@@H]3O 72120339 LRECIABFFPIQSO-CZGCYONISA-N 348.439 2.161 30 3 EEEF Cc1cc(-c2nc(-c3ccc(OCC(=O)O)c(C#N)c3)n[nH]2)ccn1 40866597 SSTLHFKNYPCBEW-UHFFFAOYSA-N 335.323 2.177 30 1 EEEF N[C@@H](CS)C(=O)Nc1ccc(Oc2cccc(C(=O)O)c2)cc1 28764756 URDQCNVUCIYXTO-AWEZNQCLSA-N 332.381 2.373 30 1 EEEF CC[C@@H]1O[C@]1(C)[C@H](OCOC)[C@@H](C)C(=O)N1C(=O)OC[C@H]1C(C)C 2356700664 DMBYGHSIWBDJGS-KAHPBISDSA-N 343.420 2.183 30 1 EEEF N#C[C@@H]1CCC[C@@H]1C(=O)[C@@H]1CN([C@@H]2CCOc3ccccc32)C[C@@H]1N 169363662 AXLLQKGXUYCBGM-VGAPYMQISA-N 339.439 2.278 30 1 EEEF COc1ccc(C(=O)NCCCC/N=C(\N)NCC=C(C)C)cc1 26743297 FXHOHLAGJWHHIN-UHFFFAOYSA-N 332.448 2.076 30 1 EEEF CC1(C)Oc2ccc3ccc(=O)oc3c2C(/C=N/NC(N)=S)=C1O 36384847 LDHVPJUNVMYGKG-CNHKJKLMSA-N 345.380 2.052 30 1 EEEF COC(=O)c1ccc(OC)cc1Oc1ncnc(O)c1/C=C/C(C)=O 72177537 SLOXIBORVSHHTG-GQCTYLIASA-N 344.323 2.372 30 1 EEEF C[C@@H]1CCC(=NN(C)c2ccccc2)c2ncc(C(=O)O)c(=O)n21 253683900 DXCAOAFKYKPQRQ-LLVKDONJSA-N 326.356 2.137 30 1 EEEF CCS(=O)(=O)c1ccc2nc(-c3ccc(N)c(C#N)c3)[nH]c2c1 587248575 BLGGOXJSQWMTMD-UHFFFAOYSA-N 326.381 2.477 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1[C@H](OC(=O)C(C)C)CC(=C)[C@]1(O)CC=C(C)[C@H]21 13325945 YNPWRXLOAYTDQM-GMKVZWAMSA-N 332.396 2.309 30 1 EEEF C=C1CC[C@H]2[C@@H]([C@@H]3[C@@H]1C1=C(C[C@@](C)(O)C1=O)C(=O)[C@@]3(C)O)C2(C)C 200479718 DGXURLBVVBVHIO-KOWFQURMSA-N 330.424 2.195 30 1 EEEF CCc1ccccc1N/N=C1/C(=O)Nc2ccc(S(=O)(=O)O)cc21 144345798 GIIOECXXSWWQLL-UHFFFAOYSA-N 345.380 2.264 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)[C@]1(C)CC(=O)CC(C)(C)[C@H]1C[C@H]3O 95919304 YTSRALVHLWIBKL-IPDBMXHFSA-N 332.440 2.275 30 1 EEEF biogenic,in-vitro CC(C)N=c1nc(-c2cc(O)ccc2F)nc(NC(C)(C)C#N)[nH]1 1857656510 ZKCSHTWHAVTEDI-UHFFFAOYSA-N 330.367 2.340 30 1 EEEF C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@H]2[C@H](O)CO 2356431753 DCMCEXCRUWBAFV-YHVBFONYSA-N 348.483 2.459 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1CCC(=C)[C@@H]1C[C@@H](OC(=O)C=C(C)CO)C(=C)[C@@H]12 2356462687 AZDMJQODBMILBW-NZKYLMMGSA-N 344.407 2.477 30 1 EEEF N=C(NN=Cc1ccc(-c2cn3ccccc3n2)cc1)N1CCOCC1 27438761 HMHGNZBLLFIVRD-UHFFFAOYSA-N 348.410 2.192 30 1 EEEF COC(=O)C1=C2[C@](C)(C[C@@H]3O[C@H]3[C@]2(C)C(=O)OC)c2ccccc21 2356695940 CCCHYPOECSYCKC-GGCQVYRISA-N 328.364 2.235 30 1 EEEF CCCCc1nc2cc(/C=C/C(=O)NO)ccc2n1[C@H]1CCNC1 34987566 SNHWQAPINSMLNB-OWNNVSBGSA-N 328.416 2.432 30 1 EEEF O=C(/C=C/C#Cc1ccc(O)cc1F)NC1=C(C(=O)O)CCCC1 1772646218 RSIXRSXTZVORGJ-XBXARRHUSA-N 329.327 2.468 30 1 EEEF C=C1CC[C@H]2[C@@](C)(CC[C@@H](O)[C@@]2(C)NC=O)[C@@H]1/C=C/C1=CCOC1=O 1857534991 VWEPTAOEXREBNO-CRBRZBHVSA-N 345.439 2.274 30 1 EEEF C=CCONC(=O)[C@H](C)N1C(=O)S/C(=C\c2ccccc2)C1=O 1857550193 XBYMOQGEFSSJTI-KBICQTFXSA-N 332.381 2.345 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100778375 QYXZQZMPZUEEML-OXPIRJGMSA-N 346.423 2.384 30 1 EEEF endogenous,in-man C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@H]1CC[C@@H]2[C@@H](O)CO 255205353 DCMCEXCRUWBAFV-NBDNVMCBSA-N 348.483 2.459 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O[C@H]([C@@H]3O)[C@H]12 33698784 OSYJLXUUZYSFTC-OOKOIGBISA-N 332.440 2.432 30 1 EEEF in-man N#Cc1ccccc1SCc1nc2cccc(S(N)(=O)=O)c2[nH]1 586965426 WFYGPWLXFLHXSF-UHFFFAOYSA-N 344.421 2.374 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@@H]([C@@H](C=O)[N+](=O)[O-])N1 587747089 PCGJRFLRAQYEJS-AKGNYGMASA-N 331.141 2.008 30 1 EEEF CCSCC[C@@H](NC(=O)[C@@H](CS)Cc1ccccc1)C(=O)O 26494168 ZYBMHXFQTKTNOS-ZIAGYGMSSA-N 341.498 2.488 30 1 EEEF COc1ccc2c3c1O[C@H]1C=C(C(C)=O)C[C@H]4[C@H](C2)N(C)CC[C@]314 195299910 FKNWJBZMTKZQMB-MZRZTIOWSA-N 325.408 2.490 30 1 EEEF C/C1=C\[C@@H]2[C@H](C[C@@H](O)/C(C)=C/[C@H]3C(=O)[C@@H](C)C[C@]3(O)C1=O)C2(C)C 238737828 NHOIUGORUWWMAP-UIHOUPDESA-N 332.440 2.441 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@H]2[C@H]3C(=O)O 257754423 ZCRLGANQNRMURE-PWWYIPCGSA-N 346.423 2.384 30 1 EEEF endogenous,in-man COc1ccc(C(=O)/C=C/c2cc(/C=C/C(=O)NO)n(C)c2)cc1 13643597 BUBFNVUAHRKJPI-AERWKNDNSA-N 326.352 2.448 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]12CC[C@H](O)[C@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 100197243 QYXZQZMPZUEEML-SHJCSGKRSA-N 346.423 2.384 30 1 EEEF in-vitro CC(C)=C1NC(=O)[C@](CC=CC[C@H](C)O)([C@@H]2CC(=O)O[C@H](C)C2)C1=O 2356490430 IIYKLCYWWXLYAF-SSHHRWTQSA-N 349.427 2.025 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](O)C[C@@H]4C(C)(C)CC[C@H](O)[C@]4(C)[C@@H]2CC[C@@H]1[C@H]3O 238762495 VSDVMWBRICFVRW-ULSFPYBTSA-N 334.456 2.067 30 1 EEEF N#Cc1ccc2nc(-c3ccc(C(C=O)C=O)c([N+](=O)[O-])c3)[nH]c2c1 587262283 PJSUDRAFGDSWTN-UHFFFAOYSA-N 334.291 2.491 30 1 EEEF COC1=CC(=O)/C(=C2/C=C(c3ccc(OC)c(OC)c3)NN2)C=C1 104026104 OAPDIGBUIIOAOU-SQFISAMPSA-N 326.352 2.076 30 3 EEEF CCN/C(=N/S(=O)(=O)c1ccc2cc[nH]c2c1)N1C[C@H](CC)C=N1 115413981 DFPUPZMYPJSLGL-GFCCVEGCSA-N 347.444 2.150 30 1 EEEF C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12CC=C[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 100891846 ZOWHLBOPCIHIHW-AODVQFRNSA-N 330.380 2.056 30 1 EEEF in-vitro C=C[C@]1(C)C=C2C(=O)C[C@@H]3C(C)(C)[C@H](O)C[C@H](O)[C@@]3(C)[C@]2(O)CC1 2356415874 ZTWPAGAVIFLSKK-ZBSOERELSA-N 334.456 2.377 30 1 EEEF C#C[C@]1(O)C[C@H](O)[C@@H]2[C@@H]3CCc4cc(O)ccc4[C@@H]3[C@@H](OC)C[C@]21C 2356613660 TYTYJGWQMLLBDD-XYIAWKELSA-N 342.435 2.208 30 1 EEEF COc1nc(N)nc(Nc2ccc(C#N)c(OCC=C(C)C)c2)n1 35010612 XIPGSHIZSJQWLT-UHFFFAOYSA-N 326.360 2.423 30 1 EEEF N#Cc1cccc2nc(CS(=O)(=O)c3ccc([N+](=O)[O-])cc3)[nH]c12 586919976 JUOWCARGFHHBGX-UHFFFAOYSA-N 342.336 2.317 30 1 EEEF C[C@@H]1C[C@H]2O[C@H]2CCC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 2356421048 XFALPAMSDFFXGY-HPEXNQPKSA-N 332.352 2.262 30 1 EEEF O=C(/C=C(\O)C(=O)O)/C=C/c1cc(C(=O)c2ccc(F)cc2)c[nH]1 103521905 XOINLIFLBUUBGT-RSIRFQHMSA-N 329.283 2.494 30 1 EEEF in-vitro C=C[C@]1(C)C=C2C(=O)C=C3[C@](C)(C(=O)O)CC[C@H](O)[C@]3(C)[C@]2(O)CC1 2356436781 ZQZVXOUQMKWMED-FLNBYBTLSA-N 346.423 2.391 30 1 EEEF C=CCn1ncc2c(Br)nc(Cc3ccccc3)n2c1=O 29408093 WGOSZRMCSXTDKO-UHFFFAOYSA-N 345.200 2.430 30 1 EEEF C=C[C@]1(C)CCC2=C(C1)C(=O)C[C@@H]1[C@]2(C)C[C@H](O)[C@H](O)[C@]1(C)CO 2356466353 BTYISKOGKBBMDI-XYWBXWKWSA-N 334.456 2.379 30 1 EEEF COC(=O)c1c(O)cc(C)c2c1C(=O)C(=O)C1=C2O[C@H](C)C1(C)C 14693105 XZOSGNOXSWMCQU-MRVPVSSYSA-N 330.336 2.409 30 1 EEEF biogenic COc1ccc(Cl)cc1C#Cc1cnc2c(C(=O)O)cnn2c1 587912997 SJJKFVGIHNHZNZ-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF CCOC1=C/C(=C/NNc2nn3cnnc3c3ccccc23)C=CC1=O 15952888 REYXYVFHHALNRU-ZRDIBKRKSA-N 348.366 2.137 30 3 EEEF CC1=C(N2[C@@H](C)[C@H]2C)C(=O)C(Br)=C(N2[C@@H](C)[C@H]2C)C1=O 100962028 RKTOSHDREXTIII-LMLFSZOESA-N 339.233 2.204 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)OC 2356436702 XBDTWBSMNXMGIJ-RUZHRRLVSA-N 346.423 2.225 30 1 EEEF C=CCNC(=S)NN=C(C)c1c(O)n(CC)c2ccccc2c1=O 2356876172 ZIAFJBDXIAGKSN-UHFFFAOYSA-N 344.440 2.101 30 1 EEEF Cc1c(O)ccc2c1[C@@H](c1cc(C#N)cnc1Cl)N[C@H](C(=O)O)C2 963511063 SMZDONVMMJRILA-SWLSCSKDSA-N 343.770 2.309 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@H]2[C@@]12C[C@@H](O)C[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100778340 HHDWSDSMWJQURA-QWFPEPMXSA-N 332.396 2.136 30 1 EEEF endogenous,in-man Nc1nc(C#CCOc2ccccc2)cn2nc(-c3ccco3)nc12 28347295 BDSUXOVMTRRHAO-UHFFFAOYSA-N 331.335 2.397 30 1 EEEF N#Cc1ccc(N2C(=O)[C@@H]3[C@H]4CC[C@@H](O4)[C@@H]3C2=O)cc1C(F)(F)F 101488344 QZRQLVZGQQVBIK-LPWJVIDDSA-N 336.269 2.244 30 1 EEEF C=C[C@](C)(O)C=C[C@@H]1[C@](C)(O)[C@H](O)[C@H](O)[C@H]2C(C)(C)CCC[C@]21C 2356783862 MHBIPUOMMSRZKQ-SMVANRBLSA-N 338.488 2.415 30 1 EEEF C[C@H]1COC2=C1C(=O)C1=C(C2=O)[C@@]23CCCC(C)(C)[C@@H]2C[C@@H]1OC3=O 49775553 QWHJJEUAHWWKRX-NECJPBOMSA-N 342.391 2.497 30 1 EEEF COCC(=O)N1[C@H](CO)[C@@H](c2ccccc2-c2ccccc2)[C@@H]1C#N 95668346 RRMULCFNGGBUJN-NSHGMRRFSA-N 336.391 2.179 30 1 EEEF N#Cc1c(N)cc2c(c1N)Cc1cc(O)c([C@H]3COCCO3)cc1O2 473244429 KJRGWHCEUMSERY-QGZVFWFLSA-N 339.351 2.213 30 1 EEEF COc1cc(-c2nc3nc(C#N)c(C#N)nc3[nH]2)cc(Cl)c1O 587045717 DVBJKCAVYLLPCJ-UHFFFAOYSA-N 326.703 2.131 30 1 EEEF CC#CC#C/C=C1\O[C@@]2(CCCCO2)[C@H](O)[C@@H]1OC(=O)CC(C)C 5412170 LEOZNWWIPMVKHH-LOGDIPMJSA-N 332.396 2.143 30 1 EEEF C[C@@H](O)[C@H]1C(O)=C(C(=O)[C@@H]2[C@H](C)C=C[C@@H]3CCCC[C@H]32)C(=O)N1C 102967701 NOYBJWXGAYWITN-YKWBPFFISA-N 333.428 2.218 30 1 EEEF NCCCNCCCNC1=CC(=O)c2cc3ccccc3cc2C1=O 101607043 DGDMKPQMKUNOQU-UHFFFAOYSA-N 337.423 2.021 30 1 EEEF CN(CCC#N)C(=O)CSC1=NN/C(=C2\C=Nc3ccccc32)O1 136100267 SLHQTFOQEROLFX-QINSGFPZSA-N 341.396 2.067 30 3 EEEF N#Cc1ccc(C(=O)N2Cc3cnnn3-c3ccccc3[C@H]2C#N)cc1 61942562 XGYLWYNKDWFNPN-GOSISDBHSA-N 340.346 2.360 30 3 EEEF C=CC1=CC(=O)[C@@H]2[C@H](CC[C@@H]3C(C)(C)[C@@H](O)[C@@H](O)[C@@H](O)[C@@]23C)[C@H]1C 100829709 XFRCVLKGZMPUFQ-HWUZOENFSA-N 334.456 2.089 30 1 EEEF endogenous,in-man COC(=O)c1cc(OC)ccc1Oc1ncnc(O)c1/C=C/C(C)=O 72176120 LMOBXFATXIKNGH-GQCTYLIASA-N 344.323 2.372 30 1 EEEF C/C1=C\[C@@H]2[C@H](C[C@@H](O)/C(C)=C/[C@H]3C(=O)[C@H](C)C[C@]3(O)C1=O)C2(C)C 238738867 NHOIUGORUWWMAP-MOJHWKQESA-N 332.440 2.441 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O[C@H]([C@H]21)[C@H]3O 257506480 OSYJLXUUZYSFTC-DRVWOCIPSA-N 332.440 2.432 30 1 EEEF endogenous,in-man C=C1C[C@@]2(OC1=O)C(=O)Nc1c([N+](=O)[O-])cc(Br)cc12 653901783 OHKOGQPSKXSACV-LBPRGKRZSA-N 339.101 2.008 30 1 EEEF Cc1cc(C)nc(N2C[C@@H]3CN(C(=O)c4ccccc4C#N)C[C@H]3C2)n1 116825029 FEMHBRHDPBAADC-IRXDYDNUSA-N 347.422 2.174 30 1 EEEF COc1ccccc1N1CCN(N/C(C)=C2\C=CC=CC2=O)CC1 104026423 YMWMOFFUDYVVHV-FOCLMDBBSA-N 325.412 2.291 30 3 EEEF CC1=C[C@@H]2[C@H](C[C@H](O)C(C)=C[C@@H]3C(=O)[C@@H](C)C[C@]3(O)C1=O)C2(C)C 2356453082 NHOIUGORUWWMAP-BVWVXVDMSA-N 332.440 2.441 30 1 EEEF C[C@H]1CC=C[C@H](O)CC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 2356584428 DRRQOEPQLQGLLP-AAEUAGOBSA-N 332.352 2.022 30 1 EEEF Cc1ccc(N/N=C2\CC[C@H](C)n3c2ncc(C(=O)O)c3=O)cc1 38153700 CGEJHGRKXOOFHL-BTNWAMHGSA-N 326.356 2.421 30 1 EEEF C=C1C[C@H](OC(=O)C(C)C)[C@H]2C(=C)C(=O)O[C@@H]2[C@@H]2[C@H]1C[C@H]1O[C@@]21C 238732958 KXPNDIVVAQWMSC-ZYKWKZBQSA-N 332.396 2.406 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)O 257447096 IPHNMKITOREFLW-XGOQZEQDSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C=C1C(=O)[C@]23C[C@@H]1CC[C@H]2[C@@]12CO[C@@H](O)[C@@H]1C(C)(C)CC[C@@H]2OC3=O 653722044 QOAOBBJDPFYUKJ-WRNHVDCISA-N 346.423 2.225 30 1 EEEF COC1=C/C(=C/NNc2nc3ccccc3s2)C=C([N+](=O)[O-])C1=O 15952519 RNUNBGKHXVPYII-CMDGGOBGSA-N 344.352 2.370 30 3 EEEF CCCCN(CC)C[C@@H](C(C)=O)[C@@H]1C(=O)O[C@@H]2C=CCC=C2C1=O 169717775 GLMLCOHRCVZCDT-BBWFWOEESA-N 333.428 2.311 30 1 EEEF COC(=O)c1ccc[n+](CC(=O)c2ccc(Br)cc2)c1 3167996 UKKNRWUYOJOKFE-UHFFFAOYSA-N 335.177 2.406 30 3 EEEF O=C1Nc2ccccc2[C@@]12/C(=N/CC1CC1)NC(=S)N2CC1CC1 146450898 SNWJRLBOESACRE-GOSISDBHSA-N 340.452 2.243 30 1 EEEF C=C1C(=O)O[C@H]2C[C@H](C)[C@H]3[C@H](O)CC[C@]3(C)[C@H](OC(=O)/C=C/C)[C@@H]12 238772873 HSXLCTYJIGXUOE-DEPPYTLOSA-N 334.412 2.389 30 1 EEEF Cc1cc2c(cc1O)[C@](CC#N)(c1ccoc1C)N[C@H](C(=O)O)C2 963526837 OTUMJCMMUFMYLU-YJBOKZPZSA-N 326.352 2.358 30 1 EEEF O=C(CCCCc1ccc2c(c1O)C(=O)c1c(O)cccc1C2)NO 13606198 OZZGKFBIZHYKBY-UHFFFAOYSA-N 341.363 2.451 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H](O)/C(C)=C/CC/C(C)=C/CC[C@@]3(CO)O[C@H]3C[C@H]12 100089883 MULWDJOXRRXULO-HAUURUDMSA-N 348.439 2.432 30 1 EEEF in-vitro O=C(/C=C/c1ccc2ncccc2c1)NCCCCCC(=O)NO 40979828 FYZGRQUAWUGKIM-CSKARUKUSA-N 327.384 2.430 30 1 EEEF NS(=O)(=O)c1ccc(N=C2C(=O)Nc3ccc(Cl)cc32)cc1 653728711 SIBLIOXEJPMNIR-UHFFFAOYSA-N 335.772 2.060 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc2[nH]c(=O)c(=O)[nH]c2c1 587907052 CJPPVFMXSUMEBC-UHFFFAOYSA-N 326.739 2.278 30 1 EEEF C=C1C[C@@]23C[C@@]1(O)CC[C@@H]2C1=C[C@H]2C[C@@](C)(C(=O)O2)[C@@H]1[C@H]3C(=O)O 2356490058 VLTQADXREMVNJX-IMMLYZMSSA-N 330.380 2.056 30 1 EEEF COc1cccc(OC)c1-c1cn(CCCCCC(=O)NO)nn1 40917869 SOWMPEPQTOSDTL-UHFFFAOYSA-N 334.376 2.028 30 1 EEEF N#C[C@@H]1CNCC[C@@]12Oc1ccccc1C(=O)[C@@H]2C(=O)c1ccco1 587593378 IXOYQXXDJKBETN-SMNXXWJPSA-N 336.347 2.226 30 1 EEEF CCOC(=O)[C@H](C#N)[C@@H]1c2cc(C)ccc2OC(=N)[C@@H]1C(=O)OCC 169719789 KQYZYWDUMYSEAD-VHDGCEQUSA-N 344.367 2.330 30 1 EEEF C=C1[C@@H]2[C@@H](C[C@H]1OC(C)=O)C(=C)C[C@H](OC(C)=O)[C@@H]1[C@H](C)C(=O)O[C@@H]12 2356535412 YQAAKILPZPSNKX-LOGUPIHXSA-N 348.395 2.180 30 1 EEEF C=CCc1cc(C)ccc1OCCCON1C(N)=NC(N)=NC1(C)C 45302823 VGNVQBSYEPBYKA-UHFFFAOYSA-N 345.447 2.105 30 1 EEEF O=C(CCCCCCC(=O)Nc1nnc(-c2cccnc2)s1)NO 299838251 UATXVOCQHGXRFA-UHFFFAOYSA-N 349.416 2.385 30 1 EEEF CC(=O)OCc1cnc(C)c(OC(C)=O)c1/C=N/Nc1ccccn1 13556318 DZQFFIOFDOGQAR-AWQFTUOYSA-N 342.355 2.219 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@]3(C)[C@@H](C[C@H]12)C(COC(=O)C(C)C)=CC[C@H]3O 13585460 QAZOZXJCRRKFMI-PPLBCVRQSA-N 334.412 2.391 30 1 EEEF N#Cc1nc(NCc2ccc(Cl)cc2)c2ncn(CCCO)c2n1 14977861 YUWVGFWHMXEGHR-UHFFFAOYSA-N 342.790 2.346 30 1 EEEF O=C1[C@@H]2[C@H](C(=O)N1/N=C\c1cccc([N+](=O)[O-])c1)[C@H]1C=C[C@H]2C12CC2 169691456 BAOWMYTUKUMZDC-VZKXQLSMSA-N 337.335 2.126 30 1 EEEF C[C@](CCc1ccc(C2=CCCC2)cc1)(C(=O)NO)S(C)(=O)=O 169708239 JFOZMRZNNNYARO-KRWDZBQOSA-N 337.441 2.495 30 1 EEEF Cc1ccccc1-n1c(CS/C(N)=N/N)nc2ccccc2c1=O 2000879 WDDXKIXOGHVZPC-UHFFFAOYSA-N 339.424 2.116 30 1 EEEF Cc1ccc(-c2ncc(F)cc2F)c2c1CCN(C(=O)N=C(N)N)C2 203410395 CLTGYVRNFWMWCO-UHFFFAOYSA-N 345.353 2.087 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@H]1CC[C@H]2[C@]12CCC[C@@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100781430 MJFVMFNFTCKAEV-NPYFDVPQSA-N 346.423 2.384 30 1 EEEF endogenous,in-man CCSC[C@@H](NC(=O)[C@@H](CS)Cc1ccccc1)C(=O)O 26491779 DDZXMZMIRUSLFJ-CHWSQXEVSA-N 327.471 2.098 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)C3=CC(=O)[C@@](C)(C[C@H](OC(=O)C=CC)[C@@H]12)O3 2356443079 ZUSPJLQZGBITEG-CPPVZRHJSA-N 346.379 2.244 30 1 EEEF C=C1[C@@H](OC(C)=O)C[C@H]2C(=C)C[C@H](OC(C)=O)[C@@H]3[C@H](C)C(=O)O[C@@H]3[C@H]12 2356535411 YQAAKILPZPSNKX-KLPXMHROSA-N 348.395 2.180 30 1 EEEF N#Cc1nc2nc(-c3cc(Cl)cc([N+](=O)[O-])c3F)[nH]c2nc1C#N 587139615 LZUYCOOKXMJPTH-UHFFFAOYSA-N 343.665 2.464 30 1 EEEF C#CCNC(=O)C[C@@H]1C[C@@H](C(C)C)[C@@H](CNC(=O)NCC)C=C1C 2356319443 GUKKXMLZFYHOPF-BBWFWOEESA-N 333.476 2.300 30 1 EEEF CC#CC#CC=C1O[C@]2(CC[C@H](OC(=O)CC(C)C)CO2)[C@@H]2O[C@H]12 2356508573 IZOBIZVXEKNCNN-JEDBISTDSA-N 330.380 2.159 30 1 EEEF COc1ccc2c(c1)C[C@H](c1nc3nc(C#N)c(C#N)nc3[nH]1)CC2 587945514 FWULXQJLTZZFPT-LLVKDONJSA-N 330.351 2.377 30 1 EEEF O=C(O)c1ccc(N/N=C\c2cc3c(cc2[N+](=O)[O-])OCO3)cc1 13144982 MCSXOTNOLOIHTL-APSNUPSMSA-N 329.268 2.468 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2CCC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 253668125 XFALPAMSDFFXGY-UHNFBRDESA-N 332.352 2.262 30 1 EEEF COc1ccc2c(c1)[n+]([O-])c(C#N)c(-c1ccc(Cl)cc1)[n+]2[O-] 40897444 DTEHYGSCZCXPJE-UHFFFAOYSA-N 327.727 2.307 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@@]45CO[C@@H](O)[C@H]4C(C)(C)CC[C@H]5OC(=O)[C@@]3(C2)[C@H]1O 2356410496 MSSXZZIDIPKYEB-UXHBGANVSA-N 348.439 2.016 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OCC(C)C)C[C@@]1(C)[C@@H]2[C@@H](C)C(=O)C[C@H]1O 2356702917 BQKSKQIZKSAQEI-SGRKQYAJSA-N 336.428 2.121 30 1 EEEF O=C(CCCCCNC(=O)c1cc(-c2ccc(F)cc2)[nH]n1)NO 1857757886 YLGBRUQGBLZQNQ-UHFFFAOYSA-N 334.351 2.011 30 1 EEEF COC1=CC(=O)[C@]2(C)c3c(O)c(C(C)=O)c(O)c(C)c3O[C@]2(OC)C1 2356815376 CQNUVEWNKCFRQU-QZTJIDSGSA-N 348.351 2.105 30 1 EEEF Cc1ccc(/C(=N/O)NC[C@H]2CCCO2)c(OCc2ccccn2)n1 72181664 WRGFVTZPPBOUEI-OAHLLOKOSA-N 342.399 2.268 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@H](c2ccc(C3=CCCCC3)cc2)[C@H]1CO 95896166 NSZKTJJQZYFHQH-GGPKGHCWSA-N 340.423 2.469 30 1 EEEF Cc1ccc(S(=O)(=O)/N=C(\NN)Nc2ccc(Cl)cc2)cc1 6010071 NFHWOGYGBKSJQM-UHFFFAOYSA-N 338.820 2.269 30 1 EEEF CC(=O)Nc1ccc(-n2nc3c(c(C#N)c2=N)CC(C)(C)OC3)cc1 169730343 RJLSIZJERHJVOJ-UHFFFAOYSA-N 337.383 2.033 30 1 EEEF CC1=CCC[C@@]2(C)O[C@@H]2[C@H]2OC(=O)[C@@H](CN3CCCCC3)[C@@H]2C[C@H]1O 1857538397 RHKZDVNMLMFSCO-BNXFAOBVSA-N 349.471 2.279 30 1 EEEF C[C@@H]1O[C@@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)OCc1ccccc1 28530235 XRLMLBLLFRZQEE-WBAXXEDZSA-N 339.391 2.245 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@@]45C=CCC(C)(C)[C@H]4[C@@H](O)O[C@H]5OC(=O)[C@@]3(C2)[C@H]1O 2356678692 PMIAIQKUXKRZIR-JFLPPNBXSA-N 346.423 2.140 30 1 EEEF COC(=O)c1c(O)cc(C)c2c1C(=O)C(=O)C1=C2O[C@@H](C)C1(C)C 14693103 XZOSGNOXSWMCQU-QMMMGPOBSA-N 330.336 2.409 30 1 EEEF biogenic C/C(=N\NC(N)=S)c1cccc(NC(=O)Cc2ccccc2)c1 299867114 PXHAPDPEMQYETR-UDWIEESQSA-N 326.425 2.425 30 1 EEEF CC#CCOc1ccc([S@@](=O)[C@H](C(=O)NO)c2ccccc2)cc1 13585966 LMLJZJGMFKPKNY-XDHUDOTRSA-N 343.404 2.443 30 1 EEEF CCc1nn2c(/C=N/NC(N)=S)c(-c3ccccc3)nc2s1 1857602184 GATZSNFZQBTYQF-LZYBPNLTSA-N 330.442 2.187 30 1 EEEF Cc1cccc(O)c1C1=CC2=C(Cl)C(=O)[C@@](C)(O)C(=O)C2=CO1 1857640985 NAHFQFLYAGOHFW-KRWDZBQOSA-N 332.739 2.351 30 1 EEEF CCC[C@@H]1O[C@H](CC(=O)O)C[C@@]23O[C@]12C(=O)c1ccccc1C3=O 2356561272 WVRWIGGCJAKRAH-AFRIBQCYSA-N 330.336 2.006 30 1 EEEF C=C[C@@H]1C(=C)CC[C@@H]2[C@@H]1CC(=O)[C@]1(O)[C@]2(C)CC[C@@H](O)[C@@]1(C)C(=O)O 2356720508 BSSPIUBSZQCUDG-RRELETGZSA-N 348.439 2.327 30 1 EEEF C=C[C@]1(CO)C[C@@H](O)[C@@H]2[C@H](CC[C@H]3[C@H]2CCC[C@]3(C)C(=O)OC)O1 40848846 YEQTWYNMVGNBHT-JUSAYDMQSA-N 338.444 2.059 30 1 EEEF Nc1ccc(S(=O)(=O)NN=C/C=C\c2ccccc2[N+](=O)[O-])cc1 253908044 WVEMQFVVHNUQTB-CEHMEXDESA-N 346.368 2.155 30 3 EEEF CCCC(CCC)(C(=O)NO)S(=O)(=O)c1ccc(OC)cc1 13520787 FQZUGHBEAWJYRZ-UHFFFAOYSA-N 329.418 2.313 30 1 EEEF Cc1ccc2nc(NC(=O)c3csc(N=C(N)N)n3)sc2c1 26156370 SPOQTQQGLATUGF-UHFFFAOYSA-N 332.414 2.218 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cc(C#N)c(C#N)cc3[nH]2)C1=O 587038203 DTGRWODNXXWEQP-ZDUSSCGKSA-N 337.364 2.099 30 1 EEEF COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CCN3C/C4=N/O)c2c1 1857565294 RVDOYCCGKHAQAJ-AQYBPFCFSA-N 327.384 2.201 30 1 EEEF O=C1OC(=Cc2ccc(O)c(O)c2)C(O)=C(c2ccc(O)cc2)C1=O 2356696747 OLZRNPOBVWGCKN-UHFFFAOYSA-N 340.287 2.240 30 1 EEEF C=C(C)CN1CCN(CC(=O)[C@@](O)(c2ccccc2)C2CCC2)CC1 22940337 BRCPZJDCSAYHDA-OAQYLSRUSA-N 342.483 2.437 30 1 EEEF COC1=CC2=C3C[C@@H]4C[C@H](OC)[C@@H](OC)C[C@H]4CN3CCC2=CC1=O 2356847091 OTLSHWIHWKUYQL-NIHZBZNOSA-N 345.439 2.446 30 1 EEEF CC(C)[C@H]1O[S@@](=O)O[C@]1(Cn1cncn1)c1ccc(Cl)cc1 26010828 NPFKMHWOXVEEPD-SOHPYSCWSA-N 341.820 2.477 30 1 EEEF CC(C)(C)OC(=O)N[C@@H](CSCc1ccccc1)C(=O)NCC#N 82064760 BXUABFHXHJNRDS-AWEZNQCLSA-N 349.456 2.453 30 1 EEEF COc1cc(/C=C/C(=O)[C@@]2(CCCN(C)C)CCOC2=O)ccc1O 299833551 PWQKWWJWZRTZJC-ZLQZBKBYSA-N 347.411 2.258 30 1 EEEF Nc1cncnc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587888769 AIRGRLLQALRZQF-UHFFFAOYSA-N 335.194 2.076 30 1 EEEF C[C@]12CC[C@@H]3[C@H]1C=C1C(=O)c4cc(O)ccc4C(=O)[C@@]1(O2)[C@]3(C)C=O 1651273 NMLFNFAGOHGLMD-ACTXYHSCSA-N 338.359 2.470 30 1 EEEF CC1(C)CCC[C@]2(C)O[C@]12/C=C/c1cc(S(C)(=O)=O)nc(N)n1 28712575 SKULGIFBFWXBLY-VKFONMJVSA-N 337.445 2.213 30 1 EEEF C=C1C[C@H](OC(C)=O)[C@@H]2[C@H](C)C(=O)O[C@@H]2[C@@H]2C(=C)[C@@H](OC(C)=O)C[C@H]12 2356535413 YQAAKILPZPSNKX-QRTGCOKOSA-N 348.395 2.180 30 1 EEEF CC[C@H](C)[C@H](NC(=O)C[C@H]1CCC(=O)[C@@H]1CC=CCC=O)C(=O)O 2356812770 BLZRWMJJRGXFHK-CFAJVAMVSA-N 337.416 2.123 30 1 EEEF C=CCN1C(=O)N2C[C@@H](CC)N=C2c2[nH]c(-c3cc(OC)no3)nc21 72108903 ODQVSYSJORWZAV-SECBINFHSA-N 342.359 2.040 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H](O)C(C)=CCCC(C)=CCC[C@@]3(CO)O[C@@H]3C[C@H]12 299808502 MULWDJOXRRXULO-NUABRCLCSA-N 348.439 2.432 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cc(F)cc(C(=O)O)c3[nH]2)C1=O 587039590 TUSCFNMYDIKZEB-SNVBAGLBSA-N 349.343 2.193 30 1 EEEF C=CCn1c(=O)c2c(nc3ccccn32)n(Cc2ccccc2)c1=O 13475106 QZTNGJKCJJXWQM-UHFFFAOYSA-N 332.363 2.045 30 1 EEEF O=C1C=CC(O)=C/C1=C\NNC(=S)N[C@@H]1C[C@H]2C[C@H]1[C@H]1C=CC[C@@H]21 104005503 NEWHOSFZGBPMPT-UOCZPHLRSA-N 343.452 2.021 30 3 EEEF C=CCO/C(O)=C1\C(C)=Nc2nnnn2[C@H]1c1cccc(OC)c1 103539585 TWODDRDYPSFNRP-MRPLLJTBSA-N 327.344 2.349 30 1 EEEF C=C1[C@H]2CC[C@@]3([C@H]4C[C@@H]5[C@]6(COC(=O)[C@]5(C)CC[C@H]6O4)[C@H]3C2)[C@@H]1O 2356785282 SEUIPTLIXVTZIG-PUTXTEPLSA-N 330.424 2.450 30 1 EEEF O=C1C=C[C@H]2O[C@H]3CC(=O)[C@@H]1[C@@H]2C31Oc2cccc3cccc(c23)O1 34059352 VFYQSNKCCXLDEP-UKBAYJJMSA-N 334.327 2.419 30 1 EEEF CCO[P@]1(=O)C(C#N)=NN(CC)C12C(=O)c1ccccc1C2=O 40402820 SMDNSXNVNQEVHJ-HSZRJFAPSA-N 331.268 2.249 30 1 EEEF N#Cc1c(O)nc(=S)[nH]c1/C=C/c1ccccc1OCC(=O)O 1857566110 JBPHSRSVCODBQO-AATRIKPKSA-N 329.337 2.350 30 1 EEEF O=C1[C@H]2[C@@H]3C=C[C@@H]([C@H]2C(=O)N1/N=C\c1cccc([N+](=O)[O-])c1)C31CC1 100556875 BAOWMYTUKUMZDC-LOHZPGLMSA-N 337.335 2.126 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H]1[C@H](OC(=O)C(O)=CCO)CC(C)=C1CC=C(C)[C@H]12 2356493434 SWIFBBRXRXNLBH-WCXIOVBPSA-N 346.379 2.117 30 1 EEEF COC1=C(C(C)C)C(=O)C=C(CN(C)C(=O)c2ccccc2)C1=O 473083065 AQZHIMCJRKKIKI-UHFFFAOYSA-N 327.380 2.393 30 1 EEEF COc1ccc(Cl)cc1C#CC1=C(Br)C(=O)NC1=O 587912179 IAAGZWAYAFHJLE-UHFFFAOYSA-N 340.560 2.006 30 1 EEEF COc1ccc(CCNC2=CC(=O)c3ncccc3C2=O)cc1OC 102958861 GBMXZBOSWWULNX-UHFFFAOYSA-N 338.363 2.194 30 1 EEEF O=C1C=CC=C/C1=C\NNC(=S)N[C@@H]1C[C@H]2C[C@H]1[C@H]1C=CC[C@@H]21 104017605 WVNYYTSFNKWSKL-VDNDKZLGSA-N 327.453 2.135 30 3 EEEF C=C(C)[C@@H]1CCC(=C)[C@@H]2C3=C(C[C@H](C)C3=O)C(=O)[C@](C)(O)[C@@H](O)[C@H]12 2356500241 RLNWZRIDRKCQGX-YSRZBGOXSA-N 330.424 2.361 30 1 EEEF C[C@@H]1CN2C[C@H]3CC[C@@]4(O)CCC5=C4[C@@]4(CC5=O)[C@@]3(C)CC[C@@H]1[C@@]24O 2356678547 KLIOZQZXDDOEMZ-QHSIBSDTSA-N 343.467 2.247 30 1 EEEF C=C[C@@](C)(O)Cc1cc(CC(=O)c2ccc(O)cc2O)c(O)cc1O 210537582 WQNWCWJUKJWMDS-LJQANCHMSA-N 344.363 2.414 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@H](c2ccc(C3=CCCCC3)cc2)[C@@H]1CO 95896167 NSZKTJJQZYFHQH-HBFSDRIKSA-N 340.423 2.469 30 1 EEEF C=C(C)C(=O)O[C@H]1C2=C(C)CC[C@@H](O)[C@]2(C)C[C@@H]2OC(=O)C(=C)[C@@H]21 238758105 LJFQOYCUYZGFOE-XVNUXHDISA-N 332.396 2.453 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](C[C@H](O)[C@H]1[C@H]2O)[C@@]1(C)CCCC(C)(C)[C@H]1C[C@H]3O 2356575633 UWJKFPFMTSZKRY-CNIUQTDNSA-N 334.456 2.067 30 1 EEEF C=C1OC(=O)c2c(O)cc(O)c(Cc3c(O)cc(C)oc3=O)c2[C@H]1C 2356722519 JVDXMGCGLWEXBZ-QMMMGPOBSA-N 344.319 2.443 30 1 EEEF COC1=CC(=O)[C@@]2(C)c3c(O)c(C(C)=O)c(O)c(C)c3O[C@@]2(OC)C1 2356815377 CQNUVEWNKCFRQU-ROUUACIJSA-N 348.351 2.105 30 1 EEEF O=C(CCC1=CCN(Cc2ccc(C(F)(F)F)cc2)C1=O)NO 84671142 MZFLRMTWMOWSNJ-UHFFFAOYSA-N 328.290 2.260 30 1 EEEF C[C@H]1C(=O)Nc2ccc(F)cc2N1S(=O)(=O)c1cccc(C#N)c1 40977515 LJCCMWZWWXOJQN-JTQLQIEISA-N 345.355 2.233 30 1 EEEF C=C1C[C@H](O)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@@H](OC(=O)/C(C)=C/C)C[C@@H]12 238763171 UINWHHMWCJPCDZ-FPEITNRTSA-N 344.407 2.475 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc2nc(C(=O)O)cn2c1 587913043 USRMKCPNYYMABV-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF CCCS(=O)(=O)N1CCC(c2nc3cccc(C#N)c3[nH]2)CC1 586953136 PAQXTTJRABALCG-UHFFFAOYSA-N 332.429 2.354 30 1 EEEF CN1CCC[C@@]2(CC1)CC(=O)c1cc(/C=C/C(=O)NO)ccc1O2 116483467 KIBFFVJPGCMKOZ-MJICGBHWSA-N 330.384 2.025 30 1 EEEF CC(C)c1ccc(CC(=O)N2CC[C@@]2(C)C(=O)NCCC#N)cc1 61929486 FYCDHWLTBVACJW-IBGZPJMESA-N 327.428 2.373 30 3 EEEF Cc1ccc2n(c1)cc(-c1ccc(/C=N/Nc3cc(N)[nH]n3)cc1)[n+]2C 26826141 KUVAPDHHALORBU-UFFVCSGVSA-N 346.418 2.491 30 1 EEEF C=C1C[C@H](OC(=O)C(C)C)[C@@H]2[C@H](C)C(=O)O[C@@H]2[C@@H]2[C@@H]1C[C@H]1O[C@@]21C 2356557720 ZEIPBAWKAWZVOR-ANBIDALOSA-N 334.412 2.485 30 1 EEEF C=C1N(S(=O)(=O)C(F)(F)F)CC[C@@]12CN(C)c1ccccc12 206037471 VYKVSAIDHRGQDR-CYBMUJFWSA-N 332.347 2.443 30 3 EEEF C=C1C[C@@]23C[C@H]1C(=O)C[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1[C@H](O)[C@H]3O 2356378094 VYSJMJOARWDSIN-NMZZMBMGSA-N 348.439 2.161 30 1 EEEF CC(C)[C@@](C#N)(CCCN1CCN(CCO)CC1)c1ccccc1 22927197 NSRKKRFXMCQGMY-FQEVSTJZSA-N 329.488 2.494 30 1 EEEF CCC1=C(C)C(=O)[C@](C)(CN2c3ccccc3[C@]3(O)CCO[C@H]23)C1=O 40764057 LFVVJMBGORZXQX-SLFFLAALSA-N 341.407 2.325 30 1 EEEF O=C1C(O)=C(c2ccc(O)c(O)c2)C(=O)C(O)=C1c1ccc(O)cc1 85592092 PNLQLFIVEMDDQE-UHFFFAOYSA-N 340.287 2.194 30 1 EEEF N#CC1(n2cc([C@@H](NC(=O)c3cnoc3)C3CCCCC3)nn2)CC1 95563298 IZPONYMTDQFPKW-HNNXBMFYSA-N 340.387 2.330 30 1 EEEF COc1ccc2c3c1O[C@@H]1C=C(C(C)=O)C[C@@H]4[C@@H](C2)N(C)CC[C@@]341 299810544 FKNWJBZMTKZQMB-MXHNKVEKSA-N 325.408 2.490 30 1 EEEF C=C1C[C@@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@H](O)CO)[C@H]2C[C@H]1CC3 299813640 FYKIZBPSTADBEK-DSVUEQLOSA-N 348.439 2.171 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3ccc([N+](=O)[O-])cc3[nH]2)C1=O 587040030 YYBXOTJLRGCPBT-LLVKDONJSA-N 332.341 2.264 30 1 EEEF C=C1C[C@@]23CC[C@H]1C[C@@H]2[C@@]12CCC[C@](C)(CO)[C@@H]1[C@@H](OC2=O)[C@@H]3O 2356553113 OMDPLJPNOXTENE-NFZKADEESA-N 332.440 2.434 30 1 EEEF C#CCO[C@H]1CCC([N+](=O)[O-])=C2N(Cc3ccc(Cl)nc3)CCN21 35273241 HMBOPPKIRGZFSB-HNNXBMFYSA-N 348.790 2.068 30 1 EEEF CCN/C(=N\S(=O)(=O)c1cccc(Cl)c1)N1CC(C)(C)C=N1 72123254 RQYRFYXSSOVCAN-UHFFFAOYSA-N 342.852 2.322 30 1 EEEF N#CCNC(=O)C1(NC(=O)c2ccc(Cl)nc2)CCCCCC1 82065654 ZUJGWDWYVMKYOY-UHFFFAOYSA-N 334.807 2.198 30 1 EEEF C=C[C@]12C[N+](C)([O-])[C@@H]3[C@H]4CO[C@H](C[C@H]41)[C@@]1(C(=O)Nc4ccccc41)[C@@H]32 238737399 LNBRLFDEFXKCAW-PUZJKJDBSA-N 338.407 2.040 30 1 EEEF CCCCCCCC(=O)NCCCc1nc2c(O)nc(O)nc2[nH]1 587228839 ZFMWVKIXUKJXGY-UHFFFAOYSA-N 335.408 2.173 30 1 EEEF CC#CCOc1ccc([S@](=O)[C@@H](C(=O)NO)c2ccccc2)cc1 13585972 LMLJZJGMFKPKNY-MZNJEOGPSA-N 343.404 2.443 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)C3=CC(=O)[C@@](C)(C[C@H](OC(=O)C(C)C)[C@H]12)O3 2356531367 WQQJRSDFQHYDRU-QHHYFVSCSA-N 346.379 2.244 30 1 EEEF N#C[C@@H]1CCCN1C(=O)[C@H]1CC=C[C@@H]2CN(Cc3ccccc3)C(=O)[C@H]21 653888062 RSPHQZYIDJUMKI-YDZRNGNQSA-N 349.434 2.352 30 1 EEEF C[C@H](O)[C@]1(c2ccc(C#N)cc2)NC[C@@H]2CC(=O)N(C)c3cccc1c32 963017399 CMVJTQXTIAWOOQ-XLDJFRKUSA-N 347.418 2.236 30 1 EEEF COCc1n[nH]c2c1[C@H](c1ccc(OC)c(OC)c1)[C@@H](C#N)C(=N)O2 169690867 GUBJGLORYWMXBN-QMTHXVAHSA-N 342.355 2.215 30 1 EEEF C=C(Cc1c(OC)ccc(C(=O)O)c1O)[C@@H]1CC[C@](C)(O)[C@@H](O)C1 27559298 JNPNGXWCEMBWHW-PSZVPEGOSA-N 336.384 2.110 30 1 EEEF C=C1[C@H]2[C@@H]3OC(=O)C(=C)[C@H]3CCC(=C)[C@]2(O)C[C@H]1OC(=O)C(C)C 2356650630 LUUJHRSUAVIZOX-RUEZSYAVSA-N 332.396 2.309 30 1 EEEF COc1ccc(C=O)c2cc(-c3nc4nc(C#N)c(C#N)[nH]c-4n3)oc12 586904597 YNJCWQZZJRAMDV-UHFFFAOYSA-N 344.290 2.282 30 1 EEEF C=CCONC(=O)CN1C(=O)S/C(=C\c2ccc(F)cc2)C1=O 1857603007 QGIIBQQFZASGRI-WQLSENKSSA-N 336.344 2.096 30 1 EEEF C=C[C@@]1(O)CN2CC[C@@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12 4097379 BSRUJCFCZKMFMB-ZNYHDOEXSA-N 340.423 2.288 30 1 EEEF endogenous,in-man N#Cc1ccccc1OCc1cn(CC(=O)c2ccc(O)cc2)nn1 61931045 XKYYQMYEDQTWBB-UHFFFAOYSA-N 334.335 2.317 30 3 EEEF C=C(C)C(=O)O[C@H]1CCC(CO)=C2[C@H]3OC(=O)C(=C)[C@@H]3CC[C@]21C 238734961 DXUUYKZZAJEBSQ-PWDMQXDWSA-N 332.396 2.455 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)C3=CC(=O)[C@@](C)(C[C@@H](OC(=O)C=CC)[C@H]12)O3 2356443081 ZUSPJLQZGBITEG-OLHCRQPDSA-N 346.379 2.244 30 1 EEEF C=C(C[C@@H]1C=C(C)C(=O)O1)[C@@H](O)COc1ccc2ccc(=O)oc2c1 15212310 BJAAKPBQJCDTGE-CVEARBPZSA-N 342.347 2.351 30 1 EEEF biogenic O=C1O/C(=C\c2ccc(O)cc2)C(=O)C(c2ccc(O)c(O)c2)=C1O 238774862 SJGOQLCKPXMLHK-AUWJEWJLSA-N 340.287 2.240 30 1 EEEF N#Cc1ccc2nc(-c3nccnc3I)[nH]c2c1 587186857 XGEIAWHDWGYDOI-UHFFFAOYSA-N 347.119 2.496 30 1 EEEF COC(=O)c1ccc(I)c2c1C(=O)C=CC2=O 1857746586 CPHZAMHHNCGPAO-UHFFFAOYSA-N 342.088 2.013 30 1 EEEF CN(CCC#N)C(=O)CN1C(=O)COc2ccc(C(C)(C)C)cc21 4686132 DDNZMZDVHZMJID-UHFFFAOYSA-N 329.400 2.082 30 1 EEEF C#CCNc1nc(C)nc(-n2c(Nc3cc[nH]n3)nc3ccccc32)n1 71316655 SSYRSGUUTKCTEB-UHFFFAOYSA-N 345.370 2.031 30 1 EEEF CC1=C(N2[C@H](C)[C@H]2C)C(=O)C(Br)=C(N2[C@@H](C)[C@H]2C)C1=O 100962037 RKTOSHDREXTIII-LDXBQPRVSA-N 339.233 2.204 30 1 EEEF C=C1C(=O)O[C@@H]2CC(=C)[C@@H]3[C@H](OC(=O)C(C)C)C[C@](C)(O)[C@@H]3C[C@@H]12 2356693951 RPFZMZXPFLBITO-QHJVRGJGSA-N 334.412 2.389 30 1 EEEF COc1ccc(-c2c(C#N)[n+]([O-])c3cc(Cl)ccc3[n+]2[O-])cc1 40914903 WWBXAHYRXSLRDB-UHFFFAOYSA-N 327.727 2.307 30 1 EEEF O=C(O)[C@H]1CNC[C@@H](CCN/N=C/c2ccccc2-n2cccc2)C1 1857618792 RJTVXEAUTBQVHF-YNFYMGOASA-N 340.427 2.101 30 1 EEEF CC(=O)O[C@H]1O[C@@H]2C=C(C)[C@H]3C[C@@H]2[C@@]13[C@@H](OC(C)=O)C(=O)C=C(C)C 29041964 QFUYTTKICOKMGU-AFOVWBNFSA-N 348.395 2.324 30 1 EEEF N#C[C@@H]1[C@H](c2ccc(-c3cccnc3)cc2)[C@@H](CO)N1C(=O)C1CC1 95896226 FYALJDMLJJPLTL-QRVBRYPASA-N 333.391 2.337 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@H](C)[C@@]2(O)C=C(C)[C@@H](C[C@H]3OC(=O)C(=C)[C@H]13)O2 525915086 PWWKARNXEFCPJO-XBFCAGORSA-N 348.395 2.036 30 1 EEEF biogenic Cc1ccc(CN2CCN(N/C=C3/C=CC(=O)C(O)=C3)CC2)cc1 13126514 OONWUYMIIDCDDO-LGMDPLHJSA-N 325.412 2.082 30 3 EEEF CCC#C[C@@](O)(C(=O)O[C@H]1C2CCN(CC2)[C@@H]1C)c1ccccc1 17250306 VOCRJOMVKAJZBC-ZTNFWEORSA-N 327.424 2.314 30 1 EEEF C[C@@H]1CN2C[C@H]3CC[C@]4(O)CC(=O)C5=C4[C@@]4(CC5)C(=O)[C@@H]1C[C@@H]2[C@@]34C 28972993 LSKAYCSMVNNFJC-BOSSYYJLSA-N 341.451 2.106 30 1 EEEF C=C1C[C@@]23CC[C@H]1C[C@@H]2[C@@]12CCC[C@](C)(CO)[C@@H]1[C@@H](OC2=O)[C@H]3O 2356553114 OMDPLJPNOXTENE-RTJRNGDUSA-N 332.440 2.434 30 1 EEEF CC1=C(OCCN2C(=O)C(=O)c3cc(F)ccc32)[C@@H](C)SC1=O 71318123 SWOPJCXOATZWAK-SECBINFHSA-N 335.356 2.308 30 1 EEEF Cc1cc(C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)NO)c(C)o1 96269518 OIQWPJQECPFTCI-INIZCTEOSA-N 341.367 2.224 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@H](c2ccccc2C2=CCCCC2)[C@@H]1CO 95797105 XJOIDJIXTAYCGR-HBFSDRIKSA-N 340.423 2.469 30 1 EEEF C=C[C@](C)(O)C=C[C@@H]1[C@](C)(O)[C@H](O)[C@H](O)[C@@H]2C(C)(C)CCC[C@]12C 2356783860 MHBIPUOMMSRZKQ-OGFPXCSUSA-N 338.488 2.415 30 1 EEEF CS(=O)(=O)[C@H](CCc1ccc(-c2ccccc2)cc1)C(=O)NO 73310473 YDXMTRBRIVQRFA-MRXNPFEDSA-N 333.409 2.205 30 1 EEEF CS(=O)(=O)c1ccc2nc(COc3ccc(C#N)cc3)[nH]c2c1 587191167 QHIHZQKILNIKLD-UHFFFAOYSA-N 327.365 2.417 30 1 EEEF COC1=CC(=O)/C(=C2\N=C(N)NC(C)=C2c2ccc(OC)cc2)C=C1 103918428 SDULKRWPCVMXNH-SDXDJHTJSA-N 337.379 2.267 30 3 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]12C[C@@H](O)C[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 100199181 HHDWSDSMWJQURA-QHBBZOLPSA-N 332.396 2.136 30 1 EEEF in-vitro CN1C(=O)[C@]2(C3=C(CN2C)C(=O)c2ccccc2C3=O)c2ccccc21 73311984 LQFKECHGKWJDBZ-OAQYLSRUSA-N 344.370 2.180 30 1 EEEF C=C(C)[C@@H]1CCC(=C)[C@@H]2C3=C(C(=O)C(C)=C[C@H]12)[C@H](O)[C@](C)(O)C3=O 2356599881 PMTAKUZIYCHAID-QOTKAZNMSA-N 328.408 2.281 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@]2(C)C[C@H]3C(=O)O[C@@H](C4=C(C)[C@H](O)C[C@H]42)[C@@H]13 238780789 NYFZEWICSQORLI-FMJWFNAKSA-N 332.396 2.143 30 1 EEEF CC(C)C[C@H](NC(=O)c1ccc(CN=[N+]=[N-])cc1)C(=O)NCC#N 299841210 YPGRIBJLIRWSAI-AWEZNQCLSA-N 328.376 2.281 30 1 EEEF CC[C@H](O)C[C@H](C)[C@@H]1O[C@]1(C)C=CC(=O)N[C@@H](CO)[C@H](C)CC 2356421455 KQYIQWJQJFWGMP-DNTJOWKISA-N 327.465 2.020 30 1 EEEF C=CCN1C(=O)N2C[C@@H](CC)N=C2c2[nH]c(-c3cc(C)n(C)n3)nc21 72107862 JTGQLHAOPMIUBM-LLVKDONJSA-N 339.403 2.085 30 1 EEEF CN(c1ccc(C(=O)NO)cc1)[C@@H]1CCN(c2ccccc2)C1=O 299860608 JKSCFHKEBJNQOU-MRXNPFEDSA-N 325.368 2.047 30 1 EEEF NNc1ccc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)nc1 587889627 QABKEIVYIPRAGG-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C[C@H]3C(C)(C)[C@@H](O)CC(=O)[C@]3(C)[C@H]2[C@H](O)C1 1857569586 SFTRIKRIJQCBGG-SJKBCMPFSA-N 332.440 2.441 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C=C3[C@@](C)([C@@H](O)CC[C@@]3(C)C(=O)O)[C@]2(O)CC1 2356436784 ZQZVXOUQMKWMED-UVBQOVKKSA-N 346.423 2.391 30 1 EEEF CNC(=O)/C(=N/OC)c1ccccc1COc1cccc(SC)n1 103195232 MVFQMEBLWPOUKK-CAPFRKAQSA-N 345.424 2.479 30 1 EEEF CC(C)=C1NC(=O)[C@](CC=CC[C@H](C)O)([C@H]2CC(=O)O[C@H](C)C2)C1=O 2356490429 IIYKLCYWWXLYAF-FGBSKUFISA-N 349.427 2.025 30 1 EEEF CNC(=O)/C(=N/OC)c1cccc([N+](=O)[O-])c1Oc1ccccc1 103184529 MKGJNTOXWWTANW-NBVRZTHBSA-N 329.312 2.484 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@@H](C(=O)OC)[C@H]1[C@@]2(C)CCC[C@@]31OC2=O 2356636505 KVXQCEAWXGANQC-OYSBAZFQSA-N 346.423 2.225 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)[C@@H]2[C@@H]3OCC4=C3[C@@](C)(CCC4=O)CC[C@]12C 2356823285 GKUCSSBQVHTTCY-RLIOBEPESA-N 334.456 2.475 30 1 EEEF C#C[C@@H]1CN2CC[C@H]1C[C@H]2COC(=O)Nc1ccccc1C(=O)OC 2356837726 LMLYDZBSOPFRQG-ILXRZTDVSA-N 342.395 2.365 30 1 EEEF C=C(C)[C@@H](O)Cc1c(O)cc2c(c1O)c(=O)c1cccc(O)c1n2C 14819118 DXPXJTFEUAMACU-AWEZNQCLSA-N 341.363 2.288 30 1 EEEF biogenic N#Cc1cncc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)n1 587890086 OSZDNBYRMQXMHH-UHFFFAOYSA-N 345.189 2.365 30 1 EEEF COc1ccc(N(C(=O)[C@@H](C)CS)[C@H](C)C(=O)O)cc1OC 28263310 QMKCAFICSCUPEE-VHSXEESVSA-N 327.402 2.076 30 1 EEEF O=C(N[C@@H](CS)Cc1ccccc1)[C@@H]1Cc2ccccc2CN1 27716339 AGLKDDGHOSRSDS-MSOLQXFVSA-N 326.465 2.358 30 1 EEEF CC=CC(=O)O[C@@H]1[C@H](O)[C@H]2O[C@@H]3C=C(C)CC[C@]3(C)[C@@]1(C)[C@@]21CO1 2356487415 AGQQMRNEWSVYSU-RCQHAYOSSA-N 334.412 2.138 30 1 EEEF CC(C)(O)C(C)(C)OB(OC(C)(C)C(C)(C)O)c1ccc(F)nc1 221635896 HMSDQJLUNQZTPO-UHFFFAOYSA-N 341.232 2.048 30 1 EEEF CN(C)CCCN(C)c1nc(N(C)CCC#N)c2sccc2n1 1911586259 JNFSCEZOWFOZJC-UHFFFAOYSA-N 332.477 2.429 30 1 EEEF C#C[C@]1(O)[C@@H](O)C[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3[C@@H](OC)C[C@@]21C 238737092 OOMBHDXDTAYDBF-YUDLKVPISA-N 342.435 2.208 30 1 EEEF CC(C)(C)[C@H]1CC(CNC(=O)/C(C#N)=N/OCc2ccccc2)=NO1 26168591 QOOCZDOCWDUISB-QFNCUCFLSA-N 342.399 2.390 30 1 EEEF C=C(C)C(=O)O[C@@H]1CCC(CO)=C2[C@@H]3OC(=O)C(=C)[C@H]3CC[C@@]21C 2356470533 DXUUYKZZAJEBSQ-NPNMTCQASA-N 332.396 2.455 30 1 EEEF C[C@@H]1CN2C[C@@H]3CC[C@]4(O)CC(=O)C5=C4[C@@]4(CC5)C(=O)[C@H]1C[C@H]2[C@@]34C 2356603689 LSKAYCSMVNNFJC-MIZVNJCRSA-N 341.451 2.106 30 1 EEEF O=C(/C=C/c1ccc2cccnc2c1)NCCCCCC(=O)NO 40420873 IXKLILPHPNZHNB-CSKARUKUSA-N 327.384 2.430 30 1 EEEF CC(C)C[C@@H](NC(=O)c1cccc(C(F)(F)F)c1)C(=O)NCC#N 82065019 YLGLXVDHNPHGMY-CYBMUJFWSA-N 341.333 2.490 30 1 EEEF CC(C)CC(=O)N[C@@H](CC(N)=O)c1nc2cc(C#N)cc(Cl)c2[nH]1 587203536 KVRCDJQKEPWOJQ-LBPRGKRZSA-N 347.806 2.167 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1CC/C(C(=O)N1CCCC1)=C\CC[C@@]1(C)O[C@@H]21 1772631703 JLALAWOIVFYLTJ-FKUVIKGSSA-N 331.412 2.365 30 1 EEEF O=C1C=C(NC2=C[C@H]3O[C@H](c4ccccc4)OC[C@@H]3OC2=O)CCC1 19924582 WIDOMGFQDHPMIW-ZIFCJYIRSA-N 341.363 2.136 30 1 EEEF CN(C)CC/N=C(\O)CN1N=C(c2ccc(Cl)cc2)CCC1=O 8556000 MYFFJIWKJDKREH-UHFFFAOYSA-N 336.823 2.185 30 1 EEEF CN1C(=O)[C@@]2(C3=C(CN2C)C(=O)c2ccccc2C3=O)c2ccccc21 73311986 LQFKECHGKWJDBZ-NRFANRHFSA-N 344.370 2.180 30 1 EEEF O=C(NO)c1cnc(Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)nc1 166623353 ZORADJKXOGUMMR-UHFFFAOYSA-N 343.221 2.266 30 1 EEEF O=C1C(Nc2ccc([N+](=O)[O-])cc2)=C(Cl)C(=O)c2ncncc21 103274478 QOASPUCDOKZVGF-UHFFFAOYSA-N 330.687 2.326 30 1 EEEF COCC(=O)N1[C@@H](C#N)[C@@H](c2ccc(C3=CCCCC3)cc2)[C@@H]1CO 95896168 NSZKTJJQZYFHQH-CMKODMSKSA-N 340.423 2.469 30 1 EEEF N#Cc1c(O)nc(SC[C@@H]2CO2)nc1-c1ccc([N+](=O)[O-])cc1 96910366 HSBFNWSCFJVKJN-JTQLQIEISA-N 330.325 2.120 30 1 EEEF O=C(C1CC1)[C@H](c1ccccc1F)N1CC[C@@H]2C(=CC(=O)[S@]2=O)C1 299851201 BGWGSGYBPUVHJJ-RLJZQAMKSA-N 347.411 2.136 30 1 EEEF CN(C)S(=O)(=O)c1cccc2nc(C#Cc3ccccc3)[nH]c12 587953652 OUMAOACBWFSTJT-UHFFFAOYSA-N 325.393 2.213 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1cc(O)ncn1 587888938 DUWRQKRFWNAULW-UHFFFAOYSA-N 336.178 2.199 30 1 EEEF CCC[C@@H]1O[C@H](CC(=O)O)C[C@@]23O[C@@]12C(=O)c1ccccc1C3=O 2356561273 WVRWIGGCJAKRAH-DWTDUGSWSA-N 330.336 2.006 30 1 EEEF C[C@@H]1C/C=C/[C@@H](O)C/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 14614734 DRRQOEPQLQGLLP-NBRMKKJYSA-N 332.352 2.022 30 1 EEEF COC1=C[C@@H]2[C@@H]3Cc4ccc(OC)c(O)c4[C@]2(CC[N+]3(C)[O-])CC1=O 85885777 IQCNMIIBBLJCAC-SLAUIZBQSA-N 345.395 2.031 30 1 EEEF O=C(O)CC/N=C(\S)[C@]1(c2cccnc2)CCCC[S@@]1=O 13651018 MBPYCZVDQXRZIJ-SPLOXXLWSA-N 326.443 2.013 30 1 EEEF CCOC(=O)C(/C=N/c1ccc(O)c(C(=O)OC)c1)=C(/O)OCC 101962984 LDGPLSSVYRFLES-ZCWJWGKDSA-N 337.328 2.250 30 1 EEEF C[C@H](N[C@H]1c2cc(C#N)ccc2OC(C)(C)[C@H]1O)C(=O)OC(C)(C)C 299846081 HTQRBOPBRPMVKW-UVBJJODRSA-N 346.427 2.451 30 1 EEEF COc1cccc([C@@]2(C#N)NCCc3ccc(C(=O)N(C)C)cc32)c1 962929701 VYYSIPMEIIMHCC-HXUWFJFHSA-N 335.407 2.310 30 1 EEEF Cc1ccnc2c1/C(=N/N=C(N)N)C[C@H](c1cc(F)ccc1F)C2 13474714 NOQLJONWLKOHDI-VHAAKXEISA-N 329.354 2.376 30 1 EEEF O=C1C(Cl)=C(NCCCN2CCCC2=O)C(=O)c2ccccc21 102971902 XCYPTXXOANJQED-UHFFFAOYSA-N 332.787 2.118 30 1 EEEF C=C(C)[C@@H]1[C@@H]2C[C@H](C)[C@@H]3CC[C@H](C)[C@]4(O)C(=O)C(=O)[C@@]1(C)C(=O)[C@]324 15150466 JQKMCBIANZSIJR-DOCLEKQUSA-N 330.424 2.339 30 1 EEEF biogenic COc1ccc(Cl)cc1C#Cc1cn(-c2ncccn2)nc1N 587909616 WRHOXVQHWJVDMR-UHFFFAOYSA-N 325.759 2.306 30 1 EEEF Nc1cnc(N)c(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)c1 587881149 HIRHIWCBPXXNPG-UHFFFAOYSA-N 349.221 2.263 30 1 EEEF COc1ccc(C)cc1NCCCc1nc2nc(C#N)c(C#N)nc2[nH]1 587228381 BUSFUXAZJMEYOP-UHFFFAOYSA-N 347.382 2.458 30 1 EEEF CC1=C(O)C(=O)C[C@]2(C)[C@@H]3CCc4cocc4[C@]3(CO)CC[C@@]12O 2356337346 YJYCGDAWLMWZRS-JCHJZTRSSA-N 332.396 2.408 30 1 EEEF C=C[C@]1(C)C(=O)C=C2C(=CC[C@H]3C(C)(C)[C@@H](O)[C@@H](O)C[C@]23C)[C@H]1O 2356432454 AZNDIKGKUJHYJB-DAEABALNSA-N 332.440 2.153 30 1 EEEF COC1=C(Br)C[C@](O)(CC#N)C(O)=C1Br 2356434411 QJGRBPFVRFQRMW-SECBINFHSA-N 338.983 2.452 30 1 EEEF C=C1[C@@H]2C[C@H](O)C(C)(C)[C@]2(O)[C@@H](O)C[C@@]23CC(=O)[C@@](C)(CC[C@@H]12)C3 2356593376 IRZVFDISJFITJT-QVIZNZKXSA-N 334.456 2.211 30 1 EEEF COc1cc2c(cc1O)C[C@H]1OC=C3[C@H]1[C@@]2(C#N)CCC31OCCO1 73165920 QCTOYFPDRIXSQO-KZNAEPCWSA-N 341.363 2.154 30 1 EEEF N#C[C@H]1[C@@H](c2ccc(-c3cccnc3)cc2)[C@H](CO)N1C(=O)C1CC1 95896225 FYALJDMLJJPLTL-GBESFXJTSA-N 333.391 2.337 30 1 EEEF COC1=C[C@@]23CCc4cc(OC)c(OC)cc4[C@@]2(CCN3C)CC1=O 95914935 XWTJDHWJXSZTLM-UXHICEINSA-N 343.423 2.465 30 1 EEEF biogenic,in-vitro C[C@]1(OC(=O)C2CCCC2)C(=O)C=C2C=C3CCCN3C=C2C1=O 13817779 FFRGFPBARHRABR-IBGZPJMESA-N 327.380 2.434 30 3 EEEF O=C(NO)c1ccc2c(c1)C[C@@H](NC(=O)c1cccc(Cl)c1)CN2 113848034 HSFAHSOUBJQFRE-CQSZACIVSA-N 345.786 2.226 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)[C@H](O)C[C@@]3(C)[C@@]1(C)[C@]21CO1 2356610170 VRHZKNFFKJZHFD-URSXXGQTSA-N 334.412 2.138 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(CO)CCC[C@](C)(CO)[C@H]1C[C@@H]3O 2356645366 NLKCAXRWGIRDDQ-KDRHOLLNSA-N 334.456 2.070 30 1 EEEF N#Cc1cccc(S(=O)(=O)N2CC(=O)Nc3ccc(Cl)cc32)c1 43075174 XVGMCKFDYWMIMN-UHFFFAOYSA-N 347.783 2.359 30 1 EEEF CC1=CC(=O)[C@@]2(CN1)N[C@@H](C)Cc1cc(Br)c(F)cc12 587791512 GBZAYDNBEDMVFK-VFZGTOFNSA-N 339.208 2.394 30 1 EEEF CC(C)NC[C@@H](O)CO/N=C1/c2ccccc2[C@H]2CCCC[C@@]12O 169342282 RTKLMTIRQZCKHN-XTRJLOQSSA-N 332.444 2.169 30 1 EEEF CC(C)C[C@@](C)(O)c1cn(C2=CC(=O)c3cccc(O)c3C2=O)nn1 1857544416 ZAWKKFCMFOXGOT-GOSISDBHSA-N 341.367 2.157 30 1 EEEF C#CCN(C)C[C@H]1CN2CC[C@H]1C[C@H]2CNC(=O)Nc1ccccc1 2356320495 MFSCSGBXHMMZNQ-LNLFQRSKSA-N 340.471 2.084 30 1 EEEF COC(=O)c1cc(C#Cc2ccc(C[C@@H](C)NC(C)=O)cc2)ccn1 113410721 GIKMVLAUUXWXFC-CQSZACIVSA-N 336.391 2.335 30 1 EEEF CS(=O)(=O)[C@@H](CCc1ccc(-c2ccccc2)cc1)C(=O)NO 73310471 YDXMTRBRIVQRFA-INIZCTEOSA-N 333.409 2.205 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3ccc([C@@H](N)N=O)cc3[nH]2)C1=O 587038489 JKUMDYFJBJYQDQ-YPMHNXCESA-N 345.384 2.079 30 1 EEEF COc1c(O)cc(O)c2c1OC/C(=C\c1ccc(O)c(O)c1)C2=O 13481949 XAVKZGJWLZVXHI-RUDMXATFSA-N 330.292 2.176 30 1 EEEF COC1=C[C@@]23CCc4cc(OC)c(OC)cc4[C@]2(CCN3C)CC1=O 2356420374 XWTJDHWJXSZTLM-PMACEKPBSA-N 343.423 2.465 30 1 EEEF C=C1C[C@@H](O)[C@@H]2O[C@@]2(C)CC[C@@H]2/C(=C/C=C/C(C)(C)O)C(=O)OC[C@@H]12 101649475 DHTWVKTXQLZELP-WHZAQKEKSA-N 348.439 2.288 30 1 EEEF O=C1CN(/N=C/c2ncc(-c3cccc(C(F)(F)F)c3)o2)C(=O)N1 26637483 QIIIGJKARGFBRP-KPSZGOFPSA-N 338.245 2.246 30 1 EEEF C=C1[C@H](O)[C@H](OC(=O)C(C)=CC)[C@@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(C)=CC[C@H]12 2356536025 MXNYEYDKNYIYGB-UCIFAOBLSA-N 344.407 2.475 30 1 EEEF C=C(C)C(=O)O[C@@H]1[C@@H]2C(=C)C(=O)O[C@@H]2CC(=C)[C@@H]2C[C@H](O)C(=C)[C@H]12 2356627894 ZQBZOPWDBPOXPR-NYXISSTPSA-N 330.380 2.085 30 1 EEEF C=C1OC(=O)c2c(O)cc(O)c(Cc3c(O)cc(C)oc3=O)c2[C@@H]1C 2356722518 JVDXMGCGLWEXBZ-MRVPVSSYSA-N 344.319 2.443 30 1 EEEF C=C1C(=O)[C@@]23[C@H](O)C[C@@H]4C(C)(C)[C@H](O)CC[C@@]4(C)[C@H]2CC[C@@H]1[C@H]3O 84588783 BAXVJERFBZODKZ-GJXLEEKZSA-N 334.456 2.067 30 1 EEEF C#CCOc1ccc(-c2nc3cc(S(=O)(=O)O)ccc3[nH]2)cc1 587563249 PZLBAHLWNFKAHC-UHFFFAOYSA-N 328.349 2.489 30 1 EEEF Cn1ncc(C#N)c1NC(=O)[C@@H]1CC(c2ccccc2Cl)=NO1 4504951 OBMDODZBSHAYHD-ZDUSSCGKSA-N 329.747 2.077 30 3 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@@]1(CCC[C@@]2(C)CO[C@@H](O)[C@H]21)COC3=O 6032275 QUUUEWBMPVGPDF-CRFTYCKYSA-N 346.423 2.226 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@H](C)[C@@]2(O)C=C(C)[C@@H](C[C@H]3OC(=O)C(=C)[C@H]13)O2 2356287793 PWWKARNXEFCPJO-UZCKPWGLSA-N 348.395 2.036 30 1 EEEF CCOC(=O)c1c(C)[nH]c(=O)c(C#N)c1-c1ccc([N+](=O)[O-])cc1 103278247 YFCKEKBCMNTKDR-UHFFFAOYSA-N 327.296 2.307 30 1 EEEF C#C[C@H]1CN2CC[C@H]1C[C@@H]2COC(=O)Nc1ccccc1C(=O)OC 8300182 LMLYDZBSOPFRQG-SOUVJXGZSA-N 342.395 2.365 30 1 EEEF biogenic C=C1C(=O)[C@@]23C(=O)[C@@H]4OC[C@]5(C=CCC(C)(C)[C@@H]45)[C@@H]2CC[C@@H]1[C@H]3O 1911580336 DXDQUOYXWQXPEJ-SDDUFPNZSA-N 328.408 2.069 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@H](c2ccccc2-c2ccccc2)[C@@H]1CO 95667883 RRMULCFNGGBUJN-HBFSDRIKSA-N 336.391 2.179 30 1 EEEF N#CC1(n2cc([C@@H](NC(=O)c3ncco3)C3CCCCC3)nn2)CC1 95560209 GISFKMXSMLGOPG-AWEZNQCLSA-N 340.387 2.330 30 1 EEEF C=C(C)[C@H]1CCC2=C[C@@H](C/C(C)=C\C(=O)[C@H](O)CC(=O)C1)OC2=O 169332471 NKBOMIIKMNCYIQ-AKCXRZHYSA-N 332.396 2.440 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)OC 2356436701 XBDTWBSMNXMGIJ-PYAKXWGRSA-N 346.423 2.225 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@@]12CO[C@@H]4OC[C@@](C)(CC[C@@H]1OC3=O)[C@H]42 103109417 QRZAIOQXVJRCBS-UZRASMLVSA-N 344.407 2.243 30 1 EEEF Cc1ccccc1S(=O)(=O)N1[C@H](CO)[C@@H](c2ccccc2)[C@@H]1C#N 95897623 UKJFDLKEHROOFG-JZXOWHBKSA-N 342.420 2.036 30 1 EEEF O=c1nc(-c2ccc(C#Cc3ccccc3)cc2)[nH]c2c1CNCC2 473086400 BVHFZCGWZJJXIU-UHFFFAOYSA-N 327.387 2.482 30 1 EEEF CS(=O)(=O)N[C@H]1CC[C@H](Oc2ccc(C#N)c(Cl)c2)CC1 653873784 JNVZVWKNRMMCCX-HAQNSBGRSA-N 328.821 2.451 30 1 EEEF CNCC#Cc1c(F)ccc2c1/C(=C/c1[nH]ccc1OC)C(=O)N2 14947101 QMIDZOGAPGBZSC-BENRWUELSA-N 325.343 2.226 30 1 EEEF C=C1C(=O)[C@@]23CC(=O)[C@@H]4C(C)(C)CCC[C@]4(C)[C@@H]2[C@@H](O)C[C@H]1[C@H]3O 2356397832 JLKBHAAAVQFJPZ-KDNVISMSSA-N 332.440 2.275 30 1 EEEF C=C(Cc1ccc(O)cc1)[C@](O)(CO)Cc1ccc(OC)cc1O 6484004 UICXJFXGPMLFAQ-LJQANCHMSA-N 330.380 2.171 30 1 EEEF biogenic C#C[C@@H]1CN2CC[C@H]1C[C@H]2CNC(=O)Nc1ccc(C(C)=O)cc1 2356641277 KRKGEQVUPUYJNG-HFTRVMKXSA-N 325.412 2.354 30 1 EEEF N#Cc1nc(NCc2ccc(F)cc2)c2c(n1)N(CCCCO)CN2 40957462 KGIBXJLXVWCOPX-UHFFFAOYSA-N 342.378 2.061 30 1 EEEF CO[C@H]1C[C@H]2O[C@]23CCN2CCCc4cc5c(cc4[C@@]23C1)OCO5 238745583 VZCXOCQQSFKKFK-JGNHQEBTSA-N 329.396 2.209 30 1 EEEF CCOc1nc(NC(=O)Cc2cccc(OC)c2)cc(N)c1C#N 14960058 JIVYDIADMNEKCM-UHFFFAOYSA-N 326.356 2.124 30 1 EEEF C=C1C(=O)[C@]23[C@@H](O)[C@@H]1[C@@H](O)C[C@H]2[C@@]1(C)CCCC(C)(C)[C@H]1C[C@H]3O 2356575636 UWJKFPFMTSZKRY-RFTWDNPXSA-N 334.456 2.067 30 1 EEEF C=C1C[C@@H](O)[C@H](O)C(=C)CC[C@@H]2/C(=C/C=C/C(C)(C)O)C(=O)OC[C@@H]12 38260612 DFVRPHGROBFFBS-KORXDNNLSA-N 348.439 2.047 30 1 EEEF CC=CC(=O)O[C@@H]1[C@H](O)[C@H]2O[C@@H]3C=C(C)CC[C@@]3(C)[C@@]1(C)[C@]21CO1 2356487413 AGQQMRNEWSVYSU-JUZBDSPUSA-N 334.412 2.138 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@@H]2[C@@]1(CCC[C@@]2(C)CO[C@@H](O)[C@@H]21)COC3=O 85508943 QUUUEWBMPVGPDF-CGYMOSLMSA-N 346.423 2.226 30 1 EEEF biogenic,in-vitro C=CCN1C(=O)S[C@@H](Cc2nc3cccc(C(=O)O)c3[nH]2)C1=O 587037920 AGSWTTBSUCRUJH-JTQLQIEISA-N 331.353 2.054 30 1 EEEF CN(O)C(=O)CCCc1ccc2c(c1O)C(=O)c1c(O)cccc1C2 13606213 GKNZLRDDKGJSJQ-UHFFFAOYSA-N 341.363 2.403 30 1 EEEF C=C1CN([C@H](C(=O)OC)C(C)C)S(=O)(=O)c2ccc(F)cc21 13830629 RSCWHTXMDKHWJQ-AWEZNQCLSA-N 327.377 2.041 30 1 EEEF N#CCCNC(=O)C1=CC(CF)(CF)Oc2ccc([N+](=O)[O-])cc21 1537648 WMVNZVFRFPHGMS-UHFFFAOYSA-N 337.282 2.078 30 1 EEEF COC(=O)[C@]1(C)CCC(=O)C(C)=C1C=CC(C)=C[C@H](O)C[C@@H](C)O 2356377840 NGPTWMZMECMCMC-FRIZHTMISA-N 336.428 2.479 30 1 EEEF COC(=O)c1cc(C#Cc2ccc(C[C@H](C)NC(C)=O)cc2)ccn1 113410723 GIKMVLAUUXWXFC-AWEZNQCLSA-N 336.391 2.335 30 1 EEEF C=C(C)C(=O)OCCOc1ccc(O)n1-c1cc(O)cc(C(=O)O)c1 587927359 TYABOXFYDRSREZ-UHFFFAOYSA-N 347.323 2.085 30 1 EEEF CC(C)(C)c1cc(I)c(O)c(CN=C(N)N)c1 27860098 RVOXYPROGRURTG-UHFFFAOYSA-N 347.200 2.068 30 1 EEEF CCC1=C(C)N[C@H](OC)C(C(=O)CN2C(=O)c3ccccc3C2=O)=C1 27206964 FLROWEGEBWIQIO-QGZVFWFLSA-N 340.379 2.038 30 1 EEEF COc1ccc(S(=O)(=O)[C@H](CC(=O)NO)c2ccccc2)cc1 29391817 SZVMBGCUMABOMY-OAHLLOKOSA-N 335.381 2.106 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@]12OC(=O)[C@](C)(CC[C@H]1O)[C@H]2[C@@H]3C(=O)OC 238776722 NZAMXUVSJOQDKJ-BTSJPBEPSA-N 346.423 2.225 30 1 EEEF CCOc1ccc(N(CC(=O)O)C(=O)[C@H](C)CS)cc1OCC 28259911 SFPRIWLQFPMFOE-LLVKDONJSA-N 341.429 2.468 30 1 EEEF CC(C)(C)NC[C@@H](O)CO/N=C(\Cl)c1nc2ccccc2o1 42922691 WBYAJYDAQSGUMZ-ICHPLGEASA-N 325.796 2.494 30 1 EEEF O=C(O)[C@@H]1CCCN(CCO/N=C/c2ccnc3ccccc23)C1 1857565878 FOTJDUOZGJMMPX-RVZJCZPVSA-N 327.384 2.382 30 1 EEEF C=CCN1C(=O)/C(=C/Nc2ccc(O)cc2)C(=O)N(CCCC)C1=O 6890873 BMTFFTLTQAIZCT-QINSGFPZSA-N 343.383 2.465 30 1 EEEF CCCCN[C@H]1C2=C(OC(C)(C)[C@@H]1O)C(=O)c1ccccc1C2=O 29134717 PWJHHLDOTFKWMM-KBXCAEBGSA-N 329.396 2.248 30 1 EEEF N#C[C@@H]1CC[C@H](c2ccccc2)N1C(=O)CNC1(CO)CCCC1 35949676 QITGSVUBMFCQQD-DLBZAZTESA-N 327.428 2.137 30 1 EEEF N#Cc1ccc(C(=O)NCCCN=c2[nH]c3ccccc3[nH]2)cc1F 473168083 JRUSPIXWYFETEM-UHFFFAOYSA-N 337.358 2.228 30 1 EEEF NS(=O)(=O)c1nc2ccc(OCC#Cc3ccccc3)cc2s1 299861079 HSDWUTHWFCNZSZ-UHFFFAOYSA-N 344.417 2.374 30 1 EEEF CNC(=O)/C(=N/OC)c1ccccc1COc1ncccc1Cl 103178780 FFYJARQBDHAHPN-XSFVSMFZSA-N 333.775 2.411 30 1 EEEF C#CCN(Cc1ccc2nc(N)[nH]c(=O)c2c1)c1ccc(C#N)cc1 26172038 MZDJMEWMEZJEBS-UHFFFAOYSA-N 329.363 2.017 30 1 EEEF CC(C)CN(CC(=O)NO)S(=O)(=O)c1ccc(C(C)(C)C)cc1 26505167 NDRLUYJPDDYOBH-UHFFFAOYSA-N 342.461 2.136 30 1 EEEF O=C(O)C[C@@H](SC1=C(Cl)C(=O)c2ccccc2C1=O)C(=O)O 49803437 SQYAJXDRTWJQHM-MRVPVSSYSA-N 340.740 2.177 30 1 EEEF CC1(C)CCC[C@@]2(C)[C@@H]3C(=O)C=C4COC[C@@H](O)[C@]4(O)[C@H]3CC[C@H]12 238755508 RPRCCSXIERFARX-ZVQJROQZSA-N 334.456 2.477 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cc4c(cc3[nH]2)OCO4)C1=O 587038153 CYWIIYYFQAENMI-GFCCVEGCSA-N 331.353 2.084 30 1 EEEF COC(=O)CC/N=C(\S)[C@]1(c2cccnc2)CCCC[S@]1=O 13651015 YOMOAZHLOLYFGF-QRQCRPRQSA-N 340.470 2.101 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(COC3=O)[C@H]2CC[C@]3(C)CO[C@@H](O2)[C@H]31 2356350121 VGHUWBCJSRMGIQ-CJCRLBDESA-N 344.407 2.243 30 1 EEEF O=C(NO)[C@@H](Cc1ccccc1)C(=O)NCc1ccc(Cl)cc1 28604497 MDFALTKCDXYVEX-HNNXBMFYSA-N 332.787 2.321 30 1 EEEF in-vivo N#Cc1cccc(-n2nnc([C@H]3CCCCN3C(=O)C3CCC3)n2)c1 49045479 RDVZDMOJYYFVOJ-MRXNPFEDSA-N 336.399 2.388 30 1 EEEF N#C[C@@H]1CCCN1C(=O)CCNC(=O)c1ccc(C(F)(F)F)cc1 84688592 VNLAQYMGUSCAEB-ZDUSSCGKSA-N 339.317 2.340 30 1 EEEF N#C[C@@H]1[C@@H](c2ccc(-c3cncnc3)cc2)[C@H](CO)N1C(=O)C1CCC1 95897719 RYHHKKTZXOEYDH-CEXWTWQISA-N 348.406 2.123 30 1 EEEF C[C@]12C(=O)C[C@H]3[C@@H](C=CC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@H]2[C@H](O)CO 2356389235 NCBLKWGLSQARQJ-WPWXJNKXSA-N 344.451 2.443 30 1 EEEF CCc1nc2n(c(=O)c1C(N)=O)[C@@H](C)CC/C2=N/Nc1ccccc1 100760742 ROUYGSNPBKRWQM-HKHLUXDBSA-N 339.399 2.076 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@H]2[C@]12CCC[C@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100826194 IPHNMKITOREFLW-MMBCHBGRSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C=C1C(=O)[C@@]23CC[C@@H]4C(C)(C)CC[C@H](O)[C@@]4(C)[C@@H]2[C@@H](O)C[C@@H]1[C@H]3O 35032234 IZMRXAKHHVUZIH-PRFYLKETSA-N 334.456 2.067 30 1 EEEF C=C1C(=O)[C@@]23[C@@H]4CC5=C(C(=O)CC5(C)C)[C@@](C)(O4)[C@@H]2CC[C@@H]1[C@H]3O 49785251 MJXXHOYVYOQSOU-KTGBWCAVSA-N 328.408 2.356 30 1 EEEF COc1nccc(N2CCC(N(C)Cc3ccccc3C#N)CC2)n1 299866257 VOTGEQAIOLRHCC-UHFFFAOYSA-N 337.427 2.458 30 1 EEEF COc1cc2c3c(c1)O[C@@]1(C(=O)Nc4cc(C#N)ccc41)[C@@H](C2)C3=O 587438240 DEYIJIKOHGYTCK-ORAYPTAESA-N 332.315 2.162 30 1 EEEF O=C1C(Br)=C(Br)C(=O)c2ccc(=O)ccc21 1631902 MXNJXAAYHKFDPH-UHFFFAOYSA-N 343.958 2.427 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)OC1)[C@H]2[C@H]3C(=O)O 100778378 QYXZQZMPZUEEML-MENMWXSUSA-N 346.423 2.384 30 1 EEEF endogenous,in-man C=C1C(=O)O[C@H]2C=C(COC(C)=O)CCC=C(C(=O)OC)CC[C@H]12 2356738315 FELNAJVVBXSDQN-CVEARBPZSA-N 334.368 2.247 30 1 EEEF C#CC=C[C@@H]1[C@H]2[C@H]3[C@H]4O[C@@H]2C[C@@H]4O[C@@]3(OC)[C@]1(Br)CC 2356795173 IKEWAOKGFUGNOH-OTFXVNSVSA-N 339.229 2.494 30 1 EEEF O=C(CS[C@H](c1ccc(Cl)c(Cl)c1)P(=O)(O)O)NO 96284895 MMODIMKCMBCKCF-SECBINFHSA-N 346.128 2.408 30 1 EEEF CNC(=O)N(CCC#N)CCCN(C(=O)N(C)C)c1ccccc1 1651314 IOCMFDMGLCPHJK-UHFFFAOYSA-N 331.420 2.120 30 1 EEEF C=CC[C@@]12CC(=O)[C@H](O)[C@@H]([C@H](c3ccc4c(c3)OCO4)[C@H]1C)[C@H]2O 2356536932 FBPLISOOTGTZGY-AOYOUIMASA-N 330.380 2.022 30 1 EEEF CC(C)C1=CC(=O)[C@]2(C)CC[C@@]3(C)C(=O)C=C(CO)[C@H](O)C[C@@H]3[C@H]12 238780000 SRUVAUDOCNEFJS-MNRMEVMPSA-N 332.440 2.443 30 1 EEEF COC(=O)c1cc2c([nH]1)C(=O)C=C1N(C(=O)OC(C)(C)C)C[C@@H]3C[C@]123 100866062 JVWWPRHIXMFAED-NIVTXAMTSA-N 344.367 2.390 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@H](NC(=O)c2ccc(C#N)cc2)[C@H]1O 40835663 FZBBUIVMCCYQOP-ZWKOTPCHSA-N 347.374 2.433 30 1 EEEF CC(C)C[C@H](NC(=O)c1ccc2c(c1)CCCC2)C(=O)NCC#N 82065353 DVCNVPRPWUDEAW-KRWDZBQOSA-N 327.428 2.350 30 1 EEEF O=C(/C=C/c1ccc(CONC(=O)Nc2ccccc2)cc1)NO 1857544042 KYUNUEOCEYKHCC-ZHACJKMWSA-N 327.340 2.459 30 1 EEEF N#C[C@@H]1CCCN1C(=O)CNC(=O)c1c(Cl)cccc1Cl 84602457 CEQDXLZRRYUVKY-VIFPVBQESA-N 326.183 2.238 30 1 EEEF CC(=O)N1CCc2[nH]c(/C=C3\C(=O)Nc4ccc(C#N)cc43)cc2C1 96272954 OUDNHJQPMQFCDI-PXNMLYILSA-N 332.363 2.284 30 1 EEEF O=C(NO)c1ccc(OCCNC(=O)c2cc3ccccc3o2)cc1 29070066 GUYCSHUDCXKIOO-UHFFFAOYSA-N 340.335 2.361 30 1 EEEF Cc1ccc(CN2C(=O)c3ccc(/C=C/C(=O)NO)cc3C2=O)cc1 28527211 BJUUWERYWRVVCG-VQHVLOKHSA-N 336.347 2.310 30 1 EEEF C[C@@H]1CN2C[C@@H]3CC[C@]4(O)CC(=O)C5=C4[C@]4(CC5)C(=O)[C@H]1C[C@H]2[C@]34C 2356603690 LSKAYCSMVNNFJC-MOCJQUDOSA-N 341.451 2.106 30 1 EEEF C/C(=N\O)c1cnc2nnn(Cc3cc4cccnc4cc3F)c2n1 96170379 VTRDOGKAJOPEHB-LSFURLLWSA-N 337.318 2.155 30 1 EEEF C=C1C[C@]23CC[C@@H]4C(CO)(CO)CC(=O)C[C@]4(C)[C@@H]2[C@@H](O)C[C@H]1C3 5843247 SRLVFQVUOGIQFP-QYXZOKGRSA-N 334.456 2.070 30 1 EEEF C=C[C@@]12CN(C)CC[C@@H]1[C@](C(=O)OC)(c1cc3ccccc3[nH]1)CO2 14693443 DRYXIMTVLUTZDF-DBVUQKKJSA-N 340.423 2.485 30 1 EEEF CCC/C=C/[C@H]1C(=O)[C@H]2O[C@@H]2C2(OCC(CC)(CC)CO2)[C@@H]1CO 102688523 TWGDZVIUZPIUAD-OBGVFFCRSA-N 338.444 2.467 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1C[C@H](O)[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1C[C@@H]3O 2356613909 BSPNTRYRRCCKFJ-SLEKXOJNSA-N 348.439 2.161 30 1 EEEF O=C(Cn1ccc(-c2ccc(C(=O)NO)s2)n1)Nc1ccccc1 38422064 CJMGSWOXEGSUKF-UHFFFAOYSA-N 342.380 2.369 30 1 EEEF O=C(NO)c1ccc(N[C@@H]2CCN(CCc3ccccc3)C2=O)cc1 169223198 OEOIWMTTYKVUJA-QGZVFWFLSA-N 339.395 2.061 30 1 EEEF C[C@@]12COS(=O)(=O)CC1=C(c1ccc(C(F)(F)F)cc1)C(=O)O2 169343889 CKKKBOVQQKRFPT-CYBMUJFWSA-N 348.298 2.135 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@H](c2ccccc2C2=CCCC2)[C@@H]1CO 95867998 OERKOXUAKKWALJ-AOIWGVFYSA-N 326.396 2.079 30 1 EEEF O=C(/C=C/c1ccc(O)cc1)[C@]1(CCN2CCCC2)CCOC1=O 299833138 OKYXTSIQTZMHBL-MEQKGCOVSA-N 329.396 2.394 30 1 EEEF C[C@@](CCc1ccccc1)(C(=O)NO)S(=O)(=O)c1ccccc1 1772576620 JNNBFIBVHIDVHP-QGZVFWFLSA-N 333.409 2.357 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@]45CCC[C@@](C)(C(=O)OC4)[C@H]5[C@H](C(=O)O)[C@@]3(C2)[C@H]1O 104371550 MJFVMFNFTCKAEV-HLJXZVOVSA-N 346.423 2.384 30 1 EEEF in-man CC(C)NC[C@H](O)CO/N=C1/c2ccccc2[C@H]2CCCC[C@]12O 26944102 RTKLMTIRQZCKHN-IZTJSQINSA-N 332.444 2.169 30 1 EEEF COc1ccc2c(c1)CCN1C(=O)/C(=C/C(=O)c3ccccc3)NC[C@H]21 96934325 LIMMLFUDPNTOJP-XLXASQRYSA-N 348.402 2.491 30 1 EEEF N#Cc1cccc(C[C@@H](NC(=O)c2cc3ccccc3[nH]2)C(=O)O)c1 621431369 UGTAZERUVHUHBW-QGZVFWFLSA-N 333.347 2.465 30 1 EEEF CSC1=N[C@H]2[C@H](N(C)C(=O)N2C)N1/N=C/C=C/c1ccccc1 1857639632 WONCCEICUAEBNN-DGIOYVCPSA-N 329.429 2.370 30 1 EEEF CC(=O)N1CCC[C@@]2(CCN(C(=O)Nc3cccc(C#N)c3)C2)C1 3955841 IBLNDEVKCZCDCP-GOSISDBHSA-N 326.400 2.425 30 1 EEEF COC(=O)[C@]1(c2cccc(OCc3ccccc3)c2)C[C@@H]1C(=O)NO 29134807 GVBYOUWYVHIZCE-APWZRJJASA-N 341.363 2.202 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)C2=CC3=C(CO)C(=O)C=C[C@@]3(C)CC[C@@]21C 2356730455 IQSIJJOWDAYBIC-SLHNCBLASA-N 332.440 2.155 30 1 EEEF Cc1ccc2c(c1)/C(=N/NC(=S)NC1CCCCC1)C(=O)N2C 40408954 KQCQJRYTCCNBEA-CYVLTUHYSA-N 330.457 2.472 30 1 EEEF Cc1cc2c(cc1O)[C@@](CC#N)(c1ccoc1C)N[C@H](C(=O)O)C2 963526835 OTUMJCMMUFMYLU-MAUKXSAKSA-N 326.352 2.358 30 1 EEEF O=C1C=Cc2ccccc2/C1=C/NNc1nc2ccccc2c(=O)n1O 13119054 CMMYVYGVASVMBD-PTNGSMBKSA-N 346.346 2.187 30 3 EEEF CN(C)/C=N\c1ncnc2c1cnn2-c1ccc(C(F)(F)F)cn1 18062156 HPIBBTRLLYUCAF-WNFQYIGGSA-N 335.293 2.451 30 1 EEEF C=C1C(=O)[C@@]23[C@H](CC[C@H]1[C@H]2O)[C@]1(C)O[C@@H]3CC2=C1C(=O)CC2(C)C 2356621034 MJXXHOYVYOQSOU-AUJVZHMZSA-N 328.408 2.356 30 1 EEEF C[C@H]1CCN(C(=O)C(C)(C)C#N)C[C@@H]1N(C)c1ncnc2[nH]ccc12 66252349 VWSCLEOQSBFMNS-JSGCOSHPSA-N 340.431 2.181 30 1 EEEF N/C(=N\O)Nc1ccc(Sc2ccc(N/C(N)=N/O)cc2)cc1 95581514 ADUYOPVBXVJZMD-UHFFFAOYSA-N 332.389 2.069 30 1 EEEF Cc1ccccc1S(=O)(=O)N1[C@H](C#N)[C@H](c2ccccc2)[C@@H]1CO 95897622 UKJFDLKEHROOFG-RYRKJORJSA-N 342.420 2.036 30 1 EEEF CC1=CC(=O)[C@@]2(CN1)Oc1ccccc1C(=O)[C@@H]2C(=O)c1ccco1 587595356 NGEPTUKSQJSQGP-VQIMIIECSA-N 337.331 2.169 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc(C(N)=O)cc([N+](=O)[O-])c1N 587900393 OXSAQTXMGOXHHR-UHFFFAOYSA-N 345.742 2.338 30 1 EEEF Cc1cn2cc(C#Cc3ccc(N4CCN(C)CC4)cc3)nc2c(C)n1 1772599957 ATURPPOWCMIIPM-UHFFFAOYSA-N 345.450 2.498 30 1 EEEF COc1ccc(S(=O)(=O)N/N=C/c2cc(Cl)ccc2O)cc1 20249597 IGLFCFBYVFVEHD-CXUHLZMHSA-N 340.788 2.367 30 1 EEEF C=C(C)[C@@H]1C[C@H]2CC[C@H]1[C@@H]1[C@H](CC[C@]1(O)CCNC(=N)NC)[C@]2(C)O 2356521806 MKBHWZDZALSUAF-RUWNHTTISA-N 349.519 2.251 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1c[nH]ccc1=O 587887902 CCJWMQOWBZQVNM-UHFFFAOYSA-N 335.190 2.392 30 1 EEEF COc1c(C)c2c(c(O)c1CC[C@H](C)CCC(=O)NO)C(=O)OC2 28870035 ZZGCYZXJPMORDY-VIFPVBQESA-N 337.372 2.234 30 1 EEEF Nc1ccc(S(=O)(=O)NN=CC=Cc2ccccc2[N+](=O)[O-])cc1 1857622041 WVEMQFVVHNUQTB-UHFFFAOYSA-N 346.368 2.155 30 1 EEEF CC(=O)OC[C@@H]1O[C@@H](C#CCCc2ccccc2)C=C[C@H]1OC(C)=O 7991924 PEMFRHXMDHFDFC-ZCNNSNEGSA-N 342.391 2.441 30 1 EEEF C=C1C[C@]23C[C@H]1[C@H](O)C[C@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 70454929 IPHNMKITOREFLW-MHKXYFPYSA-N 332.396 2.136 30 1 EEEF biogenic,in-vitro N#C[C@@H]1CCCN1C(=O)[C@@H]1CC[C@H](COc2ccccc2Cl)N1 14947548 DTSZQBAFUITGDQ-IPYPFGDCSA-N 333.819 2.354 30 1 EEEF C=C1C[C@H]2[C@@H](O)[C@@H](C)C[C@]2(O)C(=O)/C(C)=C\[C@@H]2[C@H](C[C@H]1O)C2(C)C 102945579 XYXDIXJADPYNOO-GCXWEQQCSA-N 334.456 2.233 30 1 EEEF O=C(CCc1ccc2c(ccn2S(=O)(=O)c2ccccc2)c1)NO 84759216 OZHCPGPUQWHXJS-UHFFFAOYSA-N 344.392 2.316 30 1 EEEF C[C@@H]([C@H](NC(=O)OCc1ccccc1)C(=O)NCC#N)C(F)(F)F 82064905 DQUMJPBSYXBJLB-JQWIXIFHSA-N 343.305 2.120 30 1 EEEF C=CC(=C)[C@@H](O)C[C@H]1[C@](C)(O)[C@@H](O)[C@H](O)[C@H]2C(C)(C)CCC[C@@]21C 1857601509 IBGMRNOLPKLLRL-CKSMNCTJSA-N 338.488 2.415 30 1 EEEF COCC(=O)N1[C@H](CO)[C@@H](c2ccccc2C2=CCCCC2)[C@@H]1C#N 95866712 XJOIDJIXTAYCGR-NSHGMRRFSA-N 340.423 2.469 30 1 EEEF Cc1ncoc1C(=O)NCc1ccc2cc(C(=O)NO)sc2c1F 299866620 PEMUWZHFIHWNAQ-UHFFFAOYSA-N 349.343 2.386 30 1 EEEF C=C[C@]1(C)C(=O)C=C2C(=CC[C@H]3C(C)(C)[C@H](O)[C@@H](O)C[C@]23C)[C@H]1O 2356432455 AZNDIKGKUJHYJB-LDGYFSAJSA-N 332.440 2.153 30 1 EEEF CN=C1NCC#C[C@H]2C[C@@H](C)[C@@]34CCC(C(=O)O)=C3C[C@H]2[C@@]4(C)CN1 2356353099 IDOIZYCKBKFALL-NGNZTNIOSA-N 341.455 2.012 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@@H]2[C@@H]3C=C(C)[C@H](C[C@@H]3C(C)C)[C@H]2C1=O 101880734 PBDZFTMSQJXALQ-XLWJZTARSA-N 347.484 2.021 30 1 EEEF CC1=CC(=O)C2=C(C)C[C@H](OC(C)(C)C)[C@@H]3[C@H](C)C(=O)O[C@@H]3[C@@]12O 2356331209 GFSKBOWVEKODGN-QLXAOWJFSA-N 334.412 2.328 30 1 EEEF CC(=O)O[C@H](C(=O)C=C(C)C)[C@]12[C@@H](OC(C)=O)O[C@@H]3C=C(C)[C@H]1C[C@@H]32 29041966 QFUYTTKICOKMGU-QLWJPQISSA-N 348.395 2.324 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OCC(C)C)C[C@@]1(C)[C@@H]2[C@H](C)C(=O)C[C@H]1O 2356702916 BQKSKQIZKSAQEI-CCPSRCKYSA-N 336.428 2.121 30 1 EEEF COC1=C[C@@]2(C=CC1=O)C[C@H]1c3c(cc(OC)c(O)c32)CCN1C 14618488 RICRDZJWIPYDGM-HXPMCKFVSA-N 327.380 2.241 30 1 EEEF biogenic N#C[C@H]1[C@@H](c2ccc(-c3ccncc3)cc2)[C@@H](CO)N1C(=O)C1CC1 95897876 HIKHAZJBFWQNBZ-IPMKNSEASA-N 333.391 2.337 30 1 EEEF C=C1[C@H](O)[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O[C@H]([C@@H]12)[C@@H]3O 238731051 PWCNMDCZKHGAQG-DKDWBBOZSA-N 332.440 2.432 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2CC/C=C/[C@H](O)Cc2cc(O)cc(O)c2C(=O)O1 96903592 LTYXUGJWWVZNBY-VCVDJDOKSA-N 334.368 2.054 30 1 EEEF CC(C)C1=C[C@H]2[C@@H]3[C@@H](C(C(C)C)=CC(=O)[C@@]3(C)O)[C@H]1C(=O)[C@@]2(C)O 263590572 YNYHPBIGKWCFOA-AHVXBYHZSA-N 332.440 2.297 30 3 EEEF COc1cccc([C@]2(C#N)NCCc3ccc(C(=O)N(C)C)cc32)c1 962929700 VYYSIPMEIIMHCC-FQEVSTJZSA-N 335.407 2.310 30 1 EEEF C=C1C[C@@H]2OC(=O)C(=C)[C@H]2[C@H](OC(=O)C(C)C)C[C@@]2(C)OC1=CC2=O 2356428328 HKQSOGUZSSFJSM-XWESNNAXSA-N 346.379 2.244 30 1 EEEF C=CC(C)(C)[C@]1(C)OC=C[C@@]1(C)CC(=O)[C@@H](O)[C@@H](OC)[C@@H](C)O 6494203 BSIAHHIPMGVHJM-DNBIXMRYSA-N 326.433 2.223 30 1 EEEF in-vitro O=C(O)CCCCCO/N=C\c1ccccc1OCC1OCCO1 42750698 XCKYWONXNGWBHZ-PDGQHHTCSA-N 337.372 2.434 30 1 EEEF CCn1c(C(=O)c2cc(C)cc(C#N)c2)c(C(C)C)c(=O)[nH]c1=O 43201700 AYPIJAMXGVYYRQ-UHFFFAOYSA-N 325.368 2.091 30 1 EEEF in-vivo N#CCNC(=O)[C@H](Cc1cccs1)NC(=O)OCc1ccccc1 82064881 GDDSZMNOSYFPDE-HNNXBMFYSA-N 343.408 2.225 30 1 EEEF C/C(=N\NC1=NCCN1)c1cnn(-c2ccc(C#CC3CC3)cc2)c1C 1857584637 IOJZRSDBONQIOD-ZVHZXABRSA-N 346.438 2.215 30 1 EEEF COC(=O)C1=C2Nc3ccccc3[C@]23CCN2CC[C@H]1[C@@]1(O[C@@H]1C)[C@@H]23 2356381467 NYHQYHWNIWLUDO-RHVQDJQVSA-N 338.407 2.042 30 1 EEEF C=C1[C@@H](CCC(C)=CCO)[C@]2(C)C[C@@H](O)C[C@@](C)(CO)[C@H]2C[C@H]1O 2356639998 LCWHTWNKEOSQBZ-SFUSBHMVSA-N 338.488 2.418 30 1 EEEF COC1=C[C@H]2[C@H]3Cc4cc(OC)c(OC)cc4[C@@]2(CCN3C)CC1=O 2356787135 UFPSPSKAMWHJCV-BXTJHSDWSA-N 343.423 2.321 30 1 EEEF C=CC(C)(C)[C@]1(C)OC=C[C@@]1(C)CC(=O)[C@H](O)[C@H](OC)[C@H](C)O 238736432 BSIAHHIPMGVHJM-UIVXMWCNSA-N 326.433 2.223 30 1 EEEF CC[C@H](C)[C@@H](CO)NC(=O)/C=C/[C@@]1(C)O[C@H]1[C@@H](C)C[C@H](O)CC 140073560 KQYIQWJQJFWGMP-WXDFVLQISA-N 327.465 2.020 30 1 EEEF Cn1c(=O)ccc2cc(NS(=O)(=O)c3ccccc3C#N)ccc21 1772590591 OCYPGMCMVGHLRX-UHFFFAOYSA-N 339.376 2.211 30 1 EEEF COc1cccc(/C(=N\O)c2cccc(NS(=O)(=O)N(C)C)c2)c1 27421360 IDBDUWUWWZLMNN-MSUUIHNZSA-N 349.412 2.140 30 1 EEEF C=C1[C@H]2CC=C(C)[C@H]2[C@H]2OC(=O)C(=C)[C@H]2[C@@H](OC(=O)C(C)=CC)[C@H]1O 2356536019 MXNYEYDKNYIYGB-PDCGBLAGSA-N 344.407 2.475 30 1 EEEF O=C1C=C(c2ccc(O)c(O)c2O)C(=O)c2c1cccc2[N+](=O)[O-] 71316330 RUSAERZRWGPBBY-UHFFFAOYSA-N 327.248 2.174 30 1 EEEF COC(=O)CC[C@H](N)c1nc2cc(C#N)c(C(F)(F)F)cc2[nH]1 587258329 HHZTVTNMUOJZJK-VIFPVBQESA-N 326.278 2.406 30 1 EEEF C=CCc1cc(NC(=O)NC)ccc1OC[C@@H](O)CNC(C)(C)C 169317259 UAFMUJDYUGVGJH-HNNXBMFYSA-N 335.448 2.294 30 1 EEEF Cn1c(Nc2cccc(-c3cccc(C#N)c3)c2)cc(=O)n(O)c1=O 1857571690 GZOAUJXWXHBKCR-UHFFFAOYSA-N 334.335 2.067 30 1 EEEF Cc1ccc(S(=O)(=O)Nc2cccc(/C=C/C(=O)NO)c2)cc1 29133891 QWEBHXODFLJNDE-JXMROGBWSA-N 332.381 2.314 30 1 EEEF C=CC[C@]12CC(=O)[C@@H](O)[C@H]([C@@H](c3ccc4c(c3)OCO4)[C@@H]1C)[C@H]2O 238777744 FBPLISOOTGTZGY-CEAYDYMWSA-N 330.380 2.022 30 1 EEEF C[C@]1(C=O)[C@H](O)CC[C@]2(C)[C@H]1CCC1=C[C@H]3C[C@@]12CC[C@]3(O)CO 2356324658 KZRJAXKCOWVRTH-UQEPQNNOSA-N 334.456 2.213 30 1 EEEF C=C[C@@H]1CN2CC[C@H]1C[C@H]2CNC(=O)CC1(CC(=O)O)CCCC1 2356389563 ZGYUSGIGQDEQMQ-PMPSAXMXSA-N 334.460 2.424 30 1 EEEF CC(=O)CC1=C2C(=O)O[C@]3(C)CC[C@@H]4[C@H]([C@H]([C@H]23)[C@@](C)(O)C1=O)C4(C)C 2356482938 BTLNQUGRPABJQH-RFXYXWMGSA-N 346.423 2.210 30 1 EEEF O=C(CCCCc1cn(Cc2ccc3ccccc3n2)nn1)NO 96907679 AETFDFSAMBOSFM-UHFFFAOYSA-N 325.372 2.093 30 1 EEEF C=CCNC(=O)N1C[C@@H]([C@@H](C)OC(=O)CCCc2ccccc2)C1=O 95593450 PSEWBDINEPXWQK-ZBFHGGJFSA-N 344.411 2.295 30 1 EEEF COc1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)[nH]n1 587890536 LJTOHZDRQCKCJI-UHFFFAOYSA-N 338.194 2.436 30 1 EEEF C[C@@H]1CCN(C(=O)C(C)(C)C#N)C[C@H]1N(C)c1ncnc2[nH]ccc12 66252350 VWSCLEOQSBFMNS-TZMCWYRMSA-N 340.431 2.181 30 1 EEEF O=C1C(=O)c2cccc3c2C(=C1Cl)OC[C@@H]3n1cc(C2CC2)nn1 96934586 TUYWFDDYXKGSOA-LBPRGKRZSA-N 341.754 2.448 30 1 EEEF C=C1C(=O)O[C@@H]2C3=C(C)C(=O)C[C@H]3[C@](C)(O)C[C@@H](OCC(C)C)[C@@H]12 238741143 IDJQTNTZPPTSEU-HKYLLPEISA-N 334.412 2.186 30 1 EEEF CC1(C)CCC[C@]2(C)O[C@@]12/C=C/c1cc(S(C)(=O)=O)nc(N)n1 101412206 SKULGIFBFWXBLY-MYNUTGAYSA-N 337.445 2.213 30 1 EEEF O=C(O)C1=C(Nc2ccc(CCO)cc2)C(=O)c2ccccc2C1=O 102987575 LMBCMMMWUONXKB-UHFFFAOYSA-N 337.331 2.051 30 1 EEEF C=C(C)[C@@H](Cc1c(OC)c2ccc3c(c2n(C)c1=O)OCO3)OC 14682518 GHCVBXAYFUCEKZ-CQSZACIVSA-N 331.368 2.409 30 1 EEEF biogenic C[C@@]12CC[C@H](O)[C@@H]3COC(=C31)C(=O)c1cc3c(cc12)C(=O)C=CC3=O 138962870 MYMGNUKZCJPHIG-APXLUKDGSA-N 336.343 2.131 30 1 EEEF CC#CC#CC=C1O[C@]2(CC[C@H](OC(=O)CC(C)C)CO2)[C@@H]2O[C@@H]12 2356508582 IZOBIZVXEKNCNN-WQANXHIZSA-N 330.380 2.159 30 1 EEEF C[C@H]1CC=C[C@@H](O)CC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 2356584430 DRRQOEPQLQGLLP-WCQYABFASA-N 332.352 2.022 30 1 EEEF COc1ccc(NC(=O)[C@@H](CC2CCCCC2)C(=O)NCC#N)cn1 34054168 UGTHOVYFRUNGHC-HNNXBMFYSA-N 344.415 2.255 30 1 EEEF N#Cc1cccc(-c2c[nH]c3ncnc(N4CCO[C@H](C#N)C4)c23)c1 224858117 YDRMVAPJCHICGE-CQSZACIVSA-N 330.351 2.225 30 1 EEEF CC(C)C1=CC2=C(C(=O)C1=O)[C@@]13CCCC(C)(C)[C@@H]1[C@@H](O)[C@@H]2OC3=O 49021060 NYZQYBFZGIKGRX-CLWJZODNSA-N 344.407 2.130 30 1 EEEF COC(=O)C#Cc1ccc2c3c(n(C)c(=O)c2c1)-c1ccccc1C3=O 95581349 SKAFEUQQPVTMMK-UHFFFAOYSA-N 343.338 2.274 30 1 EEEF C=C1C(=O)O[C@H]2[C@H](O)C(C)=CCCC(C)=CCC[C@@]3(CO)O[C@@H]3C[C@H]12 299808503 MULWDJOXRRXULO-VBEQINLCSA-N 348.439 2.432 30 1 EEEF C=C1C(=O)[C@@]23C[C@@H]1CC[C@H]2[C@@]12CO[C@@H]4OC[C@@](C)(CC[C@@H]1OC3=O)[C@H]42 5723112 QRZAIOQXVJRCBS-KVDSSBBXSA-N 344.407 2.243 30 1 EEEF C=C(C)C(=O)O[C@@H]1CCC(=C)[C@@H]2[C@@H]3OC(=O)[C@H](C)[C@@H]3[C@@H](O)C[C@]21C 2356480136 QHTWVJOMDDBORA-LQOFDJPTSA-N 334.412 2.389 30 1 EEEF CCOc1cc(C)nc(N[C@@H]2CCc3ccc(C(=O)NO)cc3C2)n1 113846131 WBWFGMCELMVENS-OAHLLOKOSA-N 342.399 2.272 30 1 EEEF C=CCNC(=O)c1ccc[n+](CC(=O)Nc2ccc(Cl)cc2)c1 103172208 IIWPQZHWXPANFJ-UHFFFAOYSA-O 330.795 2.182 30 1 EEEF CC1=C[C@]2(O)C(=O)C(C)=C[C@@H]3[C@H](C[C@H](O)C(C)=C[C@H]2C1=O)C3(C)C 2356565159 QSTBGARAGIHHBB-TYNWYWJLSA-N 330.424 2.361 30 1 EEEF N#C[C@H](CCCCN)NC(=O)c1ccc(OCc2ccncc2)cc1 73138582 PJEBPRWUSAIUEL-KRWDZBQOSA-N 338.411 2.412 30 1 EEEF N#Cc1ccc(-c2ccc3c(c2)OC[C@H]2[C@@H](CO)SC(=O)N32)cn1 299869358 UMOJOKQCEXAYIR-GOEBONIOSA-N 339.376 2.415 30 1 EEEF COc1cccc(CCC[C@H](CC(=O)N(C)O)CP(=O)(O)O)c1 584904754 OCDQDBAFBVPPGL-CYBMUJFWSA-N 345.332 2.050 30 1 EEEF in-vitro COc1ccc(Cl)cc1C#Cc1cnc2c(C(=O)O)nccn12 587912388 NOZDOYXCJIELJU-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF COC(=O)/C(=N\OCc1ccc(C#N)cc1)c1c(C)nn(C)c1C 6550884 XGNNQFATWLEVHS-SILNSSARSA-N 326.356 2.003 30 3 EEEF CC1=C[C@]2(O)C(=O)C(C)=C[C@@H]3[C@H](C[C@@H](O)C(C)=C[C@@H]2C1=O)C3(C)C 2356565160 QSTBGARAGIHHBB-YTMVRGIBSA-N 330.424 2.361 30 1 EEEF C=C(CC[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CC[C@@H](O)[C@@]2(C)CO)[C@@H](O)CO 2356581699 GLRQCZGXPULESM-JIFZMYKYSA-N 338.488 2.418 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C[C@@H]3C(C)(C)CC[C@H](O)[C@]3(CO)[C@]2(O)CC1 2356722673 MYLWJAXIZRHGOI-QVHQYWGISA-N 334.456 2.379 30 1 EEEF CC1=C[C@H](C)[C@H](c2cc(O)cc(O)c2)OC(=O)[C@H](C)[C@H](O)[C@H](C)C1=O 2356733727 RFQJAVYYIHIQAI-SEUDMZKHSA-N 348.395 2.480 30 1 EEEF Cc1cccc(CCC[C@H](CC(=O)N(C)O)CP(=O)(O)O)c1 584905591 LKGTWQXFDFYGBW-CQSZACIVSA-N 329.333 2.349 30 1 EEEF in-vitro C=C1[C@H]2C[C@@H](O)C(C)(C)[C@H](O)[C@@H]2C[C@@]23C[C@@](O)(CC[C@@H]12)[C@](C)(O)C3 1857746985 NIIGYOSFUYUFED-YQMODDGXSA-N 336.472 2.003 30 1 EEEF CC(C)[C@](C#N)(CCCN1CCN(CCO)CC1)c1ccccc1 22927193 NSRKKRFXMCQGMY-HXUWFJFHSA-N 329.488 2.494 30 1 EEEF O=C(c1csc(-c2cccc(O)c2O)n1)N(O)CCc1c[nH]cn1 49582925 WYVQJMXTYHVYFT-UHFFFAOYSA-N 346.368 2.019 30 1 EEEF C=C1C(=O)O[C@H]2/C=C(/C)C3=CC(=O)[C@](C)(C[C@@H](OC(=O)C(C)C)[C@@H]12)O3 238758494 WQQJRSDFQHYDRU-QUQRSYOCSA-N 346.379 2.244 30 1 EEEF O=C1C2=C(C(=O)c3ccccc31)[C@H](c1ccco1)[C@@H]([N+](=O)[O-])CO2 473115336 SAWIIIQAQQCCFO-AAEUAGOBSA-N 325.276 2.372 30 1 EEEF CCn1c2c(c(O)nc1=O)[C@H](c1ccc(C)cc1)C1=C(CCC1=O)N2 1772643186 GFYQCHZFSLHBOA-CQSZACIVSA-N 337.379 2.452 30 1 EEEF COc1ccc(C2(C#N)CCN(CC(=O)O)CC2)cc1OC(C)C 13588524 GNGUYINVAWUFIB-UHFFFAOYSA-N 332.400 2.424 30 1 EEEF C#CCNC(=O)C1=C[C@H](C2CCCCC2)C[C@H](OCCCCO)O1 13634821 XNMGFLPANXTEIP-FUHWJXTLSA-N 335.444 2.352 30 3 EEEF O=C(NO)c1cnc(NCc2ccc(F)cc2C(F)(F)F)nc1 166914350 LPCPMORCWHFGDB-UHFFFAOYSA-N 330.241 2.366 30 1 EEEF C=C(CO)[C@@H]1CC2=CC[C@H]3[C@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@@H]2[C@@H](O)C1 2356443945 FISRUIAPOPDKNG-GRLHSABHSA-N 336.472 2.028 30 1 EEEF C=C(C)[C@@H]1C[C@H]2CC[C@H]1[C@@H]1[C@H](CC[C@@]1(O)CCNC(=N)NC)[C@]2(C)O 2356521805 MKBHWZDZALSUAF-GNLOLKOISA-N 349.519 2.251 30 1 EEEF CC(C)[C@H]1O[S@](=O)O[C@@]1(Cn1cncn1)c1ccc(Cl)cc1 84711453 NPFKMHWOXVEEPD-ALLJEULLSA-N 341.820 2.477 30 1 EEEF CC1=C[C@@]2(O)C(=O)[C@](C)(O)[C@@H]3[C@@H]4[C@H](CC[C@@]3(C)C=C2C1=O)C4(C)C 198502296 UZEAKOOBNZOXDE-OOGOFMSLSA-N 330.424 2.195 30 1 EEEF C=CC[C@]1(OCc2ccccc2)C(=O)C(=O)O[C@H]1[C@@H]1COC(C)(C)O1 1646911 QUSJNYTVFAJGCT-QOKNQOGYSA-N 346.379 2.164 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 2356436700 XBDTWBSMNXMGIJ-GLZFIAKDSA-N 346.423 2.225 30 1 EEEF CCOC(=O)c1ccc(OC2=CNN/C2=C2\C=CC(=O)C=C2O)cc1 103757061 QWKSQDMYTDKOSO-SAPNQHFASA-N 340.335 2.026 30 3 EEEF CCc1nc(N)nc(N)c1-c1ccc(N2CCNCC2)c(N=[N+]=[N-])c1 26501448 AMHSFYHMKMZQJJ-UHFFFAOYSA-N 339.407 2.222 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H]1[C@@H](OC(=O)C(C)=CC)CC(=C)[C@@H]1C[C@H](O)C(=C)[C@H]12 2356486443 SDRJABGPZHYDOV-ZCVDQKGDSA-N 344.407 2.475 30 1 EEEF CO[C@@]1(C#C[C@](O)(c2ccccc2)c2ccncc2)CN2CCC1CC2 28563976 NSEVJPOKAGLQCK-VXKWHMMOSA-N 348.446 2.432 30 1 EEEF CCCCCCCCCCNCC(P(=O)(O)O)P(=O)(O)O 71317586 HRIDUOZZXIYDCR-UHFFFAOYSA-N 345.313 2.398 30 1 EEEF CC(C)C[C@H](NC(=O)c1cccc(OC(F)F)c1)C(=O)NCC#N 82065113 AMMSQOAPTFTBIG-ZDUSSCGKSA-N 339.342 2.072 30 1 EEEF CC(=O)[C@H](CCC#N)[C@]1(C)N[C@H](C(=O)O)Cc2ccc(O)c(C)c21 963549972 JPUZFQIOUALAPC-DEYYWGMASA-N 330.384 2.024 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)(CC[C@@H](O)[C@@]4(C)CO)[C@@H]2C[C@H](O)[C@H]1C3 2356417360 YYNFNCPHITUVRP-CYGWCMMDSA-N 334.456 2.068 30 1 EEEF C=C(C)[C@@H]1CCC(=C)[C@@H]2C3=C(C[C@H](C)C3=O)C(=O)[C@](C)(O)[C@H](O)[C@H]12 2356500240 RLNWZRIDRKCQGX-XDXKLNNZSA-N 330.424 2.361 30 1 EEEF C=C(C)[C@@H]1CC[C@@]23O[C@@H]2[C@@H](CC(C)=C[C@]2(O)C=C(C)C(=O)[C@H]12)OC3=O 2356529179 XCSMOAULMOLHGO-NKPKVQEGSA-N 344.407 2.248 30 1 EEEF CCn1c(N)c(-c2nc3ccccc3[nH]2)c2nc(C#N)c(C#N)nc21 653692122 KNFROIXIHWSHAP-UHFFFAOYSA-N 328.339 2.320 30 1 EEEF C=CCn1c(S)nnc1-c1nnn(Cc2ccc(Cl)cc2)c1N 957883991 KODRFIKOFOMTEI-UHFFFAOYSA-N 347.835 2.295 30 1 EEEF CC(=O)/C(=N/Nc1ccc2c(=O)cc(C)oc2c1)N1CCSCC1 103005401 AVIGRLXKCWROIP-ZPHPHTNESA-N 345.424 2.465 30 1 EEEF C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@H](O)[C@@H]1C(=C)[C@@H](C)CC[C@]21C 2356574599 GCVDFMXIDUYWBG-POTBXROMSA-N 344.407 2.167 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@]2(C)C[C@H]2C(=O)C=C(C)[C@H](O)C1=O 2356671144 PCTOPLUNRDRIQE-WESSWTGZSA-N 344.407 2.296 30 1 EEEF N=C(N)Nc1ccc(-c2ccc(-c3ccc(N=C(N)N)cn3)cc2)nc1 40394071 AVFZFICDSLCXSG-UHFFFAOYSA-N 346.398 2.021 30 1 EEEF CC(C)NC(=O)N1[C@H](CO)[C@H](c2ccc(C#CC3CC3)cc2)[C@@H]1C#N 95897426 FGRJVUDIIQYRHF-IPMKNSEASA-N 337.423 2.218 30 1 EEEF COc1ccc(NC(=O)ONC(=N)c2ccc3nonc3c2)cc1 653778470 XJSJGNVCHMWTQP-UHFFFAOYSA-N 327.300 2.310 30 1 EEEF COc1ccc(C(=O)C2=CNN/C2=C2\C=C(Cl)C=CC2=O)cc1 104015514 VDKTZIGOXNIVSW-DTQAZKPQSA-N 328.755 2.385 30 3 EEEF O=C1C=CC(O)=C/C1=C\NNC(=S)N[C@@H]1C[C@H]2C[C@H]1[C@@H]1C=CC[C@H]12 104005499 NEWHOSFZGBPMPT-NHUBMVOVSA-N 343.452 2.021 30 3 EEEF C=C1CC[C@@H](O)[C@]2(C)C[C@@H]3OC(=O)C(=C)[C@H]3[C@H](OC(=O)C(C)C)[C@@H]12 238777354 GEAKLPVKLKYFLZ-QHJVRGJGSA-N 334.412 2.389 30 1 EEEF Cc1cccc(/N=C/C2=C3NC=C(C(=O)O)C(=O)N3[C@@H](C)CC2)c1 101471332 ADFYQZZKXUPLRK-BFNDQCEFSA-N 325.368 2.492 30 1 EEEF C=C(CO)[C@@H]1CC2=CC[C@H]3[C@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@@H]2C[C@H]1O 2356464957 VJVZOSZFDKSLNA-QDWVOHSCSA-N 336.472 2.028 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1C[C@H](O)[C@H]2[C@]1(C)CCC[C@@](C)(C(=O)O)[C@@H]1[C@H](O)C3 238759762 REISIHFCXBLVLB-RYXOVRDTSA-N 348.439 2.161 30 1 EEEF N#C[C@@H]1Sc2nnc(-c3ccccc3Br)n2NC1=N 1857579258 LNXLTBJCDMOAAT-QMMMGPOBSA-N 335.190 2.226 30 1 EEEF N#Cc1ccc(CS(=O)(=O)c2nnnn2C2CCCCC2)cc1 13815204 ZIJVEPDBECDDEB-UHFFFAOYSA-N 331.401 2.024 30 1 EEEF C=CCOC(=O)c1c(C)[n+]([O-])c2cc(Cl)c(Cl)cc2[n+]1[O-] 1663174 MPFZCKDAKDLQAA-UHFFFAOYSA-N 329.139 2.065 30 1 EEEF CCOc1ccn([C@@H]2c3cc(C#N)ccc3OC(C)(C)[C@H]2O)c(=O)c1 27553917 ONNLAGFIKANGLE-MSOLQXFVSA-N 340.379 2.240 30 1 EEEF CCC(=O)C[C@H](C)[C@@H]1O[C@]1(C)C=CC(=O)N[C@@H](CO)[C@@H](C)CC 2356596957 RDWBIAZAAVLQEC-YARXLOAZSA-N 325.449 2.229 30 1 EEEF CC[S@](=O)C[C@](C)(O)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1 28015254 XXMKUOWGHUBGCA-ZAMGYDSWSA-N 348.346 2.035 30 1 EEEF N#CCNC(=O)[C@@H](CC1=CCCC1)NC(=O)OCc1ccccc1 82064863 UBZZYVLNRSNGDG-MRXNPFEDSA-N 327.384 2.422 30 1 EEEF O=C(O)Cc1cc(CC(=O)O)cc(-c2ccc(C#CCCO)s2)c1 653827942 UNUACSGLWHCXEJ-UHFFFAOYSA-N 344.388 2.403 30 1 EEEF N#Cc1ccc(N2C[C@H](CN)[C@@H](c3cc(F)ccc3F)CC2=O)cn1 169312409 LQGNBFOSBXWJMN-NHYWBVRUSA-N 342.349 2.327 30 1 EEEF C=CCn1c(O)c(C(=O)Nc2nnc(C)s2)c(=O)c2ccccc21 4337946 HAVDYZJOJZQVQT-UHFFFAOYSA-N 342.380 2.305 30 1 EEEF N#Cc1cccc(C(=O)N[C@@H]2CCC[C@H](NC(=O)c3ccccn3)C2)c1 95587696 WSQGEPYGCDINHA-SJORKVTESA-N 348.406 2.424 30 1 EEEF O=C(NO)c1ccc(Sc2ccc([N+](=O)[O-])c3nonc23)cc1 299830856 YKMQHZRYJDXZMO-UHFFFAOYSA-N 332.297 2.401 30 1 EEEF COc1ccc(S(=O)(=O)Nc2ccc(/C=C/C(=O)NO)cc2)cc1 13493379 OGJOCFPURGELIS-NYYWCZLTSA-N 348.380 2.015 30 1 EEEF COC(=O)[C@@]1(c2cccc(OCc3ccccc3)c2)C[C@H]1C(=O)NO 29134809 GVBYOUWYVHIZCE-QFBILLFUSA-N 341.363 2.202 30 1 EEEF O=C1c2ccccc2C(=O)N1C/C=N/NC(=S)Nc1ccccc1 653704154 CAHMVTNCQXNXSV-VCHYOVAHSA-N 338.392 2.255 30 1 EEEF C[C@@H]1CC/C(=N\N(C)c2ccccc2)c2ncc(C(=O)O)c(=O)n21 40641074 DXCAOAFKYKPQRQ-NUSFMGPTSA-N 326.356 2.137 30 1 EEEF CC1=CC(=O)[C@]2(CN1)N[C@H](C)Cc1cc(Br)c(F)cc12 587791510 GBZAYDNBEDMVFK-RFAUZJTJSA-N 339.208 2.394 30 1 EEEF CCCCCC[C@H](O)[C@@H]1C[C@H](OC(C)=O)C2=C(O1)[C@@H](O)CCC2=O 2356620151 GXYWRLQZWPUUNP-TUUVXOQKSA-N 340.416 2.016 30 1 EEEF CC(=O)O[C@@H]1O[C@H](OC(C)=O)[C@@H]2CC[C@H]3C(C)(C)[C@H]4C[C@]32C1=CC4=O 2356696887 YUEBDHFRUOFFJT-CKVNNJNRSA-N 348.395 2.363 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O[C@@H]([C@@H]21)[C@@H]3O 33698787 OSYJLXUUZYSFTC-HXRPTQKMSA-N 332.440 2.432 30 1 EEEF in-man N#Cc1cccc(C(=O)Nc2ccc([C@H]3CNCCO3)cc2F)n1 149931847 STLBETLOVNLVRU-MRXNPFEDSA-N 326.331 2.006 30 1 EEEF Cc1ccccc1S(=O)(=O)N1[C@H](C#N)[C@@H](c2ccccc2)[C@@H]1CO 95897624 UKJFDLKEHROOFG-SOLBZPMBSA-N 342.420 2.036 30 1 EEEF N#Cc1c(NC(=O)C2CCCCC2)[n+]([O-])c2ccc(Cl)cc2[n+]1[O-] 299827795 RTLFJSAAOHBWIX-UHFFFAOYSA-N 346.774 2.150 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](COC(C)=O)CC/C=C(/C(=O)OC)CC[C@@H]12 14453278 DRSUBRLQXQEHHE-PJWMVSAYSA-N 336.384 2.327 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)Nc2ccncc2)[C@@H]1O 15469 USLZPNFABLSDEQ-CVEARBPZSA-N 338.367 2.348 30 1 EEEF Clc1cccc(C#CCOc2nsnc2C23CN4C[C@@H]2[C@H]3C4)c1 100811720 HPTGNTPIZBKTDN-ZIAGYGMSSA-N 343.839 2.435 30 1 EEEF COC1=C/C(=C/NNC2=NC(=O)[C@H](c3ccccc3)S2)C=CC1=O 13119062 ZEHAYTYWJUVUNC-NKSUMMKUSA-N 341.392 2.004 30 3 EEEF CC=CC(=O)O[C@@H]1C[C@@H]2OC[C@]23O[C@@H]2C=C(C)C(=O)C[C@@]2(C)[C@]13C 2356397108 GUTBYIDIQSFHLV-ZOLWUENMSA-N 332.396 2.346 30 1 EEEF CCO[P@](=O)(N[C@H](CC(C)C)C(=O)NO)c1ccc(OC)cc1 100812323 KTCRMROJXXSPQJ-FATZIPQQSA-N 344.348 2.060 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C(O)=C3C(C)(C)[C@H](O)CC[C@]3(C)[C@@]2(O)[C@@H](O)C1 2356460943 PYMRQNNIAHSRKU-HCIAYHKASA-N 348.439 2.183 30 1 EEEF C[C@@H]1NC(=O)[C@]23C[C@@H](O)[C@H]4[C@@H](CCC5=CC(=O)C=C[C@@]54C)[C@@H]2CC[C@H]13 137400432 ZFDFFZSCUSDQEX-MNDZJSSJSA-N 341.451 2.380 30 1 EEEF COc1ccc(-n2c3nc(=O)[nH]c(=O)c-3cc3ccc(C#N)cc32)cc1 96282699 SYMYDNJITZGATF-UHFFFAOYSA-N 344.330 2.059 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1CCC(COC(C)=O)=C1C[C@H](OC(C)=O)C(=C)[C@@H]12 238767482 BRBKGYDAQMCZSA-DKIMLUQUSA-N 346.379 2.246 30 1 EEEF Cc1[nH]n(-c2ccccc2)c(=O)c1/C=N/c1ccc2[nH]c(=O)[nH]c2c1 169692312 ZYDIVERIGXAEEC-VXLYETTFSA-N 333.351 2.394 30 1 EEEF C=CCONC(=O)[C@@H](C)N1C(=O)S/C(=C\c2ccccc2)C1=O 1857550192 XBYMOQGEFSSJTI-COVOJHCQSA-N 332.381 2.345 30 1 EEEF C#C[C@@H]1CN2CC[C@H]1C[C@@H]2CNC(=S)Nc1ccc(OC)cc1 2356298661 RSEHFCTVVFUHHR-IJEWVQPXSA-N 329.469 2.325 30 1 EEEF CC(=O)O[C@@H]1O[C@H](OC(C)=O)[C@H]2CC[C@H]3C(C)(C)[C@H]4C[C@@]23C1=CC4=O 2356696890 YUEBDHFRUOFFJT-WKNHCFJXSA-N 348.395 2.363 30 1 EEEF C[C@@H]1C[C@@H]2O[C@@H]2C=CC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 2356447605 XTUZVEOWUSGCSV-GTTSAUCSSA-N 330.336 2.038 30 1 EEEF CC(C)[C@]1(O)C=C2C(=O)C[C@H]3[C@@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@@H]2CC1 2356337241 TVHWXCUVXSEILO-DUSDWVPTSA-N 336.472 2.459 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@@]45CO[C@@H](O)[C@H]4C(C)(C)CC[C@H]5OC(=O)[C@@]3(C2)[C@@H]1O 2356410498 MSSXZZIDIPKYEB-ZFAVNPLQSA-N 348.439 2.016 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@H]2[C@@]12C[C@@H](O)C[C@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100778339 HHDWSDSMWJQURA-FHJPPIJZSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C[C@]12C=CC(=O)C=C1[C@](O)(CO)C[C@@H]1[C@@H]2CC[C@@]2(C)C(=O)CC[C@@H]12 2356460235 NQQZWPXWZWALLC-ITWPWFMSSA-N 330.424 2.197 30 1 EEEF CC[C@]1(C)C=C2C(=O)[C@@]3(O)OC(=O)[C@@]4(CCCC(C)(C)[C@H]34)[C@@]2(O)CC1 73220665 UVVLWVQILXUIKL-SQWSIXGCSA-N 348.439 2.495 30 1 EEEF N#Cc1ccnc(Oc2nn([C@H]3C[C@H](F)C3)c3ncnc(N)c23)c1 1911580567 USPIAMGRHIPYDO-MGCOHNPYSA-N 325.307 2.140 30 1 EEEF C=C1C[C@]23CC(=O)[C@H]4[C@@]5(C)CC(=O)C[C@]46[C@@H]([C@H]2C(=O)[C@H]1C[C@H]36)N(C)C5 95910365 MAYJMKOWBZXVIJ-AONQXHEUSA-N 339.435 2.026 30 1 EEEF biogenic,in-vitro COC1=CC(=O)C(OC)=C([C@H](O)CCCCCCCCCO)C1=O 1772623627 KYPYMRTZUANJOA-CYBMUJFWSA-N 340.416 2.043 30 1 EEEF C=C1N(S(=O)(=O)C(F)(F)F)CC[C@]12CN(C)c1ccccc12 206037493 VYKVSAIDHRGQDR-ZDUSSCGKSA-N 332.347 2.443 30 3 EEEF N#C[C@@H]1C[C@H](F)CN1C(=O)[C@@H](N)Cc1ccc(C(F)(F)F)cc1 103241551 MEPRZPLBMXAVKQ-AVGNSLFASA-N 329.297 2.038 30 1 EEEF CN(C)/C(=N\C#N)C1=CC(C)(C)Oc2ccc(S(C)(=O)=O)cc21 26149993 YNRXDVYBSZMVTC-SDXDJHTJSA-N 333.413 2.086 30 1 EEEF O=C(NO)[C@@H]1C[C@@H](c2ccc(Oc3ccc(F)cc3)cc2)C(=O)N1 199800318 TUIHSDQRXNNCLL-GJZGRUSLSA-N 330.315 2.096 30 1 EEEF CC1CCC(NS(=O)(=O)Cc2nc3ccc(C#N)cc3[nH]2)CC1 586953560 UXJMWXCKVIBOHG-UHFFFAOYSA-N 332.429 2.433 30 1 EEEF N#Cc1cc(C(=O)N[C@H](CO)c2ccccc2)ccc1-c1cn[nH]c1 1772618792 ZJTWQFQDQUDRQQ-GOSISDBHSA-N 332.363 2.412 30 1 EEEF COc1cc2ncc3c(c2cc1O)n(-c1ccc(C#N)cc1)c(=O)n3C 204229150 RMHILFHVHBDHDO-UHFFFAOYSA-N 346.346 2.463 30 1 EEEF CC[C@H](C)[C@H](NC(=O)C[C@H]1CCC(=O)[C@H]1CC=CCC=O)C(=O)O 2356812771 BLZRWMJJRGXFHK-LOUJCGABSA-N 337.416 2.123 30 1 EEEF CC[C@@H](C)[C@H](NC[C@@H](N)CS)C(=O)NCc1ccc(C)cc1C 38311863 ZBVDGGZJTGDHST-XYPHTWIQSA-N 337.533 2.181 30 1 EEEF C=C1[C@H](O)[C@@]23CC[C@@H]1C[C@H]2[C@@]12CCC[C@](C)(C(=O)OC1)[C@@H]2C[C@H]3O 238739530 YCDLVBJHTHGAOX-FLOUHHNOSA-N 332.440 2.434 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(C(=O)NCCO)cc1 587905789 HZMITFVRNLOLRM-UHFFFAOYSA-N 329.783 2.471 30 1 EEEF Cc1nc(/C(=N/c2ccc(Br)cc2)Nn2cnnc2)no1 6523578 CIXWKCHWZJWWEB-UHFFFAOYSA-N 348.164 2.054 30 1 EEEF O=C(NO)c1ccc2c(c1)C[C@H](NC(=O)c1cccc(Cl)c1)CN2 113848035 HSFAHSOUBJQFRE-AWEZNQCLSA-N 345.786 2.226 30 1 EEEF O=C1C=C[C@H](O)[C@H]2[C@H]1[C@H](O)CCC21Oc2cccc3cccc(c23)O1 238757205 XKRWQYCVELDJFF-CFGMGRTJSA-N 338.359 2.194 30 1 EEEF CCCS(=O)(=O)N1CCC(c2nc3ccc(C#N)cc3[nH]2)CC1 586953144 PELLHFANFBNXQC-UHFFFAOYSA-N 332.429 2.354 30 1 EEEF C=C(CO)[C@@H]1CC2=CC[C@@H]3[C@](C)(CO)[C@H](O)CC[C@]3(C)[C@H]2C[C@@H]1O 2356464951 VJVZOSZFDKSLNA-INCXTXFYSA-N 336.472 2.028 30 1 EEEF Cc1ccc2n(c1)cc(-c1ccc(/C=N/NC3=NCCCN3)cc1)[n+]2C 26835194 PAGBNLZOAKQCRE-FSJBWODESA-N 347.446 2.012 30 1 EEEF C=C1[C@H]2C(=O)C[C@H]3[C@@](CC[C@H]4C(C)(C)[C@@H](O)CC[C@]43C)([C@H]2O)[C@@H]1O 2356522498 JGAWMQVJTGKMKT-RRNINVNESA-N 334.456 2.067 30 1 EEEF NS(=O)(=O)c1c(F)c(F)c(N/N=C/c2ccccc2)c(F)c1F 95591678 FONSQMSMSCXXDM-KPSZGOFPSA-N 347.293 2.336 30 1 EEEF COc1ccc(C2=NO[C@](C)(C(=O)NO)C2)cc1OC1CCCC1 20039 SKSQSCQKTAQENI-KRWDZBQOSA-N 334.372 2.405 30 1 EEEF C=CCCC(=O)NCCOc1ccc(C[C@@H]2SC(=O)NC2=O)cc1 26502602 WHPJZXYAGCQXGA-AWEZNQCLSA-N 348.424 2.042 30 1 EEEF CC1=C(C(=O)O)C(=O)C[C@H]2CCC[C@]3(C(=O)Nc4ccccc43)N12 111955814 QQDWEMDBMCNRPU-ZMZPIMSZSA-N 326.352 2.020 30 1 EEEF CC(=O)[C@H](O)Cc1c(O)ccc(C(=O)C=Cc2ccc(O)cc2)c1O 2356784045 MZOMYVOGPUTEFR-GOSISDBHSA-N 342.347 2.192 30 1 EEEF Cc1cc(C(=O)Nc2ccc([C@H]3CNCCO3)c(F)c2)cc(C#N)n1 149875817 QHJVJEHMHYPQPH-QGZVFWFLSA-N 340.358 2.314 30 1 EEEF N#CC1(n2cc([C@@H](NC(=O)c3cocn3)C3CCCCC3)nn2)CC1 95560591 RUCXDHDXCJCYIR-HNNXBMFYSA-N 340.387 2.330 30 1 EEEF N#Cc1cc([C@H]2N[C@@H](C(=O)O)Cc3c2cnc2ccccc32)ccn1 963229373 KMSBPESAZVWSRQ-QZTJIDSGSA-N 330.347 2.190 30 1 EEEF C=C1C[C@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@@H](O)CO)[C@@H]2C[C@@H]1CC3 169349427 FYKIZBPSTADBEK-UKSSEWCLSA-N 348.439 2.171 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]12CC[C@H](O)[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 100191913 XBDTWBSMNXMGIJ-CPSMVOCUSA-N 346.423 2.225 30 1 EEEF in-vitro O=C(CCc1ccc2c(c1)OCO2)Nc1ccc(C(=O)NO)cc1 45254401 IQNJWPAFRXXXMQ-UHFFFAOYSA-N 328.324 2.106 30 1 EEEF C=C1C[C@]23C[C@@]1(O)CC=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 238754755 QQZHQZNECSBZML-PZWCKASYSA-N 344.407 2.289 30 1 EEEF CC(=O)C1=CC[C@H]2[C@@H]3CC[C@H]4[C@H](O)[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C 2356512834 GKCFQKGBOYKBGP-LUCSZFGISA-N 348.483 2.457 30 1 EEEF CCOc1ccnc(CCNC(=S)Nc2ccc(C#N)cn2)c1F 3873317 PQSCCWFMTRVFDA-UHFFFAOYSA-N 345.403 2.415 30 1 EEEF in-vivo CCCCCCCCCO[C@@H]1C=C(C(=O)O)C[C@H](N)[C@H]1NC(C)=O 4646292 QYNCJYWGTMZSNV-GVDBMIGSSA-N 340.464 2.369 30 1 EEEF CC(C)C1=C[C@H]2C[C@@]3(C=O)[C@@H]4CC[C@@](C)(O)[C@H]4C[C@@]2(CO)[C@@]13C(=O)O 2356465761 GEHSSDSUIBHHAH-HQYDJIAXSA-N 348.439 2.018 30 1 EEEF C=C(C)C(=O)O[C@H]1CC2=C[C@H](C/C(C)=C\[C@H]3OC(=O)C(=C)[C@@H]13)OC2=O 34577860 JMUOPRSXUVOHFE-NFOXUEAISA-N 344.363 2.164 30 1 EEEF CCC#CCOC(=O)CNC(=O)c1coc(-c2ccccc2C)n1 82072285 HGEZYBKKVSTOEF-UHFFFAOYSA-N 326.352 2.336 30 1 EEEF CCOC1=C/C(=C/NNc2nncc(-c3ccccc3)n2)C=CC1=O 15953241 FNKZAWQVWVNHDA-ACCUITESSA-N 335.367 2.398 30 3 EEEF C[C@@H](/N=c1/c(NC(=O)c2ccc(C#N)cc2)c(O)c1=O)C(C)(C)C 101179024 RYODQKBZBBAMKI-JPYHIROTSA-N 325.368 2.087 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)(CCC[C@@]4(C)C=O)[C@@H]2C[C@@H](O)[C@H]1[C@H]3O 2356672640 RNQLPXGROISTQX-DQAPRGMSSA-N 332.440 2.275 30 1 EEEF O=CC(C=O)c1ccc(-c2nc3cc(F)cnc3[nH]2)cc1[N+](=O)[O-] 587261821 JRVOVFZBANLBNP-UHFFFAOYSA-N 328.259 2.154 30 1 EEEF N#C[C@H](C(=O)Nc1ccc(C(F)(F)F)cc1)C(=O)[C@H]1CCCN1 169714923 AVJJSTSKKNYXAA-NWDGAFQWSA-N 325.290 2.105 30 1 EEEF O=C(N[C@@H](Cc1ccccc1)C(=O)O)[C@@H](S)Cc1ccccc1 13747260 KIMKJXCMBALPEJ-HOTGVXAUSA-N 329.421 2.340 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@H](NC(=O)c2ccc(C#N)cc2)[C@@H]1O 40503872 FZBBUIVMCCYQOP-ROUUACIJSA-N 347.374 2.433 30 1 EEEF COC(=O)CCCC#Cc1ccc(Cn2cc(C)c(O)nc2=O)cc1 653663521 JDCPZRWDRXIXOU-UHFFFAOYSA-N 340.379 2.000 30 1 EEEF N#Cc1nc2nc(-c3cc(Br)cnc3F)[nH]c2nc1C#N 587178204 VDKGXQBNMMTHCZ-UHFFFAOYSA-N 344.107 2.060 30 1 EEEF C=C(C)[C@@H]1CC[C@]2(CO)OC(=O)C3=C(CC(C)=O)C(=O)C(C)=C[C@H]1[C@@H]32 2356411334 MMENEXZIHVFHNM-AMVBQIFNSA-N 344.407 2.298 30 1 EEEF C=C1CCC=C(C)CC[C@H]2C(=CC=CC(O)(CO)CO)COC(=O)[C@H]12 2356427347 WVMYRDBAJSJKGW-ZWKOTPCHSA-N 348.439 2.050 30 1 EEEF O=C(NO)[C@@H](CCc1ccccc1)C(=O)NCCCc1ccccc1 3919983 XKSDROXJWZNHOT-SFHVURJKSA-N 340.423 2.490 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@H]1CC[C@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100778343 MBNDVMTZEKAWKP-MOCONCIESA-N 332.396 2.136 30 1 EEEF endogenous,in-man C#C[C@]1(O)CC[C@@H]2[C@@H]3C[C@H](O)c4cc(OC)ccc4[C@@H]3C[C@@H](O)[C@@]21C 2356584249 YTRCAZOTWYOCGG-RJQKVZOFSA-N 342.435 2.377 30 1 EEEF C=C1CC[C@]2(O)OC(=O)C(C)=C2[C@H]2[C@@H]1C1=C(C[C@@H](C)C1=O)[C@H]1O[C@]12C 238768719 GALZHQYJPOPISQ-HCRWOEOASA-N 342.391 2.207 30 1 EEEF C=C[C@]1(C)C=C2C(=CC1)[C@]13C[C@@H]1CC[C@]1(C)C(=O)O[C@@](O)([C@H]13)[C@@H]2O 2356396828 XHJCBVNMOHCTOP-HPNNZRBTSA-N 328.408 2.478 30 1 EEEF COc1ccc(C2=NO[C@@](C)(C(=O)NO)C2)cc1OC1CCCC1 3812219 SKSQSCQKTAQENI-QGZVFWFLSA-N 334.372 2.405 30 1 EEEF C=C1C[C@@]23C[C@]1(O)CC[C@H]2[C@@]12C=CC[C@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100784054 UXLXLQYIDWLPKX-XJBLYOGMSA-N 330.380 2.056 30 1 EEEF endogenous,in-man CC(C)=C1NC(=O)[C@](CC=CC[C@H](C)O)([C@H]2CC(=O)O[C@@H](C)C2)C1=O 2356490432 IIYKLCYWWXLYAF-WZFJYNIESA-N 349.427 2.025 30 1 EEEF C[C@@H]1CC2=C([C@@H]1O)[C@H](O)[C@]1(C)CC[C@@H]3[C@H]([C@H](O)[C@@]1(C)C2=O)C3(C)C 2356843631 NNSBPFCEWFSYFB-VFBCAGNVSA-N 334.456 2.067 30 1 EEEF O=C1C=C2CC[C@@H]3[C@@H]([C@@H]2CC1)[C@H]1C[C@@]2(CO1)[C@H](C(=O)CO)CC[C@H]32 2356416618 ZQTXDFVYZQQLOY-MZGDTODISA-N 330.424 2.295 30 1 EEEF C[C@@H]1CN2C[C@H]3CCC4=C5[C@](O)(CC[C@@]56C(=O)[C@@H]1C[C@@H]2[C@@]36C)CC4=O 59353062 BASSTWHCAWRGHM-BOSSYYJLSA-N 341.451 2.106 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(C)C(=O)CC[C@](C)(C(=O)O)[C@@H]1C[C@@H]3O 2356487490 CLGOGJHVMHIUDO-PHPZCVMGSA-N 346.423 2.369 30 1 EEEF CCCCCCCCC[C@@H]1C[C@H](O)[C@@H](O)C=C[C@H](O)CC(=O)O1 2356721137 VKFBQLMPTJTKBZ-YVSFHVDLSA-N 328.449 2.472 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@]2(CCNC[C@H]2C#N)N1 587792181 GZQSQLGJENUGLF-XDMRBOTDSA-N 338.224 2.451 30 1 EEEF O=CC(C=O)c1ccc(-c2nc3cc4cn[nH]c4cc3[nH]2)cc1[N+](=O)[O-] 587261982 KXDPQPGYPHDQBT-UHFFFAOYSA-N 349.306 2.496 30 1 EEEF COc1ccc(C=CC(=O)c2c(O)cc(O)c(OC)c2O)cc1O 2356689961 GYEZIQDCZWTBTP-UHFFFAOYSA-N 332.308 2.422 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1CCC(=C)[C@]1(O)C[C@@H](OC(=O)C(C)C)C(=C)[C@H]21 2356650627 LUUJHRSUAVIZOX-DINLJIAVSA-N 332.396 2.309 30 1 EEEF CC[C@@H]1C=NN(/C(=N/S(=O)(=O)c2cccc(Cl)c2)N(C)C)C1 72122932 DBUZGONQGQCYAT-HKOCCSETSA-N 342.852 2.274 30 1 EEEF N#CCOC(=O)[C@H](Cc1ccccc1)NC(=O)/C=C/c1ccccc1 169347847 WXDOQYATAKOXFQ-DXRVJIQQSA-N 334.375 2.494 30 1 EEEF C#C[C@]12O[C@]1(C=O)[C@@H]1[C@H](O)C[C@@H]3C(C)(C)CCC[C@]3(C)[C@@H]1CC2=O 2356471217 RLCVKAJQPCOLQK-GRUHCGSISA-N 330.424 2.129 30 1 EEEF CC1=CCCC[C@@H]2O[C@]23CC(=O)O[C@@H]3c2c(O)ccc(O)c2[C@H]1O 2356403621 PHCAOFZRCKAKBR-DUOKCRBOSA-N 332.352 2.387 30 1 EEEF COc1cccc(C#C[C@H](O)[C@H]2[C@@H](c3ccccc3)CC(=O)N2C)c1 28461159 HEVJWFAENYQBKM-SVFBPWRDSA-N 335.403 2.422 30 1 EEEF N#Cc1nc2nc([C@@H]3CS[C@H](Cc4ccccc4)N3)[nH]c2nc1C#N 587040602 IHUXBNSHRYAUJR-UONOGXRCSA-N 347.407 2.043 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(COC3=O)[C@H]2CC[C@@]3(C)CO[C@H](O2)[C@@H]13 2356350123 VGHUWBCJSRMGIQ-QFIHHOAPSA-N 344.407 2.243 30 1 EEEF C=C1C(=O)O[C@@H]2C3=C(C)C(=O)C[C@@H]3[C@](C)(O)C[C@@H](OCC(C)C)[C@@H]12 2356491344 IDJQTNTZPPTSEU-MVGUPFISSA-N 334.412 2.186 30 1 EEEF C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@@H]2C(=CC=CC(C)(C)O)COC(=O)[C@@H]12 2356613193 CHWOLNBRUULGCY-ZPFYTHJMSA-N 348.439 2.288 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@@]2(N1)C(=O)C=CN[C@@H]2C 587792919 INJXIIPYPDFSAK-KEMUVXCRSA-N 339.208 2.392 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@]2(COC[C@@H]2C#N)N1 587739116 FRFVAZZMRPQOFX-IPURGOFSSA-N 325.181 2.488 30 1 EEEF N#CC1CN(C[C@H]2CC[C@H](c3nnn4cnc5[nH]ccc5c34)CC2)C1 1772606214 UTOILZPWKFKSCQ-MQMHXKEQSA-N 335.415 2.335 30 1 EEEF CC(C)[C@]1(O)C=C2C(=O)C[C@@H]3C(C)(C)[C@H](O)CC[C@]3(C)[C@@H]2C[C@H]1O 2356336805 NHJLCDALTNPYBE-TWQAGNNBSA-N 336.472 2.457 30 1 EEEF C[C@H]1CCC(/C=N/c2ccc(F)cc2)=C2NC=C(C(=O)O)C(=O)N21 100775129 KSRPRRVIDJZIJB-WHGJXMNKSA-N 329.331 2.322 30 1 EEEF CCCc1nc(N)nc(N)c1C#CCc1cc(OC)ccc1OC 45484447 VSWSZIRWLYCVMG-UHFFFAOYSA-N 326.400 2.205 30 1 EEEF in-vitro C=CCn1c(=O)c(NCC(C)C)c2n(c1=O)[C@H](c1ccccc1)CN2 82224353 KOJAAMGLIXQWFF-HNNXBMFYSA-N 340.427 2.279 30 1 EEEF O=C(NO)[C@H]1CCC[C@@H]1S(=O)(=O)c1ccc(Cl)c(Cl)c1 1857586719 PAVNSONEORCDOC-KWQFWETISA-N 338.212 2.441 30 1 EEEF C=C1C[C@H](OC(=O)C(C)C)[C@@H]2[C@H](C)C(=O)O[C@@H]2[C@@H]2[C@@H]1C[C@@H]1O[C@]12C 2356557722 ZEIPBAWKAWZVOR-XIAWZUSXSA-N 334.412 2.485 30 1 EEEF C=C1[C@H](O)C[C@H]2[C@](C)(C[C@@H](O)C[C@@]2(C)CO)[C@H]1CCC(C)=CCO 2356639999 LCWHTWNKEOSQBZ-YDETXVTLSA-N 338.488 2.418 30 1 EEEF C[n+]1cccc(/N=C(\O)c2ccc(C(=O)Nc3ccc[n+](C)c3)cc2)c1 33857901 PIBMEDBCFLFOGD-UHFFFAOYSA-P 348.406 2.224 30 1 EEEF Cc1nn(-c2ccc([N+](=O)[O-])cc2)c(O)c1/C=N/C[C@H]1CCCO1 101888683 WDMAQOAAIYXHRE-NGWPFTMJSA-N 330.344 2.392 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@](C)(O)C(=O)CCC(C)=C[C@@H]2OC(=O)C(=C)[C@H]21 2356754585 AYLHAROHTWZRTO-ZDXGLAPJSA-N 348.395 2.022 30 1 EEEF COc1ccc(Nc2nc(N)n(-c3ccc(C#N)cc3)n2)cc1OC 72127881 BMTGHPXGBMXSDX-UHFFFAOYSA-N 336.355 2.482 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1C[C@H]1O[C@]1(CO)CC/C=C(\C)CC/C=C(\C)[C@H]2O 40892353 MULWDJOXRRXULO-SVZQVSRYSA-N 348.439 2.432 30 1 EEEF C=C(C)C#C[C@@](O)(C(=O)O[C@@H]1CN2CCC1CC2)c1ccccc1 1641750 GBTXSVZHHMYRNF-QUCCMNQESA-N 325.408 2.091 30 1 EEEF N#Cc1ccc2c(c1)[C@@H](N1CCCCC1=O)[C@H](O)C(CF)(CF)O2 26734143 CMVGCVMVWIIPKS-CVEARBPZSA-N 336.338 2.043 30 1 EEEF N#CCNC(=O)[C@H](Cc1cccc(Cl)c1)NC(=O)c1ccccc1 43016041 NFHCBRWUVWGFHZ-INIZCTEOSA-N 341.798 2.321 30 1 EEEF N#C[C@H]1C[C@H](O)CC[C@H]1n1cc(C(N)=O)c(Nc2ccc(F)cc2)n1 221213141 USZHEZVXLJZXEW-WDBKCZKBSA-N 343.362 2.090 30 1 EEEF Nc1ccnc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)c1N 587889173 GYARNNAHWWHEFE-UHFFFAOYSA-N 349.221 2.263 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)[C@H](C)C[C@@H]2OC(=O)C(=C)[C@H]12 15165981 KYTKEOOPALLADL-RNNKMICHSA-N 346.379 2.244 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(C)(C)C)[C@H]1[C@@](C)([C@@H]2O)[C@H]2CC[C@@]1(C)O2 2356544662 XVJNAEOCXFSHRU-RQCNVRKMSA-N 336.428 2.216 30 1 EEEF O=C1C(=O)c2cccc3c2C(=C1Cl)OC[C@H]3n1cc(C2CC2)nn1 96934587 TUYWFDDYXKGSOA-GFCCVEGCSA-N 341.754 2.448 30 1 EEEF CCCCCCCOc1ccc(-n2cc(C(=O)NCCN)nn2)cc1 1772593387 HUFITZGWISIDBH-UHFFFAOYSA-N 345.447 2.305 30 1 EEEF C=C1C[C@H](O)[C@@H]2C(=C)C(=O)O[C@@H]2[C@@H]2C(=C)[C@@H](OC(=O)C(C)=CC)C[C@H]12 2356654401 UINWHHMWCJPCDZ-CMURFVSUSA-N 344.407 2.475 30 1 EEEF CCCCCCCCC#Cc1cn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]c1=O 44086533 AIBWJKBBEOYYME-DLBZAZTESA-N 348.443 2.309 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]12CO[C@@H]4OC[C@](C)(CC[C@@H]1OC3=O)[C@@H]42 95884395 QRZAIOQXVJRCBS-OSKYZRHQSA-N 344.407 2.243 30 1 EEEF biogenic,in-vitro O=C1C=C2CC[C@@H]3[C@H]([C@@H]4C[C@]5(CO4)[C@@H](C(=O)CO)CC[C@@H]35)[C@@H]2CC1 255287623 ZQTXDFVYZQQLOY-LODOXEDVSA-N 330.424 2.295 30 1 EEEF N#Cc1cc2nc(-c3cnc4ncnn4c3C(F)F)[nH]c2cc1C#N 587128203 IPDHKZXAKKOGMW-UHFFFAOYSA-N 336.265 2.349 30 1 EEEF C=CCc1cccc2[nH]c(-c3cc(S(=O)(=O)NC)cn3C)nc12 586947085 KFJVHNGTVUWQLE-UHFFFAOYSA-N 330.413 2.205 30 1 EEEF CCCCCC[C@@H](C(=O)NO)S(=O)(=O)c1ccc(OC)cc1 13585928 VMCQYTNLTZJCIG-AWEZNQCLSA-N 329.418 2.313 30 1 EEEF COc1cc(OC)nc(N2C(=O)CS[C@H]2c2ccc(C#N)cc2)n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c1c(O)cc2c(c1O)c(=O)c1cccc(O)c1n2C 14819120 DXPXJTFEUAMACU-CQSZACIVSA-N 341.363 2.288 30 1 EEEF biogenic Cc1c2c(n(CCc3ccccc3)c1C)N(C)N=C(C#N)S2(=O)=O 1860828 VFCHZXHXTNVJKS-UHFFFAOYSA-N 342.424 2.408 30 1 EEEF COC1=CC(=O)[C@]2(O)C[C@@H]3[C@H](c4ccccc4C3(C)C)[C@@H](O)C2=C1 15122217 VZQCDBNQPVXLLR-HYJFEMIMSA-N 326.392 2.213 30 1 EEEF biogenic COc1cccc(C2=NNC(=O)/C2=N\Nc2ccc(N(C)C)cc2)c1 49034001 HNJSMMNHEPKWIB-UHFFFAOYSA-N 337.383 2.063 30 1 EEEF Cc1cccc(N/N=C2\CC[C@@H](C)n3c2ncc(C(=O)O)c3=O)c1 40466752 WUHFIBQMXMWMIL-OHARDZCESA-N 326.356 2.421 30 1 EEEF C=C(C)[C@H](O)COc1cc(O)cc2c1-c1c(O)ccc(O)c1C2=O 238788801 SVLCTBWISIZGTK-CYBMUJFWSA-N 328.320 2.331 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)[C@H](C)C[C@H]2OC(=O)C(=C)[C@H]12 15165984 KYTKEOOPALLADL-VYTVBFMPSA-N 346.379 2.244 30 1 EEEF C[C@](O)(COc1ccc(F)cc1)C(=O)N1CCc2c(C#N)cccc21 169313268 URFJTFLKZYWYJR-IBGZPJMESA-N 340.354 2.416 30 1 EEEF C=CCc1cc(NC(=O)NC)ccc1OC[C@H](O)CNC(C)(C)C 169317260 UAFMUJDYUGVGJH-OAHLLOKOSA-N 335.448 2.294 30 1 EEEF C[C@@H]1C[C@]23C(=O)[C@H](C)C[C@@H]4C(C)(C)[C@@]45O[C@@](C)(C=C2C1=O)[C@@H](O)[C@@H]35 2356522874 XKHKWWYWWNXZDZ-PVQLJPOUSA-N 330.424 2.291 30 1 EEEF C=C[C@@H]1C=C2C(=O)C=C3[C@](C)(C(=O)O)CC[C@H](O)[C@]3(C)[C@@]2(O)CC1 2356788682 CHLJNZOUECQLLK-GOFXCJRXSA-N 332.396 2.001 30 1 EEEF C=C1[C@@H](O)C[C@H]2C(C)(C)[C@@H](O)CC[C@]2(C)[C@H]1C/C=C1/COC[C@H]1O 73162256 PQJNKPQZAXZXLP-HKMYURLRSA-N 336.472 2.434 30 1 EEEF CCc1nnc(/N=C(\O)CCc2nc(C3=CCN(C)CC3)no2)s1 49743453 XQSYZRLTPFPORF-UHFFFAOYSA-N 348.432 2.423 30 3 EEEF CC(=O)N1N=C(c2ccc(C#N)cc2)O[C@@H]1c1ccc([N+](=O)[O-])o1 96913469 URCDUIGRLYQTAC-OAHLLOKOSA-N 326.268 2.299 30 1 EEEF COCC(=O)N1[C@H](CO)[C@@H](c2ccccc2C2=CCCC2)[C@@H]1C#N 95867995 OERKOXUAKKWALJ-SCTDSRPQSA-N 326.396 2.079 30 1 EEEF N#Cc1ccc(-c2ccc3c(c2)OC[C@@H]2[C@@H](CO)SC(=O)N32)cn1 299869357 UMOJOKQCEXAYIR-GDBMZVCRSA-N 339.376 2.415 30 1 EEEF COc1cc[nH]c1/C=C1\C(=O)Nc2ccc(F)c(C#C[C@@H](C)O)c21 14947102 DJEJXDSNSASKPZ-WJEYQPDNSA-N 326.327 2.387 30 1 EEEF Cc1cccc(NC(=O)C2=C/C(=C3/C=C(Cl)C=CC3=O)NN2)c1 103917976 YKMNFJQFSUYWHN-BUHFOSPRSA-N 327.771 2.441 30 3 EEEF C=C(C)C(=O)O[C@@H]1CCC(=C)[C@@H]2[C@@H]3OC(=O)[C@H](C)[C@@H]3[C@H](O)C[C@]21C 2356480137 QHTWVJOMDDBORA-QHIMXNGFSA-N 334.412 2.389 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@]3(C)C[C@H](OCC(C)C)[C@H]12 2356671227 RDYCVUNQBCWGOT-FTGINLBMSA-N 336.428 2.384 30 1 EEEF C=C[C@@H]1C(=C)CC[C@@H]2[C@@H]1CC(=O)[C@@]1(O)[C@@](C)(C(=O)O)[C@@H](O)CC[C@]21C 2356720506 BSSPIUBSZQCUDG-KSVPOGTQSA-N 348.439 2.327 30 1 EEEF Cc1nc2n(c(=O)c1C(=O)O)[C@H](C)CCC2=NNc1ccccc1 253689906 PTMLSROVUJDKCJ-SNVBAGLBSA-N 326.356 2.421 30 1 EEEF C[C@@H]1NC=CC(=O)[C@]12Oc1ccccc1C(=O)[C@@H]2C(=O)c1ccco1 587597087 SBOAAVAUODSRDI-YARKZXGKSA-N 337.331 2.167 30 1 EEEF COc1ccc(S(=O)(=O)[C@](C)(CC=C(C)C)C(=O)NO)cc1 13520771 COEXRWHXVMMHEF-OAHLLOKOSA-N 327.402 2.089 30 1 EEEF CC(=O)c1cc(C)c(O)c(CC2=C(C)C(=O)C(O)=C(C)C2=O)c1O 169311932 AUXPTCQGDZVDQE-UHFFFAOYSA-N 330.336 2.452 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)Cc2ccccc2)[C@@H]1O 15467 PUIJYFMVVBJSLW-MOPGFXCFSA-N 336.391 2.490 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(C)C(=O)CC[C@](C)(C(=O)O)[C@@H]1C[C@H]3O 2356487489 CLGOGJHVMHIUDO-OSHCZGFSSA-N 346.423 2.369 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@]2(CC[C@@H]3C(=CC=CC(C)(C)O)C(=O)OC[C@@H]13)CO2 2356803327 WZDCQTZIRFGNEC-ZPHFWKLASA-N 346.423 2.306 30 1 EEEF Cc1ccc(/C=N/n2c(=O)n(-c3ccncc3)c(=O)c3ccccc32)o1 34334810 JQRASMDFBHRKFY-CIAFOILYSA-N 346.346 2.331 30 1 EEEF CCCCCCC[C@@H](O)[C@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12 89469606 ZNDOHEBDAFJMEG-OWTLIXCDSA-N 329.462 2.471 30 1 EEEF C=C1C(=O)O[C@@H]2[C@H]3C(C)=CCC3=C(C)C[C@@H](OC(=O)/C(O)=C/CO)[C@@H]12 238739249 SWIFBBRXRXNLBH-LZMZYPTJSA-N 346.379 2.117 30 1 EEEF C=C1C=CC2=C(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3C(=C)C(=O)O[C@@H]3[C@@H]12 238760357 GWTNNINCUJQCGQ-NNPSNHGLSA-N 344.363 2.020 30 1 EEEF C=C1C(=O)O[C@H]2C[C@@]3(C)OC(=CC3=O)/C(C)=C\[C@@H](OC(=O)C(C)C)[C@H]12 238746496 JHZYGPMGMMUUTG-MFRWKCHVSA-N 346.379 2.244 30 1 EEEF Cc1nc(N)cnc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587889823 YUNOWZYTPJSCTH-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF CC=C(C)C(=O)O[C@@H]1C[C@H](O)C2=CC(=O)C(C(C)(C)O)=C[C@]2(C)[C@H]1C 2356594907 LHZKEPWOCHFOLY-VDESFZGPSA-N 348.439 2.478 30 1 EEEF O=S(=O)([C@H]1O[C@H]1c1ccccc1)N1CCN(c2ccccc2)CC1 26291969 UPZFQDXXSQSJFN-ZWKOTPCHSA-N 344.436 2.236 30 1 EEEF CC(C)C[C@H](NC(=O)c1ccccc1C(F)(F)F)C(=O)NCC#N 82064976 MIZGLZUZKGZYDY-ZDUSSCGKSA-N 341.333 2.490 30 1 EEEF C=C([C@H](O)/C=C/[C@@](C)(O)CO)[C@@H]1CC(=O)[C@]2(C)[C@H]3CC[C@@H](C)[C@H]3[C@H]12 145395879 PIQKTPMDCOQYRT-HQXRUAAMSA-N 334.456 2.090 30 1 EEEF CC(C)C[C@](C)(O)c1cn(C2=CC(=O)c3cccc(O)c3C2=O)nn1 1857544417 ZAWKKFCMFOXGOT-SFHVURJKSA-N 341.367 2.157 30 1 EEEF CCCCN/C(N)=N\c1nc(-c2ccc(CNC(C)=O)o2)cs1 3923000 YECLWVVYRAOYHZ-UHFFFAOYSA-N 335.433 2.375 30 1 EEEF CCCCCCCCC[C@@H]1OC(=O)C[C@H](O)C[C@H](O)C=C[C@H]1O 2356619470 HFGOXJHLMBNOHC-VQHPVUNQSA-N 328.449 2.472 30 1 EEEF CCCCCCCCCNCC(F)(P(=O)(O)O)P(=O)(O)O 1857560326 PTZUSRHURJXIOB-UHFFFAOYSA-N 349.276 2.305 30 1 EEEF COC1=C[C@@]23CCN(C)[C@H](Cc4cc(OC)c(OC)cc42)C3=CC1=O 100266422 DBPGJIUVRZHFCM-QRWLVFNGSA-N 341.407 2.241 30 1 EEEF C=C[C@@H]1[C@]2(C)C[C@H](C(=O)[C@@]1(C)CO)[C@]1(C)O[C@H]3/C(=C\C)C(=O)O[C@H]3[C@H]21 195839292 UAVHCHBOMMAUHU-ACMOEVLOSA-N 346.423 2.042 30 1 EEEF COc1cccc(-n2cc(Cn3cc(/C=N/O)c4cccnc43)nn2)c1 653717065 KCJFBMJBKRTJDP-AWQFTUOYSA-N 348.366 2.482 30 1 EEEF N#C[C@H](c1cccnc1)N1CCN(C(=O)CCc2ccccc2)CC1 13728967 JPGLHQCUFYGSDQ-LJQANCHMSA-N 334.423 2.423 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@]4(C)CCC[C@](C)(CO)[C@@H]4CC(=O)[C@@]3([C@@H]1O)[C@@H]2O 2356407505 DBVNQUBNOIPPEM-HASVXSATSA-N 334.456 2.068 30 1 EEEF CC(C)[C@]1(O)C=C2C(=O)C[C@@H]3C(C)(C)[C@H](O)CC[C@]3(C)[C@H]2C[C@H]1O 2356336804 NHJLCDALTNPYBE-HGEBXIKFSA-N 336.472 2.457 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@H](C)[C@@]2(O)C=C(C)[C@@H](C[C@@H]3OC(=O)C(=C)[C@H]31)O2 2356287792 PWWKARNXEFCPJO-LAJWIDPJSA-N 348.395 2.036 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1CCC(COC(=O)C(C)C)=C1C[C@@H](O)C(=C)[C@@H]12 2356644496 INJHISWMTROACX-MXASKKJJSA-N 332.396 2.311 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H](C(C)=O)[C@@]3(C)[C@@H](C(C)=O)CC[C@@](C)(O)[C@H]3[C@@H](C)[C@H]12 2356678065 QRJWNJLDUSTASQ-VLJDXLDGSA-N 348.439 2.312 30 1 EEEF C=C[C@@H]1C(=C)CC[C@@H]2[C@@H]1CC(=O)[C@@]1(O)[C@@](C)(C(=O)O)[C@H](O)CC[C@]21C 2356720505 BSSPIUBSZQCUDG-HLLQXRNWSA-N 348.439 2.327 30 1 EEEF CCCc1cnc2c(C#N)c(N3CCN(c4ncccn4)CC3)ccn12 45349632 LLLLOHWLVHBXQH-UHFFFAOYSA-N 347.426 2.275 30 1 EEEF C[C@H](Sc1nc(N)cc(O)n1)c1nc2cc(C#N)c(C#N)cc2[nH]1 586961568 KEDQBTHXTBJRLN-ZETCQYMHSA-N 337.368 2.237 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@H]2C(=C)C[C@H](O)[C@@H]3C(=C)C(=O)O[C@H]3[C@H]2C1=C 2356532142 RWWQHQZKBAELGL-DZTUFKMZSA-N 330.380 2.085 30 1 EEEF COC1=CC(=O)[C@]2(C)c3c(O)c(C)c(O)c(C(C)=O)c3O[C@]2(OC)C1 2356835304 KQROSALZXGEZDK-QZTJIDSGSA-N 348.351 2.105 30 1 EEEF C=CCNC[C@@H](O)COc1ccc2c(=O)c3ccccc3oc2c1 38691906 QUAWTSJEZZGHFW-CYBMUJFWSA-N 325.364 2.462 30 1 EEEF COc1ccc(C)cc1C(=O)CCc1nc2nc(C#N)c(C#N)nc2[nH]1 587788036 ULGTUKMIJIHGSS-UHFFFAOYSA-N 346.350 2.229 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnn(CCC(=O)N(C)C)c1 587909492 SRNSFDAYTMULHG-UHFFFAOYSA-N 331.803 2.423 30 1 EEEF CC1(C)CCC[C@@]2(C)O[C@]12/C=C/c1cc(S(C)(=O)=O)nc(N)n1 101412199 SKULGIFBFWXBLY-HKFHSAMXSA-N 337.445 2.213 30 1 EEEF CCOC(=O)c1ccc(Oc2nc[nH]c(=O)c2/C=C/C(C)=O)cc1 72139895 MKRCJRKXDMLVKG-RUDMXATFSA-N 328.324 2.341 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1C[C@H](O)[C@H]2[C@]1(C)CCC[C@@](C)(C(=O)O)[C@H]1C[C@@H]3O 84618233 BSPNTRYRRCCKFJ-UCWNZCKUSA-N 348.439 2.161 30 1 EEEF C=C(C)C(=O)O[C@H]1CC(=C)[C@H]2C[C@H](O)C(=C)[C@@H]2[C@H]2OC(=O)[C@H](C)[C@@H]12 238736977 IXOAQFFFKPCXLB-LKCSHLFESA-N 332.396 2.165 30 1 EEEF C[C@@H]1C[C@H]2O[C@H]2CCCCC(=O)Cc2cc(O)cc(O)c2C(=O)O1 33981995 YXPSTSCHAVSCKS-HPEXNQPKSA-N 334.368 2.486 30 1 EEEF biogenic C=C[C@]1(C)C=C2C(=O)C[C@@H]3C(C)(C)[C@H](O)C[C@H](O)[C@]3(C)[C@]2(O)CC1 2356415873 ZTWPAGAVIFLSKK-OWJTWYAJSA-N 334.456 2.377 30 1 EEEF C=C1C(=O)[C@@]23CC(=O)[C@@H]4C(C)(C)CCC[C@]4(C)[C@@H]2[C@H](O)C[C@H]1[C@@H]3O 2356397834 JLKBHAAAVQFJPZ-WKRGYCEKSA-N 332.440 2.275 30 1 EEEF Clc1ccc(C#CCOc2nsnc2C23CN4C[C@@H]2[C@H]3C4)cc1 100829312 JVDFDVTZQWJMQV-ZIAGYGMSSA-N 343.839 2.435 30 1 EEEF CC1=NC(=N)S/C1=N\Nc1c(C)n(C)n(-c2ccccc2)c1=O 100509762 WRLIBUCLZVXFDE-VKYZZDNRSA-N 328.401 2.352 30 3 EEEF C[C@@]12CC[C@](C)(O1)[C@@H]1C(=O)N(c3cnc(C#N)c(Cl)c3)C(=O)[C@@H]12 100075917 VKOUOBLCMIKWHV-VZAMPYOESA-N 331.759 2.054 30 1 EEEF CCN1C(=O)N(CC)[C@H]2NC(=S)N(/N=C/C=C/c3ccccc3)[C@@H]21 1857645994 ZKFBHJXHPXBJBI-RNDHMKDESA-N 343.456 2.305 30 1 EEEF COc1cc2c(cc1O)[C@]1(C#N)CCC3(OCCO3)C3=CO[C@H](C2)[C@@H]31 73165922 XNLXOUVEEFCNBM-KZNAEPCWSA-N 341.363 2.154 30 1 EEEF C=C(C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H]3O[C@@]3(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 238782317 CJKLZISKIDBYNR-ZYKWKZBQSA-N 330.380 2.326 30 1 EEEF C=C1C[C@]23C[C@H]1[C@H](O)C[C@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@@H]2[C@@H]3C(=O)O 238731084 ZCRLGANQNRMURE-NEQAEMHNSA-N 346.423 2.384 30 1 EEEF C=C1CCN([C@H](C(=O)OC)C(C)C)S(=O)(=O)c2ccc(F)cc21 13661082 UPAXSQGOHNYEOQ-HNNXBMFYSA-N 341.404 2.431 30 3 EEEF N/C(=N/C(=O)NC1CCCCC1)N/N=C/c1c[nH]c2ccc(O)cc12 13741844 VXIGLOFXPSRFTP-KEBDBYFISA-N 342.403 2.154 30 1 EEEF O=C(NO)c1cnc(NCc2ccccc2OC(F)(F)F)nc1 166684918 YYASRQFJCZDIDW-UHFFFAOYSA-N 328.250 2.106 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)[C@@H](C)C[C@@H]2OC(=O)C(=C)[C@H]12 1572755 KYTKEOOPALLADL-RROPRTBTSA-N 346.379 2.244 30 1 EEEF C=C[C@]1(C)C=C2[C@H](O)[C@H](O)[C@@H]3C(C)(C)C(=O)C=C[C@]3(C)[C@]2(O)CC1 2356325942 RNZJQFGWISERJP-UXTPAWKISA-N 332.440 2.153 30 1 EEEF CCOC(=O)c1cnc2n(c1=O)CCCC/C2=N\Nc1ccccc1 28251738 FJMIRGSJANZUSJ-RCCKNPSSSA-N 340.383 2.420 30 1 EEEF C=C1[C@@H]2OC(=O)C=C(C)[C@@H]2C[C@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@@H]12 2356470958 LUHDPMVWXCNPMF-OVWQWFNUSA-N 344.407 2.477 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 504672481 PVIQXTWXWOHHFV-GLZFIAKDSA-N 344.407 2.001 30 1 EEEF biogenic COc1ccc(Cl)cc1C#Cc1c(O)nc(=O)n(CC(C)C)c1N 587912002 BKVMYBRUSLDWBO-UHFFFAOYSA-N 347.802 2.249 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2/C=C\C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 169354753 XTUZVEOWUSGCSV-OELBELFUSA-N 330.336 2.038 30 1 EEEF Oc1nc2ccc(C3=NNC(=NCc4ccncc4)SC3)cc2[nH]1 1857766945 ARBIGJGQTGEWLD-UHFFFAOYSA-N 338.396 2.260 30 1 EEEF C[C@@H]1C[C@@H]2O[C@H]2CCC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 2356421049 XFALPAMSDFFXGY-VFVAKGGASA-N 332.352 2.262 30 1 EEEF COC(=O)C1=C2Nc3ccccc3[C@]23CCN2CC[C@H]1[C@]1(O[C@H]1C)[C@@H]23 2356381468 NYHQYHWNIWLUDO-ZTAZRJFTSA-N 338.407 2.042 30 1 EEEF CC1=CCCC[C@@H]2O[C@]23CC(=O)O[C@H]3c2c(O)ccc(O)c2[C@@H]1O 2356403624 PHCAOFZRCKAKBR-PSMGESJCSA-N 332.352 2.387 30 1 EEEF O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)NO)c1ccc(F)cc1 96269525 ZGGUVSSJHHKVGJ-INIZCTEOSA-N 341.342 2.154 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N2CC[C@H](O)C2)nc1 587908485 XSCCSLJVBQUGGU-HNNXBMFYSA-N 329.787 2.109 30 1 EEEF O=C(O)[C@H]1CNC[C@H](CCN/N=C/c2ccccc2-n2cccc2)C1 1857570482 RJTVXEAUTBQVHF-KFXCQKJJSA-N 340.427 2.101 30 1 EEEF O=C(/C=C/c1cccn1Cc1ccc(F)cc1F)CC(=O)C(=O)O 103295930 DKFIIFFRTUHRER-AATRIKPKSA-N 333.290 2.441 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(C)C(=O)CC[C@@](C)(C(=O)O)[C@H]1C[C@@H]3O 72104716 CLGOGJHVMHIUDO-VRHUIZLCSA-N 346.423 2.369 30 3 EEEF COc1ccccc1Cn1cccc1/C=C/C(=O)CC(=O)C(=O)O 33818788 KCMZLWSTJLSCOT-CMDGGOBGSA-N 327.336 2.171 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(C(=O)NCC(=O)O)o1 587912437 PBKOZYUCLGVQND-UHFFFAOYSA-N 333.727 2.156 30 1 EEEF C=CCc1cccc2nc([C@@H](C)NS(=O)(=O)c3cnn(C)c3)[nH]c12 586937466 FCPZVHZOUQTAAZ-LLVKDONJSA-N 345.428 2.064 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@]2(C)CC[C@@](O)(O2)C(C)=C[C@H]2OC(=O)C(=C)[C@@H]21 253638280 JCTQUEQSHOHEPW-YXBKOPBNSA-N 348.395 2.180 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)OC 504672484 PVIQXTWXWOHHFV-UFTRZQDCSA-N 344.407 2.001 30 1 EEEF biogenic C=C(C[C@H]1C=C(C)C(=O)O1)[C@H](O)COc1ccc2ccc(=O)oc2c1 15212328 BJAAKPBQJCDTGE-JKSUJKDBSA-N 342.347 2.351 30 1 EEEF biogenic CN1CC2=C(C(=O)c3ccccc3C2=O)C12C(=O)c1ccccc1C2=O 73310820 KXMCAQURQWRSSP-UHFFFAOYSA-N 343.338 2.126 30 1 EEEF C=C[C@@]1(C)C(=O)C=C2C(=CC[C@@H]3C(C)(C)[C@@H](O)[C@H](O)C[C@@]23C)[C@H]1O 200556336 AZNDIKGKUJHYJB-DTXGANJQSA-N 332.440 2.153 30 1 EEEF CCCCCCCC[S@+](C)CC(P(=O)(O)O)P(=O)(O)O 34803955 HJUIIHFOXRYVDU-HXUWFJFHSA-O 349.346 2.277 30 1 EEEF COc1cc(N2CCC(N(C)Cc3ccccc3C#N)CC2)ncn1 299866264 VPMVRCWTRASJTG-UHFFFAOYSA-N 337.427 2.458 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)(CC[C@@H](O)[C@@]4(C)CO)[C@@H]2C[C@@H](O)[C@H]1C3 2356417362 YYNFNCPHITUVRP-GDTGPJSDSA-N 334.456 2.068 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@]1(C)CCC[C@](C)(CO)[C@H]1C[C@H]3O 2356404713 VFCKRZZDFUUVFU-DHQACITASA-N 334.456 2.068 30 1 EEEF CN(C)S(=O)(=O)c1cccc2nc(-c3ccc(O)c(C#N)c3)[nH]c12 587189024 WLUFJVXRVPLBQG-UHFFFAOYSA-N 342.380 2.057 30 1 EEEF O=C(NCc1ccc2cc(C(=O)NO)sc2c1)c1cccnc1 96928982 KXRJQBSKMVFJFP-UHFFFAOYSA-N 327.365 2.345 30 1 EEEF N#Cc1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cn1N 587885286 DQKJNUSCTZLXKJ-UHFFFAOYSA-N 347.205 2.091 30 1 EEEF Cn1c(-c2ccccn2)nc2c(N)nc(C#CC3(O)CCCCC3)nc21 13861448 GKLFVWBVLGOSKV-UHFFFAOYSA-N 348.410 2.054 30 1 EEEF COc1ccc2c3c1O[C@@H]1C=C(C(C)=O)C[C@@H]4[C@@H](C2)N(C)CC[C@]341 169295578 FKNWJBZMTKZQMB-YVTWGWGSSA-N 325.408 2.490 30 1 EEEF COc1cc(OC)nc(N2C(=O)CS[C@@H]2c2ccc(C#N)cc2)n1 169351008 ZPURGNXZGBYXOX-OAHLLOKOSA-N 342.380 2.144 30 1 EEEF CC#CCN(CCC)C(=O)[C@@]1(c2ccc3c(c2)CCO3)C[C@H]1CN 29047985 FCURKYXBYVWDLH-FXAWDEMLSA-N 326.440 2.100 30 1 EEEF C[C@H](CS)C(=O)N1C[C@H](Oc2ccc(Cl)cc2)C[C@H]1C(=O)O 27999340 XGGGHQKFFFAETI-WQAKAFBOSA-N 343.832 2.339 30 1 EEEF CCCCCCCCC[C@@H]1OC(=O)C[C@H](O)C[C@@H](O)C=C[C@@H]1O 2356619471 HFGOXJHLMBNOHC-YVSFHVDLSA-N 328.449 2.472 30 1 EEEF COCCNC(=O)Nc1cc2[nH]nc(-c3ccc(C#N)cc3)c2cn1 218534291 BPAMLTWGLIYUSH-UHFFFAOYSA-N 336.355 2.264 30 1 EEEF C=C1[C@@H]2OC(=O)[C@H]3[C@H]4[C@@](C)(CC[C@H](O)[C@@]4(C)C(=O)O)[C@@H]4CC[C@@H]1C[C@]234 238765089 CXVXNQFWGOEIMV-OISVNVOMSA-N 346.423 2.382 30 1 EEEF C=C(C)[C@@H](OC(=O)c1ccc(OC)c2ccc(OC)cc12)C(N)=O 473117509 ZMQZOYOMBNDKND-MRXNPFEDSA-N 329.352 2.444 30 1 EEEF CC#CCOc1ccc([S@](=O)[C@H](C(=O)NO)c2ccccc2)cc1 13585968 LMLJZJGMFKPKNY-BXKMTCNYSA-N 343.404 2.443 30 1 EEEF COC(=O)/C=C1\CCCN1CCc1cc2c(cc1CC#N)OCO2 1659613 NLPPGQPGOWINQJ-RVDMUPIBSA-N 328.368 2.177 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@]2(C)C[C@@H]2C(=O)C=C(C)C(=O)[C@@H]1O 2356581519 YLQIJBIUALFEAE-IJTAGJJNSA-N 344.407 2.296 30 1 EEEF N#Cc1cccc(C(=O)N[C@H]2CCC[C@H](NC(=O)c3ccccn3)C2)c1 95587694 WSQGEPYGCDINHA-IRXDYDNUSA-N 348.406 2.424 30 1 EEEF O=C1C=CC=C/C1=C\NNC1=NC(=O)[C@H](Cc2ccc(F)cc2)S1 15952885 HPUMHJYDWOJHJM-PABFRNLHSA-N 343.383 2.039 30 3 EEEF C=C1[C@@H]2C[C@H](O)C(C)(C)[C@@]2(O)[C@H](O)C[C@@]23CC(=O)[C@@](C)(CC[C@@H]12)C3 205950675 IRZVFDISJFITJT-OAAREDOUSA-N 334.456 2.211 30 1 EEEF O=CC(C=O)c1ccc(-c2nc3ccc(O)cc3[nH]2)cc1[N+](=O)[O-] 587262099 OEWRNGNHCFNVPC-UHFFFAOYSA-N 325.280 2.325 30 1 EEEF CCC/C=C/[C@@H]1C(=O)[C@H]2O[C@H]2C2(OCC(CC)(CC)CO2)[C@H]1CO 13783072 TWGDZVIUZPIUAD-MDNMDQJKSA-N 338.444 2.467 30 1 EEEF C[C@@]1(CCC(=CCO)CO)[C@@H]2CCC=C3C(=O)OC[C@@]32CC[C@H]1C=O 2356379736 GUKSFBJMSDUTIA-UHMOLFJZSA-N 348.439 2.172 30 1 EEEF N#Cc1c2n(c(=O)n(-c3ccccc3)c1=N)CCCC[C@@H]2N1CCCC1 53295975 ADVWRHQQTDKLMY-KRWDZBQOSA-N 349.438 2.311 30 1 EEEF C=CCNC(=S)NCCCCn1nc(-c2ccccc2)ccc1=O 27210635 GFMBTEXAJWSTJC-UHFFFAOYSA-N 342.468 2.341 30 1 EEEF C/C(=N/Nc1ccc(S(N)(=O)=O)cc1[N+](=O)[O-])c1ccc(C)cc1 38204516 NUHLRNDCKTWELN-BOPFTXTBSA-N 348.384 2.387 30 1 EEEF C[C@H]1NC(=O)[C@]23C[C@@H](O)[C@H]4[C@@H](CCC5=CC(=O)C=C[C@]54C)[C@@H]2CC[C@H]13 255286875 ZFDFFZSCUSDQEX-KVRQVOBHSA-N 341.451 2.380 30 1 EEEF N#Cc1c(NC(=O)c2ccco2)[n+](=O)c2ccc(Cl)cc2n1O 377845793 FHQKYYLCVTVRGQ-UHFFFAOYSA-O 331.695 2.163 30 1 EEEF C[C@]1(OC(=O)c2ccco2)C(=O)C=C2C=C(C3CC3)OC=C2C1=O 8860662 RPKPRQGWDHATHB-SFHVURJKSA-N 326.304 2.481 30 3 EEEF CO[C@@]1(C#C[C@@](O)(c2ccccc2)c2ccncc2)CN2CCC1CC2 28563972 NSEVJPOKAGLQCK-FCHUYYIVSA-N 348.446 2.432 30 1 EEEF C[C@H]1CCN(C(=O)C(C)(C)C#N)C[C@H]1N(C)c1ncnc2[nH]ccc12 66252351 VWSCLEOQSBFMNS-GXTWGEPZSA-N 340.431 2.181 30 1 EEEF COc1cc(C#N)c(OC)n1-c1nc(N2CCCCC2)ncc1F 587945082 KNFDUYGEKZAPHQ-UHFFFAOYSA-N 331.351 2.286 30 1 EEEF Cc1ncc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)c(N)n1 587881641 VAZOJSPAPJHQNZ-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF C/C(NNC(=S)NCCc1ccccc1)=C1/C=CC(=O)C=C1O 100585143 MSNWOEFSFSENHJ-NTCAYCPXSA-N 329.425 2.053 30 3 EEEF C=C1C(=O)O[C@@H]2C[C@@]3(C)OC(=CC3=O)C(C)=C[C@H](OC(=O)C(C)C)[C@@H]12 2356539288 JHZYGPMGMMUUTG-XWESNNAXSA-N 346.379 2.244 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@](C)(O)CC[C@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@@H]12 2356677098 GUGYUSGXSKYCJD-GINSCSNVSA-N 348.439 2.288 30 1 EEEF Cc1ccc(S(=O)(=O)N/N=C\c2ccc3nccnc3c2)cc1 33365807 WWCLUYJYYQVKKL-ODLFYWEKSA-N 326.381 2.251 30 1 EEEF C=C(C)[C@H]1[C@@H]2C[C@H](C)[C@H]3CC[C@H](C)[C@@]4(O)C(=O)C(=O)[C@]1(C)C(=O)[C@]234 38297842 JQKMCBIANZSIJR-DNKNUALPSA-N 330.424 2.339 30 1 EEEF COc1cc(CCN/C=C2\C=CC=CC2=O)c([N+](=O)[O-])cc1OC 136326385 UMLDLLQZGPDAJV-ACCUITESSA-N 330.340 2.323 30 3 EEEF O=C1C=C[C@]2(O[C@@H]3c4c2ccc(O)c4C(=O)[C@@H]2O[C@@H]23)c2cccc(O)c21 95563160 GLLQRSNTBBQHPX-WCIQWLHISA-N 348.310 2.129 30 1 EEEF C[C@H]1Cc2ccc(F)c(Br)c2[C@@](CCC=O)(C(=O)O)N1 587825288 CNZBBDHJVSYJER-RTHLEPHNSA-N 344.180 2.381 30 1 EEEF C=C[C@]1(C)C=C2[C@H](O)[C@H](O)[C@@H]3C(C)(C)C(=O)C=C[C@@]3(C)[C@]2(O)CC1 2356325943 RNZJQFGWISERJP-XLQBFBSWSA-N 332.440 2.153 30 1 EEEF C[C@]12C3=C(C(=O)c4occ(c41)[C@H](O)[C@@H]1O[C@H]12)[C@@H]1CC[C@H](O)[C@]1(C)CC3 2356449777 XPAHMBAVRBKIJS-XTZWBNLXSA-N 342.391 2.416 30 1 EEEF COc1ccc(CCN=C2N[C](N)c3ccccc3N2)cc1OC 2356828270 OKQMPKKRPOSOKX-UHFFFAOYSA-N 325.392 2.114 30 1 EEEF CC(=O)Nc1nc(C)c(-c2ccc(S(C)(=O)=O)c(C#N)c2)s1 84689698 UNPCEUDDZMOCCV-UHFFFAOYSA-N 335.410 2.352 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnn2cc(C(=O)O)cnc12 587911314 DGFKLVDRXOKDOD-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF NS(=O)(=O)c1ccc(N/C(S)=N/Nc2ccccc2F)cc1 28127722 KQBPCTUKTLMUPL-UHFFFAOYSA-N 340.405 2.198 30 1 EEEF CCOC(=O)[C@@H](C#N)[C@]1(CC)Oc2cc(OC)cc3c2C(=O)[C@H]1C3 587428359 OAFVAGNNVDRDRW-SNUQEOBHSA-N 329.352 2.294 30 1 EEEF COCCCCn1c(=O)cc(Nc2ccc(C)c(CS)c2)[nH]c1=O 13522364 QNMYNLZNNUENNT-UHFFFAOYSA-N 349.456 2.445 30 1 EEEF C=CCc1cc(NC(=O)NCC)ccc1OC[C@@H](O)CNC(C)C 169317297 PWYDWQHIIMXLJN-INIZCTEOSA-N 335.448 2.294 30 1 EEEF CC(C)NC[C@H](O)CO/N=C1/c2ccccc2[C@H]2CCCC[C@@]12O 169342283 RTKLMTIRQZCKHN-IZJDMMHXSA-N 332.444 2.169 30 1 EEEF O=c1[nH]c(=O)n(-c2cccc(Cl)c2)c(O)c1/C=N/c1ccccn1 169688755 GXDHEXWWCZQNIQ-DJKKODMXSA-N 342.742 2.030 30 1 EEEF O=C(NO)c1ccc(N2CCN(Cc3ccc(F)cc3)C2=O)cc1 205704673 CEFRJLUYBQEKQU-UHFFFAOYSA-N 329.331 2.387 30 1 EEEF C[C@]1(C=O)[C@H]2CC[C@@]3(C)O[C@@]14C(=O)c1ccc(O)cc1C(=O)C4=C[C@H]23 102958921 NMLFNFAGOHGLMD-LFHWYUKOSA-N 338.359 2.470 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]1(C)CCC[C@@]2(CO)C(=O)O[C@H]([C@@H]3O)[C@@H]21 85932791 RDUNXXWNAKBVER-AFQJYMIFSA-N 332.440 2.434 30 1 EEEF in-man CCOc1ccc(CCCN2CC=C(CCC(=O)NO)C2=O)cc1 95572274 SNJVYHFFCNPDCZ-UHFFFAOYSA-N 332.400 2.072 30 1 EEEF COc1cc2c(c(I)c1OC)C(=O)C=CC2=O 1857747000 RQZIZPWWWQCKJE-UHFFFAOYSA-N 344.104 2.244 30 1 EEEF C/C(=N\NC(=N)N)c1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1 1772619929 PCVIOFSWQMBTEW-AUEPDCJTSA-N 345.353 2.353 30 1 EEEF COc1ccc([N+](=O)[O-])cc1[C@@H]1NN/C(=C2/C=CC=CC2=O)S1 104034514 WXCQWCTXVHXHLQ-YVGNARHYSA-N 331.353 2.350 30 3 EEEF N#Cc1cnc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cn1 587889645 RDRLENUAZWTASU-UHFFFAOYSA-N 345.189 2.365 30 1 EEEF C=CC1=CC(=O)[C@@H]2[C@@H](CC[C@@H]3C(C)(C)[C@@H](O)[C@@H](O)[C@@H](O)[C@@]23C)[C@H]1C 100829707 XFRCVLKGZMPUFQ-NAMWVTTQSA-N 334.456 2.089 30 1 EEEF endogenous,in-man O=C1C=CC=C/C1=C1/C[C@H](C(=O)Nc2cc(Cl)ccc2O)ON1 104000989 NGLFOEZGIXQTMD-AUECHBEKSA-N 332.743 2.227 30 3 EEEF C=CC[C@@]12CC(=O)[C@H](O)[C@@H]([C@H](c3ccc(OC)c(OC)c3)[C@@H]1C)[C@H]2O 2356602596 FWKAJIVKMLFWPD-PYOZGWQMSA-N 346.423 2.310 30 1 EEEF C=C[C@](C)(O)[C@H](O)C[C@@H]1C(=C)[C@H](O)C[C@@H]2[C@@](C)(CO)CCC[C@]12C 2356651820 CYJDHAXSZJABJA-BVMALAMASA-N 338.488 2.416 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)[C@@H]2[C@@H]3OCC4=C3[C@](C)(CCC4=O)CC[C@]12C 2356823283 GKUCSSBQVHTTCY-MHZMNLEESA-N 334.456 2.475 30 1 EEEF CC1=C2OCCCCN3C(=O)[C@](O)(c4ccccc43)[C@]2(C)SC1=O 71329178 KFSYAIIGWGRHHI-QZTJIDSGSA-N 345.420 2.337 30 1 EEEF O=C(NO)[C@@H]1C[C@H](c2ccc(Oc3ccc(F)cc3)cc2)C(=O)N1 199800338 TUIHSDQRXNNCLL-CABCVRRESA-N 330.315 2.096 30 1 EEEF C=C1C[C@]2(OC1=O)C(=O)Nc1c([N+](=O)[O-])cc(Br)cc12 653901782 OHKOGQPSKXSACV-GFCCVEGCSA-N 339.101 2.008 30 1 EEEF COCCNC(=O)[C@H]1CCCC[C@@H]1c1nc2cccc(C#N)c2[nH]1 587230106 FJLCJTIIYPNMKU-KBPBESRZSA-N 326.400 2.471 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@@](CCC=O)(C(=O)O)N1 587828366 OZXIIBKYYJVMTP-CLAHSXSESA-N 344.180 2.381 30 1 EEEF CCc1ncnc(N2CCOC(C)(C)C2)c1C#Cc1ccc(N)nc1 169699819 OJKQKRMQTDFQKA-UHFFFAOYSA-N 337.427 2.031 30 1 EEEF CC(=O)N[C@@H](C)C(=O)N=C1CCN(c2ccc(Cl)c(Cl)c2)N1 1857548943 AOUJYKTVAHPJSB-QMMMGPOBSA-N 343.214 2.158 30 1 EEEF C=CCN(C)C[C@@H]1CN2CC[C@H]1C[C@@H]2CNC(=O)c1ccccc1 2356301868 ZDVHQAKIGXBAMN-IPMKNSEASA-N 327.472 2.245 30 1 EEEF Cc1ccc2c(c1)n(O)c(C#N)c(NC(=O)c1cccs1)[n+]2=O 377845791 COYVYQIJDBNBKP-UHFFFAOYSA-O 327.345 2.287 30 1 EEEF N#C[C@@H]1CNCC[C@]12Oc1ccccc1C(=O)[C@@H]2C(=O)c1ccco1 587593375 IXOYQXXDJKBETN-FXHACXQTSA-N 336.347 2.226 30 1 EEEF N#Cc1ccc([C@H]2N[C@H](C(=O)O)Cc3cccc(F)c32)c([N+](=O)[O-])c1 962891738 CNNZXQYEIVSGGQ-XJKSGUPXSA-N 341.298 2.294 30 1 EEEF C=C1C(C)(C)[C@@H]2CC[C@]1(C(=O)N1CCC(n3cc(CO)nn3)CC1)C2 207957973 SGVUKVYMMKYMBG-KUHUBIRLSA-N 344.459 2.316 30 1 EEEF Nc1ccc2cc(C(=O)NCc3ccc(C(=O)NO)cc3)ccc2c1 13441431 MKSOCNAEMAKSFX-UHFFFAOYSA-N 335.363 2.471 30 1 EEEF CC(=O)OCC[C@@H](C=CC=CC#CC#CC=CCO)OC(=O)C(C)C 2356397877 RLOXIGRNKNTVJQ-LJQANCHMSA-N 344.407 2.175 30 1 EEEF C=CC(C)(C)c1[nH]c2ccccc2c1C=c1nc(O)c(=CC)[nH]c1=O 2356323795 NZJGQSUIQDSMTO-UHFFFAOYSA-N 335.407 2.050 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)CC[C@H](O)[C@]2(C)C[C@H]2OC(=O)C(=C)[C@@H]12 2356509317 LJFQOYCUYZGFOE-NOGCVJDZSA-N 332.396 2.453 30 1 EEEF CO[C@]1(C#C[C@@](O)(c2ccccc2)c2ccccn2)CN2CCC1CC2 28563813 LLHFDYRCKMNGML-FGZHOGPDSA-N 348.446 2.432 30 1 EEEF COC1=C(O)C(=O)c2c(OC)c3c(c(O)c2C1=O)[C@@H](C)O[C@@H](C)C3 238739938 RVZCNHHDKHVNPP-NKWVEPMBSA-N 334.324 2.218 30 1 EEEF Cn1c(Nc2ccc(-c3ccc(C#N)cc3)cc2)cc(=O)n(O)c1=O 1857540032 SCUFBHSLGMPHLA-UHFFFAOYSA-N 334.335 2.067 30 1 EEEF C=C1C2=C(O)[C@@H](O)[C@H](C)C=C2C(=O)c2cc(O)c(OC)c(OC)c21 2356329702 KMJOSWUIOOZDTP-UOWDBTKRSA-N 330.336 2.368 30 1 EEEF Clc1cccc(C#CCOc2nsnc2C23CN4C[C@H]2[C@@H]3C4)c1 100811718 HPTGNTPIZBKTDN-KBPBESRZSA-N 343.839 2.435 30 1 EEEF C=C1C[C@@]23C[C@@]1(O)CC[C@@H]2C1=C[C@H]2C[C@@](C)(C(=O)O2)[C@H]1[C@H]3C(=O)O 2356490059 VLTQADXREMVNJX-RFPSBRHQSA-N 330.380 2.056 30 1 EEEF C=C(C)[C@H]1Oc2cc(O)c(C(C)=O)cc2[C@H]1OC(=O)C(=CC)CO 2356690563 CLWSKSKCEVBFSD-IAGOWNOFSA-N 332.352 2.455 30 1 EEEF N#Cc1ccccc1[C@H](O)C1=C2C=C[C@@H]3C[C@@]2(OC1=O)[C@H]1CCCCN31 1772602990 IHXMEANXHYXNKY-DYZHCLJRSA-N 348.402 2.380 30 1 EEEF C=C1C(=O)[C@@]23CC(=O)[C@@H]4C(C)(C)CCC[C@]4(C)[C@@H]2[C@H](O)C[C@H]1[C@H]3O 2356397835 JLKBHAAAVQFJPZ-ZWLMBCPCSA-N 332.440 2.275 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]12C[C@@H](O)C[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 62234985 HHDWSDSMWJQURA-GEXQUTOHSA-N 332.396 2.136 30 1 EEEF in-man N#CN[n+]1ccccc1C1=CC(CF)(CF)Oc2ccc(C#N)cc21 26737604 VPBLLQSQRUGABR-UHFFFAOYSA-N 339.325 2.372 30 1 EEEF O=C1C[C@@H](O)[C@@H](O)[C@@H]2C1=CCCC21Oc2cccc3cccc(c23)O1 299832749 QZXGWZACFKTEPU-MDASCCDHSA-N 338.359 2.338 30 1 EEEF C=C1[C@@H](C[C@H](O)[C@@H]2CC(=O)NC2=O)[C@@]2(C)CCCC(C)(C)[C@H]2C[C@H]1O 2356380055 PPQGMYUYEYHPEL-CAAHHWGJSA-N 349.471 2.170 30 1 EEEF C=C[C@](C)(O)[C@H](O)C[C@@H]1C(=C)[C@H](O)C[C@@H]2[C@@](C)(CO)CCC[C@@]12C 2356651823 CYJDHAXSZJABJA-ZSXPZZPQSA-N 338.488 2.416 30 1 EEEF COc1cccc(NS(=O)(=O)c2cccc(/C=C/C(=O)NO)c2)c1 38442896 LFJZWKWWAXYUAR-CMDGGOBGSA-N 348.380 2.015 30 1 EEEF O=C(/C=C/c1ccc2ccn(S(=O)(=O)c3ccccc3)c2c1)NO 84668648 XPOMEPVGJSNPON-VQHVLOKHSA-N 342.376 2.397 30 1 EEEF CC(=O)N[C@H](C)Cc1ccc(C#Cc2cnc(NCCF)nc2)cc1 142364067 APMTZRZHULWTDV-CQSZACIVSA-N 340.402 2.325 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@]2(C)[C@H]3CC[C@@]4(C)O[C@@]15C(=C)C(=O)O[C@@]25[C@@H]34 238762140 RAMWJTYDCGKVKM-KKAKHNJDSA-N 330.380 2.304 30 1 EEEF C#Cc1ccc2c(c1)C(=O)N1CC[C@H]1c1c(-c3nc(C)no3)ncn1-2 13781517 QBWJMTOHSYOPBE-AWEZNQCLSA-N 331.335 2.113 30 1 EEEF N#Cc1ccc(-c2ccc(N3C[C@H](CO)OC3=O)c(F)c2F)cn1 169349762 ZHHMPFXXCBIODF-LLVKDONJSA-N 331.278 2.216 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@@](C2)(C(=O)O[C@@H]2CCC(C)(C)[C@@H]4[C@H](O)OC[C@]432)[C@H]1O 2356410497 MSSXZZIDIPKYEB-YEMMUIKFSA-N 348.439 2.016 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 2356783747 MEGPPDNKNMAIJN-XULVFZLMSA-N 330.380 2.056 30 1 EEEF Cn1c(/C=C2\S/C(=N/c3nccs3)NC2=O)ccc1[N+](=O)[O-] 98082401 HYZXVTHRHNXHNH-VURMDHGXSA-N 335.370 2.281 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(C#CCO)c(OC)c1 587909217 MMFYYHZOOFBTQI-UHFFFAOYSA-N 327.767 2.496 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@@H](C1=O)[C@@]1(C)C=C[C@@]2(C(C)C)CC1 169302820 SDJYQQCUHRGBAF-GGNLRSJOSA-N 347.484 2.165 30 1 EEEF O=C(O)CO/N=C1C(=C2/C(=O)Nc3ccccc32)/Nc2ccccc2/1 1661795 MARBCYLHVIOQCF-LALPNIDTSA-N 335.319 2.281 30 1 EEEF Cn1c(Oc2ccc(-c3cccc(C#N)c3)cc2)cc(=O)n(O)c1=O 1857551463 VFLGBJJUYMXJRP-UHFFFAOYSA-N 335.319 2.115 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@](C)(CO)CCC[C@]4(C=O)[C@H]2CC[C@H]1[C@H]3O 2356462312 NGMHJAMTHJNIJX-CSEMPIMJSA-N 332.440 2.277 30 1 EEEF CCCCCC[C@H](O)[C@@H]1C[C@@H](OC(C)=O)C2=C(O1)[C@@H](O)CCC2=O 2356620150 GXYWRLQZWPUUNP-QCEMKRCNSA-N 340.416 2.016 30 1 EEEF C=C([C@H](O)C=C[C@](C)(O)CO)[C@@H]1CC(=O)[C@@]2(C)[C@H]1[C@@H]1[C@@H](C)CC[C@H]12 2356727543 PIQKTPMDCOQYRT-QUPOLLIOSA-N 334.456 2.090 30 1 EEEF O=C1Nc2ccccc2/C1=N/NC(=S)Nc1ccc(C(=O)O)cc1 73157437 XBNVUQAIJWXMDN-UHFFFAOYSA-N 340.364 2.028 30 1 EEEF N#CCNC(=O)[C@H](CC1CCCCC1)NC(=O)c1cccc(O)c1 82064539 CYGXEYUVAIJOJV-INIZCTEOSA-N 329.400 2.101 30 1 EEEF CC(C)(C)c1ccc(C(=O)NC(=O)NCCCCCC(=O)NO)cc1 49034936 XDTIBLCTJRACBX-UHFFFAOYSA-N 349.431 2.489 30 1 EEEF COC1=CC(=O)C2=C(O[C@@H](c3ccc(OC)c(OC)c3)CC2)C1=O 198729017 NGGBXUMUYRBLPC-CYBMUJFWSA-N 330.336 2.492 30 1 EEEF Cc1ccc(C(=O)/C=C\c2nc3cccc(S(N)(=O)=O)c3[nH]2)cc1 587965174 HXGQNVVWFMSKFJ-KTKRTIGZSA-N 341.392 2.415 30 1 EEEF C=C1C(=O)O[C@@H]2/C=C(/C)C3=CC(=O)[C@@](C)(C[C@H](OC(=O)C(C)C)[C@@H]12)O3 238771345 WQQJRSDFQHYDRU-MFRWKCHVSA-N 346.379 2.244 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 104365889 QYXZQZMPZUEEML-ZSQWHVHDSA-N 346.423 2.384 30 1 EEEF in-man Cc1c[nH]c2c1[C@@]13C[C@H]1CN(S(=O)(=O)c1ccccc1)C3=CC2=O 101331880 VRRYPFUNOZUDIK-SGTLLEGYSA-N 340.404 2.366 30 1 EEEF CCN/C(=N/S(=O)(=O)c1ccc2cc[nH]c2c1)N1C[C@@H](CC)C=N1 115413979 DFPUPZMYPJSLGL-LBPRGKRZSA-N 347.444 2.150 30 1 EEEF Cc1ccc(S(=O)(=O)ON/N=C2/[C@@H]3O[C@H]3[C@@H]3CCCC[C@H]23)cc1 102950941 AVTXTHBQNZOKPF-MEHSUPDVSA-N 336.413 2.148 30 1 EEEF O=C1CCCC2=C1[C@@H](c1cc3ccccc3[nH]c1=O)NC(=S)N2 103285161 LILXRXMAYLRMKZ-OAHLLOKOSA-N 325.393 2.054 30 1 EEEF NC(N)=Nc1ccc(-c2cc(C(=O)Nc3ccc(F)cc3)[nH]n2)cc1 222125115 QWKIQQKIJKJGAE-UHFFFAOYSA-N 338.346 2.373 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@@H]2[C@@H]3C[C@@H](C(C)C)[C@H](C=C3C)[C@H]2C1=O 169304351 PBDZFTMSQJXALQ-XPABHHOTSA-N 347.484 2.021 30 1 EEEF O=C(C[N+]1(C[C@@H](O)c2ccccc2)CCOCC1)c1ccccc1 36381172 KIODMQGFGSAVJP-LJQANCHMSA-N 326.416 2.450 30 1 EEEF CCCCCCCCCCc1cn(COCCO)c(=O)[nH]c1=O 43587243 YDGVIYHDHHDRKI-UHFFFAOYSA-N 326.437 2.186 30 1 EEEF CCC#C[C@](O)(C(=O)O[C@@H]1C2CCN(CC2)[C@H]1C)c1ccccc1 5458397 VOCRJOMVKAJZBC-ZAAXVRCTSA-N 327.424 2.314 30 1 EEEF CCC/C=C/[C@@H]1C(=O)[C@H]2O[C@H]2C2(OCC(CC)(CC)CO2)[C@@H]1CO 13783070 TWGDZVIUZPIUAD-NEMHTBHWSA-N 338.444 2.467 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1[C@@H](O)C[C@H]2[C@]1(C)CCC[C@](C)(CO)[C@H]1C[C@H]3O 169313020 VFCKRZZDFUUVFU-KLRAXQCPSA-N 334.456 2.068 30 1 EEEF C=C(C)[C@@H](O)Cc1c(O)c(O)cc2oc3cc(O)cc(O)c3c(=O)c12 14763103 GONMHOQVFDWXLV-JTQLQIEISA-N 344.319 2.248 30 1 EEEF biogenic,in-vitro C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(COC3=O)[C@@H]2CC[C@@]3(C)CO[C@@H](O2)[C@@H]13 40873991 VGHUWBCJSRMGIQ-OSKYZRHQSA-N 344.407 2.243 30 1 EEEF COc1ccc2nc(-c3ccc(C(C=O)C=O)c([N+](=O)[O-])c3)[nH]c2n1 587262579 YEHVXMNBUXKFTJ-UHFFFAOYSA-N 340.295 2.023 30 1 EEEF C=CCSc1nc(N)c(C(=O)Nc2ccccc2)cc1C(N)=O 20069207 ZZSAXDGBTSCJQM-UHFFFAOYSA-N 328.397 2.293 30 1 EEEF CCOC(=O)c1nc(-c2cn(C)c3c2C(=O)C(OC)=CC3=O)cs1 25991397 CRKVVPSMKCNRBO-UHFFFAOYSA-N 346.364 2.235 30 1 EEEF C=C1[C@H](O)C[C@@H]2C(C)(C)[C@H](O)CC[C@]2(C)[C@H]1CC=C1COC[C@H]1O 2356416317 PQJNKPQZAXZXLP-UMCYSPNLSA-N 336.472 2.434 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)C(=O)C=C[C@](C)(O)C[C@H](OCC(C)C)[C@@H]12 2356653592 LUEQCEAVADXVIC-DFEOGRTESA-N 334.412 2.352 30 1 EEEF C=C[C@]1(C)CCC2=C([C@H](O)C(=O)[C@@H]3C(C)(C)CC[C@H](O)[C@]23C)[C@H]1O 2356734933 KKWFUTJLCATXQH-FSPZJIPGSA-N 334.456 2.377 30 1 EEEF C=C[C@H]1CN2[C@@H]3C[C@@]45c6ccccc6N[C@]4(O3)[C@@H]2C[C@@H]1[C@@H]5C(=O)OC 238732076 VQQRVBOFQXPEAN-NORGFYCISA-N 338.407 2.102 30 1 EEEF O=C(NO)c1ccc(N2CCN(CCc3ccccc3)C2=O)cc1 205707432 FEHFKUIBPASWRG-UHFFFAOYSA-N 325.368 2.290 30 1 EEEF CC(C)C1=C[C@H]2O[C@]23[C@@]2(C)CCC4=C(COC4=O)[C@@H]2C[C@@H]2O[C@@]23C1=O 1857608356 AAQGJDXQUVCTKP-FOQSWYGASA-N 342.391 2.100 30 1 EEEF C=C1C(=O)O[C@@H]2C3=C(COC(C)=O)CC[C@H](OC(C)=O)[C@@]3(C)CC[C@@H]12 2356410447 LLUIAKNHFIRVHK-RIVXBTQJSA-N 348.395 2.470 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@@]3(O)C=C[C@@](C)(C[C@@H](OC(=O)C(C)C)[C@H]12)O3 2356625027 XJUPOHKZSDZNBE-FJWRHQQOSA-N 348.395 2.036 30 1 EEEF CC(C)C[C@H](NC(=O)c1ccc(-n2cccc2)cc1)C(=O)NCC#N 82061347 FGIOOVDQFGGWMB-KRWDZBQOSA-N 338.411 2.262 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N2CCCNCC2)nc1 587908448 WCYMKEGZEYVXBN-UHFFFAOYSA-N 342.830 2.338 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@H]2[C@@]12CO[C@@H]4OC[C@@](C)(CC[C@@H]1OC3=O)[C@@H]42 103109406 QRZAIOQXVJRCBS-WGRRBQJKSA-N 344.407 2.243 30 1 EEEF Cc1ccc2n(c1)cc(-c1ccc(/C=C/C=N/NC(=N)N)cc1)[n+]2C 26833415 GVKBLIXUALPIKG-DMRDCZSUSA-N 333.419 2.221 30 1 EEEF N#CC(Cc1ccccc1F)(Cc1ccccc1F)C(=O)NCCN 1857540665 LKKQFANZNXCTSS-UHFFFAOYSA-N 343.377 2.335 30 1 EEEF CC(=O)Oc1cc(O)cc2c1C(=O)C(=Cc1ccc(O)c(O)c1)CO2 2356816488 DBQSMZBWTHHICO-UHFFFAOYSA-N 342.303 2.387 30 1 EEEF O=C(/C=C/c1ccc(CNCCc2c[nH]c3ncccc23)cc1)NO 72114138 NPRMIAORLQQEDL-BQYQJAHWSA-N 336.395 2.414 30 1 EEEF N#CCCCCN1COc2cc3c(cc2C1=O)O[C@@H]1CCCN1C3=O 72173104 UWBONOROIYFKGA-MRXNPFEDSA-N 341.367 2.127 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2C1=CC[C@H](O)[C@](C)(C(=O)O)[C@@H]1[C@@H]3C(=O)O 2356424825 WFTRKYGVESACJS-QQJSBZPLSA-N 332.396 2.462 30 1 EEEF Cc1cccc(/N=C/C2=C3NC=C(C(=O)O)C(=O)N3[C@H](C)CC2)c1 101174678 ADFYQZZKXUPLRK-DKSCHZSNSA-N 325.368 2.492 30 1 EEEF C=C1CC[C@H]2[C@](C)(CC[C@@H](O)[C@@]2(C)CO)[C@H]1CC(=O)C1=CCOC1=O 2356711148 KPJIGLLMDBHXEB-BEUFEYIVSA-N 348.439 2.171 30 1 EEEF CCCCCCCCS(=O)(=O)C(Cl)(Cl)S(N)(=O)=O 34718005 MSEDXJWDYOYTDH-UHFFFAOYSA-N 340.294 2.139 30 1 EEEF O=C([C@@H]1CCOC1)N1CCc2nc(C#Cc3ccccc3)sc2C1 96272964 VDPVHWGVEQPQDX-OAHLLOKOSA-N 338.432 2.464 30 1 EEEF C[C@@H]1NC=CC(=O)[C@@]12N[C@H](C)Cc1ccc(F)c(Br)c12 587799524 XROGJGIIBPMHKL-OLBFVZFUSA-N 339.208 2.392 30 1 EEEF CNS(=O)(=O)c1ccc(CCc2nc3ccc(C#N)cc3[nH]2)cc1 586946801 PWOMWOBGGNEHOZ-UHFFFAOYSA-N 340.408 2.128 30 1 EEEF C/C=C/C(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)C(=O)C[C@]3(C)[C@]1(C)[C@@]21CO1 5832880 LJWZOKOFCBPNAG-LCFHQAOJSA-N 332.396 2.346 30 1 EEEF CS(=O)(=O)c1ccc(C2=CC(=O)c3ccccc3S2(=O)=O)cc1 27201904 VUEIQIDZBNSAIR-UHFFFAOYSA-N 348.401 2.101 30 1 EEEF CC(C)(C)[C@@H]1CC(CNC(=O)/C(C#N)=N/OCc2ccccc2)=NO1 26168586 QOOCZDOCWDUISB-PZBNQXIHSA-N 342.399 2.390 30 1 EEEF C=CCOC(=O)N[C@H](C)C(=O)S[C@H](Cc1ccccc1)C(=O)O 26572593 WLCVFCDRUPIJNX-DGCLKSJQSA-N 337.397 2.243 30 1 EEEF CC(C)(O)C1=CC2=C[C@H](O)[C@H]3[C@](C)(C(=O)O)CCC[C@]3(C)[C@H]2CC1=O 144812014 QMSWKASVXHXIKB-JUNANHINSA-N 348.439 2.471 30 1 EEEF CN(C)c1ccc(/C=C2\N=C(N/N=C/c3ccccc3)NC2=O)cc1 1863888 KZPGSLSYDJTVPH-XYGMCREWSA-N 333.395 2.203 30 1 EEEF CCOc1cc(C(=O)O[C@H](C(N)=O)[C@]2(C)CO2)c2cccc(C)c2c1 26482888 GMRLTVUVZPIILQ-APWZRJJASA-N 343.379 2.347 30 1 EEEF COC1=CC(=O)C(=O)c2oc3c(c21)COc1c-3ccc(OC)c1O 13380042 GRCODZNXJRUTGU-UHFFFAOYSA-N 328.276 2.306 30 1 EEEF biogenic CCOC(=O)[C@H](C#N)[C@@]1(CC)Oc2cc(OC)cc3c2C(=O)[C@H]1C3 587428361 OAFVAGNNVDRDRW-VBHSOAQHSA-N 329.352 2.294 30 1 EEEF N#Cc1nc(Nc2cc(F)cc(F)c2)c2ncn(CCCO)c2n1 72137909 ZUHQXVINLQBRFR-UHFFFAOYSA-N 330.298 2.102 30 1 EEEF C=C1C[C@]23C[C@H]1C(=O)C[C@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 238741342 PHYYFNCWOIYWTJ-BLYXBGHVSA-N 330.380 2.344 30 1 EEEF NNc1cncc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)c1 587888052 FIEWGPXGBUBSDV-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF COc1ccc(CCCc2nc3nc(C#N)c(C#N)nc3[nH]2)c(OC)c1 587929588 XVJGSOQBIIPJPR-UHFFFAOYSA-N 348.366 2.289 30 1 EEEF COc1cc([C@H]2c3c(n[nH]c3C)OC(=N)[C@@H]2C#N)cc2c1OCO2 169690886 UXHONJABCASPMN-NOZJJQNGSA-N 326.312 2.097 30 1 EEEF C[C@@]1(OC(=O)c2ccco2)C(=O)C=C2C=C(C3CC3)OC=C2C1=O 8860663 RPKPRQGWDHATHB-GOSISDBHSA-N 326.304 2.481 30 3 EEEF Cc1ccc2occ(/C=N/c3ccc(S(N)(=O)=O)cc3)c(=O)c2c1 28524777 LBYPGUINQFECHD-DJKKODMXSA-N 342.376 2.499 30 1 EEEF CC1=C2C=C3C(=O)C(O)=C([C@H](C)CO)[C@]3(C)CC[C@]2(C)C[C@H](O)C1=O 2356521435 XUINLCMVOIWOKB-NEUBXINZSA-N 346.423 2.393 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)C2=CC3=C(CO)C(=O)C=C[C@@]3(C)CC[C@]21C 2356730456 IQSIJJOWDAYBIC-SWBPCFCJSA-N 332.440 2.155 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)O 2356783746 MEGPPDNKNMAIJN-WCWNFEBDSA-N 330.380 2.056 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H](O)/C(C)=C\CC/C(C)=C/CC[C@@]3(CO)O[C@@H]3C[C@H]12 141611155 MULWDJOXRRXULO-HURKPUOJSA-N 348.439 2.432 30 1 EEEF CC#CC#COC1=C[C@@]2(CC[C@@H](OC(=O)CC(C)C)CO2)[C@@H]2O[C@H]12 238744560 RYAXKMRZPSXCFZ-AXUOBQJMSA-N 330.380 2.159 30 1 EEEF CCOC(=O)[C@H](/C=N/NC(N)=S)c1ccc(C(F)(F)F)cc1 653726140 JVTXUTBEGMHMES-NZWFQIHVSA-N 333.335 2.171 30 1 EEEF C[C@H](OS(=O)(=O)c1ccc([N+](=O)[O-])cc1)[C@@H]1CC(C)(C)OC1=O 64634099 ADFXPKPWYXFXBX-CABZTGNLSA-N 343.357 2.030 30 1 EEEF in-vitro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c1ccc(CNC(CO)(CO)CO)cc1 96906592 UIOBMGXTHDRZNG-UHFFFAOYSA-N 339.476 2.231 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(-c2nnn(C)n2)nc1 587908016 KJEXNRJIEHJIKG-UHFFFAOYSA-N 325.759 2.334 30 1 EEEF C=C[C@@H]1[C@](C)(CO)C(=O)[C@H]2C[C@@]1(C)[C@@H]1[C@@H]3OC(=O)C(=CC)[C@@H]3O[C@@]21C 2356677553 UAVHCHBOMMAUHU-DOORKKBLSA-N 346.423 2.042 30 1 EEEF C=C1C(=O)O[C@@H]2[C@H]1CC[C@H](C)[C@]1(OC(=O)CC)C=CC(=O)O[C@@]21C 72106697 RHXBMTGVDKQCFS-WOWSFRMASA-N 334.368 2.078 30 1 EEEF C=CCN1C(=O)N2C[C@H](CC)N=C2c2[nH]c(-c3cc(C)n(C)n3)nc21 72107863 JTGQLHAOPMIUBM-NSHDSACASA-N 339.403 2.085 30 1 EEEF CC#CC#C/C=C1/O[C@@]2(CCCCO2)[C@H](O)[C@H]1OC(=O)CC(C)C 85836893 LEOZNWWIPMVKHH-WOZHACCISA-N 332.396 2.143 30 1 EEEF C=C[C@@]12CN3CC[C@@H]1[C@@](C(=O)OC)(CO2)c1[nH]c2ccccc2c1C3 14421853 VQGKYGKANOEJCY-DBVUQKKJSA-N 338.407 2.369 30 1 EEEF C[C@@H]1CC=C[C@H](O)CC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 2356584431 DRRQOEPQLQGLLP-YPMHNXCESA-N 332.352 2.022 30 1 EEEF C=C([C@H](O)C=C[C@](C)(O)CO)[C@@H]1CC(=O)[C@]2(C)[C@@H]3CC[C@H](C)[C@@H]3[C@H]12 2356727494 PIQKTPMDCOQYRT-DCCMZFKYSA-N 334.456 2.090 30 1 EEEF O=C(/C=C/c1ccc(CNCCc2cnn3ccccc23)cc1)NO 72114285 SSEWZEHHFFXSEU-CMDGGOBGSA-N 336.395 2.185 30 1 EEEF O=[N+]([O-])c1ccc(S(=O)(=O)NN=CCCc2ccccc2)cc1 254102299 MCPAPVJNCYFCEH-UHFFFAOYSA-N 333.369 2.492 30 3 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)O 257447095 IPHNMKITOREFLW-NOZDNCFESA-N 332.396 2.136 30 1 EEEF endogenous,in-man CCN(CCN=c1[nH]c2ccccc2[nH]1)Cc1cc(C#N)ccc1O 1857556065 SGTNOUIJAMBVRP-UHFFFAOYSA-N 335.411 2.496 30 1 EEEF C=C1C[C@H](OCC(C)C)[C@@H]2C(=C)C(=O)O[C@@H]2C=C(C)[C@@H](O)C[C@@H]1O 2356440615 JDMDKFIKZIBCPI-TXTZMMAHSA-N 336.428 2.144 30 1 EEEF O=C1C(O)=C(c2cc(O)c(O)c(O)c2)C(=O)C(O)=C1c1ccccc1 44416879 OZTXUNBXAHGFHP-UHFFFAOYSA-N 340.287 2.194 30 1 EEEF CCOc1cc2c(-c3cccc(S(N)(=O)=O)c3)n[nH]c2cc1C#N 96270047 NMJXLTYBAJJXCO-UHFFFAOYSA-N 342.380 2.148 30 1 EEEF Cc1cccc2n1cc(/C=C/c1ccc(/C=N/NC(=N)N)cc1)[n+]2C 26823636 ZQRYAYYVPMOMJJ-BJKFPSCVSA-N 333.419 2.060 30 1 EEEF Cn1c(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cccc1=O 587891074 MHYZXYFEXHAOMV-UHFFFAOYSA-N 349.217 2.403 30 1 EEEF N#Cc1cnc(N)nc1NCC1(CO)CC(CCc2ccccc2)C1 1645708 WBDGIJDTEFRZGO-UHFFFAOYSA-N 337.427 2.364 30 1 EEEF C=C[C@H]1CC(=O)[C@@H]2Oc3c(OC)ccc4c3[C@@]23CCN(C)[C@H](C4)[C@@H]13 29463140 NTWGNEUJRLFCNI-QQDKQHTISA-N 325.408 2.345 30 1 EEEF CCN(CC)CCC[C@@H](C)Nc1ncnc2c1C(=O)C(OC)=CC2=O 27523140 CENAUQJRBYLTJY-GFCCVEGCSA-N 346.431 2.308 30 1 EEEF C=C1C[C@@]23C[C@H]1C(=O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 2356735009 PHYYFNCWOIYWTJ-TVUJFAMJSA-N 330.380 2.344 30 1 EEEF C=C[C@@]1(C)C=C2[C@@H](O)C[C@@H]3C(CO)(CO)CC(=O)C[C@@]3(C)[C@@H]2CC1 38784077 GUCMEFFLGFUFEJ-SPOLIRPYSA-N 334.456 2.236 30 1 EEEF C=CCOC(=O)c1c(C)oc2cc(OC)c(OS(=O)(=O)O)cc12 72105464 SDBUJXBLKPHHSJ-UHFFFAOYSA-N 342.325 2.274 30 1 EEEF CC(C)C[C@H](NC(=O)c1ccc(O)c(C(C)(C)C)c1)C(=O)NCC#N 82065543 GNAZYHVGFVWYTP-HNNXBMFYSA-N 345.443 2.474 30 1 EEEF C#Cc1ccc2c(c1)C(c1ccccn1)=NCc1c(C(=O)O)ncn1-2 95589034 LNWKMCTYBSXUHQ-UHFFFAOYSA-N 328.331 2.298 30 1 EEEF COC(=O)CC/N=C(\S)[C@]1(c2cccnc2)CCCC[S@@]1=O 13651014 YOMOAZHLOLYFGF-IVZQSRNASA-N 340.470 2.101 30 1 EEEF C#CCCN1c2ccccc2C(=O)N(Cc2ccccc2)S1(=O)=O 26963550 VXGBRKXMNJSVLR-UHFFFAOYSA-N 340.404 2.417 30 1 EEEF CN1CC2=C(C(=O)c3ccccc3C2=O)[C@]12C(=O)Nc1ccccc12 73298479 IBWUGLRRRIOIBF-HXUWFJFHSA-N 330.343 2.155 30 1 EEEF C=C(C)C[C@@H]1N(c2ccccc2)C(=O)[C@H]2[C@@H](C(=O)O)[C@@H]3C=C[C@@]21O3 43737349 IDZVBZRLNMBRMS-ZAHIEGGZSA-N 325.364 2.392 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnn(Cn2cc(N)cn2)c1 587909692 YXKUYPPYZITSQL-UHFFFAOYSA-N 327.775 2.229 30 1 EEEF COC1=C/C(=C/NNC2=NC(=O)[C@@H](c3ccccc3)S2)C=CC1=O 13119061 ZEHAYTYWJUVUNC-AUECHBEKSA-N 341.392 2.004 30 3 EEEF CC[C@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1 27619118 XPWASUHKKNPCDI-CVEARBPZSA-N 334.416 2.421 30 1 EEEF C#CC=C[C@@H]1[C@H]2[C@H]3[C@H]4O[C@@H]2C[C@@H]4O[C@@]3(OC)[C@@]1(Br)CC 2356795174 IKEWAOKGFUGNOH-VSPOPZGASA-N 339.229 2.494 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C(O)=C3[C@@](C)(CO)CC[C@@H](O)[C@]3(C)[C@@]2(O)CC1 14759378 YFSWTQQLSUEQBY-FZIGORSYSA-N 348.439 2.184 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)CC[C@H](O)[C@]2(C)C[C@H]2OC(=O)C(=C)[C@H]12 2356509314 LJFQOYCUYZGFOE-AFKZWXFASA-N 332.396 2.453 30 1 EEEF COc1ccc(/C=C/C(=O)c2c(C)[n+]([O-])c3ccccc3[n+]2[O-])cc1 40975723 HJSKOFCCDGEGKS-FMIVXFBMSA-N 336.347 2.320 30 1 EEEF C=C1C[C@]23C[C@H]1[C@H](O)C[C@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O[C@H]([C@@H]12)[C@@H]3O 238732023 OSYJLXUUZYSFTC-SELRSLNKSA-N 332.440 2.432 30 1 EEEF N#Cc1ccc2c(c1)CCN(S(=O)(=O)c1cccc(C(=O)O)c1)C2 95552724 GJAJUPMKLWMKNY-UHFFFAOYSA-N 342.376 2.003 30 1 EEEF O=c1[nH]nc(Cc2ccc(Cl)cc2)n1/N=C/c1ccc([N+](=O)[O-])o1 1654977 SALZHTFMSVUBNK-LZYBPNLTSA-N 347.718 2.199 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@H]1CC[C@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100781427 MJFVMFNFTCKAEV-UCWNZCKUSA-N 346.423 2.384 30 1 EEEF endogenous,in-man C=C1[C@H]2CC[C@@H]3[C@]4(C)CCC[C@]5(C)C(=O)O[C@H]([C@@H]54)[C@H](O)[C@@]3(C2)[C@H]1O 2356524092 PWCNMDCZKHGAQG-GHATWAMYSA-N 332.440 2.432 30 1 EEEF COC(=O)c1ccc2c(c1)C(=N\O)/C(=C1/C(=O)Nc3ccccc31)N2 95582435 IIVPVTOQYLXHRU-BAXAEGEVSA-N 335.319 2.440 30 1 EEEF C/N=C1/N/C(=C/c2c[nH]c3ccc(Br)cc23)C(=O)N1C 96937892 ZSWULTXENYERTM-LFYBBSHMSA-N 333.189 2.319 30 1 EEEF N#Cc1cc(Br)c2[nH]c([C@H]3CSCC(=O)N3)nc2c1 587042746 FOLNZIVGMXHCLL-SECBINFHSA-N 337.202 2.101 30 1 EEEF CCN1CCN(Cc2ccc(Nc3ncc(C#N)s3)nc2)CC1 62232907 BDRGERWUEALEAQ-UHFFFAOYSA-N 328.445 2.291 30 1 EEEF C=C1C[C@@]23C[C@@]1(O)CC[C@@H]2C1=C[C@H]2C[C@@](C)(C(=O)O2)[C@@H]1[C@@H]3C(=O)O 2356490060 VLTQADXREMVNJX-TUXRKGLZSA-N 330.380 2.056 30 1 EEEF N#Cc1nc(Cl)cc2nc(-c3ccc(CC(=O)O)c(N)c3)[nH]c12 587250684 WNYRXYAOHJDDDJ-UHFFFAOYSA-N 327.731 2.359 30 1 EEEF N#Cc1nc2nc(-c3cnc4c(F)cccc4c3N)[nH]c2nc1C#N 587176477 MCONZUQJSGCYCC-UHFFFAOYSA-N 330.286 2.033 30 1 EEEF C/C(=N\c1ccc(S(N)(=O)=O)cc1)[C@@H]1C(=O)Nc2ccccc21 169685124 DUGPEYYCVBKDIP-ZNBBLSJYSA-N 329.381 2.162 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(COC3=O)[C@H]2CC[C@]3(C)CO[C@H](O2)[C@H]31 2356350122 VGHUWBCJSRMGIQ-KWJCFAMBSA-N 344.407 2.243 30 1 EEEF C[C@H]1CCC(/C=N/c2ccccc2F)=C2NC=C(C(=O)O)C(=O)N21 100771967 KCAUDGFTUAZJFX-WHGJXMNKSA-N 329.331 2.322 30 1 EEEF COc1ccc(/C=N/N(Cc2ccccc2)/C(N)=N/[N+](=O)[O-])cc1 103171357 DGPWPEMCOQXMQF-WOJGMQOQSA-N 327.344 2.038 30 1 EEEF Cc1c(/N=C/c2c(O)cc(O)cc2O)c(=O)n(-c2ccccc2)n1C 84741560 MHSQMEITUBEVGB-VXLYETTFSA-N 339.351 2.352 30 1 EEEF O=C(CCC1=CCN(Cc2cccc(Br)c2)C1=O)NO 95574570 DOAMQZPUHRPDLK-UHFFFAOYSA-N 339.189 2.003 30 1 EEEF CN(c1ccc(C(=O)NO)cc1)[C@H]1CCN(c2ccccc2)C1=O 299860606 JKSCFHKEBJNQOU-INIZCTEOSA-N 325.368 2.047 30 1 EEEF CC(=O)OC[C@@H]1O[C@H](C#CCCc2ccccc2)C=C[C@@H]1OC(C)=O 13782948 PEMFRHXMDHFDFC-AABGKKOBSA-N 342.391 2.441 30 1 EEEF CCCCCC=CC1=C(CO)C(=O)[C@H]2O[C@]2(CC=C(C)C(=O)O)C1=O 2356716671 UJNVMSXVUCFBMB-IEBWSBKVSA-N 348.395 2.122 30 1 EEEF CC(C)C1=C(O)C(=O)C2=C(C1=O)[C@@H](O)[C@@H](O)[C@H]1C(C)(C)CCC[C@]21C 34182976 QPJRFHRTQNTKHS-PHXBYCTMSA-N 348.439 2.471 30 1 EEEF CCc1c(C)c(C#N)c2nc3ccc(NS(C)(=O)=O)cc3n2c1O 621431544 NUPMZTJRYYLUOK-UHFFFAOYSA-N 344.396 2.307 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(O[C@@H]2CCNC2)nc1 587908079 LACGUCSPFCOQQH-OAHLLOKOSA-N 329.787 2.279 30 1 EEEF Cc1ccc(S(=O)(=O)NN/C=C2\C(=O)C=Cc3ccccc32)cc1 4582553 HOCPHSQRYKSFPQ-ATVHPVEESA-N 340.404 2.415 30 3 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@@H]([C@H](C=O)[N+](=O)[O-])N1 587747121 PDDFVXQYGACOIB-LNCSFIOASA-N 331.141 2.008 30 1 EEEF CS(=O)(=O)N1CCC2(CCCN(Cc3ccc(C#N)cc3)C2)CC1 3956071 GNJRSSDTRIXAPO-UHFFFAOYSA-N 347.484 2.196 30 1 EEEF CN(CCC#N)c1nc(N(C)C2CCNCC2)nc2ccsc12 1911573643 ZZVMFUZVPCVUGH-UHFFFAOYSA-N 330.461 2.229 30 1 EEEF N#C/N=C(/NCCCc1c[nH]cn1)NCCSc1ccccc1 49089368 AAOBJKVPHPJNIH-UHFFFAOYSA-N 328.445 2.151 30 1 EEEF CC(C)C[C@H](NC(=O)c1cc(-c2ccccc2)no1)C(=O)NCC#N 82065387 XVDVVQXJUFPBBS-HNNXBMFYSA-N 340.383 2.126 30 1 EEEF N#CC1(n2cc([C@@H](NC(=O)c3ccon3)C3CCCCC3)nn2)CC1 95561787 OYIIXZYEJKKHOY-HNNXBMFYSA-N 340.387 2.330 30 1 EEEF CCO/C=N/n1cnc2c(oc3nc(C(F)(F)F)ccc32)c1=O 653695842 UTPJVIJLMZLEMX-NGYBGAFCSA-N 326.234 2.384 30 1 EEEF COc1ccccc1N1CCN(NC(C)=C2C=CC(=O)C=C2)CC1 13130334 MQCCFQLZQRGEBT-UHFFFAOYSA-N 325.412 2.291 30 3 EEEF C=C1C(=O)[C@@]23C[C@H](O)[C@@H]4C(C)(C)CCC[C@]4(C)[C@@H]2[C@H](O)C[C@H]1[C@H]3O 2356638805 RFZAFMSAZOFRSM-FEACJRBJSA-N 334.456 2.067 30 1 EEEF CC(=N)[C@@H](C#N)C(=O)CSc1nnc(-c2ccc3c(c2)OCO3)o1 36182476 NRPONSWDLHTVNL-SNVBAGLBSA-N 344.352 2.306 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@](C)(C(=O)O)CCC[C@@]4(C)[C@]2(O)[C@@H](O)C[C@@H]1C3 165978271 UVEPVLCUQGRNSH-WPUCUGSTSA-N 348.439 2.305 30 1 EEEF Cc1ccc(O)c(/C(CCN2CCN(c3ccccn3)CC2)=N/O)c1 36475946 ZWQOXMHVCXACBK-HEHNFIMWSA-N 340.427 2.486 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N2CCOCC2)nc1 587908399 TYNPJKPICPEYQH-UHFFFAOYSA-N 329.787 2.375 30 1 EEEF Cn1nc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cc1N 587890419 FXTHZIKTIOJYIO-UHFFFAOYSA-N 337.210 2.020 30 1 EEEF N[C@@H](CS)CNc1ccc(-c2cccc(-c3nnn[nH]3)c2)cc1 13471831 SGQCDCFAFCWKLD-CQSZACIVSA-N 326.429 2.203 30 1 EEEF O=C1Nc2ccc(Cl)cc2/C1=N/Nc1nc2ccccc2[nH]c1=O 45337886 GANBPYKELQFUNP-UHFFFAOYSA-N 339.742 2.345 30 1 EEEF COc1cccc2c1CCN1C(=O)/C(=C/C(=O)c3ccccc3)NC[C@H]21 96934319 HEWQOIDNNXSQSU-XUDLPTGHSA-N 348.402 2.491 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@]3(C=O)C=COC=C(COC(=O)C(C)C)[C@@H]3C[C@H]12 238782739 WEJGAPVLRYMYJQ-OLMMMNRUSA-N 346.379 2.307 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cncc2nc(O)c(O)nc12 587911279 CCXIPSYWQOKFHM-UHFFFAOYSA-N 327.727 2.498 30 1 EEEF O=C(NO)c1ccc2c(c1)C[C@H](Nc1ccc([N+](=O)[O-])cn1)CC2 113845003 HZAZIEOZGMNOQZ-CYBMUJFWSA-N 328.328 2.078 30 1 EEEF C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@H](O)[C@@H]1C(C)(C)CCC[C@]21C 2356480245 UXBITRKCDARMSM-WOGUSJMUSA-N 346.423 2.391 30 1 EEEF CC1(C)O[C@H]1CC(=O)Nc1cccnc1C(=O)Nc1nccs1 28333970 CZHUCHUJVPAVIN-JTQLQIEISA-N 332.385 2.296 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(COC3=O)[C@H]2CC[C@@]3(C)CO[C@@H](O2)[C@@H]13 101692119 VGHUWBCJSRMGIQ-XRQTXNRQSA-N 344.407 2.243 30 1 EEEF CC(C)[C@H](NC(=O)c1ccc(C#Cc2ccccc2)cc1)C(=O)NO 96910099 ZBZLOHPXIWQAKZ-SFHVURJKSA-N 336.391 2.346 30 1 EEEF N=c1c(N)c[nH]cc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587888538 MRXBDYLNQXIHAG-UHFFFAOYSA-N 349.221 2.094 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@@]2(COC[C@@H]2C#N)N1 587739119 FRFVAZZMRPQOFX-YACGNSKGSA-N 325.181 2.488 30 1 EEEF C#Cc1ccc2c(c1)C(=O)N1CC[C@H]1c1c(-c3nc(CC)no3)ncn1-2 13781518 OOTAQHRUCFIGFZ-AWEZNQCLSA-N 345.362 2.367 30 1 EEEF Cn1ccc(C(=O)N[C@]23CCC[C@](C#Cc4cnccn4)(CC2)C3)n1 205038324 VNZGTPXGIPDLPN-RBUKOAKNSA-N 335.411 2.085 30 1 EEEF CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1O[C@@H](C)C#N 29341099 BTPGDRXWEDAPAP-NSHDSACASA-N 338.839 2.285 30 1 EEEF O=C1C(Nc2ccc3c(c2)OCO3)=C(Cl)C(=O)c2ncncc21 26997106 WMDNQJQOSPJLHI-UHFFFAOYSA-N 329.699 2.147 30 1 EEEF N#CC1(C#N)N[C@H](c2ccccc2)C(C#N)(C#N)N[C@H]1c1ccccc1 23478276 QVPFDGMLHNLKDK-HDICACEKSA-N 338.374 2.234 30 1 EEEF C=C(C)C(=O)O[C@@H]1C=C(C)C2=CC(=O)[C@@](C)(C[C@H]3OC(=O)C(=C)[C@@H]13)O2 2356686318 AERIPQYYSNTIDA-GTACMHHNSA-N 344.363 2.164 30 1 EEEF O=C1C=C2O[C@]3(O)CC(=O)c4c(O)cccc4C3=C2c2cccc(O)c21 13368994 OEPGXEJLGRYQSA-HXUWFJFHSA-N 348.310 2.394 30 1 EEEF biogenic C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(COC3=O)[C@@H]2CC[C@@]3(C)CO[C@H](O2)[C@@H]13 40873989 VGHUWBCJSRMGIQ-AHIFSQJYSA-N 344.407 2.243 30 1 EEEF biogenic,in-vitro N#C/N=C(/NCCCc1c[nH]cn1)NCCc1c[nH]c2ccccc12 49014155 IICSNIJLINEWGY-UHFFFAOYSA-N 335.415 2.083 30 1 EEEF C=CC[C@]12C[C@@H](OC)[C@@H](O)[C@H]([C@@H](c3ccc4c(c3)OCO4)[C@@H]1C)[C@@H]2O 238755688 GGFOVZYLYBVWDX-WGILBSOCSA-N 346.423 2.468 30 1 EEEF N#Cc1ccc(OCc2nc3ccc(S(=O)(=O)O)cc3[nH]2)cc1 587190553 LVFSANPHIPZPBW-UHFFFAOYSA-N 329.337 2.260 30 1 EEEF Clc1ccc(-c2nnn(CC#CI)n2)cc1 3596932 TYTKRDSICMFXBP-UHFFFAOYSA-N 344.543 2.389 30 1 EEEF CCN(CC)C[C@@H](O)CO/N=C(\Cl)c1nc2ccccc2o1 43025783 QHKFDFZJKZZLAR-GMVXBXSFSA-N 325.796 2.448 30 1 EEEF C#Cc1ncc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cn1 587887520 QHYHCTRJLBVHSQ-UHFFFAOYSA-N 344.201 2.475 30 1 EEEF C[C@H](O)[C@@]1(c2ccc(C#N)cc2)NC[C@@H]2CC(=O)N(C)c3cccc1c32 963017404 CMVJTQXTIAWOOQ-YHQOMNDMSA-N 347.418 2.236 30 1 EEEF COc1ccc(CNC2=CC3=NCCc4c[nH]c(c43)C2=O)cc1OC 29124329 CFXNCWUUGSLWAF-UHFFFAOYSA-N 337.379 2.247 30 1 EEEF C=C1CC[C@H]2[C@@](C)(CC[C@@H](O)[C@@]2(C)CO)[C@H]1C(=O)CC1=CCOC1=O 2356643559 WZHWNAKOQGIEEB-PNDFQMOFSA-N 348.439 2.171 30 1 EEEF CCN(C)C(=O)c1cnc(NCCOC)nc1-c1ccc(C#N)cc1 82159000 QSXZKUZYUYFTOU-UHFFFAOYSA-N 339.399 2.165 30 1 EEEF O=C1C=Cc2ccccc2/C1=C/NN1C(=O)[C@@H]2[C@@H](C1=O)[C@H]1C=C[C@H]2CC1 136965893 CXENGHZKMYPUDO-HWPCBZPTSA-N 346.386 2.325 30 3 EEEF CC1=CC(=O)C2=C(C)C[C@H](OC(C)(C)C)[C@@H]3[C@H](C)C(=O)O[C@@H]3[C@]12O 2356331213 GFSKBOWVEKODGN-RYRSKNLTSA-N 334.412 2.328 30 1 EEEF N/C(=N\O)c1cccc(-c2cc(-c3cccc(/C(N)=N/O)c3)on2)c1 103226118 RRQOEFKOUPJUBM-UHFFFAOYSA-N 337.339 2.198 30 1 EEEF CCN(C)c1ncc(C#Cc2ccc(C[C@H](C)NC(C)=O)cc2)cn1 113412503 IGGLVNBBXXXTDP-HNNXBMFYSA-N 336.439 2.400 30 1 EEEF C=C(CC[C@@H]1C(=C)CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]21C)[C@@H](O)CO 2356581701 GLRQCZGXPULESM-YRIPFXIYSA-N 338.488 2.418 30 1 EEEF CC(C)C1=C(O)C(=O)C2=CC3=C(CO)C(=O)[C@H](O)C[C@]3(C)CC[C@@]21C 2356602719 KHEZYAOQSJJFOU-UAOJZALGSA-N 346.423 2.393 30 1 EEEF CC(C)C[C@H](OC(=O)N[C@@H]1C[C@H]1c1ccccc1)C(=O)NCC#N 82061442 OUVCVQOVGZUNNG-XHSDSOJGSA-N 329.400 2.323 30 1 EEEF COC1=C(O)C(=O)c2c(O)c3c(c(OC)c2C1=O)C[C@H](C)O[C@H]3C 40407140 UIBXAMHOHCDVSB-BQBZGAKWSA-N 334.324 2.218 30 1 EEEF biogenic COc1ccc(C[C@@H](N)CC(=O)N2[C@H](C#N)C[C@@H]3CCC[C@@H]32)cc1 299824478 HFHHWEUWEMLZGS-DFGXFYAUSA-N 327.428 2.248 30 1 EEEF COc1c(C)c2c(c(O)c1CC[C@@H](C)CCC(=O)NO)C(=O)OC2 28870032 ZZGCYZXJPMORDY-SECBINFHSA-N 337.372 2.234 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@@H]3C[C@H](OC[C@@H](C)CC)[C@H]12 2356673969 WULWDKXUHKIGSZ-MXNBKQEBSA-N 336.428 2.384 30 1 EEEF C=CCN1C(=O)c2n[nH]c(COC)c2[C@H]1c1ccc2c(c1)OCO2 199728921 GPQWXCIMIKDSIH-MRXNPFEDSA-N 327.340 2.016 30 3 EEEF C=C1C(=O)O/C2=C(\C)[C@]3(O)C=C[C@](C)(C[C@@H](OC(=O)C(C)C)[C@@H]1C2)O3 238764763 NQTBGYYRPIDDKV-LJUUEUOXSA-N 348.395 2.385 30 1 EEEF COc1ccc([C@H](O)C#C[C@H](O)c2ccccc2)c(OC)c1OC 1857760848 DDKCKMHUTOSATP-JKSUJKDBSA-N 328.364 2.483 30 1 EEEF C=C1[C@H](O)[C@@H]2O[C@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@]1(C)C(=O)C(=O)[C@]32C 2356527240 ZVWIURNWTXCECX-HUJVSYBTSA-N 330.424 2.291 30 1 EEEF C=C(C)[C@@H]1CCC(=C)[C@@H]2C3=C(C(=O)C(C)=C[C@H]12)[C@@H](O)[C@@](C)(O)C3=O 2356599882 PMTAKUZIYCHAID-SSFXFZHWSA-N 328.408 2.281 30 1 EEEF N#C[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)CNC(=O)c1cccc2ccccc12 84616477 IPKHAZSRZNIQAI-KBPBESRZSA-N 348.366 2.373 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@]2(COC[C@@H]2C#N)N1 587744415 ZUMGHCAWUGYXMG-IPURGOFSSA-N 325.181 2.488 30 1 EEEF CCSC1(SCC)C[C@@H](C(=O)O)N(C(=O)[C@@H](C)CS)C1 27991985 KQXPOBZTCGQQQT-UWVGGRQHSA-N 337.532 2.440 30 1 EEEF CC(=O)/C=C/N1C(=O)[C@@H](C)[C@H]2[C@@H]1CCN2C(=O)OCc1ccccc1 29479107 RPKPBMQJCVNPKB-BBQGHWSYSA-N 342.395 2.347 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@]2(C)C[C@H]2C(=O)C=C(C)C(=O)[C@H]1O 2356581518 YLQIJBIUALFEAE-HZHAQGHXSA-N 344.407 2.296 30 1 EEEF C=C1CC[C@H]2[C@@](C)([C@H](O)CC(=O)[C@@]2(C)CO)[C@@H]1CCC1=CCOC1=O 73275158 QEUIMVOANWYOHE-CTZQRVGRSA-N 348.439 2.171 30 1 EEEF CCSCC[C@H](N)C(=O)N[C@H](C#N)Cc1c[nH]c2ccccc12 49032531 IGUDMUOUKIZCPL-ZFWWWQNUSA-N 330.457 2.189 30 1 EEEF CC(C)O[C@@H]1Oc2ccc(O)c3c2[C@]1(C)[C@@H]1C(=O)C=C(CO)C1=C3 2356722742 ORBWSHDOOZYCPR-UHOSZYNNSA-N 328.364 2.308 30 1 EEEF COc1ccc(N/C(C[N+](=O)[O-])=N\CCCn2ccnc2)cc1OC 45317413 AMITUFJDCDQXGV-UHFFFAOYSA-N 347.375 2.078 30 1 EEEF COc1cc(Nc2ncc(C(=O)NO)cn2)cc(C(F)(F)F)c1 146122220 AGHMPPAFDIFEMJ-UHFFFAOYSA-N 328.250 2.367 30 1 EEEF N#CC1(n2cc([C@@H](NC(=O)c3cn[nH]c3)C3CCCCC3)nn2)CC1 95564037 SYDGGPNMAZALGO-HNNXBMFYSA-N 339.403 2.065 30 1 EEEF Oc1ccc(O)c(/C=N\NC(=S)N[C@H]2C[C@@H]3C[C@@H]2[C@@H]2C=CC[C@@H]32)c1 169355913 OFXIRPMFRVBDKI-AILRCOGZSA-N 343.452 2.497 30 1 EEEF C=C1[C@@H](C[C@@H](O)[C@@H]2CC(=O)NC2=O)[C@@]2(C)CCCC(C)(C)[C@H]2C[C@H]1O 2356380057 PPQGMYUYEYHPEL-UMCQMYNOSA-N 349.471 2.170 30 1 EEEF Nc1cccc(-c2cc(C(=O)NCCCCCCC(=O)NO)no2)c1 33132728 BYKMCJLDXBMWTO-UHFFFAOYSA-N 346.387 2.110 30 1 EEEF O=C(/C=C/c1ccc2c(c1)CN(CCc1cnn3ccccc13)C2)NO 72176496 KMTIRMHMRODSJK-FNORWQNLSA-N 348.406 2.411 30 1 EEEF CN1CCc2cn(C)c3c2C1=C/C(=N/CCc1ccc(O)cc1)C3=O 377811868 OLEMIURMTKKFSE-PGMHBOJBSA-N 335.407 2.440 30 1 EEEF Cc1cn(C/C(=N/Nc2ccccc2)c2ccccc2)c(=O)[nH]c1=O 103215340 IXZYFBKIAYKLGQ-XLNRJJMWSA-N 334.379 2.361 30 1 EEEF C=CCN1C(=O)CN(CC2CCNCC2)C(=O)c2cc(Cl)ccc21 95561615 VHZBCYGTJRJSIP-UHFFFAOYSA-N 347.846 2.314 30 1 EEEF N#Cc1cc2nc([C@H]3CSCC(=O)N3)[nH]c2cc1C(F)(F)F 587042231 BDMPWYJTPWNGTN-SNVBAGLBSA-N 326.303 2.357 30 1 EEEF CN(C)S(=O)(=O)c1cccc2[nH]c(-c3ccc(F)cc3C#N)nc12 587158184 LONNMDAXPQHEJJ-UHFFFAOYSA-N 344.371 2.491 30 1 EEEF COc1ccc([C@@H](O)C#C[C@@H](O)c2ccccc2)c(OC)c1OC 1857760845 DDKCKMHUTOSATP-CVEARBPZSA-N 328.364 2.483 30 1 EEEF NC(N)=Nc1nc(C(=O)Nc2nc3ccc(F)cc3s2)cs1 26152317 WMEVVDCVWQEWJJ-UHFFFAOYSA-N 336.377 2.049 30 1 EEEF C=C(CO)[C@]1(O)C=C2C(=O)C[C@H](C(C)C)[C@]2(C)C[C@@H]2OC(=O)C[C@@]21C 2356423705 CMFMNGXFTLTMOH-FLYSZBIRSA-N 348.439 2.169 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](CC(C)=CC(=O)[C@@H](O)CC(=O)C1)OC2=O 2356723586 NKBOMIIKMNCYIQ-QBIMZIAESA-N 332.396 2.440 30 1 EEEF Cc1nc(NS(C)(=O)=O)sc1-c1nc2cccc(C#N)c2[nH]1 586951401 LMWOKXCLDUTPBK-UHFFFAOYSA-N 333.398 2.238 30 1 EEEF COCCNCCc1cn(CC/N=C2\C[C@H]3CC[C@]2(C)C3(C)C)nn1 1772657849 LYUCEYCSLNCISQ-PLJJGOEBSA-N 347.507 2.344 30 1 EEEF CS(=O)(=O)Nc1ccc(/N=C/[C@H]2C(=O)Nc3ccccc32)cc1 169726566 VSYGALGQXZUTRS-NGWPFTMJSA-N 329.381 2.496 30 1 EEEF CCCOc1ccc(C(=O)N[C@H](CC(C)C)C(=O)NCC#N)cc1 82065227 ZVZJBOKRXXMOMU-MRXNPFEDSA-N 331.416 2.260 30 1 EEEF CC#CC#COC1=C[C@]2(CC[C@@H](OC(=O)CC(C)C)CO2)[C@@H]2O[C@H]12 5158077 RYAXKMRZPSXCFZ-UTRMSSBJSA-N 330.380 2.159 30 1 EEEF biogenic,in-vitro CC1(C)CCN(C(=O)CC#N)[C@@]12CCN(c1ncnc3[nH]ccc13)C2 169698986 IRKRUMKFBUIGLS-GOSISDBHSA-N 338.415 2.079 30 1 EEEF C[C@]12C=CC(=O)C=C1[C@](O)(CO)C[C@@H]1[C@@H]2CC[C@@]2(C)C(=O)CC[C@H]12 2356460236 NQQZWPXWZWALLC-JTZLQOMOSA-N 330.424 2.197 30 1 EEEF CC(C)COC(=O)[C@H](C)/N=C/C=C/N[C@@H](C)C(=O)OCC(C)C 45337749 HSXWDUUJSUEGEA-YMQGILBXSA-N 326.437 2.336 30 1 EEEF CS(=O)(=O)Nc1ccc(O)c(-c2nc3cccc(C#N)c3[nH]2)c1 586948699 SRSGXHURLHRIRM-UHFFFAOYSA-N 328.353 2.179 30 1 EEEF COc1c2c(c(O)c3c1C(=O)C1=C(C[C@H](C)O[C@@H]1C)C3=O)OCO2 103296514 QKLVHWJTSFVTRV-NKWVEPMBSA-N 332.308 2.002 30 1 EEEF Cc1ccc(-c2nnc(Nc3ncc(C(=O)NO)cn3)s2)cc1 72123504 ZVDKZXQXTLMMGF-UHFFFAOYSA-N 328.357 2.166 30 1 EEEF CCC/C=C/[C@@H]1C(=O)[C@@H]2O[C@@H]2C2(OCC(CC)(CC)CO2)[C@H]1CO 253993278 TWGDZVIUZPIUAD-WJYOYXOKSA-N 338.444 2.467 30 1 EEEF C=C1CC[C@@H]2[C@H]([C@@H]3[C@@H]1C1=C(C[C@@](C)(O)C1=O)C(=O)[C@]3(C)O)C2(C)C 2356415983 DGXURLBVVBVHIO-VFQIYLTMSA-N 330.424 2.195 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@H]2C[C@@H](CC(C)=C[C@H]3OC(=O)C(=C)[C@@H]31)OC2=O 2356536258 HOZUUHWHCWNMPV-QCODTGAPSA-N 346.379 2.244 30 1 EEEF Cc1nc(C(=O)Nc2ccc([C@H]3CNCCO3)cc2F)ccc1C#N 149958757 SBASBXAJQPUXDZ-QGZVFWFLSA-N 340.358 2.314 30 1 EEEF CC1=CC(=O)[C@]2(CN1)N[C@@H](C)Cc1cc(Br)c(F)cc12 587791507 GBZAYDNBEDMVFK-BJOHPYRUSA-N 339.208 2.394 30 1 EEEF Cc1cc2c(cc1O)[C@]1(Cc3ccccc3[C@@H]1C#N)N[C@H](C(=O)O)C2 963553105 RLECXGGYOMJNLF-ZWOKBUDYSA-N 334.375 2.358 30 1 EEEF Cn1cc(C(=O)c2ccc(F)cc2)cc1/C=C/C(=O)CC(=O)C(=O)O 13674094 MWHNLHLQSBEVQO-VOTSOKGWSA-N 343.310 2.021 30 1 EEEF COc1ccc(C/N=C(\S)NCCCn2ccnc2)cc1OC 13679606 XYENOKGNKNXUGG-UHFFFAOYSA-N 334.445 2.366 30 1 EEEF C=C[C@H]1CC(=O)[C@@H]2Oc3c(OC)ccc4c3[C@@]23CCN(C)[C@@H](C4)[C@@H]13 167846093 NTWGNEUJRLFCNI-PVPCKKGCSA-N 325.408 2.345 30 1 EEEF CC(C)S(=O)(=O)N[C@@H]1Cc2ccc(-c3cncc(C#N)c3)cc2C1 62224520 KGEABTFMCTZXTF-GOSISDBHSA-N 341.436 2.415 30 1 EEEF CC=CC#CC#CC=CC(=O)OCCCC#CC#CC=CC(=O)OC 2356536599 YZENRRRDZBYNCT-UHFFFAOYSA-N 334.371 2.185 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@]2(C)C[C@@H]2C(=O)C=C(C)C(=O)[C@H]1O 2356581521 YLQIJBIUALFEAE-SJYTYEEDSA-N 344.407 2.296 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)CC[C@H]3C(=C)C(=O)O[C@@H]3[C@H]2[C@]2(C)O[C@H]12 238780305 DVCUGTJISUVHTF-ZHFGEGHCSA-N 330.380 2.470 30 1 EEEF N#Cc1nc2nc(Cc3csc(-c4ccco4)n3)[nH]c2nc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endogenous,in-man O=C[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)CCCc1ccccc1 13738812 ATHGZTRCNIYYSU-ROUUACIJSA-N 342.439 2.190 30 1 EEEF N/C(=N\O)c1ccc(-c2cc(-c3cccc(/C(N)=N/O)c3)on2)cc1 103226161 QEMWFOWYBXYHDD-UHFFFAOYSA-N 337.339 2.198 30 1 EEEF COc1cc(/C=C2\C(=O)c3ccc(N)cc3C2=O)cc(OC)c1O 26497077 XKHLGRCZHXGPIF-WLRTZDKTSA-N 325.320 2.454 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@@H](O)C[C@@H](O)C(=C)C[C@H](OCC(C)C)[C@H]12 2356440612 JDMDKFIKZIBCPI-ICUGJSFKSA-N 336.428 2.144 30 1 EEEF C#C[C@]12O[C@]1(C=O)[C@H]1[C@H](CC2=O)[C@]2(C)CCCC(C)(C)[C@H]2C[C@H]1O 2356471219 RLCVKAJQPCOLQK-YGAKERMQSA-N 330.424 2.129 30 1 EEEF C=CCN1C(=O)N2C[C@H](CC)N=C2c2[nH]c(-c3cc(C)nn3C)nc21 72110305 IDCILQLKRDAWDC-NSHDSACASA-N 339.403 2.085 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1[C@H](OC(=O)C(C)C)C[C@@](C)(O)[C@@H]1CC=C(C)[C@H]21 13325531 SLWRMDVPXSTKON-WLQXYJQWSA-N 334.412 2.389 30 1 EEEF C=C1CC[C@H]2[C@](C)(CC[C@@H](O)[C@@]2(C)CO)[C@H]1C(=O)CC1=CCOC1=O 2356643558 WZHWNAKOQGIEEB-NIMBFUQJSA-N 348.439 2.171 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@@H]2[C@]1(C)C(=O)CC[C@@](C)(C(=O)O)[C@H]1C[C@@H]3O 72104714 CLGOGJHVMHIUDO-PSFOJYCLSA-N 346.423 2.369 30 3 EEEF C=CCc1cccc2nc([C@H](CC(N)=O)NC(=O)CC(C)C)[nH]c12 587202857 HFPYZOCZEUVCES-AWEZNQCLSA-N 328.416 2.370 30 1 EEEF CC(C)C1=C(O)C(=O)C2=CC3=C(CO)C(=O)[C@H](O)C[C@@]3(C)CC[C@]21C 2356602718 KHEZYAOQSJJFOU-JSNMRZPZSA-N 346.423 2.393 30 1 EEEF O=C(/C=C/c1ccc(CNCCc2c[nH]c3cccnc23)cc1)NO 72113201 IFTQEXVGUHQLPH-BQYQJAHWSA-N 336.395 2.414 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@@H]2[C@]1(C)C(=O)CC[C@@](C)(C(=O)O)[C@@H]1C[C@@H]3O 72104715 CLGOGJHVMHIUDO-RZXHAHPMSA-N 346.423 2.369 30 3 EEEF COc1ccc(S(=O)(=O)N/N=C(\C)c2nc3ccccc3[nH]2)cc1 1911583959 OVYIPLPIMZQIBT-YBFXNURJSA-N 344.396 2.274 30 1 EEEF CCC(=O)C[C@H](C)[C@@H]1O[C@]1(C)/C=C/C(=O)N[C@H](CO)[C@@H](C)CC 140073830 RDWBIAZAAVLQEC-PXRYMEDMSA-N 325.449 2.229 30 1 EEEF C=C(C)C(=O)O[C@H]1CC2=C[C@H](C/C(C)=C/[C@H]3OC(=O)C(=C)[C@@H]13)OC2=O 95100128 JMUOPRSXUVOHFE-HRDMCZAFSA-N 344.363 2.164 30 1 EEEF C=C1C(=O)O[C@@H]2[C@H]1[C@@H](C)[C@H]1[C@](C)(O)CC[C@@H](C(C)=O)[C@]1(C)[C@@H]2C(C)=O 523041775 QRJWNJLDUSTASQ-XFQPZBRPSA-N 348.439 2.312 30 1 EEEF biogenic CS(=O)(=O)Nc1ccc(C(=O)/C=C/c2ccc(O)c(O)c2)cc1 43172872 VTJGOZYUTLWLLA-KRXBUXKQSA-N 333.365 2.365 30 1 EEEF C#Cc1ccc2c(c1)C(=O)N1CCC[C@H]1c1c(C(=O)OCC)ncn1-2 13781508 AGSFVTKORUUQJP-HNNXBMFYSA-N 335.363 2.321 30 1 EEEF CCCCN[C@@H]1C2=C(OC(C)(C)[C@H]1O)C(=O)c1ccccc1C2=O 29134723 PWJHHLDOTFKWMM-KDOFPFPSSA-N 329.396 2.248 30 1 EEEF C[C@H](OS(=O)(=O)c1ccc([N+](=O)[O-])cc1)[C@H]1CC(C)(C)OC1=O 64634101 ADFXPKPWYXFXBX-JOYOIKCWSA-N 343.357 2.030 30 1 EEEF in-vitro C[C@@H](C=O)NC(=O)[C@H](Cc1ccccc1)NC(=O)Nc1ccccc1 82061188 IOBSHJKFMZWHDJ-YOEHRIQHSA-N 339.395 2.123 30 1 EEEF N#Cc1cccnc1NCc1cccc(-c2nc3c[nH]c(=N)[nH]c-3n2)c1 587229441 GSDWLSVKOKUAHE-UHFFFAOYSA-N 342.366 2.263 30 1 EEEF C=C(C)C(=O)O[C@@H]1CC(=C)[C@@H]2C[C@H](O)C(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 13326256 ZGDWDAMVZDRRQA-YHPRMOQLSA-N 330.380 2.085 30 1 EEEF biogenic N#C[C@@H]1C[C@H](F)CN1C(=O)[C@@H](N)Cc1ccccc1C(F)(F)F 103242319 GGXMRDYJBWYCMY-GVXVVHGQSA-N 329.297 2.038 30 1 EEEF COc1ccccc1C(=O)/C=C1\NC[C@H]2c3ccccc3CCN2C1=O 96934349 PBSPRMMNFZKZHW-FSEPTYSPSA-N 348.402 2.491 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(S(N)(=O)=O)s1 587918297 LCXNBMWDUZEXRU-UHFFFAOYSA-N 327.814 2.457 30 1 EEEF N#Cc1cccc(COc2ccc(-n3cc(C(=O)O)nn3)cc2C#N)c1 1772643417 ULHCCZWXAHHVRI-UHFFFAOYSA-N 345.318 2.288 30 1 EEEF Cc1cc(C)n(-c2nc(SCC(N)=O)c(C#N)c3c2CCCC3)n1 66077307 HIDKHOJLJSWPKX-UHFFFAOYSA-N 341.440 2.212 30 1 EEEF C#Cc1cc2c(cc1O)[C@]1(C#N)CCC3(OCCO3)C3=CO[C@H](C2)[C@@H]31 96916991 ONSGVYWHERRIEK-GUDVDZBRSA-N 335.359 2.127 30 1 EEEF Clc1cccc(C#CCOc2nsnc2C23CN4C[C@H]2[C@H]3C4)c1 13798000 HPTGNTPIZBKTDN-VMZNBEPHSA-N 343.839 2.435 30 1 EEEF CCN(C)c1nccc(C#Cc2ccc(C[C@H](C)NC(C)=O)cc2)n1 169706344 IGNDEIPSSYUMSI-HNNXBMFYSA-N 336.439 2.400 30 1 EEEF O=C(O)[C@@H]1CCCN(CCO/N=C/c2ccccc2-n2cccn2)C1 1857544651 HIELEYYSSNZACD-RBYWHNRPSA-N 342.399 2.019 30 1 EEEF COc1ccc(N/C(O)=N/S(=O)(=O)c2ccc(OC)cc2)cc1 26476187 YHXADIZXPHWGKQ-UHFFFAOYSA-N 336.369 2.419 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N2CCC(O)CC2)nc1 587908070 KUZMVBXOVAXFTL-UHFFFAOYSA-N 343.814 2.500 30 1 EEEF C[C@@H]1CCC(/C=N/c2ccc(F)cc2)=C2NC=C(C(=O)O)C(=O)N21 100775127 KSRPRRVIDJZIJB-OQOREVAYSA-N 329.331 2.322 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](n2ncc3ccccc3c2=O)[C@@H]1O 27557296 UMDKMLKKBGABSS-MSOLQXFVSA-N 347.374 2.389 30 1 EEEF C=C1[C@@H](OC(=O)C=C(C)CO)C[C@H]2C(=C)CC[C@@H]3C(=C)C(=O)O[C@H]3[C@H]12 2356462688 AZDMJQODBMILBW-WHEVEAIOSA-N 344.407 2.477 30 1 EEEF C[C@H](O)C[C@H]1O[C@@H]1C=CC=Cc1cc2cc(O)cc(O)c2c(=O)o1 2356744596 TYXXEQMKBIKKOL-AMKSKSKJSA-N 330.336 2.312 30 1 EEEF C=CCN(C)CC[C@@H]1CC[C@@H](O)[C@H](C(=O)N(C)Cc2ccccc2)O1 2356876134 ZHTXQABDTNBAGM-IPMKNSEASA-N 346.471 2.061 30 1 EEEF CC(C)C1=C[C@@H]2[C@@H]3[C@@H](C(C(C)C)=CC(=O)[C@]3(C)O)[C@H]1C(=O)[C@@]2(C)O 238772002 YNYHPBIGKWCFOA-GLMCPCGLSA-N 332.440 2.297 30 1 EEEF CCCCC1=C(N2CC2)C(=O)c2nc3n(c2C1=O)CC[C@@H]3OC(C)=O 13605730 CKHIGJCCWYNDSH-LBPRGKRZSA-N 343.383 2.030 30 1 EEEF CC(=O)CC1=C2C(=O)O[C@]3(C)CC[C@@H]4[C@H]([C@H]([C@@H]23)[C@](C)(O)C1=O)C4(C)C 2356482937 BTLNQUGRPABJQH-RALKJSRBSA-N 346.423 2.210 30 1 EEEF C#C[C@]1(O)CC[C@@H]2[C@@H]3C[C@H](O)c4cc(OC)ccc4[C@@H]3C[C@H](O)[C@]21C 2356584250 YTRCAZOTWYOCGG-ZICUHAMLSA-N 342.435 2.377 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 62234987 HHDWSDSMWJQURA-CUFSAKGESA-N 332.396 2.136 30 1 EEEF in-man C[C@@H]1CC(=O)C2=C(CC[C@]34O[C@]23C(=O)c2cccc(O)c2[C@H]4O)C1 2356796807 NNMGLXNJGVNRCH-CFHYLDRMSA-N 326.348 2.219 30 1 EEEF CC(C)(C)C(=O)N[C@@H](Cc1ccc(Br)cc1)C(=O)NO 653801245 CMKKIEWVWXTANS-NSHDSACASA-N 343.221 2.028 30 1 EEEF O=C(CCCCCCC(=O)N[C@@H]1CCN(Cc2ccccc2)C1)NO 1772658181 XXKNJZXNYLJBDM-QGZVFWFLSA-N 347.459 2.223 30 1 EEEF CC1(C)OC(c2ccc(S(N)(=O)=O)cc2)=C(c2ccco2)C1=O 13559391 YCFUZEFTLBDSHJ-UHFFFAOYSA-N 333.365 2.173 30 1 EEEF COc1ccc(-c2c(C#N)c(N)nc(SCCO)c2C#N)cc1 13612605 LWIZMQXDGANRMC-UHFFFAOYSA-N 326.381 2.167 30 1 EEEF CCOc1nn(-c2ccc(Cl)cc2)c(O)c1/C=N/CC(=O)OC 101659338 ZDRDGNHIMOJBSI-CAOOACKPSA-N 337.763 2.222 30 1 EEEF CC(C)[C@@]12O[C@@H]1C=C1[C@@]3(C)CCC4=C(COC4=O)[C@H]3C[C@@H]3O[C@]13C2=O 64512408 NDBFYINIVHOHLP-JPEKPBGJSA-N 342.391 2.100 30 1 EEEF CCC/C=C/[C@@H]1C(=O)[C@@H]2O[C@H]2C2(OCC(CC)(CC)CO2)[C@@H]1CO 253993274 TWGDZVIUZPIUAD-IOJDNRJCSA-N 338.444 2.467 30 1 EEEF COc1cccc(C[C@H](CS)C(=O)Nc2c[nH]c(C(=O)O)c2)c1 11688387 XRMVSIGVJPNKLV-LLVKDONJSA-N 334.397 2.449 30 1 EEEF C=C(C)[C@@H]1C[C@@H]2[C@@H](CC[C@]2(O)CCNC(=N)NC)[C@@]2(O)CC=C[C@H]1C2 2356676439 SYAVXIORAFJRNU-YGPNDZQQSA-N 347.503 2.171 30 1 EEEF CC=CC=CC1=CC2=CC(=O)[C@](C)(OC(=O)C[C@H](C)O)C(=O)C2=CO1 2356859860 TZCZFKHZYAXVCK-BUXKBTBVSA-N 344.363 2.068 30 1 EEEF CC(C)C[C@@H](NC(=O)c1ccc(-n2cccc2)cc1)C(=O)NCC#N 82061349 FGIOOVDQFGGWMB-QGZVFWFLSA-N 338.411 2.262 30 1 EEEF COC1=C[C@H]2[C@H]3Cc4ccc(OC)c(O)c4[C@]2(CCN3C)CC1=O 138939212 INYYVPJSBIVGPH-XEKQOVJPSA-N 329.396 2.018 30 1 EEEF COCC(=O)N1[C@@H](C#N)[C@@H](c2ccccc2-c2ccccc2)[C@@H]1CO 95668353 RRMULCFNGGBUJN-CMKODMSKSA-N 336.391 2.179 30 1 EEEF CCc1ncnc(N2CCC3(CC2)COC3)c1C#Cc1ccc(N)nc1 149402372 QNIWKMMGDVFCEO-UHFFFAOYSA-N 349.438 2.033 30 1 EEEF C=CC[C@]1(OCc2ccccc2)C(=O)C(=O)O[C@@H]1[C@H]1COC(C)(C)O1 5538963 QUSJNYTVFAJGCT-OGWOLHLISA-N 346.379 2.164 30 1 EEEF C[C@H]1C[C@@H]2O[C@@H]2/C=C\C=C\C(=O)Cc2cc(O)cc(O)c2C(=O)O1 14614731 XTUZVEOWUSGCSV-RZCUTACJSA-N 330.336 2.038 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(=O)C(C)=CC)CC(=C)[C@H]1[C@H]2C(C)=C[C@@H]1O 2356530237 JEAWGNYMYMHNGM-ZDRBWGSPSA-N 344.407 2.475 30 1 EEEF COc1ccc(NC(C)(C)c2nc3nc(C#N)c(C#N)nc3[nH]2)cc1 587200967 CKPCHVIGYKNWPO-UHFFFAOYSA-N 333.355 2.452 30 1 EEEF Cc1nc(N)cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)n1 587890175 TWJJRGAEDVJMNG-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF O=C(O)COc1ccc2c(c1)O/C(=C\c1ccccc1C(=O)O)C2=O 1772656605 LPRINWBOYGBWAP-CHHVJCJISA-N 340.287 2.464 30 1 EEEF O=C(c1ccc(O)cc1)[C@H]1O[C@@H]1C[C@H](O)CCc1ccc(O)cc1 14594461 SFLXZEYRHVXOSA-LMMKCTJWSA-N 328.364 2.432 30 1 EEEF Cc1cc2c(nc1N1CCC(OC[C@@]3(C)C[C@H]3C#N)CC1)CNC2=O 1857642158 UTONXMAOIHKISP-ORAYPTAESA-N 340.427 2.169 30 1 EEEF O=C(NO)c1cnc(Nc2nnc(-c3ccccc3Cl)o2)nc1 72122910 XWHMNBPQBJZXBX-UHFFFAOYSA-N 332.707 2.043 30 1 EEEF N#Cc1ccc(N2C(=O)[C@@H]3[C@H]4CC[C@H](O4)[C@@H]3C2=O)cc1C(F)(F)F 29126974 QZRQLVZGQQVBIK-MPZDIEGVSA-N 336.269 2.244 30 1 EEEF C[C@H]1NC(=O)[C@]23C[C@H](O)[C@H]4[C@@H](CCC5=CC(=O)C=C[C@@]54C)[C@@H]2CC[C@@H]13 2356663880 ZFDFFZSCUSDQEX-GJIQRYEPSA-N 341.451 2.380 30 1 EEEF CN(O)C(=O)C[C@@H](CP(=O)(O)O)c1ccc(Cl)c(Cl)c1 299844581 HRVAZZLZVPKODL-QMMMGPOBSA-N 342.115 2.492 30 1 EEEF O=C(c1ccccc1)c1ccccc1N=Cc1c(O)nc(=O)[nH]c1O 1779604113 IDGMVBMQUQUQAZ-UHFFFAOYSA-N 335.319 2.163 30 1 EEEF CCc1ccc2[nH]c3nc(NN/C=C4\C=CC(=O)C=C4O)nnc3c2c1 13125012 SJWMVTNWERXCDG-PKNBQFBNSA-N 348.366 2.450 30 3 EEEF C=C(C)[C@@H]1CC[C@]2(CO)OC(=O)C3=C(CC(C)=O)C(=O)C(C)=C[C@@H]1[C@H]32 2356411335 MMENEXZIHVFHNM-WBFDFMGXSA-N 344.407 2.298 30 1 EEEF CC1CCC(NS(=O)(=O)Cc2nc3cccc(C#N)c3[nH]2)CC1 586953608 WHDVKIXWHAVFRE-UHFFFAOYSA-N 332.429 2.433 30 1 EEEF COc1ccc(C(=O)C#Cc2ccc(S(C)(=O)=O)cc2)cc1OC 13683364 OZHWLRKHAHPLNY-UHFFFAOYSA-N 344.388 2.342 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1C[C@H]1O[C@]1(CO)CC/C=C(/C)CC/C=C(/C)[C@H]2O 169292508 MULWDJOXRRXULO-ISGKGXORSA-N 348.439 2.432 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)[C@@H]3[C@H](O)CC[C@]3(C)[C@H](OC(=O)C=CC)[C@@H]12 2356549664 HSXLCTYJIGXUOE-SGQJJRJLSA-N 334.412 2.389 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)[C@H](O)C[C@@]3(C)[C@@]1(C)[C@@]21CO1 2356610163 VRHZKNFFKJZHFD-ANPJLTAGSA-N 334.412 2.138 30 1 EEEF CC(C)(O)C#Cc1cc2c(cc1F)OCCc1sc(C(N)=O)nc1-2 215739486 ZBBIOQGXTIRGKU-UHFFFAOYSA-N 346.383 2.105 30 1 EEEF CC1=CC(=O)[C@@]2(CN1)N[C@@H](C)Cc1ccc(F)c(Br)c12 587799460 XHIZTKJYJVNHTR-BJOHPYRUSA-N 339.208 2.394 30 1 EEEF C=CC[C@@H]1C(=O)N(C(C)=O)[C@H]2CCN(C(=O)OCc3ccccc3)[C@H]12 26487906 PHAYEXZAKQRIHL-YESZJQIVSA-N 342.395 2.347 30 1 EEEF CCO[C@]12C[C@]3(C)[C@H](CC1=C(C)C(=O)O2)C(C)=CC(=O)[C@@H]3OC(C)=O 2356500628 YDUWTFHAUBSRIH-HQJJXPTPSA-N 348.395 2.470 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@](C)(O)CC[C@@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@H]12 2356677099 GUGYUSGXSKYCJD-IWQSFCKSSA-N 348.439 2.288 30 1 EEEF CCCCC(=O)O[C@@H]1CCn2c1nc1c2C(=O)C(C)=C(N2CC2)C1=O 38792489 SSAUGKDFJRHWJM-LLVKDONJSA-N 343.383 2.030 30 1 EEEF C=CCc1cc(NC(=O)NCC)ccc1OC[C@H](O)CNC(C)C 169317298 PWYDWQHIIMXLJN-MRXNPFEDSA-N 335.448 2.294 30 1 EEEF CC[C@H](C)[C@H](NC[C@@H](N)CS)C(=O)NCc1ccc(C)cc1C 27315782 ZBVDGGZJTGDHST-XKQJLSEDSA-N 337.533 2.181 30 1 EEEF C=C(CO)[C@@H]1C=C2[C@H](O)C[C@H]3[C@](C)(CO)[C@@H](O)CC[C@]3(C)[C@H]2CC1 238772753 YKSOUKMSKAWWQG-ULBBQPHTSA-N 336.472 2.028 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3ccc(C(=O)O)cc3[nH]2)C1=O 587038454 IHMKVWZVBKMWQR-LLVKDONJSA-N 331.353 2.054 30 1 EEEF CS(=O)(=O)c1ccc(C#CC(=O)c2cccc([N+](=O)[O-])c2)cc1 13683400 ICDXCUKKRNRWNN-UHFFFAOYSA-N 329.333 2.233 30 1 EEEF Clc1ccc(-c2nnnn2CC#CI)cc1 3596930 LHOJVOLOJVLHEW-UHFFFAOYSA-N 344.543 2.389 30 1 EEEF O=S(=O)([C@H]1O[C@H]1c1ccc(Cl)c(Cl)c1)N1CCOCC1 26379610 VDROCDVBBSIMQF-NWDGAFQWSA-N 338.212 2.053 30 1 EEEF C=C1COC(=O)[C@]12C[C@]1(C)[C@@H](C)CC[C@H](O)[C@@H]1[C@H]2OC(=O)C(C)C 38784247 VSLKGPYHLGIYBG-ZUHYYECNSA-N 336.428 2.471 30 1 EEEF biogenic,in-vitro C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@@H]2/C(=C/C=C/C(C)(C)O)C(=O)OC[C@@H]12 85641376 DHTWVKTXQLZELP-GTWYZVCQSA-N 348.439 2.288 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@@](C2)([C@@H](C(=O)O)[C@H]2[C@@]4(C)CCC[C@@]32COC4=O)[C@@H]1O 257483225 MJFVMFNFTCKAEV-OMJJOCQZSA-N 346.423 2.384 30 1 EEEF endogenous,in-man C=CC(C)(C)c1[nH]c2ccccc2c1/C=c1\[nH]c(=O)c2cccn2c1=O 205634632 WXBLMCVYDMVHHI-VBKFSLOCSA-N 345.402 2.480 30 1 EEEF CC(C)C(O)(C#Cc1cn2nc(-c3ccco3)nc2c(N)n1)C(C)C 28342647 ZEJVIIQJNKJHOJ-UHFFFAOYSA-N 339.399 2.361 30 1 EEEF C[C@@H]1CC=C[C@@H](O)CC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 2356584429 DRRQOEPQLQGLLP-DGCLKSJQSA-N 332.352 2.022 30 1 EEEF C=C[C@@H]1C=C2C(=O)C=C3[C@](C)(C(=O)O)CC[C@H](O)[C@]3(C)[C@]2(O)CC1 2356788681 CHLJNZOUECQLLK-CYMZCZABSA-N 332.396 2.001 30 1 EEEF COc1cncc2nc(-c3ccc(C(C=O)C=O)c([N+](=O)[O-])c3)[nH]c12 587262680 ZGYIXQRFKNULKC-UHFFFAOYSA-N 340.295 2.023 30 1 EEEF COC(=O)[C@]1(CC(=O)c2ccc(C#N)cc2)NCCc2c(C)ccnc21 963072819 OEPWJBWNTBPHER-HXUWFJFHSA-N 349.390 2.049 30 1 EEEF CCSCC[C@@H](NC(=O)[C@H](CS)Cc1ccccc1)C(=O)O 26494854 ZYBMHXFQTKTNOS-UONOGXRCSA-N 341.498 2.488 30 1 EEEF C=CC[C@H]1C(=O)N(C(C)=O)[C@H]2CCN(C(=O)OCc3ccccc3)[C@@H]21 26487894 PHAYEXZAKQRIHL-IXDOHACOSA-N 342.395 2.347 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1[C@@H](OC(C)=O)C[C@@]1(C)[C@H](OC(C)=O)CCC(=C)[C@@H]21 40394040 IDVKLEJKBPWDKI-NGXVOCDNSA-N 348.395 2.324 30 1 EEEF C=CCN(C[C@@H]1Oc2cc(OC)cc3c2C(=O)[C@H]1C3)C(=O)OCC 587431044 YEUBKLJITZIBGN-ZFWWWQNUSA-N 331.368 2.456 30 1 EEEF C/C(=N\NC(=S)NNC(=S)Nc1ccccc1)c1ccccn1 13650656 CVCPNJREWHGQQL-WOJGMQOQSA-N 344.469 2.171 30 1 EEEF CCC(=O)C[C@H](C)[C@@H]1O[C@]1(C)C=CC(=O)N[C@H](CO)[C@H](C)CC 2356596881 RDWBIAZAAVLQEC-IPUKNANDSA-N 325.449 2.229 30 1 EEEF COC1=CC(=O)[C@@]2(C)c3c(O)c(C)c(O)c(C(C)=O)c3O[C@@]2(OC)C1 2356835305 KQROSALZXGEZDK-ROUUACIJSA-N 348.351 2.105 30 1 EEEF CCCCc1nc2cc(/C=C/C(=O)NO)ccc2n1CCN(C)C 34987454 FDTJPEFUCCISMT-CSKARUKUSA-N 330.432 2.459 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@@H](c2ccccc2-c2ccccc2)[C@@H]1CO 95667887 RRMULCFNGGBUJN-WSTZPKSXSA-N 336.391 2.179 30 1 EEEF CC=CC=CC(=O)NCCC[C@H]1NC(O)=C(C(=O)C=CC=CC)C1=O 2356700596 UOPXXWDGQCFNHZ-CQSZACIVSA-N 344.411 2.027 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@H](C(=C)C)C(=O)C=C(C)C(=O)[C@H]1O 2356843915 NQSGQBPUUPHFQJ-WFEDQXDTSA-N 344.407 2.462 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)[C@@H](C)C[C@H]2OC(=O)C(=C)[C@H]12 15165986 KYTKEOOPALLADL-VJEJJEIOSA-N 346.379 2.244 30 1 EEEF biogenic C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@H](O)[C@H]1C(C)(C)CCC[C@@]21C 2356480243 UXBITRKCDARMSM-CAIZAGQASA-N 346.423 2.391 30 1 EEEF CCCCCC=CC1=C(CO)C(=O)[C@@H]2O[C@@]2(CC=C(C)C(=O)O)C1=O 2356716670 UJNVMSXVUCFBMB-HKUYNNGSSA-N 348.395 2.122 30 1 EEEF N#Cc1cc([C@@]23CO[C@@H](CF)C[C@H]2CSC(N)=N3)c(F)cc1F 223174069 LGJIPDMTLWEFJV-FEUHOPSXSA-N 341.358 2.468 30 1 EEEF CCO[P@](=O)(N[C@@H](CC(C)C)C(=O)NO)c1ccc(OC)cc1 84462391 KTCRMROJXXSPQJ-PSLXWICFSA-N 344.348 2.060 30 1 EEEF C=C1C[C@H](OC(C)=O)[C@H]2[C@H](C)C(=O)O[C@@H]2[C@H]2C(=C)[C@@H](OC(C)=O)C[C@@H]12 238759441 YQAAKILPZPSNKX-QZXJSLGOSA-N 348.395 2.180 30 1 EEEF CN(C)c1ccc(-c2c(C#N)c(N)nc(SCCO)c2C#N)cc1 13612613 IMNHXHGQBWALSD-UHFFFAOYSA-N 339.424 2.225 30 1 EEEF CC1=C[C@H](C)[C@H](c2cc(O)cc(O)c2)OC(=O)[C@H](C)[C@@H](O)[C@@H](C)C1=O 2356733728 RFQJAVYYIHIQAI-XDEUHCRFSA-N 348.395 2.480 30 1 EEEF Cc1cc(C(=O)Nc2ccc([C@H]3CNCCO3)cc2F)cc(C#N)n1 149956792 DVGXXSVCMOQXEN-QGZVFWFLSA-N 340.358 2.314 30 1 EEEF C[C@@H]1C[C@@H]2O[C@H]2CCCCC(=O)Cc2cc(O)cc(O)c2C(=O)O1 33981997 YXPSTSCHAVSCKS-VFVAKGGASA-N 334.368 2.486 30 3 EEEF biogenic CN(C)S(=O)(=O)c1ccc2nc(-c3cc(O)cc(C#N)c3)[nH]c2c1 587191823 SCISALRQEGYKFD-UHFFFAOYSA-N 342.380 2.057 30 1 EEEF C#CCO[C@@H]1CCC([N+](=O)[O-])=C2N(Cc3ccc(Cl)nc3)CCN21 35273235 HMBOPPKIRGZFSB-OAHLLOKOSA-N 348.790 2.068 30 1 EEEF Cc1ccc(/C(=N/O)N2CC[C@@H](N(C)C)C2)c(Oc2cccnc2)n1 72101684 RFNNXGWSOILSGH-GICLCMKGSA-N 341.415 2.349 30 1 EEEF CCC/C=C/[C@H]1C(=O)[C@@H]2O[C@@H]2C2(OCC(CC)(CC)CO2)[C@@H]1CO 169305747 TWGDZVIUZPIUAD-GGUMPTNQSA-N 338.444 2.467 30 1 EEEF CC(=O)O[C@H](C)[C@H](C=C1C=C(C)C2=NCC[C@H]3O[C@]123)OC(=O)C(C)C 2356476657 MRUZXUQKRAPYFF-XIEZEKGWSA-N 347.411 2.374 30 1 EEEF Cc1cc(C)n(-c2c(C)n(C)n(-c3ccccc3)c2=O)c(=O)c1C#N 40919301 XBJCEWQBKMHVLM-UHFFFAOYSA-N 334.379 2.124 30 1 EEEF O=C(NCc1ccc2cc(C(=O)NO)sc2c1F)c1ccc[nH]1 299866073 OINZGHKFVKGQAY-UHFFFAOYSA-N 333.344 2.418 30 1 EEEF NC(=O)c1ncc(N[C@@H]2CCCC[C@@H]2N)cc1C#Cc1ccccc1 1772605990 LIMBNPSYRMFDCL-ZWKOTPCHSA-N 334.423 2.262 30 1 EEEF C=C1C[C@@]23C[C@]1(O)CC[C@@H]2[C@@]12C=CC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 5249427 UXLXLQYIDWLPKX-FEFNBBSZSA-N 330.380 2.056 30 1 EEEF in-man Cc1cccc(C#C[C@@]2(O)C[C@@H]3CC[C@H](C2)N3/C(=N/C#N)N(C)C)c1 103293054 MJGIIYBLRIBHES-BNCBEYCFSA-N 336.439 2.103 30 1 EEEF C[C@H](CO)C1=C(O)C(=O)C2=C(C[C@H](O)[C@H]3C(C)(C)CCC[C@]23C)C1=O 504703445 KSXQZHNLPHBARZ-LTIAJNLGSA-N 348.439 2.473 30 1 EEEF biogenic C[C@@H]1CN2C[C@H]3CCC4=C5[C@@]6(CC[C@@]5(O)CC4=O)C(=O)[C@@H]1C[C@@H]2[C@@]36C 34634570 BASSTWHCAWRGHM-QXLLIFFRSA-N 341.451 2.106 30 1 EEEF C=C1CCN([C@@H](C(=O)OC)C(C)C)S(=O)(=O)c2ccc(F)cc21 13661080 UPAXSQGOHNYEOQ-OAHLLOKOSA-N 341.404 2.431 30 3 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@@H]3C[C@@H](C(C)C)[C@H](C=C3C)[C@@H]2C1=O 169304343 PBDZFTMSQJXALQ-AICCOOGYSA-N 347.484 2.021 30 1 EEEF COc1ccc2c(c1OC(C)=O)C1=CC(=O)CC[C@@]13CCN[C@@H]3C2 1611738 ITOZXSNVASSYGQ-VQIMIIECSA-N 327.380 2.271 30 1 EEEF C=C[C@]1(C)C=C2C(=CC1)[C@]13C[C@@H]1CC[C@]1(C)C(=O)O[C@](O)([C@H]2O)[C@@H]13 2356396827 XHJCBVNMOHCTOP-ARSJYVCHSA-N 328.408 2.478 30 1 EEEF O=S(=O)(O)c1ccccc1/C=N/NC(=S)NC1CCCCC1 28705933 PGUXBNKRFJREGX-XNTDXEJSSA-N 341.458 2.064 30 1 EEEF C=C(C)[C@@H]1C[C@@H]2[C@H](CC[C@@]2(O)CCNC(=N)NC)[C@@]2(O)CC=C[C@H]1C2 2356676437 SYAVXIORAFJRNU-FKAIMOKRSA-N 347.503 2.171 30 1 EEEF COc1cccc2c1O[C@@H]1C=C(OC[C@@]3(C)CO3)C=C(O)[C@H]1C2=O 64475218 GLCNXGRTIKCJRG-RKVPGOIHSA-N 330.336 2.400 30 1 EEEF O=C(/C=C/c1cccc2c1ccn2S(=O)(=O)c1ccccc1)NO 84670757 HQWYZXOINNDBDH-MDZDMXLPSA-N 342.376 2.397 30 1 EEEF CC1=C(CCCNC(=O)NO)C2=C(C)C3(CC3)[C@@](C)(O)C(=O)C2=C1 45302893 DXKOALYLEOGGFP-KRWDZBQOSA-N 332.400 2.142 30 1 EEEF CN1C(=O)/C(=N\c2ccc(S(N)(=O)=O)cc2)c2cc(Cl)ccc21 653722928 YFJSMGRSYXMILP-JXAWBTAJSA-N 349.799 2.085 30 1 EEEF C=C(CSC1=CC(=O)C(NC[C@@H](C)O)=CC1=O)c1ccccc1 1857646179 FHDTYBNNTDWHFG-CYBMUJFWSA-N 329.421 2.323 30 1 EEEF COCC(=O)N1CCCN(c2nc3c(C)cccc3cc2C#N)CC1 1356858 OLZHCDOWXLKZAF-UHFFFAOYSA-N 338.411 2.100 30 3 EEEF CCCCCCCCC[C@@H]1C[C@H](O)[C@H](O)C=C[C@H](O)CC(=O)O1 2356721134 VKFBQLMPTJTKBZ-HZMVEIRTSA-N 328.449 2.472 30 1 EEEF N#Cc1ccc(OCc2c(-c3ccccc3)nnn2CC(=O)O)cc1 61897615 IIFZCPHDHFIGEB-UHFFFAOYSA-N 334.335 2.480 30 3 EEEF C=C1[C@H]2CC[C@@]3([C@H]1O)[C@H](C2)[C@@]12CCC[C@@](C)(COC1=O)[C@H]2C[C@H]3O 14775484 RBBBGTLGABWVIR-YXDHVPQLSA-N 332.440 2.434 30 1 EEEF biogenic Cc1ccc(S(=O)(=O)Nc2ccc(C(=O)OCC#N)cc2)cc1 84604378 FWHZGCPCQPNJJP-UHFFFAOYSA-N 330.365 2.476 30 1 EEEF C=C1C(=O)O[C@@H]2/C=C(\COC(C)=O)CC/C=C(/C(=O)OC)CC[C@@H]12 238734906 FELNAJVVBXSDQN-XZGLEPSUSA-N 334.368 2.247 30 1 EEEF CCOC(=O)[C@H](C#N)[C@]1(CC)Oc2cc(OC)cc3c2C(=O)[C@H]1C3 587428356 OAFVAGNNVDRDRW-FHSNZYRGSA-N 329.352 2.294 30 1 EEEF Cn1cc(C2=C(c3ccc(S(C)(=O)=O)cc3)OC(C)(C)C2=O)cn1 13559366 DTRYICGYNFHUCW-UHFFFAOYSA-N 346.408 2.070 30 1 EEEF CSC1=N[C@H]2[C@@H](N(C)C(=O)N2C)N1/N=C/C=C/c1ccccc1 1857639631 WONCCEICUAEBNN-BLCCDTLPSA-N 329.429 2.370 30 1 EEEF Cc1ccc(S(=O)(=O)OCC(=O)Nc2ccc(C(=O)O)cc2)cc1 117743289 VFXZKUBIEUPBQV-UHFFFAOYSA-N 349.364 2.037 30 1 EEEF C[C@@H]1C[C@H]2O[C@H]2/C=C/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 104958843 XTUZVEOWUSGCSV-GQQIQUMISA-N 330.336 2.038 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(=O)C(C)=CC)CC(=C)[C@@H]1[C@H](O)C=C(C)[C@@H]21 2356530236 JEAWGNYMYMHNGM-WJQMWINMSA-N 344.407 2.475 30 1 EEEF C=C1CC(=O)[C@@H](O)CC(=O)C[C@@H](C(=C)C)CCC2=C[C@@H](C1)OC2=O 2356537249 LRZNKDYERIHNCD-XCRHUMRWSA-N 332.396 2.440 30 1 EEEF C=C1[C@@H](CCC(C)=CCO)[C@@]2(C)C[C@@H](O)C[C@@](C)(CO)[C@H]2C[C@H]1O 2356639996 LCWHTWNKEOSQBZ-GPBSYSOESA-N 338.488 2.418 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OCC(C)C)C[C@]1(C)[C@H](O)CC(=O)[C@H](C)[C@@H]21 2356702918 BQKSKQIZKSAQEI-WWOVGWMFSA-N 336.428 2.121 30 1 EEEF N#C[C@H]1C[C@@H](N)CC[C@@H]1n1cc(C(N)=O)c(Nc2ccc(F)cc2)n1 221156539 CVGYTGPFEWIONX-GMXABZIVSA-N 342.378 2.057 30 1 EEEF N#Cc1c(-c2cccs2)[n+](=O)c2ccc(C3OCCO3)cc2n1O 1772571063 XRJMYYGGEODYDJ-UHFFFAOYSA-N 342.356 2.439 30 1 EEEF COC(=O)c1ccc[n+](CC(=O)Nc2ccc(OC(F)F)cc2)c1 3539613 GYLBFNOJMLTPTF-UHFFFAOYSA-O 337.302 2.001 30 3 EEEF COc1ccccc1N1C(=O)[C@H]2[C@@H]3C[C@H]([C@H](S)[C@H]3S)[C@@H]2C1=O 104653583 LUMFAWHJRRAZQX-CGUMJLSSSA-N 335.450 2.047 30 1 EEEF Cn1c(C#N)ccc1S(=O)(=O)NCc1c(F)cccc1Cl 29046362 LPBWLOBWMUTDJC-UHFFFAOYSA-N 327.768 2.168 30 1 EEEF COc1ccc(C(=O)O[C@@H]2c3cocc3[C@H](CC=O)[C@H]2O)cc1OC 2356737454 SFCCTINUDYTREN-YMRXKLBXSA-N 346.335 2.242 30 1 EEEF Cc1ccccc1S(=O)(=O)N1CCC(CCCC(=O)NO)CC1 73138355 OVTDKFZUCPHOKB-UHFFFAOYSA-N 340.445 2.071 30 1 EEEF CC(C)C[C@H](C(=O)NCC#N)c1cccc(N2CCN(C)CC2)c1 82061722 GCMRYWPWBAOWRM-SFHVURJKSA-N 328.460 2.208 30 1 EEEF CCCCS(=O)(=O)C1=CC(=O)c2c(OC)ccc(OC)c2C1=O 95588001 AZLLTSTUILWUGH-UHFFFAOYSA-N 338.381 2.182 30 1 EEEF COc1nccc(N2CCC(N(C)Cc3ccc(C#N)cc3)CC2)n1 299865199 SRQPCSHEGGSFOG-UHFFFAOYSA-N 337.427 2.458 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1C[C@H]1O[C@]1(CO)CC/C=C(/C)CC/C=C(\C)[C@H]2O 169292509 MULWDJOXRRXULO-QCQAQYAYSA-N 348.439 2.432 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@@H](C1=O)[C@@]1(C(C)C)C=C[C@@]2(C)CC1 169302819 SDJYQQCUHRGBAF-QISBLDNZSA-N 347.484 2.165 30 1 EEEF CC#CC#CC=C1O[C@]2(CCCCO2)[C@@H](O)[C@@H]1OC(=O)CC(C)C 2356472879 LEOZNWWIPMVKHH-CEXWTWQISA-N 332.396 2.143 30 1 EEEF N#C[C@H]1CCC[C@H]1Nc1nc(N2CCCCC2)nc2c(=O)[nH]ccc12 96285203 ZNXONFKMMRQSLC-TZMCWYRMSA-N 338.415 2.413 30 1 EEEF CN(c1ccc(/C=C/C(=O)NO)cc1)S(=O)(=O)c1ccccc1 3873568 IAMCGWXEUBEXCF-FMIVXFBMSA-N 332.381 2.030 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@H](C)[C@@]2(O)C=C(C)[C@@H](C[C@H]3OC(=O)C(=C)[C@@H]13)O2 2356287791 PWWKARNXEFCPJO-IXVYEQEWSA-N 348.395 2.036 30 1 EEEF COc1ccc(Cl)cc1-c1cc(N(C)C)c(C(=O)N=C(N)N)o1 28822461 UOZFXXWTYCZGOA-UHFFFAOYSA-N 336.779 2.088 30 1 EEEF CC1=C/C(=C2/C=C(C(=O)NCc3ccc(C)cc3)NN2)C(=O)C(C)=C1 103917387 LONJJDCCGDIEOB-WUKNDPDISA-N 335.407 2.332 30 3 EEEF C=C1CC[C@H]2[C@](C)(CC[C@@H](O)[C@@]2(C)CO)[C@@H]1C(=O)CC1=CCOC1=O 2356643560 WZHWNAKOQGIEEB-VYMYIBDJSA-N 348.439 2.171 30 1 EEEF C=C[C@@H]1[C@](C)(CO)C(=O)[C@H]2C[C@@]1(C)[C@@H]1[C@@H]3OC(=O)C(=CC)[C@H]3O[C@@]21C 2356677552 UAVHCHBOMMAUHU-CPFUJPQVSA-N 346.423 2.042 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 257434382 HHDWSDSMWJQURA-XUGKGZAYSA-N 332.396 2.136 30 1 EEEF endogenous,in-man O=C(CCCCNC(=O)c1cc2c(cn1)[nH]c1ccccc12)NO 653808769 ULDYLBYAHNSSLV-UHFFFAOYSA-N 326.356 2.122 30 1 EEEF CN(C)S(=O)(=O)c1cccc2nc(-c3ccc(C#N)c(F)c3)[nH]c12 587143653 VOMDXZHLCIHRKF-UHFFFAOYSA-N 344.371 2.491 30 1 EEEF C=C1C[C@H](OC(=O)C(C)C)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@@H](O)C[C@@H]12 5715382 KCMNJMYYSFJSAZ-NQLMQOPMSA-N 332.396 2.165 30 1 EEEF biogenic C=C1C(=O)[C@]23[C@@H](O)[C@H]1CC[C@H]2[C@]1(C)C[C@@H](O)CC(C)(C)[C@H]1C[C@H]3O 14812493 XIGJIFFLTSZIKL-PFUVPPBISA-N 334.456 2.067 30 1 EEEF biogenic,in-vitro CCOC1=C/C(=C/c2c(C)[nH]oc2=O)C=C(Br)C1=O 100559603 UXVUSPTVUOYYBU-XBXARRHUSA-N 326.146 2.442 30 3 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@H](C1=O)[C@]1(C(C)C)C=C[C@@]2(C)CC1 45245120 SDJYQQCUHRGBAF-COCCGSRQSA-N 347.484 2.165 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O[C@H]([C@H]21)[C@@H]3O 257506482 OSYJLXUUZYSFTC-PZQFXNGHSA-N 332.440 2.432 30 1 EEEF endogenous,in-man CCN(C)c1nccc(C#Cc2ccc(C[C@@H](C)NC(C)=O)cc2)n1 169706343 IGNDEIPSSYUMSI-OAHLLOKOSA-N 336.439 2.400 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@]4(C)CC[C@H](O)[C@](C)(C(=O)O)[C@@H]4[C@@H]4C(=O)O[C@H]1[C@]43C2 2356691280 CXVXNQFWGOEIMV-YKMNBBTESA-N 346.423 2.382 30 1 EEEF Cc1cc(NC(=O)Cc2nn(C)c(=O)c3ccccc23)ccc1C#N 95593863 CEPAJPMUOJNHKP-UHFFFAOYSA-N 332.363 2.295 30 1 EEEF C=C1C(=O)O[C@H]2C3=C(C)[C@H](OC(C)=O)C[C@H](OC(C)=O)[C@]3(C)CC[C@@H]12 238743446 MIAIYIMCGDSXLY-QHNLCMDKSA-N 348.395 2.468 30 1 EEEF Cn1c(=O)ccc2cc(S(=O)(=O)Nc3ccccc3C#N)ccc21 1772614407 WSWLHCOQPUZBPG-UHFFFAOYSA-N 339.376 2.211 30 1 EEEF COc1ccnc2c1/C(=N/N=C(N)N)C[C@H](c1ccccc1Cl)C2 13474676 UNUUDMGTESLXRG-CONVLBPTSA-N 343.818 2.451 30 1 EEEF C#Cc1ccc2c(c1)C(=O)N1CCC[C@@H]1c1c(C(=O)OCC)ncn1-2 13781509 AGSFVTKORUUQJP-OAHLLOKOSA-N 335.363 2.321 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]1(C)CC(=O)CC(CO)(CO)[C@@H]1[C@@H](O)C3 169605232 PEFAJEOIPQAJGS-FLYCALMHSA-N 334.456 2.070 30 1 EEEF C#CCOc1c(OC)cc(/C=C/C(=O)N2CCC=CC2=O)cc1OC 1857651654 XTCDTSNHOVEPFN-CMDGGOBGSA-N 341.363 2.044 30 1 EEEF C[C@@H]1CC2=C(C1=O)[C@H](O)[C@]1(C)CC[C@@H]3[C@H]([C@@H](O)[C@@]1(C)C2=O)C3(C)C 2356876550 ZLWDXUVVPOSFGG-GGFGCPBASA-N 332.440 2.275 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(C(=O)N(C)CC(=O)O)o1 587912628 UEPQLLAPSPNDEF-UHFFFAOYSA-N 347.754 2.498 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@@H]([C@H](C=O)[N+](=O)[O-])N1 587747105 PCGJRFLRAQYEJS-PUQNFTFYSA-N 331.141 2.008 30 1 EEEF CC[C@@H](CO)Nc1ccc2ncc(-c3cccc(/C=N/O)c3)n2n1 1772632740 FTGAOPZDJRWUTG-FRSZACSASA-N 325.372 2.387 30 1 EEEF CC1=C[C@H](CC#N)[C@H](C(C)C)C[C@H]1CC(=O)N1CCN(CCO)CC1 2356318004 ITEREEYPHAIAQL-FHWLQOOXSA-N 347.503 2.281 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2CC/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 101452152 XFALPAMSDFFXGY-XLFSOCHTSA-N 332.352 2.262 30 1 EEEF CNC(=O)/C(=N/OC)c1ccccc1Oc1ccccc1[N+](=O)[O-] 103196038 YWIMKKODSDZNIR-OBGWFSINSA-N 329.312 2.484 30 1 EEEF Cn1c(-c2ccco2)nc2c(N)nc(C#CC3(O)CCCCC3)nc21 13861446 PGKBTOTUGNMPMG-UHFFFAOYSA-N 337.383 2.252 30 1 EEEF C=C1[C@@H]2C[C@H](O)C(C)(C)[C@@]2(O)CC[C@@]23C[C@@H](CC[C@@H]12)[C@@](O)(CO)C3 1857567842 OPXSAGTVGJPWQJ-KNEKMNIZSA-N 336.472 2.004 30 1 EEEF O=C(/C=C\c1cc(C(=O)c2cccc(F)c2)c[nH]1)/C=C(/O)C(=O)O 103521895 WQEAOCAOIXLGFY-DAXCDELTSA-N 329.283 2.494 30 1 EEEF in-vitro C=C1[C@H](O)[C@@H]2O[C@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@]1(C)[C@H](O)C(=O)[C@]32C 2356479222 ILPXHKMIZLTLAS-BJIWLQFHSA-N 332.440 2.083 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)C2=CC3=C(CO)C(=O)CC[C@@]3(C)CC[C@]21C 2356514868 OTUPIQJUQWGDQX-SWBPCFCJSA-N 334.456 2.379 30 1 EEEF C=C[C@]12CCN3Cc4c([nH]c5ccccc45)[C@@](C(=O)OC)(CO1)[C@H]2C3 2356726297 JWWNAZIXKUAPOM-PWIZWCRZSA-N 338.407 2.369 30 1 EEEF O=C(CCCCSc1nc(CCc2ccccc2)cc(=O)[nH]1)NO 35050414 IUOHZSUJFJLNKN-UHFFFAOYSA-N 347.440 2.323 30 1 EEEF C=C1[C@H](O)[C@H]2O[C@@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@@]1(C)C(=O)C(=O)[C@]32C 198332510 ZVWIURNWTXCECX-XBILFIRESA-N 330.424 2.291 30 1 EEEF C=C1C[C@@]23CC[C@@H]4[C@@](C)(CO)C(=O)CC[C@@]4(C)[C@@H]2C[C@@H]1[C@@H](O)C3=O 238754925 KNDILSYJEZUPHC-MOXYVQQRSA-N 332.440 2.277 30 1 EEEF O=C(CCCCCCNC(=O)c1ccc2nc(O)ccc2c1)NO 299839983 UFTSJQJNTKASLO-UHFFFAOYSA-N 331.372 2.126 30 1 EEEF N#Cc1ccc2c(c1)O[C@H](COc1ccc(F)c(C(N)=O)c1F)CO2 1772599461 CPBXVUMNRJTINE-JTQLQIEISA-N 346.289 2.154 30 1 EEEF C=C1C[C@@H](OC(=O)/C(C)=C\C)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(C)=C[C@@H](O)[C@@H]12 13326022 JEAWGNYMYMHNGM-OHOUSIRRSA-N 344.407 2.475 30 1 EEEF biogenic C=C(C[C@@H]1C=C(C)C(=O)O1)[C@H](O)COc1ccc2ccc(=O)oc2c1 15212319 BJAAKPBQJCDTGE-HZPDHXFCSA-N 342.347 2.351 30 1 EEEF biogenic COc1ccc(C2=NNC(=O)/C2=N\Nc2ccc(N(C)C)cc2)cc1 49032790 NQXGSYVZOZRSRU-UHFFFAOYSA-N 337.383 2.063 30 1 EEEF Nc1cc(N)c(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cn1 587887382 LLWBMTZNHWDWHQ-UHFFFAOYSA-N 349.221 2.263 30 1 EEEF CN(C)CCN=C(C=C1C=Cc2ccccc2N1C)NCCN(C)C 1857540732 ZKHGZFKQTDKCAO-UHFFFAOYSA-N 341.503 2.145 30 1 EEEF CC(C)c1ccn(C2(C(=O)O)CCN(c3cc(C#N)ccn3)CC2)n1 72423808 NZKNFLKUMFZOBL-UHFFFAOYSA-N 339.399 2.353 30 1 EEEF C=CCNC[C@H](O)COc1ccc2oc3ccccc3c(=O)c2c1 40935494 QRNFFCPQVMWMRT-ZDUSSCGKSA-N 325.364 2.462 30 1 EEEF C=CCN1[C@H]2CC[C@@H]1C[C@H](OC(=O)c1ccccc1)[C@H]2C(=O)OC 36177531 OLKZDWYIZCZYLB-QZWWFDLISA-N 329.396 2.424 30 1 EEEF CC1=C2OCCCCN3C(=O)[C@@](O)(c4ccccc43)[C@@]2(C)SC1=O 71329176 KFSYAIIGWGRHHI-ROUUACIJSA-N 345.420 2.337 30 1 EEEF CC(=O)Nc1cc2c(c(N3CCCC3)c1C#N)C[C@H](O)C(C)(C)O2 40466260 IRAYJRZRRDKDHD-INIZCTEOSA-N 329.400 2.191 30 1 EEEF COCC/N=C1\Sc2ccccc2[C@@H]2C[C@H]3[C@H](CON3C)CN12 199734449 JEODAKNDZOTWMS-HAVDKEDOSA-N 333.457 2.403 30 3 EEEF C=C1C(=O)O[C@H]2C[C@@H](C)[C@H]3[C@@H](O)CC[C@@]3(C)[C@@H](OC(=O)/C=C\C)[C@@H]12 238787540 HSXLCTYJIGXUOE-CGNCQPNSSA-N 334.412 2.389 30 1 EEEF CC(Cc1ccccc1)=NNS(=O)(=O)c1ccc([N+](=O)[O-])cc1 254096146 MDLYJQMAOSZFKC-UHFFFAOYSA-N 333.369 2.492 30 3 EEEF O=C(O)[C@@H]1Cc2cccc(F)c2[C@H](c2cccc(OC[C@@H]3CO3)c2)N1 962903170 VSHFMNJQRIDHIY-HFTRVMKXSA-N 343.354 2.292 30 1 EEEF C[C@@]1(OC(=O)C2CCCC2)C(=O)C=C2C=C3CCCN3C=C2C1=O 13817776 FFRGFPBARHRABR-LJQANCHMSA-N 327.380 2.434 30 3 EEEF COc1cc(O)c2c(c1)CC(=O)/C=C/C=C/[C@H]1O[C@@H]1C[C@@H](C)OC2=O 141129757 BXYHHINRBKIWCZ-LCOXQCEFSA-N 344.363 2.341 30 1 EEEF Nc1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cnc1N 587887684 YIOGPUYHLOHWAL-UHFFFAOYSA-N 349.221 2.263 30 1 EEEF COc1ccc(Cl)cc1C#Cc1c(C)c(C#N)c(=O)n(N)c1C 587912355 MKBHRHIQLXEBSA-UHFFFAOYSA-N 327.771 2.112 30 1 EEEF COC(=O)C[C@H]1C(=O)C=CN(Cc2cccc(C(F)(F)F)c2)C1=O 957624380 NDWZIJCCDQUZRN-LBPRGKRZSA-N 341.285 2.310 30 1 EEEF C/C(=N\n1c(Cc2ccccc2)n[nH]c1=O)c1ccc([N+](=O)[O-])cc1 6010068 QWIVSHVLOHHWQT-UDWIEESQSA-N 337.339 2.343 30 1 EEEF C=C1C(=O)[C@]23[C@@H](CC[C@H]1[C@H]2O)[C@]1(C)CCC(=O)C(C)(C)[C@H]1C[C@H]3O 95099134 UCDVIBNDYLUWFP-QBFXEHAUSA-N 332.440 2.275 30 1 EEEF biogenic,in-vitro O=C(CCCCCCC(=O)Nc1nnc(-c2ccncc2)s1)NO 299838300 UMQIXWPRZLKPHU-UHFFFAOYSA-N 349.416 2.385 30 1 EEEF COC(=O)[C@H](C=O)[C@@H]1N[C@@H](C)Cc2cc(Br)c(F)cc21 587804281 DKWOWZAXZYXXJE-JVQVWZCXSA-N 344.180 2.152 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N)nc1C(OC)OC 587903417 QENIKOQRTSQGCD-UHFFFAOYSA-N 333.775 2.412 30 1 EEEF C=CCn1c(O)c(C(CC)=Nc2ccc(C(=O)O)cc2)c(O)nc1=O 1779685993 UDGQDBZPNOSMRB-UHFFFAOYSA-N 343.339 2.070 30 1 EEEF CC1=C[C@@H]2[C@H](CCC3=C[C@@H](C[C@]4(C)O[C@@H]4[C@@H](O)[C@@H]1O)OC3=O)C2(C)C 2356815659 CUCOPNHAVGPVDH-UJCHLWPXSA-N 348.439 2.120 30 1 EEEF CCCCCC[C@H](C(=O)NO)S(=O)(=O)c1ccc(OC)cc1 13585930 VMCQYTNLTZJCIG-CQSZACIVSA-N 329.418 2.313 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]3C(C)=CCC3=C(C)C[C@@H](OC(=O)C(O)=CCO)[C@@H]12 2356493432 SWIFBBRXRXNLBH-QBPKDAKJSA-N 346.379 2.117 30 1 EEEF C=C1C[C@@]23C[C@H]1CC(=O)[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1[C@@H](O)[C@H]3O 2356684937 ZAPSETLSDTWUQE-LYKAYCHNSA-N 348.439 2.161 30 1 EEEF COc1ccccc1C[C@H]1S/C(=N/N=C/c2ccco2)NC1=O 5006071 JZGWNEGPTUVELP-NGWPFTMJSA-N 329.381 2.452 30 3 EEEF C[C@]12COS(=O)(=O)CC1=C(c1ccc(C(F)(F)F)cc1)C(=O)O2 169343890 CKKKBOVQQKRFPT-ZDUSSCGKSA-N 348.298 2.135 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2C1=CC[C@H](O)[C@](C)(C(=O)O)[C@@H]1[C@H]3C(=O)O 2356424822 WFTRKYGVESACJS-CKIXCMMDSA-N 332.396 2.462 30 1 EEEF COC(=O)C[C@]1([C@H](O)C=C(C)CCC=C(C)C)C[C@H](O)C=CC1=O 2356635824 LRHXPNHCPURRDF-SZVBFZGTSA-N 336.428 2.479 30 1 EEEF O=C(/C=N/O)NCCCNc1c2c(nc3ccccc13)CCCC2 149623378 QCQKNGOPTIWUSF-CIAFOILYSA-N 326.400 2.492 30 1 EEEF O=CCC[C@@]1(C(=O)O)Oc2ccccc2C(=O)[C@@H]1C(=O)c1ccco1 587603583 NTVWIXHUYWRWHD-RDTXWAMCSA-N 342.303 2.156 30 1 EEEF CC(C)C[C@H]1CC(=O)N(OS(=O)(=O)/C=C/c2ccccc2)C1=O 102187280 VGLWWYDLFOPKIU-VFNNOXKTSA-N 337.397 2.340 30 1 EEEF CC(=O)C1=CC[C@@H]2[C@@H]3CC[C@H]4[C@H](O)[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C 2356512831 GKCFQKGBOYKBGP-BPXCDGJQSA-N 348.483 2.457 30 1 EEEF O=S(=O)(C1CC1)N1CCc2nc(C#Cc3ccccc3)sc2C1 96272998 NGMIVBPHHSRQBE-UHFFFAOYSA-N 344.461 2.393 30 1 EEEF C=C[C@]12CCN3Cc4c([nH]c5ccccc45)[C@](C(=O)OC)(CO1)[C@H]2C3 238763409 JWWNAZIXKUAPOM-DBVUQKKJSA-N 338.407 2.369 30 1 EEEF C/C(=N\NC(N)=S)c1ccc(NC(=O)Cc2ccccc2)cc1 299871402 YKYDZQOBOHVVRZ-UDWIEESQSA-N 326.425 2.425 30 1 EEEF C=CCOC1=CC(=O)C2=C(C1=O)[C@]13CCC[C@](C)(C(=O)OC1)[C@@H]3C=C2 653762386 QVGIIFRXJSJHFU-RYGJVYDSSA-N 340.375 2.441 30 1 EEEF Cc1c[nH]c2c1[C@]13C[C@@H]1CN(S(=O)(=O)c1ccccc1)C3=CC2=O 101331877 VRRYPFUNOZUDIK-KZULUSFZSA-N 340.404 2.366 30 1 EEEF CC(C)=CC/N=C(/N)NCCCCNC(=O)/C=C/c1ccccc1 27731743 DPQOKCQXDPYGLS-ZHACJKMWSA-N 328.460 2.467 30 1 EEEF CCc1ncnc(N2CCC(C)(O)CC2)c1C#Cc1ccc(C)nc1 149155810 KKXZMSWJJDMCHB-UHFFFAOYSA-N 336.439 2.493 30 1 EEEF N#Cc1cc(Br)c2[nH]c([C@@H]3CSCC(=O)N3)nc2c1 587042750 FOLNZIVGMXHCLL-VIFPVBQESA-N 337.202 2.101 30 1 EEEF O=CCCc1cc2c(O)nc(O)nc2nc1Cc1ccc(F)cc1 587370948 YZXAUNSXVTXKEA-UHFFFAOYSA-N 327.315 2.297 30 1 EEEF CC(C)[C@@H](C(=O)NO)c1ccc2c(c1O)C(=O)c1c(O)cccc1C2 13606203 BOQGERWXXRKMKH-CQSZACIVSA-N 341.363 2.478 30 1 EEEF O=C1C=C(CSC(=S)N2CCOCC2)C(=O)c2ccccc21 1857637911 PFXAJMXCZAQORA-UHFFFAOYSA-N 333.434 2.342 30 1 EEEF N#Cc1cc(-c2ccc(F)cc2)n(-c2ccc(S(N)(=O)=O)cc2)n1 20206 UUGSJYRNELHGOL-UHFFFAOYSA-N 342.355 2.197 30 1 EEEF Cn1cc(/C=C/C(=O)c2ccc3c(c2)CCO3)cc1/C=C/C(=O)NO 40392796 LPVOYQFZOICNIL-XIIDOLPRSA-N 338.363 2.375 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)C2=CC3=C(CO)C(=O)CC[C@]3(C)CC[C@@]21C 2356514866 OTUPIQJUQWGDQX-OBKDMQGPSA-N 334.456 2.379 30 1 EEEF Cc1ccc2c(c1)/C(=N/NC(=S)NCc1ccccc1)C(=O)N2C 40402362 LXBQDXKSFBLSLB-SILNSSARSA-N 338.436 2.340 30 1 EEEF C=C1C[C@@H](OC(=O)/C(C)=C/C)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(C)=C[C@@H](O)[C@@H]12 238763667 JEAWGNYMYMHNGM-NYVXQQPPSA-N 344.407 2.475 30 1 EEEF biogenic COC(=O)/C=C\C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587876786 MYDMJMDQWYUTLA-HYXAFXHYSA-N 326.179 2.385 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1C[C@H]1O[C@]1(CO)CC/C=C(\C)CC/C=C(/C)[C@H]2O 169292510 MULWDJOXRRXULO-VBNQUTPGSA-N 348.439 2.432 30 1 EEEF CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@H](C#N)CC#N 89469518 NHZZJQFLKHUHMA-GJZGRUSLSA-N 342.399 2.044 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 257527885 QYXZQZMPZUEEML-JFUOKHFQSA-N 346.423 2.384 30 1 EEEF endogenous,in-man CN(Cc1nc2ccc(F)cc2[nH]1)S(=O)(=O)c1ccc(C#N)cc1 586928702 HODMSYZHMLCSSY-UHFFFAOYSA-N 344.371 2.394 30 1 EEEF N#Cc1nc2nc(-c3ccc(N)cc3C(F)(F)F)[nH]c2nc1C#N 587095864 YCNSCNRHOBEVEU-UHFFFAOYSA-N 329.245 2.364 30 1 EEEF CC[C@@H](O)c1c(C/C=C/CO)cc2c(c1OC)C(=O)C=C(OC)C2=O 28366691 RUMPUGDOZMKASN-URWSZGRFSA-N 346.379 2.139 30 1 EEEF C#C[C@]1(O)CC[C@@H]2[C@@H]3C[C@H](O)c4cc(OC)ccc4[C@@H]3C[C@@H](O)[C@]21C 2356584247 YTRCAZOTWYOCGG-OOMDKVSHSA-N 342.435 2.377 30 1 EEEF CC(C)[C@@H]1CC[C@]23C[C@@H]4[C@H](C)C(=O)[C@@H]5O[C@@]54[C@]2(C)C(=O)[C@@H](O)[C@]13C 2356871566 YCAWNFYZBRTGCT-ALPXENHLSA-N 332.440 2.371 30 1 EEEF CCOC(=O)N/C(=N\[C@@H](CC(C)C)C(=O)NCC#N)c1ccccc1 82065503 YEQIFUJPOGUAFN-HNNXBMFYSA-N 344.415 2.234 30 1 EEEF O=C(O)c1ccc([C@](O)(S)c2c3ccccc3cc[n+]2[O-])cc1 142971889 LMPACTCGFSUJLK-KRWDZBQOSA-N 327.361 2.295 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@@H]2[C@@H]3C(=O)O 257754424 ZCRLGANQNRMURE-QVIXOJIWSA-N 346.423 2.384 30 1 EEEF endogenous,in-man CCOc1ccc(Br)cc1/C(C)=N\NC1=NCCN1 13110967 BJBBLXXEJYVLNN-MFOYZWKCSA-N 325.210 2.121 30 3 EEEF COc1ccc(C2=NO[C@H](CC(=O)NO)C2)cc1OC1CCCC1 13777047 VSPGQUIYSBELGU-ZDUSSCGKSA-N 334.372 2.405 30 1 EEEF CCOC(=O)C1=C(C)OC(=N)[C@@H](C#N)[C@@H]1c1ccc(O)c(OC)c1 169688823 DYQABFBTVAQABQ-NHYWBVRUSA-N 330.340 2.469 30 1 EEEF CC1=C[C@@H](O)CC(CO)=CC[C@H]2CCC3=C(C(=O)[C@H]1[C@H]3O)C2(C)C 2356536675 PLSLPANFUZMMNZ-MMNPAVHPSA-N 332.440 2.299 30 1 EEEF C=C(CC[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CC[C@@H](O)[C@@]2(C)CO)[C@H](O)CO 2356581700 GLRQCZGXPULESM-NADOGSGZSA-N 338.488 2.418 30 1 EEEF COC(=O)C[C@]1([C@@H](O)C=C(C)CCC=C(C)C)C[C@@H](O)C=CC1=O 2356635825 LRHXPNHCPURRDF-VDZJLULYSA-N 336.428 2.479 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H]1[C@H](OC(C)(C)C)[C@H]1[C@]3(C)CC[C@@H](O3)[C@]1(C)[C@@H]2O 238751178 XVJNAEOCXFSHRU-TZFBGNBJSA-N 336.428 2.216 30 1 EEEF C=C1C(C)(C)[C@H]2CC[C@]1(C(=O)N1CCC(n3cc(CO)nn3)CC1)C2 20863320 SGVUKVYMMKYMBG-LIRRHRJNSA-N 344.459 2.316 30 1 EEEF COC1=CC(=O)[C@@]2(C)c3c(O)c(C(C)=O)c(O)c(C)c3O[C@]2(OC)C1 2356815378 CQNUVEWNKCFRQU-ZWKOTPCHSA-N 348.351 2.105 30 1 EEEF C[C@H](N[C@@H]1c2cc(C#N)ccc2OC(C)(C)[C@H]1O)C(=O)OC(C)(C)C 96941779 HTQRBOPBRPMVKW-XZJROXQQSA-N 346.427 2.451 30 1 EEEF COC1=CC(=O)C[C@@H](C)[C@]12Oc1cc(OC)c(F)c(OC)c1C2=O 1772631972 SZGBPAXKMROYML-RBHXEPJQSA-N 336.315 2.296 30 1 EEEF C=C(CO)[C@H]1CC[C@H]2C(=CC[C@H]3[C@](C)(CO)[C@@H](O)CC[C@]23C)[C@H]1O 13301748 OCSPOCDQHVVGDZ-WRUREIOSSA-N 336.472 2.028 30 1 EEEF C#CCN(Cc1ccc2nc(C)[nH]c(=O)c2c1)c1cccc(CO)c1 13746723 LLPXTZCJCHQBHT-UHFFFAOYSA-N 333.391 2.364 30 1 EEEF Cc1cc(C)c2c(c1)[C@H](/C=N/c1ccc(S(N)(=O)=O)cc1)C(=O)N2 169727359 SMEQORQWGKNBGU-OMPOGXFXSA-N 343.408 2.389 30 1 EEEF C=C(C)[C@@H]1CC[C@@]23O[C@@H]2[C@@H](CC(C)=C[C@@]2(O)C=C(C)C(=O)[C@@H]12)OC3=O 2356529177 XCSMOAULMOLHGO-GZOAKEPSSA-N 344.407 2.248 30 1 EEEF COC(=O)C1=C2[C@](C)(C(=O)OC)[C@H]3O[C@H]3C[C@]2(C)c2ccccc21 2356695943 CCCHYPOECSYCKC-SRRFXAJZSA-N 328.364 2.235 30 1 EEEF CCCCCC=CC1=C(CO)C(=O)[C@@H]2O[C@]2(CC=C(C)C(=O)O)C1=O 2356716673 UJNVMSXVUCFBMB-PKOBYXMFSA-N 348.395 2.122 30 1 EEEF CC(C)C[C@H](NC(=O)Nc1cccc(Br)c1)C(=O)NO 95592164 VMXFKZHHUWAWFR-NSHDSACASA-N 344.209 2.491 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)OC1)[C@@H]2[C@@H]3C(=O)O 257527886 QYXZQZMPZUEEML-MVTVPBHXSA-N 346.423 2.384 30 1 EEEF endogenous,in-man COc1ccc(Cl)cc1C#CC1=C(Br)C(=O)O[C@@H]1O 587911988 AVHHOCJXRILQNR-LBPRGKRZSA-N 343.560 2.224 30 1 EEEF N#Cc1cc([C@@H]2N[C@H](C(=O)O)Cc3c2cnc2ccccc32)ccn1 963229375 KMSBPESAZVWSRQ-ROUUACIJSA-N 330.347 2.190 30 1 EEEF N#Cc1ccc(-c2c[nH]ccc2=NS(=O)(=O)C(F)(F)F)cc1 1772616937 PNEHLXCEEHUQLF-UHFFFAOYSA-N 327.287 2.304 30 1 EEEF N#C[C@@H](C(=O)Nc1ccc(C(F)(F)F)cc1)C(=O)[C@@H]1CCOC1 169714929 QRECZZCVBQCIIJ-BXKDBHETSA-N 326.274 2.389 30 1 EEEF C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12CCC[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 100200832 OXFPYCSNYOFUCH-AODVQFRNSA-N 332.396 2.280 30 1 EEEF in-vitro C=C1C[C@H](OC(=O)C(C)C)[C@@H]2[C@H](C)C(=O)O[C@@H]2[C@@H]2[C@@H]1C[C@H]1O[C@]21C 2356557719 ZEIPBAWKAWZVOR-ADIMXDBFSA-N 334.412 2.485 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)C(=O)O[C@]2(O)C[C@@]23O[C@@H]2CC[C@H](C)[C@@]13C 36378620 YQSCJMNPXRPKAC-MCGVNIGDSA-N 348.395 2.014 30 1 EEEF C=C(CC[C@H](O)C(C)(C)O)[C@H](O)COc1ccc2ccc(=O)oc2c1 14587284 GOOJJMAKBXRBIG-WBVHZDCISA-N 348.395 2.001 30 1 EEEF biogenic O=C(NO)c1ccc(Cn2nnc(-c3nccc4ccccc34)n2)cc1 1857588624 DZXJHWRZRYDOJK-UHFFFAOYSA-N 346.350 2.056 30 1 EEEF N#Cc1cc(F)ccc1Cn1ccc2c3c(ncc21)C(=O)N(O)CC3 71316158 KMNNURYLRSRLOU-UHFFFAOYSA-N 336.326 2.483 30 1 EEEF N#Cc1cc2nc([C@@H](N)Cc3ccc(O)c([N+](=O)[O-])c3)[nH]c2cc1C#N 587265853 RUVIGCDKLCGQTN-LBPRGKRZSA-N 348.322 2.163 30 1 EEEF CC(=O)OC[C@H]1O[C@H](C#Cc2ccc(C)cc2C)C=C[C@@H]1OC(C)=O 13783121 FLENGSMTXSLATM-HSALFYBXSA-N 342.391 2.473 30 1 EEEF CNC[C@@H](O)CN1CCc2c(cccc2Oc2ccc(C#N)cc2)C1 1857574759 ZSZHFVBJHDAIQK-QGZVFWFLSA-N 337.423 2.289 30 1 EEEF O=C(/C=C/c1cc(C(=O)c2cccc(F)c2)c[nH]1)/C=C(/O)C(=O)O 103521897 WQEAOCAOIXLGFY-SPXDXPJOSA-N 329.283 2.494 30 1 EEEF in-vitro N/C(=N\O)c1ccc(-c2cc(-c3cccc(/C(N)=N/O)c3)no2)cc1 103226137 UVGKQYSJILDIGL-UHFFFAOYSA-N 337.339 2.198 30 1 EEEF COc1cccc(C2=NN3C(=NN/C3=C3\C=CC=CC3=O)SC2)c1 141095682 BRPNXGSQMFWEOM-SSZFMOIBSA-N 338.392 2.229 30 3 EEEF CNS(=O)(=O)c1cncc(C#Cc2cc(Cl)ccc2OC)c1 587918584 YJXIMAQCSUZRNG-UHFFFAOYSA-N 336.800 2.052 30 1 EEEF CC(C)(C)OC(=O)N1CC[C@]2(NCCc3ccc(O)cc32)[C@@H](C=O)C1 963351245 FUNVDCFOCWPYPX-KUHUBIRLSA-N 346.427 2.189 30 1 EEEF CCCCCC[C@H](O)[C@@H]1C[C@@H](OC(C)=O)C2=C(O1)[C@H](O)CCC2=O 2356620149 GXYWRLQZWPUUNP-DRPJVOAASA-N 340.416 2.016 30 1 EEEF N#C[C@H]1C[C@H](O)CC[C@@H]1n1cc(C(N)=O)c(Nc2ccc(F)cc2)n1 221213193 USZHEZVXLJZXEW-YVLXSGLVSA-N 343.362 2.090 30 1 EEEF NC(=S)N/N=C/c1cc2c(cc1O)OCC(c1ccc(O)cc1)=C2 1772608770 DWWBYKFVZUXIMS-UFWORHAWSA-N 341.392 2.198 30 1 EEEF CS(=O)(=O)[C@@](CCc1ccccc1)(Cc1ccccc1)C(=O)NO 1772630503 AGQCHBYZAKENRE-SFHVURJKSA-N 347.436 2.151 30 1 EEEF CN(C)CC/N=C1\c2ccccc2CS(=O)(=O)c2ccccc21 27101385 WIANMMWHIDRGPS-VHEBQXMUSA-N 328.437 2.373 30 1 EEEF C=C1[C@@H](CCC2=CCOC2=O)[C@]2(C)CCC(=O)[C@@](C)(CO)[C@H]2C[C@H]1O 73277573 IGGFMMASJSMUMP-ZGMAETJZSA-N 348.439 2.171 30 1 EEEF C=CCN1CCN(c2ccc([C@H]3CC(C(=O)OCC)=NO3)cc2)CC1 40917466 RHXISXRGOQBKAI-GOSISDBHSA-N 343.427 2.375 30 1 EEEF N#Cc1ccc(-c2ccc(N3C[C@H](CN)OC3=O)cc2F)cc1O 1857754061 FRCJLAUTRKXCFY-ZDUSSCGKSA-N 327.315 2.354 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@H]2[C@@]12CCC[C@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100826192 IPHNMKITOREFLW-PHDAHLEGSA-N 332.396 2.136 30 1 EEEF endogenous,in-man COC(=O)c1ccc(CNC(=O)c2cc(/C=C/C(C)=O)c[nH]2)cc1 40875777 JECMRNJVESVFQX-ONEGZZNKSA-N 326.352 2.334 30 1 EEEF CC1(C)OC(=O)C(c2nc3cc(C#N)c(C(F)(F)F)cc3[nH]2)=C1N 587255810 XUBQCHZAYYAXKL-UHFFFAOYSA-N 336.273 2.459 30 1 EEEF CC(C)NC(=N)N/C(N)=N\OCCCSc1ccc(F)cc1 27305784 IQRDSKBFGMIQSH-UHFFFAOYSA-N 327.429 2.077 30 1 EEEF O=C(/C=C/C(Br)=C/c1ccccc1)C1=C(O)CNC1=O 26014069 IUGVVSPEFVOLME-VEQVDCDKSA-N 334.169 2.490 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(C)C(=O)CC[C@](C)(C(=O)O)[C@H]1C[C@H]3O 2356487488 CLGOGJHVMHIUDO-MZUJIBFDSA-N 346.423 2.369 30 1 EEEF CCCCCCCCC[C@@H]1C[C@H](O)[C@@H](O)C=C[C@@H](O)CC(=O)O1 2356721135 VKFBQLMPTJTKBZ-NCOADZHNSA-N 328.449 2.472 30 1 EEEF COc1ccc2c(c1O)[C@@]13CCN(C)[C@@](OC)(C1)C(=O)C=C3C=C2 238740726 SYDFEGUVBXTQEP-RBUKOAKNSA-N 327.380 2.243 30 1 EEEF N#Cc1ccc([N+](=O)[O-])c([C@@H]2N[C@H](C(=O)O)Cc3cc(F)ccc32)c1 962897298 CHTOBEJKVIAQST-GOEBONIOSA-N 341.298 2.294 30 1 EEEF N#Cc1cccc(Nc2nccc(-c3c(CO)nn4ncccc34)n2)c1 1857541024 UAPPEWOATNYUIK-UHFFFAOYSA-N 343.350 2.294 30 1 EEEF COC1=CC(=O)/C(=C2\NNC=C2c2cnn(-c3ccccc3)c2)C=C1 100470213 RYHBSHZFMLLDEX-MNDPQUGUSA-N 332.363 2.244 30 3 EEEF O=C(NO)c1cnc(Nc2nnc(-c3ccc(Cl)cc3)o2)nc1 72126270 PMEDBASTGOEEIH-UHFFFAOYSA-N 332.707 2.043 30 1 EEEF C[C@H](O)C[C@H]1O[C@H]1C=CC=Cc1cc2cc(O)cc(O)c2c(=O)o1 2356744597 TYXXEQMKBIKKOL-CIISACIHSA-N 330.336 2.312 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@]2(N1)C(=O)C=CN[C@@H]2C 587799523 XROGJGIIBPMHKL-KEMUVXCRSA-N 339.208 2.392 30 1 EEEF COC1=CC(=O)C(OC)=C([C@@H](O)CCCCCCCCCO)C1=O 1772623628 KYPYMRTZUANJOA-ZDUSSCGKSA-N 340.416 2.043 30 1 EEEF C[C@H](C(=O)NO)N1CC[C@@](C)(c2ccc(OC(C)(C)C)cc2)C1=O 13491925 GIIDEADTCZPLKY-XIKOKIGWSA-N 334.416 2.248 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@]2(C)CC[C@@](O)(O2)/C(C)=C\[C@H]2OC(=O)C(=C)[C@@H]21 13585379 JCTQUEQSHOHEPW-QDHYIOMWSA-N 348.395 2.180 30 1 EEEF NCc1ccc(C/N=C2/[C@@H]3[C@H]4C[C@@H]5[C@@H]3C3(OCCO3)[C@@H]3[C@H]2[C@H]4[C@@H]53)cc1 1857586247 PNPIPQKWOXPTBU-RIGIIJMXSA-N 336.435 2.217 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]12C[C@H](O)C[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 100205870 HHDWSDSMWJQURA-GBNXXHSSSA-N 332.396 2.136 30 1 EEEF in-vitro O=C1C(NCCc2c[nH]c3ccccc23)=CC2=NCCn3cnc1c32 28710319 YOOAUTHLCVXVKN-UHFFFAOYSA-N 331.379 2.080 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@](C)(O)C(=O)CCC(C)=C[C@H]2OC(=O)C(=C)[C@@H]21 2356754586 AYLHAROHTWZRTO-ZLHSVIROSA-N 348.395 2.022 30 1 EEEF N#C[C@H]1C[C@@H](O)CC[C@H]1n1cc(C(N)=O)c(Nc2ccc(F)cc2)n1 221213021 USZHEZVXLJZXEW-RIEGTJTDSA-N 343.362 2.090 30 1 EEEF O=c1c2ccccc2c(/C=N/n2cnnc2)c(O)n1-c1ccccc1 169689264 BLIVQXOTLFDMKN-UFFVCSGVSA-N 331.335 2.170 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@]2(C)O[C@@H]2CC[C@@]2(C)O[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 105397386 SXIIWHLYYYECJX-MTXIWTEZSA-N 348.395 2.071 30 1 EEEF N#C[C@H]1Sc2nnc(-c3ccccc3Br)n2NC1=N 1857579257 LNXLTBJCDMOAAT-MRVPVSSYSA-N 335.190 2.226 30 1 EEEF O=C1C=CC(O)=C/C1=C\NNC(=S)N[C@@H]1C[C@H]2C[C@H]1[C@@H]1C=CC[C@@H]12 104005506 NEWHOSFZGBPMPT-OOCVSKKRSA-N 343.452 2.021 30 3 EEEF C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1C(=O)CC1=CCOC1=O 103579661 WZHWNAKOQGIEEB-NDLGOLERSA-N 348.439 2.171 30 1 EEEF biogenic,in-vitro C[C@H](O)[C@@H]1C(O)=C(C(=O)[C@@H]2[C@H](C)C=C[C@@H]3CCCC[C@H]32)C(=O)N1C 102967708 NOYBJWXGAYWITN-FHBCKGOSSA-N 333.428 2.218 30 1 EEEF C#C[C@]1(O)CC[C@H]2[C@H]3[C@H](CC[C@@]21C)c1ccc(O)cc1[C@@H](O)[C@H]3O 66258840 RVQCOPCGQWZNJQ-UIUSIFNCSA-N 328.408 2.074 30 1 EEEF O=C1C=C[C@]2(O[C@@H]3c4c2ccc(O)c4C(=O)[C@H]2O[C@H]23)c2cccc(O)c21 2356482042 GLLQRSNTBBQHPX-ZRNYENFQSA-N 348.310 2.129 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@@H]3C[C@H](OC[C@@H](C)CC)[C@@H]12 2356673968 WULWDKXUHKIGSZ-JOMCMIFOSA-N 336.428 2.384 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1CCC(=C)[C@]1(O)C[C@H](OC(=O)C(C)C)C(=C)[C@H]21 238737318 LUUJHRSUAVIZOX-KSPMYQCISA-N 332.396 2.309 30 1 EEEF Cc1ccc(C(=O)/C=C/c2nc3ccc(S(N)(=O)=O)cc3[nH]2)cc1 587965275 IZPOYDZNOLOYNG-CMDGGOBGSA-N 341.392 2.415 30 1 EEEF N#CCC[C@]1(c2cccnc2)N[C@H](C(=O)O)Cc2cccc(F)c21 962898671 MFAIZCRLGMMKKH-MAUKXSAKSA-N 325.343 2.367 30 1 EEEF CC(C)C[C@H](NC(=O)[C@H](CS)Cc1ccccc1)S(=O)(=O)O 13449704 IFOJNPIPERNZBH-UONOGXRCSA-N 345.486 2.151 30 1 EEEF O=C1[C@H]2[C@H](C(=O)N1/N=C\c1cccc([N+](=O)[O-])c1)[C@H]1C=C[C@H]2C12CC2 104320841 BAOWMYTUKUMZDC-BVOGPVHYSA-N 337.335 2.126 30 1 EEEF O=C1C=Cc2ccccc2/C1=N/Nc1cccc(S(=O)(=O)O)c1 100536101 MEVGLBAVTZFMIV-VLGSPTGOSA-N 328.349 2.345 30 3 EEEF C=C(CO)[C@@H]1CC2=CC[C@H]3[C@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@@H]2[C@H](O)C1 2356443944 FISRUIAPOPDKNG-GCNBINEPSA-N 336.472 2.028 30 1 EEEF CC1=C2C=C3C(=O)C(O)=C([C@H](C)CO)[C@]3(C)CC[C@]2(C)C[C@@H](O)C1=O 2356521434 XUINLCMVOIWOKB-CIPQGIMKSA-N 346.423 2.393 30 1 EEEF COCC(=O)N1[C@@H](C#N)[C@@H](c2ccc(C3=CCCC3)cc2)[C@@H]1CO 95897807 SMEVBYXHWQHXGK-JENIJYKNSA-N 326.396 2.079 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@H](C(=O)O)[C@H]1[C@@]2(C)CCC[C@@]31COC2=O 257483224 MJFVMFNFTCKAEV-MHFUMCDTSA-N 346.423 2.384 30 1 EEEF endogenous,in-man N#Cc1nc(Cl)cc2nc(CNc3ncccc3[N+](=O)[O-])[nH]c12 587269232 TXFGWIQGDIRWFS-UHFFFAOYSA-N 329.707 2.398 30 1 EEEF CC(=O)OC[C@H]1O[C@@H](C#Cc2ccc(C)cc2C)C=C[C@@H]1OC(C)=O 13783120 FLENGSMTXSLATM-SLFFLAALSA-N 342.391 2.473 30 1 EEEF C=C[C@]1(O)CN2CC[C@@H]1C[C@@H]2[C@@H](O)c1ccnc2ccc(OC)cc12 22061177 BSRUJCFCZKMFMB-YFMMTPMMSA-N 340.423 2.288 30 1 EEEF CCCC(=O)C=CC1=C(O)C(=O)c2cc(OC)c(O)c(O)c2C1=O 2356628275 NERSELQTDRDIKE-UHFFFAOYSA-N 332.308 2.223 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cc(Cl)nc(C#N)c3[nH]2)C1=O 587038421 HPEOYMAWPNIRIQ-SECBINFHSA-N 347.787 2.275 30 1 EEEF COc1ccc2cc(C(=O)NCCCCCCC(=O)NO)[nH]c2c1 13490062 ZPPIORLLXVVXBL-UHFFFAOYSA-N 333.388 2.362 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](n2c(=O)[nH]c3ccccc32)[C@@H]1O 13742831 STLDVTNEXNAGBC-SJORKVTESA-N 335.363 2.323 30 1 EEEF C[n+]1cscc1COc1ccc(/C=N/NC(=N)N2CCCC2)cc1 26825596 ITLNUMJVLJXMTN-VXLYETTFSA-N 344.464 2.106 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1C[C@H](O)[C@H]2[C@]1(C)CCC[C@@](C)(C(=O)O)[C@H]1C[C@H]3O 238744701 BSPNTRYRRCCKFJ-PTAFSMAPSA-N 348.439 2.161 30 1 EEEF CN[C@H](C(N)=O)c1cccc(C#Cc2cc(Cl)ccc2OC)c1 587904146 CVVFUNGZVCXIMX-KRWDZBQOSA-N 328.799 2.494 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@@](C)(C=O)CCC[C@@]4(C)[C@@H]2C[C@H](O)[C@@H]1[C@H]3O 169313029 RNQLPXGROISTQX-DTMCMCHMSA-N 332.440 2.275 30 1 EEEF Oc1ccc(O)c(/C=N\NC(=S)N[C@@H]2C[C@@H]3C[C@@H]2[C@@H]2C=CC[C@@H]32)c1 169355911 OFXIRPMFRVBDKI-DMLHEFTMSA-N 343.452 2.497 30 1 EEEF CN(CC(=O)[C@H](Cc1ccccc1)C(=O)NO)Cc1ccccc1 101071048 VMWDFCRHJFIGQM-KRWDZBQOSA-N 326.396 2.052 30 1 EEEF CN(O)C(=O)c1cn(C)c2c1CCc1cnc(NC3CCCC3)nc1-2 64527152 YQMXFJYNHFPIRQ-UHFFFAOYSA-N 341.415 2.396 30 1 EEEF C=C1C[C@@]23C[C@@]1(C)CC[C@@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 2356832914 JXHBGFBFCVSITH-UVFNWPQNSA-N 344.407 2.302 30 1 EEEF COC1=CC2=C3C[C@@H]4CC[C@H](OC)[C@@H](OC)[C@H]4CN3CCC2=CC1=O 2356845133 OBXUDMPYADNLEQ-IBBHNLMTSA-N 345.439 2.446 30 1 EEEF C#CCOc1ccc(CON(C)C(=O)c2cccn2C)cc1OC 71341938 UZVMQYHHPOYVRW-UHFFFAOYSA-N 328.368 2.250 30 1 EEEF C=C1[C@@H]2CC[C@H]3[C@@]45CCC[C@@](C)(C(=O)O4)[C@H]5[C@H](C(=O)O)[C@]3(C2)[C@@H]1O 238753741 MBNDVMTZEKAWKP-CFHXUCNZSA-N 332.396 2.136 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1cccc[n+]1[O-] 587890550 LVXIJVJBOYLIPT-UHFFFAOYSA-N 335.190 2.337 30 1 EEEF COc1cccc(/C=N\n2c(S)nnc2-c2cc(C)n[nH]2)c1OC 15987700 SIXRKWYQNDFFSK-PXNMLYILSA-N 344.400 2.165 30 1 EEEF Oc1ccc(O)c(/C=N/NC(=S)N[C@@H]2C[C@@H]3C[C@@H]2[C@@H]2C=CC[C@@H]32)c1 169355912 OFXIRPMFRVBDKI-DPMCSYOXSA-N 343.452 2.497 30 1 EEEF CC1=CCC[C@@]2(C)O[C@@H]2[C@H]2OC(=O)[C@@H](Cn3cnc(CO)c3)[C@@H]2CC1 1857743065 LEZDFUSTWQETNC-YTGMWSOZSA-N 346.427 2.211 30 1 EEEF COc1ccc2c(c1)c(OC(C)C)c(/C(O)=N/c1nn[nH]n1)n2C 28767005 RYOUDBDJJZJETN-UHFFFAOYSA-N 330.348 2.124 30 1 EEEF COc1ccc(C[C@H](NC(=O)[C@@H](CS)CC(C)C)C(=O)O)cc1 98207849 PRPWYZNFKBFGFI-HIFRSBDPSA-N 339.457 2.399 30 1 EEEF in-vitro COc1ccc(/C=C/C(=O)c2ccc(OC)c(S(N)(=O)=O)c2)cc1 1857541535 VKDNVWRDFOWZJU-WEVVVXLNSA-N 347.392 2.247 30 1 EEEF CCOC(=O)Cc1cc(O)cc(O)c1C(=O)/C=C/C=C/C[C@H](C)O 238768055 QVACWFLAVQMDNR-QFGJERFKSA-N 334.368 2.269 30 1 EEEF N#Cc1nc2nc(Cn3cc(-c4ccc(F)cc4)cn3)[nH]c2nc1C#N 587164853 DFXZIDSPZUYTBP-UHFFFAOYSA-N 344.313 2.147 30 1 EEEF COc1cc(NC(=O)N2CCCc3ccc(C=O)nc32)ncc1C#N 1772621570 ALHYZSHKUANXLF-UHFFFAOYSA-N 337.339 2.154 30 1 EEEF C=CCN1[C@@H]2CC[C@@H]1[C@@H](C(=O)OC)[C@@H](OC(=O)c1ccccc1)C2 100645136 OLKZDWYIZCZYLB-WCXIOVBPSA-N 329.396 2.424 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100776678 ZCRLGANQNRMURE-NZRFLNHFSA-N 346.423 2.384 30 1 EEEF endogenous,in-man CC(C)C[C@H](NC(=O)N1CCCc2ccccc21)C(=O)NCC#N 82065424 VNNHWECZYQAMSO-HNNXBMFYSA-N 328.416 2.203 30 1 EEEF CN[C@@H](C(N)=O)c1cccc(C#Cc2cc(Cl)ccc2OC)c1 587904147 CVVFUNGZVCXIMX-QGZVFWFLSA-N 328.799 2.494 30 1 EEEF COc1ccccc1C(=O)/C=C/c1cc(/C=C/C(=O)NO)n(C)c1 13643591 GMDLUFKQPDBUPT-FIFLTTCUSA-N 326.352 2.448 30 1 EEEF COc1ccc(/C=N\n2c(S)nnc2-c2[nH]nc3c2CCC3)cc1 15987677 UIVRHCVKOOLZCY-MFOYZWKCSA-N 340.412 2.336 30 1 EEEF C=C(C)C(=O)O[C@@H]1CCC(CO)=C2[C@@H]3OC(=O)C(=C)[C@@H]3CC[C@]21C 2356470536 DXUUYKZZAJEBSQ-ZDXGLAPJSA-N 332.396 2.455 30 1 EEEF OCC#CCSc1cnc2ccccc2c1SCC#CCO 40898342 MTMJANUOYZUQSL-UHFFFAOYSA-N 329.446 2.410 30 1 EEEF O=C(/C=C/c1cccn(Cc2ccc(Br)cc2)c1=O)NO 143931679 BWIOBTZYSHRQEN-VMPITWQZSA-N 349.184 2.178 30 1 EEEF COc1ncc2nc(-c3cc(F)cc(F)c3)c(=O)n(CCC#N)c2n1 4238457 OLGNBUIZJFTAJA-UHFFFAOYSA-N 343.293 2.054 30 1 EEEF O=C(NO)[C@@H]1CN(Cc2ccc(Oc3ccc(F)cc3)cc2)C(=O)N1 9078 NBBPYGNNDFCNNP-HNNXBMFYSA-N 345.330 2.017 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@H]2C(=C)C[C@H](O)[C@@H]3[C@H](C)C(=O)O[C@@H]3[C@H]2C1=C 2356488759 ZNXKZMIVEDDWGE-DRGPRHNLSA-N 332.396 2.165 30 1 EEEF C=C(C)C(=O)O[C@@H]1CC(=C)[C@@H]2C[C@H](O)[C@H](C)[C@@H]2[C@H]2OC(=O)C(=C)[C@@H]12 2356664663 FQKDBWKMFCRELP-LRPRVFIZSA-N 332.396 2.165 30 1 EEEF Cn1cc(-c2ccc([C@H](NC(=O)OC(C)(C)C)C(=O)NO)cc2)cn1 584905026 SASAIIBKYJIJKV-AWEZNQCLSA-N 346.387 2.158 30 1 EEEF in-vitro C=CCN(C)C[C@H]1CN2CC[C@H]1C[C@H]2CNC(=O)c1ccccc1 2356301866 ZDVHQAKIGXBAMN-FHWLQOOXSA-N 327.472 2.245 30 1 EEEF C=C1CO[C@H]2[C@H]3C(=O)C[C@H](C(C)C)[C@@]3(C)C[C@@H](O)[C@]3(C)CC(=O)O[C@]123 238737146 WEESDXVSTZNCSH-QUDJOTQDSA-N 348.439 2.266 30 1 EEEF COc1cccc2c1CCN1C(=O)/C(=C/C(=O)c3ccccc3)NC[C@@H]21 96934320 HEWQOIDNNXSQSU-FSEPTYSPSA-N 348.402 2.491 30 1 EEEF C=C1[C@@H]2CC[C@@H]3C[C@@]2(CC[C@]2(O)[C@@H]1C[C@H](O)[C@@]2(C)CO)C[C@@]3(C)O 1857611588 ADOSBXBBIYJRSB-FWMLDDLOSA-N 336.472 2.004 30 1 EEEF C=C1C2=C(C(=O)N1OC)[C@H](O)[C@@](C)(O)[C@@H](CCCCCCC)O2 2356342527 FLJXRCWDXADIBL-PVUWLOKVSA-N 325.405 2.029 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1C[C@@H]1O[C@]1(CO)CC/C=C(\C)CC/C=C(\C)[C@H]2O 100089877 MULWDJOXRRXULO-HUUDZGMYSA-N 348.439 2.432 30 1 EEEF in-vitro CNC(=O)c1noc([C@H](CCCC2CCCCC2)CC(=O)NO)n1 34020988 OIXMXOATOMTGIL-GFCCVEGCSA-N 338.408 2.159 30 1 EEEF C/C=C(/C)C(=O)O[C@H]1C[C@@H](O)C2=CC(=O)C(C(C)(C)O)=C[C@]2(C)[C@H]1C 36453013 LHZKEPWOCHFOLY-XSBSUDOJSA-N 348.439 2.478 30 1 EEEF N#Cc1ncc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cn1 587887317 KCBQXMLBHGHOCZ-UHFFFAOYSA-N 345.189 2.365 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C(O)=C3C(C)(C)[C@H](O)CC[C@]3(C)[C@]2(O)[C@H](O)C1 2356460944 PYMRQNNIAHSRKU-OVWHTBOBSA-N 348.439 2.183 30 1 EEEF C=CCn1c(O)c(C(C)=Nc2ccc3c(c2)CCC3)c(O)nc1=O 1779673418 JVLOSLNORBEEJG-UHFFFAOYSA-N 325.368 2.470 30 1 EEEF CC1=C[C@]2(O)C(=C[C@](C)(O)CC[C@@H]3[C@H](C[C@H](C)[C@H]2O)C3(C)C)C1=O 2356515846 CZUBZNDQQZRXMB-CIKRZWDRSA-N 334.456 2.377 30 1 EEEF C=CC[C@@]12CC(=O)[C@H](O)[C@@H]([C@H](c3ccc4c(c3)OCO4)[C@@H]1C)[C@H]2O 2356536936 FBPLISOOTGTZGY-HLQYOEHKSA-N 330.380 2.022 30 1 EEEF COC1=C[C@@H]2[C@H]3Cc4cc(OC)c(OC)cc4[C@@]2(CCN3C)CC1=O 2356787136 UFPSPSKAMWHJCV-STXHMFSFSA-N 343.423 2.321 30 1 EEEF CC(C)C[C@H](C(=O)NCC#N)n1cnc2c(Cl)nc(Cl)nc21 82061652 XUYTXMWETIBUJD-MRVPVSSYSA-N 341.202 2.360 30 1 EEEF O=C(NO)c1ccc(NC(=S)N/N=C/c2ccc(F)cc2)cc1 1857595658 ZAMXIYWEQCJUEI-RQZCQDPDSA-N 332.360 2.265 30 1 EEEF C=C1[C@H](O)[C@@]23CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]4(C)[C@H]2CC(=O)[C@H]1[C@H]3O 2356522496 JGAWMQVJTGKMKT-OIVXZBPLSA-N 334.456 2.067 30 1 EEEF C=C1[C@H](O)[C@@]23C(=O)C[C@@H]4C(C)(C)[C@H](O)CC[C@]4(C)[C@H]2C[C@@H]1C[C@@H]3O 2356634484 FYHBINXIARYPCI-RKZIWCSJSA-N 334.456 2.067 30 1 EEEF O=C1C=CC(=O)C2=C1[C@@H](O)CCC21Oc2cccc3cccc(c23)O1 44361447 QRNNOWVUVIEQSM-ZDUSSCGKSA-N 334.327 2.467 30 1 EEEF Cc1nc2n(c(=O)c1C(=O)O)[C@@H](C)CCC2=NNc1ccccc1 253689901 PTMLSROVUJDKCJ-JTQLQIEISA-N 326.356 2.421 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@H]2C[C@@H](CC(C)=C[C@H]3OC(=O)C(=C)[C@H]31)OC2=O 2356536256 HOZUUHWHCWNMPV-OXGONZEZSA-N 346.379 2.244 30 1 EEEF CCC[C@@H]1O[C@H](CC(=O)O)C[C@]23O[C@]12C(=O)c1ccccc1C3=O 2356561274 WVRWIGGCJAKRAH-HJGRGVKTSA-N 330.336 2.006 30 1 EEEF C=C(CC[C@@H]1C(=C)CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]21C)[C@H](O)CO 2356581698 GLRQCZGXPULESM-FFDFYAMSSA-N 338.488 2.418 30 1 EEEF C=C1C(=O)O[C@@H](CCCCCCCC)[C@@H]1C(=O)NCC(=O)OC 43462759 JUAJBMRRDLRYEZ-DZGCQCFKSA-N 325.405 2.124 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@]12CCC[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 85800271 IPHNMKITOREFLW-MKMQNPNCSA-N 332.396 2.136 30 1 EEEF in-man COc1ccc(Cl)cc1C#Cc1ccc2c(c1)[nH]c(=O)c(=O)n2C 587908634 DLSPGSFNKLGFDO-UHFFFAOYSA-N 340.766 2.289 30 1 EEEF COc1ccc(/C=C/C(=O)c2ccc(OCC(=O)O)cc2O)cc1O 27429725 RAWLIJWXNBWLSQ-QHHAFSJGSA-N 344.319 2.466 30 1 EEEF C=C(C)[C@@H]1Oc2cc(O)c(C(C)=O)cc2[C@@H]1OC(=O)C(=CC)CO 2356690564 CLWSKSKCEVBFSD-IRXDYDNUSA-N 332.352 2.455 30 1 EEEF COCC(=O)N1[C@@H](C#N)[C@@H](c2ccccc2C2=CCCC2)[C@@H]1CO 95867993 OERKOXUAKKWALJ-JENIJYKNSA-N 326.396 2.079 30 1 EEEF Oc1ccc(O)c(C=NNC(=S)N[C@@H]2C[C@H]3C[C@H]2[C@H]2C=CC[C@H]32)c1 254047240 OFXIRPMFRVBDKI-QPHLWMPCSA-N 343.452 2.497 30 1 EEEF Cc1c(C(=O)/C=C/c2ccc([N+](=O)[O-])o2)[n+](=O)c2ccccc2n1O 653723929 QEMBEDRMQZOXHK-SOFGYWHQSA-N 342.287 2.499 30 1 EEEF CCCCCC[C@@]1(C)SC(=O)C=C1OCC(=O)NCC(=O)OC 13609091 LOIBXRPPXRGNAR-MRXNPFEDSA-N 343.445 2.179 30 1 EEEF C[C@](O)(COc1ccccc1F)C(=O)N1CCc2c(C#N)cccc21 169313272 DVYDOAZUHWNKGO-IBGZPJMESA-N 340.354 2.416 30 1 EEEF Cc1ccc2[nH]c(=O)c([C@@H]3NC(=S)NC4=C3C(=O)CCC4)cc2c1 103285171 MLDAFGSUVHDXHC-INIZCTEOSA-N 339.420 2.362 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC=C2[C@@]12CC[C@@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 85800121 BSBICXIQCTXPMN-SHGZESKZSA-N 330.380 2.056 30 1 EEEF in-man C=C1CCCN(C(=O)/C=C/c2cc(OC)c(OC)c(OC)c2)C1=O 1857766781 CLFSJTWMNIHALI-BQYQJAHWSA-N 331.368 2.431 30 1 EEEF C#C[C@@H]1CN2CC[C@H]1C[C@@H]2CNC(=O)Nc1cc(OC)cc(OC)c1 2356300802 SDRGEMKIXHLRFZ-IJEWVQPXSA-N 343.427 2.169 30 1 EEEF COC(=O)/C=C/C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587876785 MYDMJMDQWYUTLA-HWKANZROSA-N 326.179 2.385 30 1 EEEF COC(=O)[C@]1(C)CCC(=O)C(C)=C1C=CC(C)=C[C@@H](O)C[C@H](C)O 2356377841 NGPTWMZMECMCMC-ZBQZNYHESA-N 336.428 2.479 30 1 EEEF C[C@@]1(CCC(=CCO)CO)[C@@H]2CCC=C3C(=O)OC[C@]32CC[C@H]1C=O 2356379733 GUKSFBJMSDUTIA-LWCVALJOSA-N 348.439 2.172 30 1 EEEF O=S(=O)(N/N=C\c1ccc2c(c1)OCO2)c1ccc(Cl)cc1 33285579 BPIOJCNNAOQBHP-PXNMLYILSA-N 338.772 2.381 30 3 EEEF C=C1C[C@@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@H](O)CO)[C@@H]2C[C@@H]1CC3 96085984 FYKIZBPSTADBEK-STNJDDFNSA-N 348.439 2.171 30 1 EEEF O=C(CS[C@@H](c1ccc(Cl)c(Cl)c1)P(=O)(O)O)NO 96284894 MMODIMKCMBCKCF-VIFPVBQESA-N 346.128 2.408 30 1 EEEF C=C1[C@@H]2CC[C@@H]3C[C@@]2(CC[C@]2(O)[C@@H]1C[C@H](O)C2(C)C)C[C@]3(O)CO 1857582398 OPXSAGTVGJPWQJ-IZVMADOGSA-N 336.472 2.004 30 1 EEEF C=C(C)C(=O)O[C@@H]1CC(=C)[C@@H]2C[C@H](O)[C@H](C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 2356664664 FQKDBWKMFCRELP-SSEINGGUSA-N 332.396 2.165 30 1 EEEF N#Cc1cccc(OCc2cn(CC(=O)c3ccc(O)cc3)nn2)c1 72136023 YRBMRCJCWGQISO-UHFFFAOYSA-N 334.335 2.317 30 1 EEEF N#C[C@@H]1CCCN1C(=O)C1(NC(=O)c2ccnc3ccccc23)CC1 169310671 QMSPXZINNSNSNF-ZDUSSCGKSA-N 334.379 2.012 30 1 EEEF Cc1cccc2c1NC(=O)[C@H]2/C=N/c1ccc(S(N)(=O)=O)cc1 169727076 SKFOKDNXKMEDPH-RMNBPEERSA-N 329.381 2.081 30 1 EEEF CSC1=N[C@@H]2[C@H](N(C)C(=O)N2C)N1/N=C/C=C/c1ccccc1 1857639633 WONCCEICUAEBNN-LBECQDLKSA-N 329.429 2.370 30 1 EEEF O=C(NO)c1sc(N2CCOCC2)cc1OCCc1ccccc1 1857761002 BGLBQNIKANBQRX-UHFFFAOYSA-N 348.424 2.325 30 1 EEEF CO[C@]1(C#C[C@](O)(c2ccccc2)c2cccnc2)CN2CCC1CC2 28563572 ZGBSEJYQXDWFRF-YADHBBJMSA-N 348.446 2.432 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@@H](C(=O)O)[C@H]1[C@]32CCC[C@@]1(C)C(=O)O2 104365810 MBNDVMTZEKAWKP-PNZYVUTDSA-N 332.396 2.136 30 1 EEEF in-man CC(C)[C@@H]1[C@H](O)[C@H](O)[C@@H]2[C@@H]3OCC4=C3[C@](C)(CCC4=O)CC[C@@]12C 2356823284 GKUCSSBQVHTTCY-PBQUBUBMSA-N 334.456 2.475 30 1 EEEF C=CCc1cc(-c2c(O)ccc(C[C@H](O)CO)c2OC)ccc1O 238732470 WPDLBOXRXKKCRE-HNNXBMFYSA-N 330.380 2.398 30 1 EEEF C=CC1=CC(=O)[C@@H]2[C@H](CC[C@@H]3C(C)(C)[C@@H](O)[C@@H](O)[C@@H](O)[C@@]23C)[C@@H]1C 14777610 XFRCVLKGZMPUFQ-LUGPCSGRSA-N 334.456 2.089 30 1 EEEF endogenous,in-man N#Cc1ncn(-c2ccc(O)cc2)c1/N=C/c1c(O)cc(O)cc1O 169350308 MGNMKOBAFRZFHU-UFWORHAWSA-N 336.307 2.317 30 1 EEEF C[C@@H]1C[C@H]2O[C@H]2/C=C/C=C\C(=O)Cc2cc(O)cc(O)c2C(=O)O1 104958837 XTUZVEOWUSGCSV-ODJCJXHMSA-N 330.336 2.038 30 1 EEEF COc1ccc(OC)c(N/N=C2/C(=O)Nc3ccccc3C2=O)c1 104023549 OPLMDWLFOXTUTL-HMMYKYKNSA-N 325.324 2.307 30 3 EEEF C=C(C)C(=O)O[C@@H]1C[C@](C)(O)C(=O)CCC(C)=C[C@@H]2OC(=O)C(=C)[C@@H]21 2356754582 AYLHAROHTWZRTO-MVWRLGRASA-N 348.395 2.022 30 1 EEEF C#CCNC(=O)C1CCN(c2cc(C)nc(-c3ccccc3)n2)CC1 5000446 WEVUFLJMHRESRW-UHFFFAOYSA-N 334.423 2.418 30 3 EEEF C=C1C[C@H](OCC(C)C)[C@@H]2C(=C)C(=O)O[C@@H]2C=C(C)[C@@H](O)CC1=O 2356483574 PJRAJKIGBHSJPR-FJIDUMEYSA-N 334.412 2.352 30 1 EEEF C=C1CO[C@H]2[C@@H]3C(=O)C[C@@H](C(C)C)[C@]3(C)C[C@H]3OC(=O)C[C@@]3(C)[C@@]12O 40877742 FNWXCFNQVRNNMR-AAQVCALCSA-N 348.439 2.266 30 1 EEEF N#C[C@H](Cc1ccc(NC(=N)N)cc1)NC(=O)OCc1ccccc1 49111835 LITMQKSVCWTOSP-INIZCTEOSA-N 337.383 2.353 30 1 EEEF O=C(CCCCCONC(=O)Nc1cnc2ccccc2c1)NO 95593564 WIIHTSGYTBNRBX-UHFFFAOYSA-N 332.360 2.354 30 1 EEEF O=C([C@H]1CCOC1)N1CCc2nc(C#Cc3ccccc3)sc2C1 96272965 VDPVHWGVEQPQDX-HNNXBMFYSA-N 338.432 2.464 30 1 EEEF C=CCOC(=O)N1C[C@@H]([C@@H](C)OC(=O)NCCc2ccccc2)C1=O 95596681 PEQWZABNJSPNBV-HIFRSBDPSA-N 346.383 2.125 30 1 EEEF C=CC[C@@]1(CNC(=O)OCC)NCCc2ccc(C(=O)N(C)C)cc21 962921878 FNNQCQNSAYHPFV-IBGZPJMESA-N 345.443 2.052 30 1 EEEF NS(=O)(=O)c1ccc(N/N=C/c2ccc(N3CCCC3)cc2)cc1 1857560484 UZKZXHGELYWRPO-CPNJWEJPSA-N 344.440 2.380 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](N/C(=N/C#N)c2cccnc2)[C@@H]1O 3935494 RYJXYHFVDXMIRD-SJORKVTESA-N 347.378 2.044 30 1 EEEF CO/N=C(\CN1CCN(c2ccccn2)CC1)c1ccc(F)cc1 36216671 FHPKNBFLJRFJBV-HEHNFIMWSA-N 328.391 2.393 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1CCC(=C)[C@H]1[C@@H]2C(=C)[C@@H](O)[C@@H]1OC(=O)C(C)C 238764351 PVMRWMPTZVVVJM-JQVOGXOBSA-N 332.396 2.165 30 1 EEEF COC1=C[C@@H]2[C@@H]3Cc4ccc(C(C)=O)c(O)c4[C@]2(CCN3C)CC1=O 95627891 DWQIEUYIJNZWSH-QEEYODRMSA-N 341.407 2.212 30 1 EEEF COc1ccc(N2C(=S)[C@@H](C#N)C(=O)N[C@@H]2c2ccco2)cc1 169688083 PSLDKXQWVTXHEX-JSGCOSHPSA-N 327.365 2.390 30 1 EEEF C=C1C[C@@]23C[C@@]1(C)CC[C@@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 2356832912 JXHBGFBFCVSITH-IQAXHZPKSA-N 344.407 2.302 30 1 EEEF CC(C)C1=CC(=O)[C@]2(C)CC[C@@]3(C)C(=O)C=C(CO)[C@H](O)C[C@H]3[C@H]12 238747123 SRUVAUDOCNEFJS-DJLVLGKWSA-N 332.440 2.443 30 1 EEEF C=C1C[C@H](O)[C@@H]2C(=C)C(=O)O[C@@H]2[C@@H]2C(=C)[C@H](OC(=O)C=C(C)C)C[C@H]12 2356441756 DDKWVHFIPPNJCX-NUTUMTGBSA-N 344.407 2.475 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1cc(CO)on1 587890599 ODCKSUNNGRNSDX-UHFFFAOYSA-N 339.178 2.184 30 1 EEEF CC1=C(CCc2nnnn2CCCC#N)C(=O)c2ccccc2C1=O 1857549034 XHBZUGKIGSTCGG-UHFFFAOYSA-N 335.367 2.305 30 1 EEEF N#Cc1cccc(-c2cc(NC(=O)[C@@]3(F)CCCN(C#N)C3)on2)c1 1857540551 AXIFCCZGQFOIJY-QGZVFWFLSA-N 339.330 2.437 30 1 EEEF O=C1OC(=Cc2ccc(O)cc2)C(=O)C(c2ccc(O)c(O)c2)=C1O 2356545419 SJGOQLCKPXMLHK-UHFFFAOYSA-N 340.287 2.240 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)[C@H](O)C[C@]3(C)[C@@]1(C)[C@]21CO1 2356610167 VRHZKNFFKJZHFD-QIGARABOSA-N 334.412 2.138 30 1 EEEF COc1ccccc1Oc1ncccc1/C(=N/O)N1CCOCC1 72185557 XGLGGDADHNBCCD-MNDPQUGUSA-N 329.356 2.351 30 1 EEEF C=C1[C@H](O)C[C@@H]2[C@](C)(CO)C[C@@H](O)C[C@@]2(C)[C@H]1CC/C(C)=C\CO 40845210 LCWHTWNKEOSQBZ-LITYEMHZSA-N 338.488 2.418 30 1 EEEF C=CCN1[C@H]2CC[C@@H]1C[C@H](OC(=O)c1ccccc1)[C@@H]2C(=O)OC 36177527 OLKZDWYIZCZYLB-LTIDMASMSA-N 329.396 2.424 30 1 EEEF CCN/C(=N\S(=O)(=O)c1ccccc1Cl)N1C[C@@H](CC)C=N1 72126896 MVMXJZAAQMLRNG-NSHDSACASA-N 342.852 2.322 30 1 EEEF CC(C)NC[C@H](O)CO/N=C1/c2ccccc2[C@@H]2CCCC[C@@]12O 169342280 RTKLMTIRQZCKHN-GLCWXTKRSA-N 332.444 2.169 30 1 EEEF N#Cc1ccc(CNc2c(NCc3ccc(C#N)cc3)c(=O)c2=O)cc1 100768166 HGBUKQMYZZVMLQ-UHFFFAOYSA-N 342.358 2.250 30 1 EEEF C/C(N)=C1/C(=O)[C@@H]2[C@@H]3c4c[nH]c5cccc(c45)C[C@H]3C(C)(C)N2C1=O 105565808 AFOUSJMOYMLOPA-PBWZNQHMSA-N 335.407 2.229 30 1 EEEF C=C(C)[C@@H]1Oc2cc(O)c(C(C)=O)cc2[C@H]1OC(=O)C(=CC)CO 2356690562 CLWSKSKCEVBFSD-DLBZAZTESA-N 332.352 2.455 30 1 EEEF C=CCn1c(=O)c(NCC2CC2)c2n(c1=O)[C@H](c1ccccc1)CN2 82209185 LYGRWWDVQGTXPY-HNNXBMFYSA-N 338.411 2.033 30 1 EEEF N#Cc1nc(NCc2ccc(F)cc2)c2ncn(CCCCO)c2n1 14977850 JLNFUUXMZSXOJU-UHFFFAOYSA-N 340.362 2.222 30 1 EEEF C[C@H]1CC(=O)C2=C(CC[C@@]34O[C@]23C(=O)c2cccc(O)c2[C@@H]4O)C1 100266981 NNMGLXNJGVNRCH-JGVKMKRASA-N 326.348 2.219 30 1 EEEF CN(CC(=O)[C@@H](Cc1ccccc1)C(=O)NO)Cc1ccccc1 101071043 VMWDFCRHJFIGQM-QGZVFWFLSA-N 326.396 2.052 30 1 EEEF CC=C(C)C(=O)O[C@@H]1CCN2C[C@H]3C[C@@H](CN4C=CC(=O)C[C@@H]34)[C@H]2C1 2356436105 ANLPQANGWMODSI-XWCCPHMRSA-N 344.455 2.136 30 1 EEEF CS(=O)(=O)N1Cc2ccccc2C[C@H]1/C(O)=N/Cc1ccco1 213572 FVMDWQCAHRVRNX-HNNXBMFYSA-N 334.397 2.123 30 1 EEEF C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@@H]2C(=CC=CC(C)(C)O)COC(=O)[C@H]12 2356613191 CHWOLNBRUULGCY-QOSLBHJFSA-N 348.439 2.288 30 1 EEEF C#C[C@]1(O)C[C@H](O)[C@@H]2[C@@H]3CCc4cc(O)ccc4[C@@H]3[C@H](OC)C[C@@]21C 2356613658 TYTYJGWQMLLBDD-LZZNHIFKSA-N 342.435 2.208 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)C(C)=C[C@@H]2OC(=O)C(=C)[C@@H]21 2356740550 RYBHZNMPMHOBAR-QMYADUOMSA-N 344.363 2.164 30 1 EEEF Cc1cc2c(cc1O)[C@](CC#N)(c1cccc(C#N)c1)N[C@H](C(=O)O)C2 963511651 URBIROOJYLTIAR-PXNSSMCTSA-N 347.374 2.328 30 1 EEEF NS(=O)(=O)c1ccc(/N=C/C2=C(O)c3ccccc3C2=O)cc1 27956 UUMCKCDORAVKRP-GIJQJNRQSA-N 328.349 2.202 30 1 EEEF C=CCc1cc(NC(=O)NCC)ccc1OC[C@H](O)CNC1CC1 169317311 IBRIYEJEZDJIDG-MRXNPFEDSA-N 333.432 2.048 30 1 EEEF C=C(C)C[C@@H]1N(c2ccccc2)C(=O)[C@H]2[C@H](C(=O)O)[C@@H]3C=C[C@@]21O3 207846 IDZVBZRLNMBRMS-DBDOFBCQSA-N 325.364 2.392 30 1 EEEF CC(C)[C@@H](C=O)c1c(O[C@@H](O)C(C)(C)O)ccc2ccc(=O)oc12 2356496201 FOMXOHFJUKCTAU-SJKOYZFVSA-N 334.368 2.200 30 1 EEEF C=C1C[C@H](O)[C@@H]2C(=C)C(=O)O[C@@H]2[C@@H]2C(=C)[C@H](OC(=O)C(C)=CC)C[C@H]12 2356654402 UINWHHMWCJPCDZ-NWCWSAAOSA-N 344.407 2.475 30 1 EEEF CN(C)c1ccc(CNC(=O)NCCCCCCC(=O)NO)cc1 29133776 WLBQLWWJBPUGKF-UHFFFAOYSA-N 336.436 2.008 30 1 EEEF N#Cc1ccc2c(c1)CC[C@@H]2N1C[C@H](N)[C@H](C(=O)[C@H]2CCC[C@H]2C#N)C1 261190765 ZAWGLJVNJZBVID-UVBQOVKKSA-N 348.450 2.314 30 1 EEEF CCOC(=O)c1csc(-c2cn(C)c3c2C(=O)C(OC)=CC3=O)n1 1653383 URTSZPDLWLNZKK-UHFFFAOYSA-N 346.364 2.235 30 1 EEEF C=C[C@@H]1CN2CC[C@H]1C[C@@H]2CNC(=O)CC1(CC(=O)O)CCCC1 2356389562 ZGYUSGIGQDEQMQ-OWCLPIDISA-N 334.460 2.424 30 1 EEEF C[C@@H]1C[C@@H]2O[C@H]2/C=C\C=C\C(=O)Cc2cc(O)cc(O)c2C(=O)O1 105575694 XTUZVEOWUSGCSV-YAXHDAAQSA-N 330.336 2.038 30 1 EEEF C=C1C[C@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)O 100783027 BSBICXIQCTXPMN-OKPFSBKOSA-N 330.380 2.056 30 1 EEEF endogenous,in-man C=C1C[C@@H]2O[C@@H]2[C@]2(CC[C@@H]3C(=CC=CC(C)(C)O)C(=O)OC[C@H]13)CO2 2356803326 WZDCQTZIRFGNEC-JMPGWDFISA-N 346.423 2.306 30 1 EEEF COC(=O)/C=C\C(C#N)(C#N)/N=C/c1ccc(Br)s1 31899149 AHWONDOEVCTSBF-LZHMDJDISA-N 338.186 2.445 30 1 EEEF COc1ccc(N/N=C2\CC[C@H](C)n3c2ncc(C(=O)O)c3=O)cc1 40639355 MCLKGGAIIDSSHM-GODZOQJBSA-N 342.355 2.121 30 1 EEEF N#CC1(OC(=O)[C@H]2C[C@]3(CN2)C(=O)Nc2ccccc23)CCCCC1 95575049 VRCMTLQTPNLTIN-DNVCBOLYSA-N 339.395 2.008 30 1 EEEF in-vitro Cc1cnc(N)c(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)n1 587890195 UXIYQQAGGYDJMM-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF COc1cc(O)c2c(c1OC)OCC(=Cc1ccc(O)c(O)c1)C2=O 2356566766 TXCALKWMXKVGOY-UHFFFAOYSA-N 344.319 2.479 30 1 EEEF CC=C(C)C(=O)O[C@@H]1C[C@H](O)C2=CC(=O)C(C(C)(C)O)=C[C@@]2(C)[C@H]1C 2356594905 LHZKEPWOCHFOLY-QIYNHLNTSA-N 348.439 2.478 30 1 EEEF CC1=C(OCCN2C(=O)C(=O)c3cc(F)ccc32)[C@H](C)SC1=O 71318124 SWOPJCXOATZWAK-VIFPVBQESA-N 335.356 2.308 30 1 EEEF CC(=O)Nc1nc2nn(-c3ccccc3)c(NC(C)=O)c2cc1C#N 43017189 ASHKDGWGEMYKIM-UHFFFAOYSA-N 334.339 2.209 30 1 EEEF C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@H]2/C(=C/C=C/C(C)(C)O)C(=O)OC[C@H]12 238759807 DHTWVKTXQLZELP-ASBBGEPWSA-N 348.439 2.288 30 1 EEEF C=CCc1cccc2nc(CS(=O)(=O)Cc3ccnn3C)[nH]c12 586923817 WPRZFNGPLQXVPG-UHFFFAOYSA-N 330.413 2.140 30 1 EEEF CN1C(=O)[C@H](NC(=O)c2cc3cc(C#N)ccc3[nH]2)Cc2ccccc21 13587904 VDFAECYBULQGGS-QGZVFWFLSA-N 344.374 2.357 30 1 EEEF CC(=N)[C@H](C#N)C(=O)CSc1nnc(-c2ccc3c(c2)OCO3)o1 17511577 NRPONSWDLHTVNL-JTQLQIEISA-N 344.352 2.306 30 1 EEEF Cc1ccc(Nc2c(N[C@H](C)CCCCC(=O)NO)c(=O)c2=O)cc1 1857766677 ZPCDSQXLCVDHBZ-GFCCVEGCSA-N 345.399 2.201 30 1 EEEF C[C@@H]1C[C@H]2O[C@H]2/C=C\C=C\C(=O)Cc2cc(O)cc(O)c2C(=O)O1 104958840 XTUZVEOWUSGCSV-OGVBHEQLSA-N 330.336 2.038 30 1 EEEF C[C@]1(CC/C(=C/CO)CO)[C@H](C=O)CC[C@@]23COC(=O)C2=CCC[C@@H]31 61924482 GUKSFBJMSDUTIA-HSTHLEMDSA-N 348.439 2.172 30 3 EEEF C/N=C1/N/C(=C\c2c[nH]c3cccc(Br)c23)C(=O)N1C 84689510 IPEDGFQBWJGPBU-WDZFZDKYSA-N 333.189 2.319 30 1 EEEF Cc1ncc(N)nc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587890232 WPLXUSQAMCIKNV-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF C=C[C@H](CCc1ccc(C(=O)OCC)cc1)c1c(N)nc(N)[nH]c1=O 1662804 FGBZUJXPLVUXJQ-GFCCVEGCSA-N 342.399 2.013 30 1 EEEF CCCCCCNC(=S)N/N=C1\C(=O)Nc2ccc([N+](=O)[O-])cc21 103203161 ADMLLUXSRNZJRV-UHFFFAOYSA-N 349.416 2.295 30 1 EEEF N#CC1(n2cc([C@@H](NC(=O)c3ccno3)C3CCCCC3)nn2)CC1 95557809 ILQNJICQCLUHMS-HNNXBMFYSA-N 340.387 2.330 30 1 EEEF COC(=O)[C@]1(C)CCC(=O)C(C)=C1/C=C/C(C)=C/[C@H](O)C[C@H](C)O 238739424 NGPTWMZMECMCMC-HINRZXSKSA-N 336.428 2.479 30 1 EEEF COc1ccc2c(c1)CCN(CCC#Cc1nccs1)C[C@@H]2O 1857567095 VWUUYLGPLYILTF-KRWDZBQOSA-N 328.437 2.485 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H]1[C@@H](OC(=O)C(C)=CC)CC(=C)[C@@H]1C[C@@H](O)C(=C)[C@H]12 2356486442 SDRJABGPZHYDOV-OXODIDRGSA-N 344.407 2.475 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)[C@@H]3C=CC(=O)[C@]3(C)[C@@H](OC(=O)C(C)C)[C@@H]12 2356636025 SKAOENNHESXSCC-CTZJGSBNSA-N 332.396 2.453 30 1 EEEF Cc1ccc2[nH]c(=O)c(/C=N/c3ccc(S(N)(=O)=O)cc3)cc2c1 95593902 XPJIFIJGPFNFPX-VXLYETTFSA-N 341.392 2.235 30 1 EEEF COc1cc2c3c(c1)O[C@@]1(CCCC(=O)/C1=C/N(C)C)[C@@H](C2)C3=O 587427253 CTRDIESGJSGEEB-BAAFFPTESA-N 327.380 2.380 30 1 EEEF N#Cc1ccc([N+](=O)[O-])c([C@H]2N[C@H](C(=O)O)Cc3cc(F)ccc32)c1 962897299 CHTOBEJKVIAQST-HOCLYGCPSA-N 341.298 2.294 30 1 EEEF Nc1ccc(C#Cc2ccc(OCCOCCOCCO)cc2)cc1 28644637 LYZYLYXIXRTVLV-UHFFFAOYSA-N 341.407 2.073 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@H]2C[C@H](C/C(C)=C/[C@H]3OC(=O)C(=C)[C@@H]31)OC2=O 238770800 HOZUUHWHCWNMPV-WSQXHVFGSA-N 346.379 2.244 30 1 EEEF O=C(NO)c1cc2n(c1)CCN(C(=O)c1cc3ccccc3s1)C2 299837750 PKOFMNJPOQAOMK-UHFFFAOYSA-N 341.392 2.478 30 1 EEEF O=CC(C=O)c1ccc(-c2nc3nc(Cl)c[nH]c-3n2)cc1[N+](=O)[O-] 587261987 LAZCTFDQGAWGHD-UHFFFAOYSA-N 345.702 2.015 30 1 EEEF Cn1nc(-c2ccc(/C=N/NC(N)=S)s2)cc1C(F)(F)F 13474206 JGLNNLSEGJOSBP-FZSIALSZSA-N 333.364 2.335 30 1 EEEF C=C(C)[C@@H](O)Cc1c(OC)c2ccc(OC)c(OC)c2n(C)c1=O 14679263 NGOMVQJSMUMPNB-ZDUSSCGKSA-N 333.384 2.044 30 1 EEEF biogenic C=C1C[C@H]2O[C@H]2[C@@](C)(O)CC[C@@H]2C3=C[C@H]([C@H]4OC4(C)C)O[C@@H]3OC[C@@H]12 166804603 PVAIAJLEMKCLCA-SYAZFZFOSA-N 348.439 2.336 30 1 EEEF C=C(C)CN1CCN(CC(=O)[C@](O)(c2ccccc2)C2CCC2)CC1 22940334 BRCPZJDCSAYHDA-NRFANRHFSA-N 342.483 2.437 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)[C@@H]3[C@H](O)CC[C@]3(C)[C@H](OC(=O)C=CC)[C@H]12 2356549656 HSXLCTYJIGXUOE-GJASKRQVSA-N 334.412 2.389 30 1 EEEF N#C[C@H](Cc1ccccc1)NC(=O)[C@@H]1C[C@@](F)(c2ccccc2)CN1 48998445 DVNLMXZGWUFTRG-BJLQDIEVSA-N 337.398 2.464 30 1 EEEF CC(=O)OCC[C@@H](/C=C/C=C\C#CC#C/C=C/CO)OC(=O)C(C)C 238776705 RLOXIGRNKNTVJQ-QQBKXEKPSA-N 344.407 2.175 30 1 EEEF COc1cc(C(C)C)c(Oc2cnc(N)nc2N)cc1C#CCCO 35298370 CEILJYAMAMSKMQ-UHFFFAOYSA-N 342.399 2.299 30 1 EEEF C=CCN1C(=O)c2n[nH]c(COC)c2[C@@H]1c1ccc2c(c1)OCO2 199728950 GPQWXCIMIKDSIH-INIZCTEOSA-N 327.340 2.016 30 3 EEEF O=C(O)CNC(=O)c1ccc(NC(=S)NN=C2CCCCC2)cc1 96921921 JNOPYSQEVVJPMR-UHFFFAOYSA-N 348.428 2.108 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@@H]1O)[C@H](C(=O)O)[C@H]1[C@@]2(C)CCC[C@@]31OC2=O 257480368 MBNDVMTZEKAWKP-YELGJAPSSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C[C@H](O)[C@@]1(c2ccc(C#N)cc2)NC[C@H]2CC(=O)N(C)c3cccc1c32 963017390 CMVJTQXTIAWOOQ-KUUHDYPXSA-N 347.418 2.236 30 1 EEEF O=C(CCCCCONC(=O)Nc1ccc2ncccc2c1)NO 1772602487 IMMRWUUOUHVTLU-UHFFFAOYSA-N 332.360 2.354 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@H]2[C@]12OC(=O)[C@](C)(CC[C@@H]1O)[C@@H]2[C@H]3C(=O)O 100823413 JKQCGVABHHQYKQ-JJCNOTPNSA-N 332.396 2.136 30 1 EEEF endogenous,in-man CN(Cc1nc2cccc(F)c2[nH]1)S(=O)(=O)c1ccc(C#N)cc1 586929734 ZPQOSOUURICVDC-UHFFFAOYSA-N 344.371 2.394 30 1 EEEF COc1cc(O)c2c(c1)CC(=O)/C=C\C=C/[C@H]1O[C@@H]1C[C@@H](C)OC2=O 169293679 BXYHHINRBKIWCZ-HLOVCJOASA-N 344.363 2.341 30 1 EEEF C[C@@H](O)CNC1=CC(=O)C(SC/C=C/c2ccc(F)cc2)=CC1=O 1857644659 WLWPMOHLSSYRSE-QAVQXKDTSA-N 347.411 2.462 30 1 EEEF C=C(C#CC1=C[C@H](O)[C@H](O)[C@@H](O)[C@H]1O)CCC=C(C)CCC=C(C)C 2356334233 CADYTUXNRNXAES-TUFLPTIASA-N 346.467 2.403 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@H]1[C@@H]2O)C(=C)[C@@H](C(C)(C)CCCO)C[C@H]3O 2356737578 FBXNWXLXYGRNOE-UUAZSLMCSA-N 334.456 2.235 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 85800269 IPHNMKITOREFLW-GEXQUTOHSA-N 332.396 2.136 30 1 EEEF in-man CC(=O)O[C@@H]1O[C@@H](OC(C)=O)[C@H]2CC[C@@H]3C(C)(C)[C@@H]4C[C@]23C1=CC4=O 238773061 YUEBDHFRUOFFJT-CEYVNIKCSA-N 348.395 2.363 30 1 EEEF CC(C)C1=C[C@H]2[C@H]3[C@@H](C(C(C)C)=CC(=O)[C@]3(C)O)[C@@H]1C(=O)[C@]2(C)O 95910616 YNYHPBIGKWCFOA-FUALLXEGSA-N 332.440 2.297 30 1 EEEF biogenic,in-vitro CC(=O)OC[C@@H]1O[C@@H](C#CCCc2ccccc2)C=C[C@@H]1OC(C)=O 7991926 PEMFRHXMDHFDFC-UFYCRDLUSA-N 342.391 2.441 30 1 EEEF O=C1c2ncc3c(ccn3Cc3ncc(F)cc3F)c2CCN1O 71296584 ZKBGNAQOFJQDBQ-UHFFFAOYSA-N 330.294 2.145 30 1 EEEF CNc1nc(OC)c(C(=O)O)cc1C#Cc1cc(Cl)ccc1OC 587903440 RGANTPQYOXJMGJ-UHFFFAOYSA-N 346.770 2.892 30 1 EEEF C=C1CN([C@@H](C(=O)OC)C(C)C)S(=O)(=O)c2ccc(F)cc21 13830627 RSCWHTXMDKHWJQ-CQSZACIVSA-N 327.377 2.041 30 1 EEEF Nc1nc(C#C[C@H](O)c2ccccc2)cn2nc(-c3ccco3)nc12 28336044 XXJQIXOJIYQSOW-AWEZNQCLSA-N 331.335 2.052 30 1 EEEF C=CCc1cc(-c2c(O)ccc(C[C@@H](O)CO)c2OC)ccc1O 2356562414 WPDLBOXRXKKCRE-OAHLLOKOSA-N 330.380 2.398 30 1 EEEF CN1CCN(c2cnc3c(c2)[C@@H](O)c2cccc(C#N)c2C=C3)CC1 45320728 QXASWNILIRQNPV-FQEVSTJZSA-N 332.407 2.271 30 1 EEEF C#CCOC(=O)c1ccc(O)c(NC(=O)COc2ccccc2)c1 299826233 FQUJUCMFSVMNTO-UHFFFAOYSA-N 325.320 2.200 30 1 EEEF C#CCN1CCC[C@H](CNS(=O)(=O)c2ccc3ccccc3c2)C1 1772640106 UWQSVNKQBCCLCY-MRXNPFEDSA-N 342.464 2.463 30 1 EEEF Cn1ccc(C(=O)N[C@@]23CCC[C@@](C#Cc4cnccn4)(CC2)C3)n1 205038290 VNZGTPXGIPDLPN-MOPGFXCFSA-N 335.411 2.085 30 1 EEEF CCC#C[C@@](O)(C(=O)OC1C[C@@H]2CC[C@@H](C1)N2C)c1ccccc1 101161042 CPSOCUUSNHHZOV-ZWOKBUDYSA-N 327.424 2.456 30 1 EEEF CC[C@H](C)N1CC(=O)/C(=C(/O)c2cc(OC)c(OC)cc2OC)C1=O 103272113 LTFSRMGIRPJUCJ-PXSDHIKXSA-N 349.383 2.191 30 1 EEEF CC(C)O[C@@H]1Oc2ccc(O)c3c2[C@@]1(C)[C@H]1C(=O)C=C(CO)C1=C3 2356722739 ORBWSHDOOZYCPR-BHIYHBOVSA-N 328.364 2.308 30 1 EEEF C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1cc(=O)[nH]c2ccc(OC)cc12 238765815 FRZGROVVMXMITN-OCCRYCDCSA-N 340.423 2.467 30 1 EEEF N#Cc1nc2nc([C@H](CN)Cc3ccc(Cl)cc3)[nH]c2nc1C#N 587069278 HMXMPBDYVSJMIZ-JTQLQIEISA-N 337.774 2.035 30 1 EEEF CCCOc1ccc(C(=O)N[C@@H](CC(C)C)C(=O)NCC#N)cc1 82065226 ZVZJBOKRXXMOMU-INIZCTEOSA-N 331.416 2.260 30 1 EEEF C/C(=N\Nc1ccc([N+](=O)[O-])cc1[N+](=O)[O-])c1c(C(=O)O)noc1C 45336926 QFCXOQVIKAPQMZ-MKMNVTDBSA-N 349.259 2.334 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc(S(N)(=O)=O)ccc1C#N 587918532 VVNASCNPNGFYAE-UHFFFAOYSA-N 346.795 2.267 30 1 EEEF C=C1C[C@@H](O)[C@@H]2O[C@]2(C)CC[C@@H]2/C(=C\C=C\C(C)(C)O)COC(=O)[C@@H]12 165583596 CHWOLNBRUULGCY-ABBOCTBQSA-N 348.439 2.288 30 1 EEEF COc1ccccc1N/N=C1\CC[C@H](C)n2c1ncc(C(=O)O)c2=O 40466641 VOSMIVRLZSSJJP-JGASNLTESA-N 342.355 2.121 30 1 EEEF CC(=O)N[C@@H](C)Cc1ccc(C#Cc2cnc(NCCF)nc2)cc1 142363879 APMTZRZHULWTDV-AWEZNQCLSA-N 340.402 2.325 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3ccc([C@@H](N)N=O)cc3[nH]2)C1=O 587038486 JKUMDYFJBJYQDQ-AAEUAGOBSA-N 345.384 2.079 30 1 EEEF CCCCSc1nnc2n(/N=C/c3ccc(O)c(OC)c3)cnn12 3092644 AERHDVFJNPRXNL-CXUHLZMHSA-N 346.416 2.414 30 1 EEEF CC(C)C[C@@H](NC(=O)[C@@H](CS)Cc1ccccc1)S(=O)(=O)O 13449690 IFOJNPIPERNZBH-KGLIPLIRSA-N 345.486 2.151 30 1 EEEF O=C1/C(=N\O)c2ccccc2N1Cc1cc(F)cc2c1OCOC2 43024859 DLOJGGLBTWYPMI-CYVLTUHYSA-N 328.299 2.417 30 1 EEEF CN1C(=O)[C@@H](CN2CCCCC2)C[C@H]1C#Cc1ccc2c(c1)CCO2 40845864 BSAYMXGAHRLDCA-RTBURBONSA-N 338.451 2.306 30 1 EEEF C=CCNC(=O)c1cc(S(=O)(=O)N2CCC[C@H](C)C2)ccc1F 3020440 HSDQTTDKCDZKIL-LBPRGKRZSA-N 340.420 2.162 30 1 EEEF CCOC(=O)c1c2n(c(=N)c3c(F)c(C#N)c(F)c(F)c13)CCN2 102826911 BMKCZVPGJXZQJN-UHFFFAOYSA-N 336.273 2.012 30 1 EEEF NCCCNCCCNCCC/N=C1/CCCc2ccccc2N1 64447457 LNYAJVAJCCBZND-UHFFFAOYSA-N 331.508 2.142 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1CCC(COC(C)=O)=C1C[C@H](OC(C)=O)C(=C)[C@@H]12 2356674993 BRBKGYDAQMCZSA-LAVFITLUSA-N 346.379 2.246 30 1 EEEF C=CCn1cc(C(=O)NC2CCCCC2)c(=O)c2c(C)nn(C)c21 95594048 XDQKZKVOUNRTNF-UHFFFAOYSA-N 328.416 2.292 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cccc(C(=O)OC)c3[nH]2)C1=O 587039457 RWYIFQLPOLNNSW-NSHDSACASA-N 345.380 2.142 30 1 EEEF Cc1nn(C)c(C)c1-c1[nH]c2ccc(S(C)(=O)=O)cc2c1C#N 587650799 TUQFOSAPFRDDBT-UHFFFAOYSA-N 328.397 2.460 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cncc(N2CCOCC2)n1 587910714 PDHVHPQKIKEKJA-UHFFFAOYSA-N 329.787 2.375 30 1 EEEF COC1=C[C@@]23CCc4ccc(O)c(OC)c4[C@]2(CCN3C)CC1=O 2356394473 AQJBMLRXZGTSTA-OALUTQOASA-N 329.396 2.162 30 1 EEEF CN(C)c1cc(F)cc(C#Cc2cncc(OC[C@@H]3CCN3)c2)c1 103281519 RAILHHVYJQPGHG-KRWDZBQOSA-N 325.387 2.427 30 1 EEEF C=C1C[C@@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)OC 2356549654 CSOGGDRRRLWUTQ-CIEHUNCWSA-N 344.407 2.145 30 1 EEEF CC(C)NC(=O)N1[C@@H](C#N)[C@H](c2ccc(C#CC3CC3)cc2)[C@@H]1CO 95897423 FGRJVUDIIQYRHF-FHWLQOOXSA-N 337.423 2.218 30 1 EEEF COc1cc2c3c(c1OC)[C@@]1(C=CC(=O)C[C@H]1OC)C[C@H]3NCC2 238784051 YUAGGKXKMLLGQC-MUKKUYKPSA-N 329.396 2.076 30 1 EEEF C=C(CN(C)C)c1nc2ccc(S(=O)(=O)NCCCC)cc2[nH]1 587190648 LYHDJVMWEVGNKU-UHFFFAOYSA-N 336.461 2.216 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@H]([C@H](C=O)[N+](=O)[O-])N1 587747106 PCGJRFLRAQYEJS-ZIGWGHGNSA-N 331.141 2.008 30 1 EEEF N#Cc1ncncc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587880563 RHZPOUXJZQPYRT-UHFFFAOYSA-N 345.189 2.365 30 1 EEEF O=C(O)[C@@H]1Cc2cccc(F)c2[C@H](c2cccc(OC[C@H]3CO3)c2)N1 962903174 VSHFMNJQRIDHIY-ZVZYQTTQSA-N 343.354 2.292 30 1 EEEF CN(C)c1ccc(/N=N/c2ccc(S(=O)(=O)N=C(N)N)cc2)cc1 13808058 YZEIJACSIWBHRG-VHEBQXMUSA-N 346.416 2.130 30 1 EEEF C=C(C(=O)OC)[C@@H]1CC[C@H](C)[C@H]2C(=C(C)C(=O)[C@H]2NC(=O)CC#N)C1 1857587985 NQNCANDIMITCMY-ZPNMRXEQSA-N 344.411 2.066 30 1 EEEF O=C(CN(Cc1ccc(F)cc1)Cc1cccc(C(=O)O)c1)NO 1857762164 WHBVPGFJEUKXSS-UHFFFAOYSA-N 332.331 2.032 30 1 EEEF COC(=O)c1ccc(C(=O)C#Cc2ccc(S(C)(=O)=O)cc2)cc1 13683372 LSHKKTLXXOBXIY-UHFFFAOYSA-N 342.372 2.111 30 1 EEEF Cc1cc(=O)[nH]c(N/N=C/c2ccc(OC(=O)c3ccco3)cc2)n1 8685594 DXOVHEFATUMIFI-VCHYOVAHSA-N 338.323 2.337 30 3 EEEF CCOC(=O)c1ccccc1Oc1nc[nH]c(=O)c1/C=C/C(C)=O 72178004 SKIYONJRQKGOFW-CMDGGOBGSA-N 328.324 2.341 30 1 EEEF O=C(O)c1ccc(S(=O)(=O)NN=Cc2c[nH]c3ccccc23)cc1 254095563 BMKQAVSHJVGEBQ-UHFFFAOYSA-N 343.364 2.179 30 1 EEEF C[C@H]1C[C@@H]2O[C@H]2CC/C=C\C(=O)Cc2cc(O)cc(O)c2C(=O)O1 226001256 XFALPAMSDFFXGY-OLTQPBGBSA-N 332.352 2.262 30 1 EEEF C=C1[C@@H]2CC[C@@H]3[C@](C2)(C(=O)O[C@H]2O[C@@H](O)[C@H]4C(C)(C)CCC[C@]432)[C@@H]1O 238762644 CXNYLUJFZZXBEK-TZKJZBJJSA-N 348.439 2.364 30 1 EEEF N#Cc1ccccc1[C@@H](O)C1=C2C=C[C@@H]3C[C@@]2(OC1=O)[C@H]1CCCCN31 1772602991 IHXMEANXHYXNKY-QTRJSKNGSA-N 348.402 2.380 30 1 EEEF N#Cc1cn(-c2ccc(C(=O)O)c(O)c2)c2cc(OCCO)ccc12 202394051 KVHZZCLQUFOLDB-UHFFFAOYSA-N 338.319 2.277 30 1 EEEF O=S(=O)(/N=C(/c1ccccc1F)N1CCOCC1)c1ccccc1 103961769 JWMIXMCHFBTRPB-ZPHPHTNESA-N 348.399 2.293 30 1 EEEF C=C1C2=C(O)[C@@H](O)[C@@H](C)C=C2C(=O)c2cc(OC)c(O)c(OC)c21 2356329922 NCHXGWSVVROJJA-WJWGPLDTSA-N 330.336 2.368 30 1 EEEF C=C1C[C@@]23C[C@]1(O)CC[C@H]2[C@@]12C=CC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100784056 UXLXLQYIDWLPKX-JIJCMNDFSA-N 330.380 2.056 30 1 EEEF endogenous,in-man N=C(N/N=C\c1ccc(-c2cn3ccccc3n2)cc1)N1CCOCC1 40496331 HMHGNZBLLFIVRD-BKUYFWCQSA-N 348.410 2.192 30 1 EEEF C#CCN1C(=O)[C@@]2(Oc3cc(OC)cc4c3C(=O)[C@H]2C4)c2ccccc21 587436632 SNXCODTWZHXKHU-QVKFZJNVSA-N 345.354 2.318 30 1 EEEF O=C(CCCCCCC(=O)N[C@H]1CCN(Cc2ccccc2)C1)NO 1772616156 XXKNJZXNYLJBDM-KRWDZBQOSA-N 347.459 2.223 30 1 EEEF COc1ccc(/N=C/C2=C3NC=C(C(=O)O)C(=O)N3[C@@H](C)CC2)cc1 102199460 MYYOXKVMGJMRFT-LOMXTUQMSA-N 341.367 2.192 30 1 EEEF C=C1CC[C@H]2CCC3=C(C(=O)[C@@H](C(C)=C[C@H](O)[C@@H]1O)[C@@H]3O)C2(C)C 2356571489 SMYOLHGQHZBFAQ-LZDZAVHKSA-N 332.440 2.297 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@@H]3C[C@H](OC[C@H](C)CC)[C@H]12 2356673967 WULWDKXUHKIGSZ-GLKSWKLWSA-N 336.428 2.384 30 1 EEEF COc1ccc(NC(=O)[C@H](CC2CCCCC2)C(=O)NCC#N)cn1 34054169 UGTHOVYFRUNGHC-OAHLLOKOSA-N 344.415 2.255 30 1 EEEF N#Cc1c(N)cc2c(c1N)Cc1cc(O)c([C@@H]3COCCO3)cc1O2 473244421 KJRGWHCEUMSERY-KRWDZBQOSA-N 339.351 2.213 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H](O)/C(C)=C/CC/C(C)=C\CC[C@@]3(CO)O[C@@H]3C[C@H]12 141611376 MULWDJOXRRXULO-GIHWZMRWSA-N 348.439 2.432 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cn2cc(C(=O)O)nc2cn1 587912603 LMAXJNLDMZQPFY-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF CC#CC#C/C=C1/O[C@]2(CC[C@H](OC(=O)CC(C)C)CO2)[C@@H]2O[C@H]12 1658904 IZOBIZVXEKNCNN-ZNQIEUMMSA-N 330.380 2.159 30 1 EEEF CN(c1ncnc2[nH]ccc12)[C@H]1CN(C(=S)CC#N)CC12CC2 1857656279 HPAFFYYHJGRTJG-LBPRGKRZSA-N 326.429 2.100 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@H]2[C@]12OC(=O)[C@@](C)(CC[C@H]1O)[C@@H]2[C@H]3C(=O)O 100823410 JKQCGVABHHQYKQ-MMBCHBGRSA-N 332.396 2.136 30 1 EEEF endogenous,in-man Nc1nc(C#C[C@@H](O)c2ccccc2)cn2nc(-c3ccco3)nc12 28336038 XXJQIXOJIYQSOW-CQSZACIVSA-N 331.335 2.052 30 1 EEEF C/C(O)=N\c1cnc(-c2cccc(C(=O)N3CCOCC3)c2)cn1 61926981 HKELTVMNTVDWNI-UHFFFAOYSA-N 326.356 2.224 30 3 EEEF C=C1[C@H]2CC[C@@H]3[C@@](C2)(C(=O)O[C@@H]2O[C@H](O)[C@@H]4C(C)(C)CC=C[C@@]234)[C@H]1O 2356678693 PMIAIQKUXKRZIR-UJDOOQKOSA-N 346.423 2.140 30 1 EEEF C=CCN(C)C[C@@H]1CN2CC[C@H]1C[C@H]2CNC(=O)c1cccs1 2356813809 BURJLYWVSNLLMI-XHSDSOJGSA-N 333.501 2.306 30 1 EEEF C=C[C@]1(C)C[C@H](O)[C@]2(C)[C@@H](C1)C(=O)C[C@@]1(O)[C@H]2[C@@H](O)CCC1(C)C 95919197 NEFSWJVXCIDEAS-KDRYUTBCSA-N 336.472 2.457 30 1 EEEF biogenic,in-vitro COc1cc(C2(c3nc4nc(C#N)c(C#N)nc4[nH]3)CC2)ccc1C 587928174 ZLVNSQFDVVUTED-UHFFFAOYSA-N 330.351 2.493 30 1 EEEF NC(=O)c1ccc(NC2=C(Cl)C(=O)c3ccncc3C2=O)cc1 28641686 DJYLBNSTXXFAOA-UHFFFAOYSA-N 327.727 2.122 30 1 EEEF C[C@@H]1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@@]12CO[C@@H](CC1=O)C(C)(C)C2=C(O)C3=O 2356509593 UZPIZMWEFRPQNY-WRQQBYJWSA-N 344.407 2.387 30 1 EEEF C=C(C)[C@@H]1CC[C@]2(CO)OC(=O)C3=C(CC(C)=O)C(=O)C(C)=C[C@@H]1[C@@H]32 238786072 MMENEXZIHVFHNM-FGTCXIJOSA-N 344.407 2.298 30 1 EEEF C=C1C(=O)O[C@H]2/C=C(\C)C3=CC(=O)[C@](C)(C[C@@H](OC(=O)C(C)C)[C@@H]12)O3 238789151 WQQJRSDFQHYDRU-VQDUKUHFSA-N 346.379 2.244 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@@]2(CCNC[C@@H]2C#N)N1 587792179 GZQSQLGJENUGLF-VPJDZLOFSA-N 338.224 2.451 30 1 EEEF COc1ccc(/C=N\n2c(S)nnc2-c2cc(C)n[nH]2)cc1OC 15987768 DEWWGIUNKWRKEG-PXNMLYILSA-N 344.400 2.165 30 1 EEEF COc1ccc(CCNC2=CC(=O)c3cccnc3C2=O)cc1OC 103234347 CDXRFBSQCYLAAH-UHFFFAOYSA-N 338.363 2.194 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C[C@@H]3C(C)(C)CC[C@H](O)[C@@]3(CO)[C@]2(O)CC1 2356722672 MYLWJAXIZRHGOI-JVJLKXRTSA-N 334.456 2.379 30 1 EEEF C=C[C@]1(C)CCC2=C([C@H](O)C(=O)[C@@H]3C(C)(C)CC[C@H](O)[C@@]23C)[C@@H]1O 2356734936 KKWFUTJLCATXQH-ZOONWIMQSA-N 334.456 2.377 30 1 EEEF C=C[C@H]1CN2CC[C@H]1C[C@@H]2CNC(=O)CC1(CC(=O)O)CCCC1 8300565 ZGYUSGIGQDEQMQ-HRCADAONSA-N 334.460 2.424 30 1 EEEF biogenic C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]12CC[C@@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 71757706 RSQSQJNRHICNNH-MHKXYFPYSA-N 332.396 2.136 30 1 EEEF COC(=O)[C@]1(C#N)[C@H](C)C(=O)N(C(C)C)[C@@H]1c1ccc(OC)cc1 206021195 TXCKQOLNVKVBRC-CDHAZOANSA-N 330.384 2.306 30 3 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H](O)C(=C)C[C@H](OCC(C)C)[C@H]12 2356440614 JDMDKFIKZIBCPI-SFFUCWETSA-N 336.428 2.144 30 1 EEEF C[C@@H](CS)C(=O)N1C[C@H](Oc2ccc(Cl)cc2)C[C@H]1C(=O)O 27999335 XGGGHQKFFFAETI-BIMULSAOSA-N 343.832 2.339 30 1 EEEF C=CCN1CC[C@]23CC(=O)CC[C@@]2(O)[C@H]1Cc1cccc(OC)c13 64436463 FHSGIWCXRGXYGB-MISYRCLQSA-N 327.424 2.234 30 1 EEEF CCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O 85426329 CMQAWGIRCVKCMC-GFCCVEGCSA-N 326.326 2.141 30 1 EEEF in-vitro COc1ccc(/C(=N/C(=S)NCCO)Nc2ccccc2)cc1 84635528 WQDBVUMTWGLYQS-UHFFFAOYSA-N 329.425 2.421 30 1 EEEF C=CCSc1nnc(CCC)n1N1C(=O)c2ccccc2C1=O 84704306 VNOUDDARQMAXQD-UHFFFAOYSA-N 328.397 2.441 30 1 EEEF CCCCCCCCNC(=O)n1cc(C(F)(F)F)c(=O)[nH]c1=O 95586118 WHQYZSQAVZUYNA-UHFFFAOYSA-N 335.326 2.474 30 1 EEEF C=CC[C@]12CC(=O)[C@@H](O)[C@H]([C@H](c3ccc4c(c3)OCO4)[C@H]1C)[C@H]2O 685935797 FBPLISOOTGTZGY-OPKPJAOZSA-N 330.380 2.022 30 1 EEEF biogenic,in-vitro N#Cc1ccc(COc2ccc(-n3cc(C(=O)O)nn3)cc2C#N)cc1 1772627366 KHUHBVGFWSVVEG-UHFFFAOYSA-N 345.318 2.288 30 1 EEEF C=CCNC(=N)N/N=C/c1ccc(-c2cn3ccccc3[n+]2C)cc1 26826151 RKDHRMHVXRMTBM-LPYMAVHISA-N 333.419 2.065 30 1 EEEF C=C1[C@@H]2CC[C@@]3(C)C[C@@]2(CC3=O)C[C@H](O)[C@]2(O)[C@@H]1C[C@@H](O)C2(C)C 2356593377 IRZVFDISJFITJT-YGAKERMQSA-N 334.456 2.211 30 1 EEEF COc1ccc(CSC[C@H](NC(=O)[C@H](C)CS)C(=O)O)cc1 40864274 IDGYKBNUWJVOHV-MFKMUULPSA-N 343.470 2.064 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@@H]2[C@@H]3C[C@@H](C(C)C)[C@@H](C=C3C)[C@H]2C1=O 195180968 PBDZFTMSQJXALQ-NJVJYBDUSA-N 347.484 2.021 30 1 EEEF C#Cc1cccc2c1[C@]1(Oc3cc(OC)cc4c3C(=O)[C@H]1C4)C(=O)N2 587442837 YVUBPNZZQZOSMN-XCLFUZPHSA-N 331.327 2.272 30 1 EEEF C=CCn1c(=O)c2[nH]c(Cc3ccccc3)nc2n(CCCC)c1=O 13553789 TVFWUWYFKDMSAG-UHFFFAOYSA-N 338.411 2.463 30 1 EEEF N#Cc1ccc(Oc2ccc3nc(C(=O)NCC(N)=O)ccc3c2)cc1 584629815 PCRRCENYZZROOI-UHFFFAOYSA-N 346.346 2.114 30 1 EEEF C=C[C@]1(C)C=C2[C@H](O)[C@H](O)[C@@H]3C(C)(C)C(=O)C=C[C@@]3(C)[C@@]2(O)CC1 2356325941 RNZJQFGWISERJP-LOBZHTCKSA-N 332.440 2.153 30 1 EEEF COc1cc(/C=N/N=c2\[nH]ccs2)cc(Br)c1O 75264889 HZZZMYNJCUUSPE-MKMNVTDBSA-N 328.191 2.488 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1[C@H](OC(=O)/C(C)=C/C)[C@H](O)C(=C)[C@@H]1CC=C(C)[C@@H]12 238745245 MXNYEYDKNYIYGB-VXWYHLEQSA-N 344.407 2.475 30 1 EEEF Cc1ccccc1S(=O)(=O)N1[C@H](C#N)[C@@H](c2ccccc2)[C@H]1CO 95897625 UKJFDLKEHROOFG-JFIYKMOQSA-N 342.420 2.036 30 1 EEEF C/N=C1/N/C(=C\c2c[nH]c3cc(Br)ccc23)C(=O)N1C 13371045 WIJJEZADZQGDSE-XGICHPGQSA-N 333.189 2.319 30 1 EEEF CC(C)C1=CC2=C(C(=O)C1=O)[C@@]13CCCC(C)(C)[C@@H]1[C@@H](OC3=O)C2=O 1857602638 WXHCWOOFKNPNJE-ZWOKBUDYSA-N 342.391 2.338 30 1 EEEF C=C1[C@@H]2CC[C@H]3[C@]45CO[C@H](CC4=O)C(C)(C)C5=C(O)C(=O)[C@]3(C2)[C@@H]1O 84733750 LRBFGRIVMPSVAV-JYDRGEROSA-N 344.407 2.099 30 1 EEEF O=C(/C=C/c1ccc(CN(CCO)Cc2ccccc2)cc1)NO 45245589 YWUMRABPVTUCGP-ZHACJKMWSA-N 326.396 2.200 30 1 EEEF C=CCCC(=O)N1C[C@@H]([C@@H](C)OC(=O)NCCc2ccccc2)C1=O 95593579 QXHATDIZTLQPCL-ZBFHGGJFSA-N 344.411 2.295 30 1 EEEF CCC(=O)NC[C@H]1N[C@H](CO)[C@@H]1c1ccc(-c2cccc(C#N)c2)cc1 95895241 IZVWTPQWCZYKCV-SFHLNBCPSA-N 349.434 2.168 30 1 EEEF Cc1cccc(/C=N/NC(=N)N/N=C/c2cccc(C)c2O)c1O 653731225 ODGLHYKYAFZBLX-LQGKIZFRSA-N 325.372 2.197 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc([N+](=O)[O-])c2nnnn2c1 587912068 AEVIDHHJSRIIBL-UHFFFAOYSA-N 329.703 2.094 30 1 EEEF CCN1C(=O)N(CC)[C@H]2[C@@H]1NC(=O)N2/N=C/C=C/c1ccccc1 1857754173 NRUADQHKBGCFCV-SZTJSXAJSA-N 327.388 2.140 30 1 EEEF C#C[C@@H]1CN2CC[C@H]1C[C@H]2CNC(=S)Nc1ccc(OC)cc1 2356298662 RSEHFCTVVFUHHR-YCPHGPKFSA-N 329.469 2.325 30 1 EEEF CC[S@](=O)C[C@@](C)(O)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1 28015244 XXMKUOWGHUBGCA-JCQPUDPBSA-N 348.346 2.035 30 1 EEEF CC(=O)N1CC[C@H]2[C@@H](CO)Nc3ccc(C#Cc4cccnc4)cc3[C@H]21 95878790 ZFWVHLMUMICASE-WMQCIHAUSA-N 347.418 2.177 30 1 EEEF O=C1C=CC=C/C1=C1/C[C@@H](C(=O)Nc2cc(Cl)ccc2O)ON1 104000994 NGLFOEZGIXQTMD-NKSUMMKUSA-N 332.743 2.227 30 3 EEEF CC=CC1=CC(=O)C([C@H]2OC(=O)c3cc(OC)cc(OC)c32)=CC1=O 2356725649 JDJRBGGOYNOXOV-GOSISDBHSA-N 340.331 2.496 30 1 EEEF CCCCCCCCCCCC(=O)NCCC[N+](N)(N)CC(=O)O 87528576 AWLNSWJVBZROPZ-UHFFFAOYSA-O 345.508 2.062 30 1 EEEF in-vitro N#C[C@H]1[C@H](c2ccc(-c3cccnc3)cc2)[C@H](CO)N1C(=O)C1CC1 95896224 FYALJDMLJJPLTL-FHWLQOOXSA-N 333.391 2.337 30 1 EEEF Cc1ccccc1S(=O)(=O)N1[C@@H](C#N)[C@@H](c2ccccc2)[C@@H]1CO 95897619 UKJFDLKEHROOFG-XYJFISCASA-N 342.420 2.036 30 1 EEEF CO[C@H](C)[C@]1(CC#N)N[C@@H](C(=O)C(F)(F)F)Cc2ccccc21 962728257 DHTCGHMJWKFPMC-YVLXSGLVSA-N 326.318 2.476 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(C)=O)C[C@]1(C)[C@H](OC(C)=O)CCC(=C)[C@@H]21 2356431878 IDVKLEJKBPWDKI-FTGINLBMSA-N 348.395 2.324 30 1 EEEF Cc1c[nH]c2c1[C@]13C[C@H]1CN(S(=O)(=O)c1ccccc1)C3=CC2=O 27703818 VRRYPFUNOZUDIK-KPZWWZAWSA-N 340.404 2.366 30 1 EEEF CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1O[C@H](C)C#N 29341102 BTPGDRXWEDAPAP-LLVKDONJSA-N 338.839 2.285 30 1 EEEF C=C1C[C@]23C[C@H]1[C@H](O)C[C@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 238742251 ZCRLGANQNRMURE-GZUHGUOESA-N 346.423 2.384 30 1 EEEF Cc1ccccc1S(=O)(=O)N1[C@H](CO)[C@H](c2ccccc2)[C@@H]1C#N 95897626 UKJFDLKEHROOFG-LZLYRXPVSA-N 342.420 2.036 30 1 EEEF N#Cc1cccc(CN2CC[C@H]3CO[C@@H](CN4CCCC4)[C@@H]3C2)c1 299842876 JQPKVYRPIBQALQ-ZCNNSNEGSA-N 325.456 2.491 30 1 EEEF CCn1c2c(c(O)nc1=O)[C@@H](c1ccc(C)cc1)C1=C(CCC1=O)N2 1772643185 GFYQCHZFSLHBOA-AWEZNQCLSA-N 337.379 2.452 30 1 EEEF O=C1C=C2CC[C@@H]3[C@H]([C@H]4C[C@]5(CO4)[C@H]3CC[C@H]5C(=O)CO)[C@H]2CC1 2356416619 ZQTXDFVYZQQLOY-UMTOMPLCSA-N 330.424 2.295 30 1 EEEF C=C1C[C@@]23C[C@H]1C(=O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 2356735008 PHYYFNCWOIYWTJ-MVUGAQQQSA-N 330.380 2.344 30 1 EEEF C#CCN1C(=O)[C@@]2(CC(=O)c3cc(C)cc(N)c3O2)c2ccccc21 587401628 URMCMTZQJLXXDG-HXUWFJFHSA-N 332.359 2.418 30 1 EEEF N#C[C@H](C(=O)Nc1ccc(C(F)(F)F)cc1)C(=O)[C@@H]1CCCN1 169714921 AVJJSTSKKNYXAA-RYUDHWBXSA-N 325.290 2.105 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)OC 2356675178 JTSAEZNOAXDDOQ-VMOJUYBOSA-N 346.423 2.225 30 1 EEEF COc1ccc(NS(=O)(=O)c2cccc(/C=C/C(=O)NO)c2)cc1 34021543 WFTGONGCXPFUHR-BJMVGYQFSA-N 348.380 2.015 30 1 EEEF COc1ccc(/C=C\C(=O)c2c(O)cc(O)c(OC)c2O)cc1O 85540915 GYEZIQDCZWTBTP-HYXAFXHYSA-N 332.308 2.422 30 1 EEEF biogenic,in-vitro C=C1C[C@H]2O[C@H]2[C@@](C)(O)CC[C@@H]2/C(=C\C=C\C(C)(C)O)C(=O)OC[C@@H]12 197456058 GUGYUSGXSKYCJD-VIJRLTMVSA-N 348.439 2.288 30 1 EEEF CC1([C@H]2CC(=O)N(CCOc3ccc(F)c(C#N)c3)C2)CCNCC1 1772574430 JNLBXUGTFLPZTB-HNNXBMFYSA-N 345.418 2.314 30 1 EEEF C=C(C)C(=O)O[C@@H]1C=C(C)C2=CC(=O)[C@@](C)(C[C@@H]3OC(=O)C(=C)[C@@H]31)O2 2356686321 AERIPQYYSNTIDA-QHHYFVSCSA-N 344.363 2.164 30 1 EEEF C=C(C)[C@H]1Oc2cc(O)c(C(C)=O)cc2[C@@H]1OC(=O)C(=CC)CO 2356690565 CLWSKSKCEVBFSD-SJORKVTESA-N 332.352 2.455 30 1 EEEF CN1CCC[C@]2(CC1)CC(=O)c1cc(/C=C/C(=O)NO)ccc1O2 116483464 KIBFFVJPGCMKOZ-JXTAAOLFSA-N 330.384 2.025 30 1 EEEF C=C1[C@@H]2CC[C@@H]3[C@](C2)(C(=O)O[C@H]2CC[C@@]4(C)CO[C@H]5OC[C@]23[C@H]54)[C@@H]1O 70450911 QALWKTNRDDDECH-FUNDCJPPSA-N 346.423 2.034 30 1 EEEF biogenic,in-vitro COc1ccc(C2=NO[C@@H](CC(=O)NO)C2)cc1OC1CCCC1 13777045 VSPGQUIYSBELGU-CYBMUJFWSA-N 334.372 2.405 30 1 EEEF CC1(C)C(=O)c2ccc(C#N)cc2[C@@H](NC(=O)c2cccnc2)[C@@H]1O 13832179 CQCYEPGUBMOZLF-WBVHZDCISA-N 335.363 2.008 30 1 EEEF Fc1cc(F)cc(C#CCOc2nsnc2C23CN4C[C@@H]2[C@H]3C4)c1 100829325 RWIBKAGXMHMEFU-ZIAGYGMSSA-N 345.374 2.060 30 1 EEEF CC(C)NC(=N)N/C(N)=N\OCCCOc1ccc2ccccc2c1 27306059 VCCPUPMPIMKFHW-UHFFFAOYSA-N 343.431 2.377 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@@]1(C)[C@H](C[C@@H]3O)[C@@](C)(C(=O)O)CC[C@H]1O 2356410451 LRECIABFFPIQSO-MYOSGADTSA-N 348.439 2.161 30 1 EEEF O/N=C(/c1cccnc1OCc1ccccc1F)N1CCOCC1 72183396 LQKFRLHUFCBNRE-SILNSSARSA-N 331.347 2.268 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@H]([C@@H](C=O)[N+](=O)[O-])N1 587747116 PDDFVXQYGACOIB-JPWUCKPDSA-N 331.141 2.008 30 1 EEEF N#C[C@@H](C(=O)Nc1ccc(C(F)(F)F)cc1)C(=O)[C@H]1CCCN1 169714922 AVJJSTSKKNYXAA-VXGBXAGGSA-N 325.290 2.105 30 1 EEEF O=C1C(=O)C(c2ccc(O)cc2)=C2OCOC2=C1c1ccc(O)cc1 14652659 DELWCYFARBLJMK-UHFFFAOYSA-N 336.299 2.376 30 1 EEEF biogenic O=C1C=CC(Cl)=CC1=NC(=O)C1=C(c2ccccc2)NNS1 263592145 ANROAGRWVVWTPE-UHFFFAOYSA-N 331.784 2.340 30 3 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N2CCC[C@@H](O)C2)nc1 587908291 PKHOMRZPOBXYFS-MRXNPFEDSA-N 343.814 2.500 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3ccc([C@H](N)N=O)cc3[nH]2)C1=O 587038488 JKUMDYFJBJYQDQ-WCQYABFASA-N 345.384 2.079 30 1 EEEF C=C1C(=O)[C@@]23C[C@H](O)[C@@H]4C(C)(C)CCC[C@@]4(C)[C@@H]2[C@@H](O)C[C@@H]1[C@H]3O 169313027 RFZAFMSAZOFRSM-CFVHAWITSA-N 334.456 2.067 30 1 EEEF N=C(NO)c1ccc(-c2ccc(-c3ccc(/C(N)=N/O)cn3)o2)cc1 27527231 PWQXNELAQYAVRT-UHFFFAOYSA-N 337.339 2.407 30 1 EEEF COc1ccccc1N1C(=O)[C@@H]2[C@@H]3C[C@H]([C@H](S)[C@H]3S)[C@@H]2C1=O 104653579 LUMFAWHJRRAZQX-JNRGUFKGSA-N 335.450 2.047 30 1 EEEF C=C1[C@H](O)[C@@H]2O[C@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@]1(C)[C@H](O)C(=O)[C@@]32C 2356479223 ILPXHKMIZLTLAS-CSLWSXCPSA-N 332.440 2.083 30 1 EEEF C[C@@H]1NC(=O)[C@]23C[C@H](O)[C@H]4[C@@H](CCC5=CC(=O)C=C[C@@]54C)[C@@H]2CC[C@@H]13 2356663881 ZFDFFZSCUSDQEX-NUOORUCRSA-N 341.451 2.380 30 1 EEEF C[C@H]1COC(=O)[C@]2(O)C3=C(C(=O)[C@H]12)[C@H](O)C[C@H]1C(C)(C)CCC[C@]31C 137458509 MQVLZPBBUQPAEZ-OFCLWNRWSA-N 348.439 2.003 30 1 EEEF O=C(C#Cc1ccc(/C=N/OCc2ccc([N+](=O)[O-])cc2)cc1)NO 40895811 OSJPFXGKTUJNDX-WOJGMQOQSA-N 339.307 2.002 30 1 EEEF CC(C)Oc1cc(=NC(=O)n2ccc3ccc(C=O)nc32)[nH]cc1C#N 1857656886 YSBCKATZEDDWLC-UHFFFAOYSA-N 349.350 2.405 30 1 EEEF CCc1cc(O)cc(C)c1[C@@H]1CN[C@H](C(=O)N2CCC[C@H]2C#N)C1 28714258 WTKNIKWBYCOFSL-ZOBUZTSGSA-N 327.428 2.223 30 1 EEEF CC(=O)NCc1cccc(-c2csc(NC(=N)NCCC#N)n2)c1 26989891 PZDNEHQFKBCQRT-UHFFFAOYSA-N 342.428 2.296 30 1 EEEF C=C[C@@H]1CN2[C@H]3C[C@]45c6ccccc6N[C@@]4(O3)[C@H]2C[C@H]1[C@@H]5C(=O)OC 2356762801 VQQRVBOFQXPEAN-BDOALPTKSA-N 338.407 2.102 30 1 EEEF C[C@@H]1CC2=C([C@@H]1O)[C@H](O)[C@]1(C)CC[C@@H]3[C@H]([C@H](O)[C@]1(C)C2=O)C3(C)C 2356843630 NNSBPFCEWFSYFB-OGLLIMPRSA-N 334.456 2.067 30 1 EEEF CC(C)(O)C#Cc1cc2c(cc1F)C1CC(C1)n1cc(C(N)=O)nc1-2 219437862 YWEPDHYSJZIHIS-UHFFFAOYSA-N 339.370 2.343 30 1 EEEF C=C1CC[C@@H](O)[C@]2(C)C[C@H](OC(=O)C(C)C)[C@H]3C(=C)C(=O)O[C@@H]3[C@@H]12 13486884 KPKVDWQJGWXVTN-QHJVRGJGSA-N 334.412 2.389 30 1 EEEF N#Cc1cccc(CS(=O)(=O)c2nnnn2C2CCCCC2)c1 13815207 WLZQJOYUWIZUOI-UHFFFAOYSA-N 331.401 2.024 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@@H]2OC[C@]23O[C@@H]2C=C(C)C(=O)C[C@]2(C)[C@]13C 2356397106 GUTBYIDIQSFHLV-BXCFQTICSA-N 332.396 2.346 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(COC(C)=O)CCC=CC[C@H](OC(C)=O)[C@H]12 2356401884 RTCARLYNKKVHJD-BBWFWOEESA-N 334.368 2.246 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@]4(C)CCC[C@]5(C)C(=O)O[C@@H]([C@@H](O)[C@@]3(C2)[C@H]1O)[C@@H]54 2356524091 PWCNMDCZKHGAQG-FRXNJVHESA-N 332.440 2.432 30 1 EEEF C=CC[C@]1(OCc2ccccc2)C(=O)C(=O)O[C@H]1[C@H]1COC(C)(C)O1 5538971 QUSJNYTVFAJGCT-ALKREAHSSA-N 346.379 2.164 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@@]1(CCC[C@@]2(C)C(=O)OC[C@H]21)COC3=O 15166338 BPNWWFAFERHJNL-BGDAJJDDSA-N 344.407 2.434 30 1 EEEF biogenic,in-vitro Cc1ccc(-c2c3c([nH]c(=N)c2C#N)C(C)(C)OS3(=O)=O)cc1 1857611644 KRMHGDKWHYTBRD-UHFFFAOYSA-N 329.381 2.295 30 1 EEEF CCOC(=O)c1nc(O)c(C#N)cc1C(=O)c1ccc(OC)cc1 1911573019 NNGXPMUYTNVKIJ-UHFFFAOYSA-N 326.308 2.075 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2/C=C/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 137040142 XTUZVEOWUSGCSV-NYOBOZBLSA-N 330.336 2.038 30 1 EEEF COc1cccc2c1[C@H](O)[C@@]1(O)CCC3=C(C(=O)C[C@H](C)C3)[C@@H]1[C@H]2O 85593804 GOUAMPBBOSYLQB-MHCXLAJTSA-N 344.407 2.212 30 1 EEEF C=C1C(=O)O[C@H]2C[C@@]3(C)OC(=CC3=O)/C(C)=C\[C@H](OC(=O)C(C)C)[C@H]12 238761044 JHZYGPMGMMUUTG-IWOODGOJSA-N 346.379 2.244 30 1 EEEF N#C[C@@H]1CNCC[C@@]12Oc1ccccc1C(=O)[C@H]2C(=O)c1ccco1 587593377 IXOYQXXDJKBETN-RNRVQEDPSA-N 336.347 2.226 30 1 EEEF CC(C)[C@]1(O)C=C2C(=O)C[C@@H]3[C@](C)(CO)[C@H](O)CC[C@@]3(C)[C@H]2CC1 2356337242 TVHWXCUVXSEILO-FTNYQUAISA-N 336.472 2.459 30 1 EEEF COC(=O)[C@]1(c2cccc(Oc3ccccc3)c2)C[C@H]1C(=O)NO 29134747 CPYMYVGMNPHMIG-YJBOKZPZSA-N 327.336 2.415 30 1 EEEF C=C1C[C@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@H](O)CO)[C@H]2C[C@@H]1CC3 102830921 FYKIZBPSTADBEK-ZOTMLPGNSA-N 348.439 2.171 30 1 EEEF C=C1C[C@@]23C[C@@]1(O)CC[C@@H]2C1=C[C@H]2C[C@@](C)(C(=O)O2)[C@H]1[C@@H]3C(=O)O 2356490061 VLTQADXREMVNJX-YKUMSJBTSA-N 330.380 2.056 30 1 EEEF C=CC[C@]12C[C@H](OC)[C@H](O)[C@H]([C@@H]1O)[C@H](c1ccc3c(c1)OCO3)[C@@H]2C 2356606167 GGFOVZYLYBVWDX-KPGZDJIMSA-N 346.423 2.468 30 1 EEEF COC(=O)c1ccc([C@@H]2C(=C(C)O)C(=O)C[C@](C)(O)[C@@H]2C(C)=O)cc1 2356845337 ODUNWFFBMKIIDY-LMMKCTJWSA-N 346.379 2.318 30 1 EEEF COCCNc1c(CC(C)(C)C)nc2ccc(/C=C/C(=O)NO)cn12 136783762 UGRWKQBWMIKPKM-SOFGYWHQSA-N 346.431 2.500 30 1 EEEF O=C1O[C@@H]2C=CCC=C2C(=O)[C@@H]1Cc1c(O)c2ccccc2oc1=O 169692522 FMTPOCAUOVRPJN-DZGCQCFKSA-N 338.315 2.038 30 1 EEEF NC1=C(c2nc3ccccc3s2)C(=O)CN1C1CCC(O)CC1 3260605 XTBFOXVYXVCSCM-UHFFFAOYSA-N 329.425 2.112 30 3 EEEF C=C[C@]1(C)C=C2[C@@H](O)[C@]3(O)OC(=O)[C@@]4(CCCC(C)(C)[C@H]34)[C@@]2(O)CC1 105556116 XJXDJAQAAAVDCT-PBOOBJRZSA-N 348.439 2.063 30 1 EEEF C=C1C[C@H](OCC(C)C)[C@@H]2C(=C)C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]1O 2356440613 JDMDKFIKZIBCPI-RZFLPCETSA-N 336.428 2.144 30 1 EEEF C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@H]2C(=CC=CC(C)(C)O)COC(=O)[C@@H]12 2356613190 CHWOLNBRUULGCY-DRCYAFTPSA-N 348.439 2.288 30 1 EEEF Cc1ccccc1S(=O)(=O)N1[C@@H](C#N)[C@H](c2ccccc2)[C@@H]1CO 95897621 UKJFDLKEHROOFG-BQFCYCMXSA-N 342.420 2.036 30 1 EEEF CC1=CC(=O)[C@@]2(CN1)N[C@H](C)Cc1cc(Br)c(F)cc12 587791509 GBZAYDNBEDMVFK-PSLIRLAXSA-N 339.208 2.394 30 1 EEEF C=C1[C@H](O)[C@H](OC(=O)C(C)=CC)[C@@H]2C(=C)C(=O)O[C@@H]2[C@@H]2C(C)=CC[C@@H]12 2356536022 MXNYEYDKNYIYGB-PYTCMNEWSA-N 344.407 2.475 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@@]3(C)OC(=CC3=O)C(C)=C[C@@H](OC(=O)C(C)C)[C@H]12 2356539285 JHZYGPMGMMUUTG-GTACMHHNSA-N 346.379 2.244 30 1 EEEF C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1C(=O)/C=C1\CCOC1=O 40421063 ZSJFBGURGMRHII-NLJJMKPZSA-N 348.439 2.171 30 1 EEEF C[C@](Cc1ccccc1)(C(=O)NO)C(=O)NCCc1ccccc1 13528317 AZWBRVJQJIHTAP-LJQANCHMSA-N 326.396 2.100 30 1 EEEF COc1cc[nH]c1/C=C1\C(=O)Nc2ccc(F)c(C#C[C@H](C)O)c21 14947103 DJEJXDSNSASKPZ-JMZICWNOSA-N 326.327 2.387 30 1 EEEF CC1=C[C@]2(O)C(=O)[C@](C)(O)[C@@H]3[C@@H]4[C@@H](CC[C@@]3(C)C=C2C1=O)C4(C)C 2356419499 UZEAKOOBNZOXDE-FRPGKDQYSA-N 330.424 2.195 30 1 EEEF COc1ccc(Cl)cc1NC(=O)C1=C/C(=C2/C=CC=CC2=O)NN1 103917951 PKBJMXHXGSIAIA-VAWYXSNFSA-N 343.770 2.228 30 3 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)c2ccc(C#N)cc2)[C@H]1O 40835661 FZBBUIVMCCYQOP-QZTJIDSGSA-N 347.374 2.433 30 1 EEEF C=C1CC[C@H]2C[C@H](O)C3=C(C(=O)[C@@H](C(C)=C[C@H](O)C1)[C@@H]3O)C2(C)C 2356605253 YZCJZJQRTRSJHJ-DTFBLWLJSA-N 332.440 2.297 30 1 EEEF CC(C)C(=O)OC[C@]1(c2ccc(CO)cc2OC(=O)C(C)C)CO1 2356626983 RILHKBOOMVZSPB-GOSISDBHSA-N 336.384 2.165 30 1 EEEF C=C1[C@H](O)[C@]23CC(=O)[C@H]4C(C)(C)[C@@H](O)CC[C@@]4(C)[C@H]2[C@@H](O)C[C@H]1C3 2356406446 WSZHSVSVZWABOB-CBBNJUKASA-N 334.456 2.067 30 1 EEEF C[C@]12CC[C@@](C)(O1)[C@@H]1C(=O)N(c3cnc(C#N)c(Cl)c3)C(=O)[C@@H]12 100075915 VKOUOBLCMIKWHV-NOXHYTERSA-N 331.759 2.054 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]3C(C)=CCC3=C(C)C[C@H](OC(=O)C(O)=CCO)[C@@H]12 2356493435 SWIFBBRXRXNLBH-YLFCFFPRSA-N 346.379 2.117 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@@]3(O)C=C[C@@](C)(C[C@H](OC(=O)C(C)C)[C@@H]12)O3 2356625026 XJUPOHKZSDZNBE-BHCCHWJASA-N 348.395 2.036 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(NS(N)(=O)=O)cc1 587919851 ZAUMCCNZJGOPPT-UHFFFAOYSA-N 336.800 2.364 30 1 EEEF COc1cc(O)c2c3c(c(O)cc(C)c13)C1=C(C)C(=O)C[C@]1(O)C2=O 1857647798 LLCALCWSGAGWQS-LJQANCHMSA-N 340.331 2.242 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)OC 2356436703 XBDTWBSMNXMGIJ-UFTRZQDCSA-N 346.423 2.225 30 1 EEEF CCO[P@@](=O)(N[C@@H](CC(C)C)C(=O)NO)c1ccc(OC)cc1 84462392 KTCRMROJXXSPQJ-LFVRLGFBSA-N 344.348 2.060 30 1 EEEF COc1ccc(N/N=C2\CC[C@@H](C)n3c2ncc(C(=O)O)c3=O)cc1 40639353 MCLKGGAIIDSSHM-AGYNKUJHSA-N 342.355 2.121 30 1 EEEF C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@H]12 2356435468 DHTWVKTXQLZELP-BOXKXSMZSA-N 348.439 2.288 30 1 EEEF CCNc1nc2cc(Cl)c(C#CCNC(N)=O)cc2nc1NCC 115765020 WCHTXJYTMDNRFS-UHFFFAOYSA-N 346.822 2.167 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@]4(C)CCC[C@]5(C)C(=O)O[C@@H]([C@@H](O)[C@@]3(C2)[C@@H]1O)[C@@H]54 2356524093 PWCNMDCZKHGAQG-KEWQTTDESA-N 332.440 2.432 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(COC(C)=O)CCC=C(C(=O)OC)CC[C@H]12 2356738320 FELNAJVVBXSDQN-HZPDHXFCSA-N 334.368 2.247 30 1 EEEF CC1=C[C@@H]2[C@H](CCC3=C[C@@H](C[C@]4(C)O[C@@H]4[C@H](O)[C@@H]1O)OC3=O)C2(C)C 2356815658 CUCOPNHAVGPVDH-RADYHQQDSA-N 348.439 2.120 30 1 EEEF COc1c(C#N)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2 27410807 WYNGKRRKXMHYLE-YCRREMRBSA-N 331.324 2.296 30 1 EEEF COC1=C[C@@]2(CCC1=O)C[C@H]1c3c(cc(OC)c(O)c32)CCN1C 14618495 MHXSUTPVPBOLJW-HXPMCKFVSA-N 329.396 2.465 30 1 EEEF biogenic COCC(=O)N1[C@H](CO)[C@H](c2ccccc2C2=CCCC2)[C@@H]1C#N 95867997 OERKOXUAKKWALJ-YQVWRLOYSA-N 326.396 2.079 30 1 EEEF Cc1cc2c(cc1O)[C@@]1(Cc3ccccc3[C@H]1C#N)N[C@H](C(=O)O)C2 963553100 RLECXGGYOMJNLF-FUHIMQAGSA-N 334.375 2.358 30 1 EEEF O=C(NO)[C@@H](Cc1ccccc1)C(=O)NCCCc1ccccc1 3919984 CQGGQNFRJIAPHA-KRWDZBQOSA-N 326.396 2.100 30 1 EEEF in-vivo C=C1C[C@@]23C[C@H]1[C@H](O)C=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 2356783748 MEGPPDNKNMAIJN-YHYKXTBLSA-N 330.380 2.056 30 1 EEEF C/C1=C/CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)[C@@H](CNCCCCN)[C@@H]2CC1 40980818 ZMDVEVDXHVWYSY-RVWSHRBGSA-N 336.476 2.151 30 1 EEEF COc1ccc(Cl)cc1C#Cc1nc(S(C)(=O)=O)ccc1N 587917827 ULDYLSHXRAYQIQ-UHFFFAOYSA-N 336.800 2.129 30 1 EEEF N#CCC(=O)N1CCC[C@]12CCN(c1c(Cl)cnc3[nH]ncc13)C2 169699029 UPPRBFBTNAYEJK-MRXNPFEDSA-N 344.806 2.096 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(COC(C)=O)CCC=CC[C@@H](OC(C)=O)[C@H]12 2356401887 RTCARLYNKKVHJD-ZACQAIPSSA-N 334.368 2.246 30 1 EEEF CCc1ccc2nc(NC(=O)c3csc(N=C(N)N)n3)sc2c1 26143536 NTVWLCSCCDTUGO-UHFFFAOYSA-N 346.441 2.472 30 1 EEEF C[C@H]1C(=O)[C@@]23C[C@H]1CC[C@H]2[C@@]12CO[C@@H](CC1=O)C(C)(C)C2=C(O)C3=O 2356509590 UZPIZMWEFRPQNY-BSZXBUEXSA-N 344.407 2.387 30 1 EEEF CO[C@](C)(C(=O)O)C1=C[C@]2(C)C(=CC1=O)CC[C@H](OC(C)=O)[C@H]2C 2356656321 RDRVOBNXHXPXJL-PLDWSREQSA-N 336.384 2.280 30 1 EEEF C[C@@]12CC[C@H](O)[C@@H]3COC(=C31)C(=O)c1cc3c(cc12)[C@H](O)CCC3=O 14723541 QBIVTXOPBMJYTJ-DVNRBFFJSA-N 340.375 2.206 30 1 EEEF CC(C)C[C@H](NC(=O)c1ccc(F)cc1Cl)C(=O)NCC#N 1857637895 MVEFFDSUROUVSQ-ZDUSSCGKSA-N 325.771 2.263 30 1 EEEF C=C1CC[C@@H]2[C@H]([C@@H]3[C@@H]1C1=C(C[C@](C)(O)C1=O)C(=O)[C@]3(C)O)C2(C)C 2356415984 DGXURLBVVBVHIO-VVCJYACQSA-N 330.424 2.195 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)OC 2356675176 JTSAEZNOAXDDOQ-MVTVPBHXSA-N 346.423 2.225 30 1 EEEF C/N=C1/N/C(=C\c2c[nH]c3ccc(Br)cc23)C(=O)N1C 84689512 ZSWULTXENYERTM-XGICHPGQSA-N 333.189 2.319 30 1 EEEF N#C[C@@H]1C[C@H](F)CN1C(=O)CNC(=O)c1cccc2ccccc12 84616479 JIRNJLZNEMWKIK-KBPBESRZSA-N 325.343 2.032 30 1 EEEF COc1ccc(/C=C2\CNC/C(=C\c3ccc(OC)nc3)C2=O)cn1 98083937 QPDMSISWIKFFSI-BGPOSVGRSA-N 337.379 2.133 30 1 EEEF C=C1C(=O)[C@@]23[C@H](O)C[C@@H]4C(C)(C)CCC[C@@]4(C(=O)O)[C@@H]2CC[C@@H]1[C@H]3O 238789035 VBQWGSKSQFBYOX-SDDUFPNZSA-N 348.439 2.161 30 1 EEEF C=CCOC(=O)NCCCc1cc(=O)oc2c(C=O)c(O)ccc12 169348336 KQVNKJFKBRITEO-UHFFFAOYSA-N 331.324 2.156 30 1 EEEF O=C1O[C@H]2C=CCC=C2C(=O)[C@@H]1Cc1c(O)c2ccccc2oc1=O 169692524 FMTPOCAUOVRPJN-ZFWWWQNUSA-N 338.315 2.038 30 1 EEEF N#C[C@@H]1CCC[C@H]1C(=O)[C@@H]1CN([C@@H]2CCOc3ccccc32)C[C@@H]1N 28955127 AXLLQKGXUYCBGM-XGAARHLOSA-N 339.439 2.278 30 1 EEEF CC1=C[C@H](C)[C@H](c2cc(O)cc(O)c2)OC(=O)[C@H](C)[C@H](O)[C@@H](C)C1=O 2356733726 RFQJAVYYIHIQAI-KGADELSOSA-N 348.395 2.480 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)[C@@H]2[C@@H]3OCC4=C3[C@@](C)(CCC4=O)CC[C@@]12C 2356823286 GKUCSSBQVHTTCY-VVRJILRHSA-N 334.456 2.475 30 1 EEEF Cc1ccc2n(c1)cc(/C=C/c1ccc(/C=N/NC(=N)NO)cc1)[n+]2C 40472472 ORWLNGOHRNHGHI-UXQBEKABSA-N 349.418 2.080 30 1 EEEF N#Cc1c(-c2cccc(C=O)c2)[nH]c2nc(N)nc(N3CCCC3)c12 263621280 YJUYKLYWYFTFQN-UHFFFAOYSA-N 332.367 2.491 30 1 EEEF in-vitro COc1ccc(N/N=C2/C(=O)ON=C2c2ccc(OC)cc2)cc1 103749901 KQSDSJLMWVZWCX-KNTRCKAVSA-N 325.324 2.433 30 3 EEEF CC#CC#CC=C1O[C@]2(CC[C@H](OC(=O)CC(C)C)CO2)[C@H]2O[C@H]12 2356508576 IZOBIZVXEKNCNN-KLIQENQMSA-N 330.380 2.159 30 1 EEEF COC1=C[C@]23CCN(C)[C@H](Cc4ccc(OC)c(O)c42)[C@H]3CC1=O 35788950 OWDQPILTDJLGCN-VPZZIHKRSA-N 329.396 2.018 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)[C@]1(C)C[C@H](O)CC(C)(C)[C@H]1C[C@H]3O 95919303 XIGJIFFLTSZIKL-UCBWXSKUSA-N 334.456 2.067 30 1 EEEF biogenic,in-vitro C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@@H](C(=O)O)[C@@H]1[C@]2(C)CCC[C@]31OC2=O 85800288 MBNDVMTZEKAWKP-QOTGHQEKSA-N 332.396 2.136 30 1 EEEF in-man C#CCN1CCc2nc3nc(N4CCCCC4)c(C#N)cc3c(N)c2C1 84604056 UQPSZGFXWACLJE-UHFFFAOYSA-N 346.438 2.065 30 1 EEEF CON=C1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12 1857573267 BAQAFPOIHHYAJW-YXKWSERDSA-N 341.411 2.373 30 1 EEEF C[C@H](CO)C1=C2CC[C@H](CO)C3=C(C[C@]2(C)CC1)[C@H](C)[C@H](O)C3=O 2356325642 QNDHAMGPYFFBHA-JFCCEXRQSA-N 334.456 2.380 30 1 EEEF CSCC[C@@H](NC(=O)[C@H](CS)Cc1ccccc1)C(=O)O 26479183 HNZBQOSYCFLCAE-QWHCGFSZSA-N 327.471 2.098 30 1 EEEF C=C1[C@H](O)[C@@H]2O[C@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@]1(C)[C@@H](O)C(=O)[C@]32C 2356479225 ILPXHKMIZLTLAS-PNORCLHNSA-N 332.440 2.083 30 1 EEEF COC(=O)C[C@]1([C@@H](O)C=C(C)CCC=C(C)C)C[C@H](O)C=CC1=O 2356635822 LRHXPNHCPURRDF-HHXXYDBFSA-N 336.428 2.479 30 1 EEEF COc1ccc(N/C(=N\C(=S)NCCO)c2ccccc2)cc1 84634704 QTBPIFNVQIHRJS-UHFFFAOYSA-N 329.425 2.421 30 1 EEEF Cn1cc(-c2ccc([C@@H](NC(=O)OC(C)(C)C)C(=O)NO)cc2)cn1 653788038 SASAIIBKYJIJKV-CQSZACIVSA-N 346.387 2.158 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H](O)/C(C)=C\CC/C(C)=C\CC[C@@]3(CO)O[C@@H]3C[C@H]12 169292312 MULWDJOXRRXULO-SLPGJBBRSA-N 348.439 2.432 30 1 EEEF C=C1[C@H](O)[C@@H]2O[C@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@@]1(C)C(=O)C(=O)[C@]32C 2356527239 ZVWIURNWTXCECX-HTGARLIXSA-N 330.424 2.291 30 1 EEEF C/C1=C/CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)[C@@H](CN3CCOCC3)[C@@H]2CC1 43021014 VHSZRNXTICCEKT-ONPCBYPWSA-N 335.444 2.154 30 1 EEEF CO[C@H](C)COC1CCC(c2nc3nc(C#N)c(C#N)nc3[nH]2)CC1 587952472 ROYBRFZTYSOJEZ-VOMCLLRMSA-N 340.387 2.174 30 1 EEEF N#Cc1c(-c2cccnc2)[nH]c(N2CCc3ccccc3C2)nc1=O 3649610 UAKQQHPMNZOIIF-UHFFFAOYSA-N 329.363 2.266 30 1 EEEF C=CC[C@]12CC(=O)[C@H](O)[C@H]([C@@H]1O)[C@H](c1ccc3c(c1)OCO3)[C@H]2C 2356536940 FBPLISOOTGTZGY-NRGNYIQLSA-N 330.380 2.022 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)[C@@H]3[C@H](O)CC[C@]3(C)[C@@H](OC(=O)C=CC)[C@@H]12 2356549660 HSXLCTYJIGXUOE-JCHGNXKVSA-N 334.412 2.389 30 1 EEEF COc1ccc(N(C(=O)[C@H](C)CS)[C@H](C)C(=O)O)cc1OC 28263318 QMKCAFICSCUPEE-NXEZZACHSA-N 327.402 2.076 30 1 EEEF C=C[C@]1(O)CN2CC[C@@H]1C[C@H]2[C@@H](O)c1ccnc2ccc(OC)cc12 195191231 BSRUJCFCZKMFMB-UOWJPWOOSA-N 340.423 2.288 30 1 EEEF NCc1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)c[nH]1 587889302 XOOCJJVHUPOJAI-UHFFFAOYSA-N 336.222 2.491 30 1 EEEF COc1ccc([C@H](O)C#C[C@@H](O)c2ccccc2)c(OC)c1OC 1857760847 DDKCKMHUTOSATP-HZPDHXFCSA-N 328.364 2.483 30 1 EEEF C=C1[C@H]2OC(=O)C=C(C)[C@H]2C[C@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@@H]12 2356470956 LUHDPMVWXCNPMF-MUQADHOPSA-N 344.407 2.477 30 1 EEEF CCCC[C@H](CC(=O)NO)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C 5887619 XNOOIEVKOZAJEO-OLZOCXBDSA-N 342.436 2.021 30 1 EEEF investigational COc1ccc2c3c1O[C@H]1C=C(C(C)=O)C[C@H]4[C@@H](C2)N(C)CC[C@]314 27711478 FKNWJBZMTKZQMB-NVALYEJGSA-N 325.408 2.490 30 1 EEEF O=C1C[C@H](O)[C@H](O)[C@H]2C1=CCCC21Oc2cccc3cccc(c23)O1 2356649602 QZXGWZACFKTEPU-KYNGSXCRSA-N 338.359 2.338 30 1 EEEF C[C@@H]1CC(=O)C2=C(CC[C@]34O[C@]23C(=O)c2cccc(O)c2[C@@H]4O)C1 2356796814 NNMGLXNJGVNRCH-TYRHLMEOSA-N 326.348 2.219 30 1 EEEF COC1=C[C@@]23CCc4ccc(O)c(OC)c4[C@@]2(CCN3C)CC1=O 238788317 AQJBMLRXZGTSTA-MOPGFXCFSA-N 329.396 2.162 30 1 EEEF COc1ccc(Cl)cc1C#CC1=C(Br)[C@@H](O)OC1=O 587912069 FPSASRYNGNZTSH-ZDUSSCGKSA-N 343.560 2.224 30 1 EEEF NC(=O)c1cccc2c1O/C(=C\c1ccc(OC[C@@H]3CO3)cc1)C2=O 169348815 SHMSNUPWFZACTQ-KHAFMBKQSA-N 337.331 2.179 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H]1[C@@H](O)CC(=C)[C@@H]1C[C@@H](OC(=O)C=C(C)C)C(=C)[C@H]12 2356441757 DDKWVHFIPPNJCX-YWBBLYAYSA-N 344.407 2.475 30 1 EEEF C=C(C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@@H](O)C(=C)[C@@H]2[C@H]2OC(=O)[C@@H](C)[C@H]12 40872451 IXOAQFFFKPCXLB-OPCFMFSHSA-N 332.396 2.165 30 1 EEEF COc1cc(C#N)ccc1/N=c1\c(O)c(O)\c1=N/[C@H](C)C(C)(C)C 13806480 QKJKPCKSVVTOOK-ADOJQYPFSA-N 327.384 2.421 30 1 EEEF C[C@]1(CCC(=CCO)CO)[C@H](C=O)CC[C@]23COC(=O)C2=CCC[C@@H]31 2356379735 GUKSFBJMSDUTIA-RKOGWWSCSA-N 348.439 2.172 30 1 EEEF CC1=C[C@H](OC=C2C(=O)O[C@@H]3C4=C(C[C@H]23)C(=O)CCC4(C)C)OC1=O 2356498062 HZXNZCJZYALICU-HQQWDMGQSA-N 344.363 2.347 30 1 EEEF COCCN/C(=N\O)c1ccc(C)nc1OCc1cccc(F)c1 72103446 GFOLPFWYJYQZIU-UHFFFAOYSA-N 333.363 2.480 30 1 EEEF COC1=C[C@@]2(CCC1=O)C[C@@H]1c3c(cc(OC)c(O)c32)CCN1C 14618497 MHXSUTPVPBOLJW-CWTRNNRKSA-N 329.396 2.465 30 1 EEEF biogenic N#Cc1nc(Cl)cc2nc(Cc3ccc(C(=O)O)cc3N)[nH]c12 587249350 IYJRYVKUQLVYAL-UHFFFAOYSA-N 327.731 2.354 30 1 EEEF O=C1O/C(=C/c2ccc(O)c(O)c2)C(=O)C(c2ccc(O)cc2)=C1O 15263894 MCSQVSPITLWUGY-RIYZIHGNSA-N 340.287 2.240 30 1 EEEF endogenous,world Oc1ccc(O)c(/C=N/NC(=S)N[C@H]2C[C@@H]3C[C@@H]2[C@@H]2C=CC[C@@H]32)c1 169355914 OFXIRPMFRVBDKI-QVQINHMRSA-N 343.452 2.497 30 1 EEEF Cc1c2c(n(CCc3ccccc3)c1C)NN=C(C#N)S2(=O)=O 1653546 URYPMWFGKXFEHU-UHFFFAOYSA-N 328.397 2.384 30 1 EEEF O=C1C=CC=C/C1=C\NNC(=S)N[C@@H]1C[C@H]2C[C@H]1[C@H]1C=CC[C@H]21 104017616 WVNYYTSFNKWSKL-XYKFUVPZSA-N 327.453 2.135 30 3 EEEF Cc1nc(OCc2cc(N3CCOCC3)cc(NCC#N)n2)oc1C 43078158 RLZOTVNEVAYHGA-UHFFFAOYSA-N 343.387 2.038 30 1 EEEF C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@@H](O)[C@H]1C(=C)[C@H](C)CC[C@]21C 238745006 GCVDFMXIDUYWBG-MEEPCEMDSA-N 344.407 2.167 30 1 EEEF N#C[C@@H]1CCCN1C(=O)CNC(=O)c1ccnc2cc(Cl)ccc12 96270274 NERXNBIHCGOYFQ-LBPRGKRZSA-N 342.786 2.133 30 1 EEEF O=C(CCCCc1cn(Cc2ccc(F)c(Cl)c2)nn1)NO 96907685 HGKUDYGHIXGMSJ-UHFFFAOYSA-N 326.759 2.337 30 1 EEEF C[C@H]1Cc2cc(Br)c(F)cc2[C@]2(COC=CC2=O)N1 587836681 XGVUTVUEYPXGQD-RTHLEPHNSA-N 326.165 2.431 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc2ncn(N)c(=O)c2c1 587909581 ZMSUWOKKOIETCG-UHFFFAOYSA-N 325.755 2.172 30 1 EEEF CCNC(=N)N/N=C/c1ccc(/C=C/c2cn3ccccc3[n+]2C)cc1 26821779 FZTFWXKVSDZHAG-OKTVNARPSA-N 347.446 2.402 30 1 EEEF C[C@]12C3=C(C(=O)c4occ(c41)[C@H](O)[C@@H]1O[C@H]12)[C@@H]1CC[C@H](O)[C@@]1(C)CC3 2356449774 XPAHMBAVRBKIJS-FETISLTMSA-N 342.391 2.416 30 1 EEEF C=C1[C@@H](O)CC2=C(COC(=O)C(C)C)CC[C@@H]3C(=C)C(=O)O[C@H]3[C@H]12 2356644497 INJHISWMTROACX-XLNGHYISSA-N 332.396 2.311 30 1 EEEF C=C(C)C(=O)O[C@@H]1[C@@H]2C(=C)C(=O)O[C@@H]2CC(C)=C2CC[C@H](O)[C@]21C 238773131 RMPQKZFNZPUCJG-INJPQVFBSA-N 332.396 2.453 30 1 EEEF CN(C)CC/N=C(/C=C1/C=Cc2ccccc2N1C)NCCN(C)C 377605861 ZKHGZFKQTDKCAO-VLGSPTGOSA-N 341.503 2.145 30 1 EEEF C#CCNC(=O)c1ccc(NC(=O)c2ccc(OC)cc2OC)cc1 473111457 BEAUWYDQWUVVSQ-UHFFFAOYSA-N 338.363 2.319 30 1 EEEF CS(=O)(=O)[C@](CCc1ccccc1)(Cc1ccccc1)C(=O)NO 1772630502 AGQCHBYZAKENRE-GOSISDBHSA-N 347.436 2.151 30 1 EEEF Cc1ncnc2c1/C(=N/N=C(N)N)C[C@H](c1ccccc1Cl)C2 13474683 SJVDKRAFRLTANA-CONVLBPTSA-N 328.807 2.146 30 1 EEEF CC(C)(CC(=O)Nc1ccc(F)cc1)NCC(=O)N1CCC[C@H]1C#N 36310914 OCUFROZKYDZPGE-HNNXBMFYSA-N 346.406 2.037 30 1 EEEF N#CC1(c2cc(-c3cnc(N)nc3)nc(N3CC4CC3C4)n2)CCC1 221231190 WNKNJRXJFOCYQM-UHFFFAOYSA-N 333.399 2.060 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@H]2C(=C)C[C@H](O)[C@H]3C(=C)C(=O)O[C@@H]3[C@H]2C1=C 238766814 RWWQHQZKBAELGL-NQLMQOPMSA-N 330.380 2.085 30 1 EEEF C=C[C@]1(C)C=C2[C@H](O)[C@H](O)[C@H]3C(C)(C)CC[C@@H](O)[C@]3(C)[C@@]2(O)CC1 96086190 MDMNBGISPKQWRE-KNEKMNIZSA-N 336.472 2.169 30 1 EEEF C[C@@]1(Nc2ccc(C(=O)NO)cc2)CCN(c2ccccc2)C1=O 200964355 LNFNYVNCDUDQFX-GOSISDBHSA-N 325.368 2.413 30 1 EEEF CC1=CC(=O)[C@]2(CN1)N[C@H](C)Cc1ccc(F)c(Br)c12 587799462 XHIZTKJYJVNHTR-PSLIRLAXSA-N 339.208 2.394 30 1 EEEF CN1C(SCC(=O)c2ccccc2)=NNC1=C1C=CC(=O)C=C1 104026162 KYIKZOGFMWXIHE-UHFFFAOYSA-N 325.393 2.315 30 3 EEEF COc1ccc([N+](=O)[O-])cc1[C@H]1NN/C(=C2/C=CC=CC2=O)S1 104034519 WXCQWCTXVHXHLQ-IPJDOKCGSA-N 331.353 2.350 30 3 EEEF C=C1C[C@@]23CC[C@H]1C[C@@H]2[C@@]12CCC[C@](C)(CO)[C@H]1[C@@H](OC2=O)[C@H]3O 2356553115 OMDPLJPNOXTENE-TVJCRXAUSA-N 332.440 2.434 30 1 EEEF COc1cccc(N/N=C2\C(O)=NN=C2c2cnccc2OC)c1 49050500 MFGWNLPRMHPFJF-UHFFFAOYSA-N 325.328 2.241 30 1 EEEF COc1ccc2c(c1OC(C)=O)C1=CC(=O)CC[C@]13CCN[C@@H]3C2 1611736 ITOZXSNVASSYGQ-APWZRJJASA-N 327.380 2.271 30 1 EEEF C[C@H](O)[C@@H]1C(=O)C(=C(O)[C@H]2[C@H]3CCCC[C@@H]3C=C[C@H]2C)C(=O)N1C 2356417408 ACUUAFHILDALFB-QLBXMJNRSA-N 333.428 2.218 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@@]2(COC=CC2=O)N1 587836682 XGVUTVUEYPXGQD-XLKFXECMSA-N 326.165 2.431 30 1 EEEF C=C[C@H]1CC(=O)[C@H]2Oc3c(OC)ccc4c3[C@@]23CCN(C)[C@@H](C4)[C@H]13 253696501 NTWGNEUJRLFCNI-YYDUELQBSA-N 325.408 2.345 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(C(N)=O)c([N+](=O)[O-])c1 587908928 FJWMALMREJQVJS-UHFFFAOYSA-N 331.715 2.151 30 1 EEEF CC1=NC=C(CO)/C(=C/NNc2c(F)c(F)c(F)c(F)c2F)C1=O 103864831 LHXRZOQIMDIBIF-CLTKARDFSA-N 347.243 2.102 30 3 EEEF C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)C(CO)=C[C@@]43C)[C@H]1CC[C@@]2(C)O 2356867879 WXBPWNNGZDXSDG-DWBADUGPSA-N 346.467 2.379 30 1 EEEF CC(=O)N1N=C(c2ccc(C#N)cc2)O[C@H]1c1ccc([N+](=O)[O-])o1 96913468 URCDUIGRLYQTAC-HNNXBMFYSA-N 326.268 2.299 30 1 EEEF CC1(C)OC(=O)C(c2nc3cc(C#N)cc(Br)c3[nH]2)=C1N 587254009 OQJDGVYDZQIKQQ-UHFFFAOYSA-N 347.172 2.202 30 1 EEEF COc1ccc(C(=O)Oc2cccc3c2C(=O)C=C(N2CC2)C3=O)cc1 29392504 UHTQQZGOJWTVHN-UHFFFAOYSA-N 349.342 2.493 30 1 EEEF C=C1C[C@@]23C[C@@]1(O)CC=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 2356473032 QQZHQZNECSBZML-FIXWDHIASA-N 344.407 2.289 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@](C)(O)CC[C@@H]2C3=C[C@H]([C@@H]4OC4(C)C)O[C@@H]3OC[C@H]12 2356515462 PVAIAJLEMKCLCA-JEFPHDMESA-N 348.439 2.336 30 1 EEEF CC(C)C[C@H](NC(=O)Nc1ccc2ncsc2c1)C(=O)NCC#N 82061201 OSCXONMVMFKLLT-ZDUSSCGKSA-N 345.428 2.472 30 1 EEEF C/C=C1/CN2CC[C@@]34C5=CC(=O)C=CC5=N[C@@]23CC[C@@H]1[C@H]4C(=O)OC 95909425 LKDWBLMHMZGRGJ-NFRBHMALSA-N 338.407 2.054 30 1 EEEF biogenic,in-vitro C#Cc1ccc2c(c1)CN(S(=O)(=O)c1cccc(C(=O)O)c1)CC2 95554129 DTKGFUCTXXESLR-UHFFFAOYSA-N 341.388 2.113 30 1 EEEF CC1=CC(=O)[C@]2(CN1)Oc1ccccc1C(=O)[C@H]2C(=O)c1ccco1 587595352 NGEPTUKSQJSQGP-LPHOPBHVSA-N 337.331 2.169 30 1 EEEF NC(=O)C1=C(Nc2ccccc2)O/C(=C\c2c[nH]c3ncccc23)C1=O 1772614867 XMEKFXKOTJZXOA-ZROIWOOFSA-N 346.346 2.312 30 1 EEEF O=C(O)[C@H]1CCCN(CCO/N=C/c2ccc3ccccc3n2)C1 1857555748 RAYNQXJPOQHGHK-UZUMKDMXSA-N 327.384 2.382 30 1 EEEF N/C(=N\O)c1ccc(-c2cc(-c3ccc(/C(N)=N/O)cc3)on2)cc1 103228004 IAKKLRJVFMNTOP-UHFFFAOYSA-N 337.339 2.198 30 1 EEEF CO[C@]1(C#C[C@](O)(c2ccccc2)c2ccncc2)CN2CCC1CC2 28563978 NSEVJPOKAGLQCK-YADHBBJMSA-N 348.446 2.432 30 1 EEEF C=C1C[C@H](OCC(C)C)[C@@H]2C(=C)C(=O)O[C@@H]2C=C(C)[C@H](O)CC1=O 2356483576 PJRAJKIGBHSJPR-XDNAFOTISA-N 334.412 2.352 30 1 EEEF C=C(C)[C@H](O)Cc1c(OC)c2cc(OC)cc(OC)c2n(C)c1=O 14682494 BPIVYUXQDVOPES-CQSZACIVSA-N 333.384 2.044 30 1 EEEF biogenic CN(C)S(=O)(=O)c1ccc2nc(-c3ccc(C#N)c(F)c3)[nH]c2c1 587143019 KFKUTFSAYHEMIE-UHFFFAOYSA-N 344.371 2.491 30 1 EEEF CN(C)c1ccc(NC(=O)NCCCCCNC(=O)CS)cc1 28136486 GNEUGLGVTJXIJM-UHFFFAOYSA-N 338.477 2.090 30 1 EEEF COc1ccc(N(C(=O)[C@H](C)CS)[C@@H](C)C(=O)O)cc1OC 28263313 QMKCAFICSCUPEE-ZJUUUORDSA-N 327.402 2.076 30 1 EEEF CC1(C)N=C(N)N=C(N)N1c1cccc(COc2cccc(C#N)c2)c1 13740728 UHSFYDTWKATRPP-UHFFFAOYSA-N 348.410 2.323 30 1 EEEF O=C1C=CC(=C2NN=C(SCC(=O)Nc3ccccc3)O2)C=C1 104026242 VBVBBAXOXNXJKT-UHFFFAOYSA-N 327.365 2.156 30 3 EEEF C=C1C[C@]23C[C@H]1[C@@H](O)C[C@H]2[C@]1(C)CCC[C@]2(C)C(=O)O[C@H]([C@H]21)[C@H]3O 100780474 OSYJLXUUZYSFTC-YZVWYEERSA-N 332.440 2.432 30 1 EEEF endogenous,in-man CC1=C[C@@H]2[C@H](C[C@H](O)C(C)=C[C@@H]3C(=O)[C@H](C)C[C@@]3(O)C1=O)C2(C)C 2356453083 NHOIUGORUWWMAP-CLQYMUMGSA-N 332.440 2.441 30 1 EEEF COC(=O)c1ccc([C@@H]2C(=C(C)O)C(=O)C[C@@](C)(O)[C@H]2C(C)=O)cc1 2356845338 ODUNWFFBMKIIDY-ZIFCJYIRSA-N 346.379 2.318 30 1 EEEF C=C(CO)[C@]12C=C3C(=O)C[C@@H](C(C)C)[C@]3(C)C[C@@H](O)[C@@]1(C)CC(=O)O2 40980038 LAUXGJSHPLNZHD-LVQIXTDASA-N 348.439 2.169 30 1 EEEF COCCNc1nc2c(s1)Cc1cc(/C=C/C(=O)NO)ccc1-2 96923429 CZEPBMRUABSSIM-HWKANZROSA-N 331.397 2.291 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc2c(cc1Cl)=C(O)C(=O)N=2 587907419 LRTDJMPJCWQGCT-UHFFFAOYSA-N 346.169 2.228 30 1 EEEF C=C[C@@H]1CC[C@H]2[C@@H]3CC(=O)[C@@]4(O)C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C 2356429461 VQFKUKMXFNCVKK-UWKUKEDQSA-N 348.483 2.457 30 1 EEEF C#C[C@]12O[C@]1(C=O)[C@@H]1[C@H](O)C[C@@H]3C(C)(C)CCC[C@@]3(C)[C@@H]1CC2=O 2356471216 RLCVKAJQPCOLQK-FRHKILPWSA-N 330.424 2.129 30 1 EEEF CCOc1ccccc1CCn1cccc(/C=C/C(=O)NO)c1=O 143877189 ABVYHBVBEQAYRY-MDZDMXLPSA-N 328.368 2.008 30 1 EEEF CCO[C@@]12C[C@@]3(C)[C@H](CC1=C(C)C(=O)O2)C(C)=CC(=O)[C@@H]3OC(C)=O 238775688 YDUWTFHAUBSRIH-SKSLQVBQSA-N 348.395 2.470 30 1 EEEF Cc1ncnc(N)c1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587880434 LLCSWUNQUVWFLD-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF CCCCC1=C(N2CC2)C(=O)c2nc3n(c2C1=O)CC[C@H]3OC(C)=O 13605732 CKHIGJCCWYNDSH-GFCCVEGCSA-N 343.383 2.030 30 1 EEEF CC(=O)O[C@H]1[C@@H](N2CCCC2=O)c2cc(C#N)ccc2OC1(C)C 26283936 MUCIVWGGWJZCBJ-IRXDYDNUSA-N 328.368 2.324 30 1 EEEF O=C1C2=CCCC3(Oc4cccc5cccc(c45)O3)[C@@H]2[C@H](O)[C@H]2O[C@@H]12 2356793057 GZNZGNSOLGAMAJ-DSLXNQLJSA-N 336.343 2.355 30 1 EEEF COc1cc2c(cc1OC)CN(CCCn1ccnc1/C=N/O)CC2 299820128 FYSCEUYDPKSCFS-UDWIEESQSA-N 344.415 2.157 30 1 EEEF COc1cc2c3c(c1)O[C@@]1(CCCC(=O)/C1=C\N(C)C)[C@@H](C2)C3=O 587427257 CTRDIESGJSGEEB-XRXWLHDISA-N 327.380 2.380 30 1 EEEF N#Cc1nc(Cl)cc2nc(CCCn3ccc([N+](=O)[O-])n3)[nH]c12 587273123 IDCSIWCFRFLIQL-UHFFFAOYSA-N 331.723 2.220 30 1 EEEF O=C(/C=C/c1ccc(/C=C(/C(=O)NC2CC2)c2cccnc2)cc1)NO 59275928 KYZXBACRIINGFW-WKZRCPIQSA-N 349.390 2.419 30 1 EEEF O=C(/C=C/c1ccc(CNCCc2cnc3ccccn23)cc1)NO 72114284 UNPUPHZKXHNIRL-CMDGGOBGSA-N 336.395 2.185 30 1 EEEF O=C(CN1C(=O)S/C(=C\c2ccc3ccccc3c2)C1=O)NO 45497729 BIIFIGCDDOXBDY-JYRVWZFOSA-N 328.349 2.382 30 1 EEEF C=CC[C@@](C)(N)c1nc2cc(I)cnc2[nH]1 587258144 ZITUXLDHHLRNDX-LLVKDONJSA-N 328.157 2.313 30 1 EEEF Nc1cnncc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587889341 YFHOKKLTZHIDSY-UHFFFAOYSA-N 335.194 2.076 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@H](C1=O)[C@]1(C(C)C)C=C[C@]2(C)CC1 101869773 SDJYQQCUHRGBAF-XHSVMWQWSA-N 347.484 2.165 30 1 EEEF C=C1C(=O)O[C@@H]2CC(=C)[C@@H]3[C@H](OC(=O)C(C)C)C[C@](C)(O)[C@@H]3C[C@H]12 2356693946 RPFZMZXPFLBITO-LAOQMUKWSA-N 334.412 2.389 30 1 EEEF C[C@](Cc1ccccc1)(C(=O)NO)C(=O)NCc1ccc(F)cc1 45283684 MTWFVXDQVQRQQS-GOSISDBHSA-N 330.359 2.196 30 1 EEEF COc1cc(N2CCC(N(C)Cc3ccc(C#N)cc3)CC2)ncn1 299866084 VEUXXZWECYYYLG-UHFFFAOYSA-N 337.427 2.458 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(=O)C(C)=CC)CC(=C)[C@@H]1[C@H](O)C=C(C)[C@H]21 2356530238 JEAWGNYMYMHNGM-ZXLDYLNASA-N 344.407 2.475 30 1 EEEF O=C(C=C[C@H](O)Cc1ccc(O)c(O)c1)CCc1ccc(O)c(O)c1 2356632589 PAUUCJGSDZNVOR-HNNXBMFYSA-N 344.363 2.171 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@@H]1O)[C@H](C(=O)OC)[C@H]1[C@@]2(C)CCC[C@@]31OC2=O 2356636504 KVXQCEAWXGANQC-HXJIOFMHSA-N 346.423 2.225 30 1 EEEF C[C@H](CO)C1=C(O)C(=O)C2=C(C[C@H](O)[C@@H]3C(C)(C)CCC[C@]23C)C1=O 504703447 KSXQZHNLPHBARZ-UAYYFRRASA-N 348.439 2.473 30 1 EEEF biogenic COc1ccc2cc(C(=O)NCCCCCCC(=O)NO)ccc2n1 299840203 VVZXDYPDBYYVAY-UHFFFAOYSA-N 345.399 2.429 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@]1(C)CCC[C@](C)(CO)[C@H]1C[C@@H]3O 2356404714 VFCKRZZDFUUVFU-LBMYDTJDSA-N 334.456 2.068 30 1 EEEF CC=CC=CC1=CC2=CC(=O)[C@@](C)(OC(=O)C[C@H](C)O)C(=O)C2=CO1 2356859862 TZCZFKHZYAXVCK-HXPMCKFVSA-N 344.363 2.068 30 1 EEEF C[C@@H]1NC=CC(=O)[C@@]12Oc1ccccc1C(=O)[C@@H]2C(=O)c1ccco1 587597084 SBOAAVAUODSRDI-MAAWUACBSA-N 337.331 2.167 30 1 EEEF N#CCN1C(=O)N(Cc2ccccc2)S(=O)(=O)c2ccsc21 6579760 PAXZBLWNIORLCR-UHFFFAOYSA-N 333.394 2.403 30 1 EEEF CCCC/C(=N/CCO)C1=C(O)[C@H](C(=O)OC)C(C)(C)CC1=O 101865093 WUMJQCTZODTZAB-JVVDOCDTSA-N 325.405 2.210 30 1 EEEF C[C@@H]1CC2=C([C@@H]1O)[C@H](O)[C@]1(C)CC[C@@H]3[C@H]([C@@H](O)[C@]1(C)C2=O)C3(C)C 2356843632 NNSBPFCEWFSYFB-WWVIOCMQSA-N 334.456 2.067 30 1 EEEF CC=CC(=O)O[C@H]1[C@@H](O)[C@@]2(C)[C@]3(CO3)[C@@H]1O[C@@H]1C=C(C)CC[C@@]12C 2356845520 OFRDWLCMCXXLSX-WDSBDPLQSA-N 334.412 2.138 30 1 EEEF N#Cc1ccc(N(CC(N)=O)CC(F)(F)F)cc1C(F)(F)F 135667803 ZDYGKWOTFUOWOA-UHFFFAOYSA-N 325.212 2.431 30 1 EEEF CN(C)S(=O)(=O)c1ccc2nc(-c3ccc(O)c(C#N)c3)[nH]c2c1 587187750 KFBAHKKYNPWHBO-UHFFFAOYSA-N 342.380 2.057 30 1 EEEF Cc1cc(-c2n[nH]c(=S)n2/N=C\c2cccc([N+](=O)[O-])c2)n[nH]1 13142219 ACOMVPZJUCMYRR-AUWJEWJLSA-N 329.345 2.430 30 1 EEEF O=C([C@H]1CSC(c2ncccc2O)=N1)N(O)Cc1ccccc1 26736436 ICFWJGZOILOKNF-GFCCVEGCSA-N 329.381 2.067 30 1 EEEF C[C@@H](O)C[C@H]1O[C@@H]1/C=C/C=C/c1cc2cc(O)cc(O)c2c(=O)o1 238771810 TYXXEQMKBIKKOL-NYOBOZBLSA-N 330.336 2.312 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(COC(C)=O)CCC=CC[C@H](OC(C)=O)[C@@H]12 2356401886 RTCARLYNKKVHJD-GVDBMIGSSA-N 334.368 2.246 30 1 EEEF COc1ccc([C@@]2(C#N)C[C@@H]3C[C@H](C(=O)NO)C[C@@H]3C2)cc1OC 100776242 FRZCXGDYYXKYJH-TZTHQDNISA-N 330.384 2.407 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@@]3(C)OC(=CC3=O)C(C)=C[C@H](OC(=O)C(C)C)[C@H]12 2356539287 JHZYGPMGMMUUTG-QMYADUOMSA-N 346.379 2.244 30 1 EEEF C=C1[C@@H]2CC[C@@]3(C)C[C@@]2(CC3=O)C[C@H](O)[C@]2(O)[C@@H]1C[C@H](O)C2(C)C 2356593375 IRZVFDISJFITJT-MJMBBHLVSA-N 334.456 2.211 30 1 EEEF O=C(NO)c1cnc(Nc2nnc(-c3cccc(Cl)c3)o2)nc1 72126865 UINFPRVMOHNRFK-UHFFFAOYSA-N 332.707 2.043 30 1 EEEF C=CCN1C(=S)N[C@@H]2c3ccccc3O[C@@]1(C)[C@@H]2C(=O)OCC 95784800 YAXHXOXPWVFUPU-VBQJREDUSA-N 332.425 2.392 30 1 EEEF COc1ccc(F)cc1[C@@H]1C/C(=N\N=C(N)N)c2c(C)ccnc2C1 13474712 WHMSZUDKRHONNW-DJYLNSBBSA-N 341.390 2.245 30 1 EEEF CCN1C(=O)N(CC)[C@H]2[C@H]1NC(=S)N2/N=C/C=C/c1ccccc1 1857645996 ZKFBHJXHPXBJBI-XUMQJTEQSA-N 343.456 2.305 30 1 EEEF N#CCC[C@@H]1NC(=O)c2ccccc2-n2c1nc1ccccc1c2=O 1857759398 JJFMDWQPUDJAHC-HNNXBMFYSA-N 330.347 2.474 30 1 EEEF COCC(=O)N1[C@H](CO)[C@H](c2ccccc2-c2ccccc2)[C@@H]1C#N 95668246 RRMULCFNGGBUJN-NLWGTHIKSA-N 336.391 2.179 30 1 EEEF N#C[C@H](c1ccc(Cl)cc1)c1c(O)nc2ccc(N)cc2[n+]1[O-] 17188009 BRRIKBOQJWSCHX-GFCCVEGCSA-N 326.743 2.465 30 1 EEEF O=N[C@H](Cc1ccc(F)c(Br)c1)C(=O)NCCS 169727921 XMEVZQFDGLJAGD-SNVBAGLBSA-N 335.198 2.312 30 1 EEEF COc1ccc(CCCc2nc3nc(C#N)c(C#N)nc3[nH]2)cc1OC 587926347 XPSNDKYBXDVCSK-UHFFFAOYSA-N 348.366 2.289 30 1 EEEF Cn1c(=O)ccc2cc(S(=O)(=O)Nc3ccc(C#N)cc3)ccc21 1772607332 BXGJNRVCUDKEGW-UHFFFAOYSA-N 339.376 2.211 30 1 EEEF CNC(=O)/C(=N/OC)c1ccccc1COc1cccc(N(C)C)c1 103193727 FMNYETGKVNNCOE-DYTRJAOYSA-N 341.411 2.428 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@](C)(O)CC[C@@H]2C3=C[C@H]([C@@H]4OC4(C)C)O[C@@H]3OC[C@@H]12 2356515463 PVAIAJLEMKCLCA-JRWCCFCNSA-N 348.439 2.336 30 1 EEEF C=C1[C@H]2C[C@H](O)[C@@]3(C(=O)C[C@@H]4C(C)(C)[C@H](O)CC[C@]4(C)[C@H]3C2)[C@@H]1O 2356634483 FYHBINXIARYPCI-QHPFIRHMSA-N 334.456 2.067 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 85800122 BSBICXIQCTXPMN-TZAGEXTKSA-N 330.380 2.056 30 1 EEEF in-man CC(=O)N1CC[C@@H]2[C@H](CO)Nc3ccc(C#Cc4cccnc4)cc3[C@@H]21 95878791 ZFWVHLMUMICASE-JRGCBEDISA-N 347.418 2.177 30 1 EEEF C[n+]1c2ccccc2c(CN[C@@H](CS)C(=O)O)c2ccccc21 17193388 MIWGSRCJYBHQTP-HNNXBMFYSA-O 327.429 2.290 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1CCC(C(=O)N1CCCC1)=CCC[C@@]1(C)O[C@@H]21 1857628085 JLALAWOIVFYLTJ-IUVQAAGXSA-N 331.412 2.365 30 1 EEEF NC(N)=Nc1nc(-c2cccc(NC(=O)C(F)(F)F)c2)cs1 45190038 AMPMCJAZCJUFSD-UHFFFAOYSA-N 329.307 2.216 30 1 EEEF COC(=O)c1ccc2nc(C#Cc3ccc([N+](=O)[O-])c(C)c3)[nH]c2n1 587262447 TYXUNLMUIZHFGL-UHFFFAOYSA-N 336.307 2.361 30 1 EEEF CN(C)CCNC(=O)c1cccc2c(N)c3cccc(C#N)c3nc12 27724586 FQBXOIPUBUQMBY-UHFFFAOYSA-N 333.395 2.133 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1C[C@H](O)[C@H]2[C@]1(C)CCC(=O)C(C)(C)[C@H]1[C@@H](O)C3 28638512 ONIKMXSBGJJNBQ-ATEWWHSOSA-N 332.440 2.275 30 1 EEEF biogenic,in-vitro CC(C)[C@@]1(O)C=C2C(=O)C[C@@H]3C(C)(C)[C@H](O)CC[C@@]3(C)[C@@H]2C[C@H]1O 473090211 NHJLCDALTNPYBE-FNYOEWHISA-N 336.472 2.457 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@@](CCC=O)(C(=O)O)N1 587825286 CNZBBDHJVSYJER-CLAHSXSESA-N 344.180 2.381 30 1 EEEF CCNC1=C(NC(=O)c2ccc(F)cc2)C(=O)c2ccccc2C1=O 5501931 ZFGAEDYHZYWSJN-UHFFFAOYSA-N 338.338 2.456 30 1 EEEF CCOC(=O)C1=C(C)OC(=N)[C@H](C#N)[C@@H]1c1ccc(O)c(OC)c1 169688824 DYQABFBTVAQABQ-ABAIWWIYSA-N 330.340 2.469 30 1 EEEF O=C(O)[C@H]1CNC[C@@H](CN/N=C/c2ccc(-c3ccccc3)o2)C1 1857614886 OBVMXCMYXAYBOD-AYERNOBWSA-N 327.384 2.180 30 1 EEEF C=C1C(=O)O[C@@H]2[C@H](O)C(C)=CCCC(C)=CCC[C@]3(CO)O[C@@H]3C[C@H]12 2356381448 MULWDJOXRRXULO-YFYQMDMQSA-N 348.439 2.432 30 1 EEEF CC=CC(=O)O[C@@H]1[C@H](O)[C@H]2O[C@@H]3C=C(C)CC[C@]3(C)[C@@]1(C)[C@]21CO1 2356487416 AGQQMRNEWSVYSU-YTCBWULZSA-N 334.412 2.138 30 1 EEEF C=C1[C@H](O)[C@@H]2O[C@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@]1(C)C(=O)C(=O)[C@@]32C 2356527241 ZVWIURNWTXCECX-SQONHMEMSA-N 330.424 2.291 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)C(=O)O[C@]2(O)C[C@]23O[C@H]2CC[C@H](C)[C@@]13C 36378619 YQSCJMNPXRPKAC-LCFYEYMSSA-N 348.395 2.014 30 1 EEEF N#Cc1c(NC(=O)c2cccs2)[n+](=O)c2ccc(F)cc2n1O 377845801 LMOWZLZJWNQEGG-UHFFFAOYSA-O 331.308 2.118 30 1 EEEF COC1CCC2(CC1)Cc1ccc(C#N)cc1[C@]21N=C(N)N(C)O1 169700448 AOZVUBOFLFKDDG-IUPXNIOVSA-N 326.400 2.034 30 1 EEEF COc1cccc(-n2ncc3c(N/N=C/c4ccncc4)ncnc32)n1 3938379 DMFMOTPKXUXNGS-ZVBGSRNCSA-N 346.354 2.060 30 1 EEEF C=CC(C)(C)[C@]1(C)OC=C[C@@]1(C)CC(=O)[C@@H](O)[C@@H](OC)[C@H](C)O 6487389 BSIAHHIPMGVHJM-WAHHTSEKSA-N 326.433 2.223 30 1 EEEF in-vitro O=C(N[C@@H](CS)Cc1ccccc1)[C@H]1Cc2ccccc2CN1 27716346 AGLKDDGHOSRSDS-QZTJIDSGSA-N 326.465 2.358 30 1 EEEF Cc1nc2ccc(C#CC3(O)CCCCC3)cc2n1-c1ncnc(N)n1 98208222 RSIUBEYNBJJYTG-UHFFFAOYSA-N 348.410 2.148 30 1 EEEF in-vitro C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)/C(C)=C\[C@H]2OC(=O)C(=C)[C@@H]21 4098031 RYBHZNMPMHOBAR-IRNKKCRZSA-N 344.363 2.164 30 1 EEEF biogenic,in-vivo C=CCN1[C@H](CO)[C@H](c2ccc(C#CC3(O)CCCC3)cc2)[C@@H]1C#N 203473543 OGQPIMPPSUTJPG-XUVXKRRUSA-N 336.435 2.181 30 3 EEEF N#CC1CN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)C1 27882258 FZTKTSSAIRNNIM-UHFFFAOYSA-N 345.305 2.273 30 1 EEEF C=C1C[C@H](O)[C@@H]2C(=C)C(=O)O[C@@H]2[C@@H]2C(=C)[C@@H](OC(=O)C=C(C)C)C[C@H]12 2356441754 DDKWVHFIPPNJCX-CKDIOHLVSA-N 344.407 2.475 30 1 EEEF CC(C)C1=C(O)C(=O)C2=CC3=C(CO)C(=O)[C@H](O)C[C@]3(C)CC[C@]21C 2356602720 KHEZYAOQSJJFOU-VOBQZIQPSA-N 346.423 2.393 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](C)[C@H]1[C@@](C)([C@@H](C(C)=O)CC[C@@]1(C)O)[C@H]2C(C)=O 2356678066 QRJWNJLDUSTASQ-ZVVOPSNKSA-N 348.439 2.312 30 1 EEEF CN1CCN(c2cnc3c(c2)[C@H](O)c2cccc(C#N)c2C=C3)CC1 45320732 QXASWNILIRQNPV-HXUWFJFHSA-N 332.407 2.271 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 85799967 ZCRLGANQNRMURE-YPCFBZKNSA-N 346.423 2.384 30 1 EEEF in-man COc1cc2c(c(OC)c1)C(=O)C(=O)C(CC1(C)OCCCO1)=C2 1630442 KDUMZSZKLZBDOQ-UHFFFAOYSA-N 332.352 2.396 30 1 EEEF C[C@@H](O)[C@@H]1C(O)=C(C(=O)[C@@H]2[C@H](C)C=C[C@@H]3CCCC[C@H]32)C(=O)N1C 102967703 NOYBJWXGAYWITN-DPHWGNNJSA-N 333.428 2.218 30 1 EEEF N#Cc1cnn(-c2nc3ccccc3c(=O)n2-c2ccccc2)c1N 103168780 IHMXGYJHPBBOCG-UHFFFAOYSA-N 328.335 2.025 30 1 EEEF COC(=O)[C@]1(c2cccc(OCc3ccccc3)c2)C[C@H]1C(=O)NO 29134811 GVBYOUWYVHIZCE-LPHOPBHVSA-N 341.363 2.202 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)[C@H](C)C[C@H]2OC(=O)C(=C)[C@@H]12 254133137 KYTKEOOPALLADL-CIHIYUMESA-N 346.379 2.244 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@@](C)(CO)CCC[C@@]4(C=O)[C@@H]2CC[C@@H]1[C@H]3O 169313032 NGMHJAMTHJNIJX-NXXFDJNYSA-N 332.440 2.277 30 1 EEEF CC1(C)CCN(C(=O)CC#N)[C@]12CCN(c1ncnc3[nH]ccc13)C2 169698987 IRKRUMKFBUIGLS-SFHVURJKSA-N 338.415 2.079 30 1 EEEF C/C(N)=C1/C(=O)[C@@H]2[C@H]3c4c[nH]c5cccc(c45)C[C@H]3C(C)(C)N2C1=O 105565804 AFOUSJMOYMLOPA-CIGIFLASSA-N 335.407 2.229 30 1 EEEF O=C1C[N+]([O-])=C(c2ccccc2)c2cc(Cl)ccc2N1CCO 26158148 PGPNWDVJEQVPBV-UHFFFAOYSA-N 330.771 2.027 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1C[C@H](O)[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1C[C@H]3O 2356613906 BSPNTRYRRCCKFJ-HOWQZWNXSA-N 348.439 2.161 30 1 EEEF C=C1C[C@]23CC(=O)[C@H]4[C@]56CCC[C@@]4(C)C(=O)N(C)[C@@H]5[C@H]2C[C@H]1C(=O)[C@H]36 238775287 YLHNZWYZUIPWIF-FWJCKRHVSA-N 339.435 2.374 30 1 EEEF CC(C)NS(=O)(=O)c1c[nH]c(-c2nc3c(C#N)cccc3[nH]2)c1 586934936 AYYNBAAOMJUSMN-UHFFFAOYSA-N 329.385 2.116 30 1 EEEF N#CCNC(=O)C1(NC(=O)[C@H]2C[C@@H]2c2ccccc2)CCCCC1 169329185 OZKIIHXGQDWWDV-CVEARBPZSA-N 325.412 2.249 30 1 EEEF Cc1cc(C#N)ccc1-c1cnn2c1C[C@@H](Oc1ncc(C#N)cn1)C2 1857638034 CZYSZPKHECVEPV-OAHLLOKOSA-N 342.362 2.396 30 1 EEEF CC1=C(C(=O)O)C(=O)C[C@@H]2CCC[C@@]3(C(=O)Nc4ccccc43)N12 103558964 QQDWEMDBMCNRPU-BBATYDOGSA-N 326.352 2.020 30 1 EEEF biogenic,in-vitro C=C1[C@H]2OC(=O)C=C(C)[C@@H]2C[C@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@@H]12 2356470957 LUHDPMVWXCNPMF-NBOOPKSLSA-N 344.407 2.477 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@@H]3C[C@H](OCC(C)=CC)[C@H]12 2356499439 DMVINTHATJOGFW-HTPGKPQGSA-N 334.412 2.304 30 1 EEEF COc1ccc(S(=O)(=O)[C@@H](CC(=O)NO)C2CCCCC2)cc1 29395923 NATAMMXFTCDJKF-HNNXBMFYSA-N 341.429 2.313 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cc4c(cc3[nH]2)OCCO4)C1=O 587038636 KGVYMNGWHUTTAD-CYBMUJFWSA-N 345.380 2.127 30 1 EEEF C=CCN(c1cc(OC)c2[nH]cc(C)c2c1[N+](=O)[O-])S(C)(=O)=O 5922556 AMLCYZHBZIOVGO-UHFFFAOYSA-N 339.373 2.345 30 1 EEEF C=CC[C@@]12C[C@H](OC)[C@H](O)[C@@H]([C@H](c3ccc4c(c3)OCO4)[C@H]1C)[C@H]2O 2356606165 GGFOVZYLYBVWDX-DGTJJKBJSA-N 346.423 2.468 30 1 EEEF O=C(NO)c1ccc(NC(=O)C2(c3ccccc3)CCOCC2)cc1 1911577736 BDDFTHXWMIKMQG-UHFFFAOYSA-N 340.379 2.493 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc2ncc(C(=O)O)n2c1 587912563 KRTCEPNPVCSKLN-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF N#Cc1ccc([C@H](O)C2=C3C=C[C@@H]4C[C@@]3(OC2=O)[C@H]2CCCCN42)cc1 1772599225 QFVVQFMCFLHDCD-DOSUHQCWSA-N 348.402 2.380 30 1 EEEF C[C@@H]1CC2=C([C@@H]1O)[C@H](O)[C@]1(C)CC[C@@H]3[C@H]([C@@H](O)[C@@]1(C)C2=O)C3(C)C 2356843629 NNSBPFCEWFSYFB-GQPYSQPKSA-N 334.456 2.067 30 1 EEEF COC1=C[C@]23CCN(C)[C@H](Cc4cc(OC)c(OC)cc42)C3=CC1=O 36375305 DBPGJIUVRZHFCM-FOIQADDNSA-N 341.407 2.241 30 1 EEEF COC1=C[C@]23CCN(C)[C@H](Cc4ccc(OC)c(O)c42)[C@@H]3CC1=O 38214211 OWDQPILTDJLGCN-QUJCMNEKSA-N 329.396 2.018 30 1 EEEF biogenic,in-vitro CC(C)C[C@@H]1CC(=O)N(OS(=O)(=O)/C=C/c2ccccc2)C1=O 40368906 VGLWWYDLFOPKIU-MYSGNRETSA-N 337.397 2.340 30 1 EEEF Cc1onc(N)c1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587880190 GWMMNHODECWWHU-UHFFFAOYSA-N 338.194 2.582 30 1 EEEF COc1ccc(N2C(=S)[C@H](C#N)C(=O)N[C@@H]2c2ccco2)cc1 169688084 PSLDKXQWVTXHEX-OCCSQVGLSA-N 327.365 2.390 30 1 EEEF O=C(c1cc2ccn(Cc3ccc(F)cc3)c2cn1)N(O)CCCO 34640561 HIIHFGJAMHWFDH-UHFFFAOYSA-N 343.358 2.438 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1CCC(=C)[C@@H]1C[C@H](OC(C)=O)[C@@H](COC(C)=O)[C@@H]12 137399519 ZDLGBDAERSQVPY-SOMFZHDCSA-N 348.395 2.181 30 1 EEEF C=CC1=CC(=O)[C@@H]2[C@@H](CC[C@@H]3C(C)(C)[C@H](O)[C@H](O)[C@H](O)[C@]23C)[C@@H]1C 86007149 XFRCVLKGZMPUFQ-YNUUYJBFSA-N 334.456 2.089 30 1 EEEF in-man COCC(=O)N1[C@H](C#N)[C@H](c2ccc(C3=CCCC3)cc2)[C@H]1CO 95897806 SMEVBYXHWQHXGK-LMMKCTJWSA-N 326.396 2.079 30 1 EEEF C/C1=C\CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)[C@@H](CNCCCCN)[C@@H]2CC1 141174261 ZMDVEVDXHVWYSY-BWWWVOLUSA-N 336.476 2.151 30 1 EEEF CN(/N=C/c1cnn2ccc(Cl)nc12)S(=O)(=O)c1ccccc1 473112764 GGBHZIZDAKPCPO-CXUHLZMHSA-N 349.803 2.037 30 1 EEEF C#CCN1C(=O)[C@]2(CC(=O)c3cc(C)cc(N)c3O2)c2ccccc21 587401627 URMCMTZQJLXXDG-FQEVSTJZSA-N 332.359 2.418 30 1 EEEF O=C(/C=C/c1cccn1Cc1ccc([N+](=O)[O-])cc1)CC(=O)C(=O)O 29465971 UENLGQCTAOVPBW-BQYQJAHWSA-N 342.307 2.071 30 1 EEEF CC(C)Oc1c(Br)csc1/C(O)=N/c1nn[nH]n1 26287840 GVGHSRDTZCPOBD-UHFFFAOYSA-N 332.183 2.447 30 1 EEEF CCOCc1nc2c(=N)[nH]c3cc(C#N)ccc3c2n1CC(C)(C)O 1911570360 ZGJAPHADBJAWID-UHFFFAOYSA-N 339.399 2.176 30 1 EEEF Cc1cccc(S(=O)(=O)N2CCC(CCCC(=O)NO)CC2)c1 73137932 XFTBVOPSQWCKEG-UHFFFAOYSA-N 340.445 2.071 30 1 EEEF C=CCN1CCN(c2ccc([C@@H]3CC(C(=O)OCC)=NO3)cc2)CC1 40917464 RHXISXRGOQBKAI-SFHVURJKSA-N 343.427 2.375 30 1 EEEF CCC/C=C/[C@@H]1C(=O)[C@@H]2O[C@H]2C2(OCC(CC)(CC)CO2)[C@H]1CO 198013670 TWGDZVIUZPIUAD-UHTQQLPRSA-N 338.444 2.467 30 1 EEEF CC=C(C)C(=O)O[C@@H]1CCN2C[C@H]3C[C@@H](CN4C=CC(=O)C[C@H]34)[C@@H]2C1 2356436102 ANLPQANGWMODSI-CGHHPOIWSA-N 344.455 2.136 30 1 EEEF CS(=O)(=O)N1CCC2(CCN(Cc3ccc(C#N)cc3)CC2)CC1 4237934 AURSRBAFRMWTLH-UHFFFAOYSA-N 347.484 2.196 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@](C)(C(=O)OC1)[C@H]2[C@H]3C(=O)O 100778377 QYXZQZMPZUEEML-YOWPGMQCSA-N 346.423 2.384 30 1 EEEF endogenous,in-man C=C1C(=O)O[C@@H]2C3=C(C)C(=O)C[C@@H]3[C@](C)(O)C[C@@H](OCC(C)C)[C@H]12 2356491341 IDJQTNTZPPTSEU-FYKYKLLDSA-N 334.412 2.186 30 1 EEEF CCCCn1c(=O)c(C#N)nn(-c2cccc(C(F)(F)F)c2)c1=O 49020489 UKVJBAHKBGRBSK-UHFFFAOYSA-N 338.289 2.085 30 1 EEEF N#C[C@H]1[C@H](c2ccc(-c3cncnc3)cc2)[C@@H](CO)N1C(=O)C1CCC1 95897721 RYHHKKTZXOEYDH-OTWHNJEPSA-N 348.406 2.123 30 1 EEEF CN(Cc1nc2ccc(C#N)cc2[nH]1)S(=O)(=O)c1ccc(F)cc1 587170769 SDYSLTWUSCZLHA-UHFFFAOYSA-N 344.371 2.394 30 1 EEEF C=C1[C@H]2C[C@H](O)[C@@H]3[C@]4(C)CC[C@H](O)C(C)(C)[C@H]4C(=O)C[C@@]3(C2)[C@@H]1O 2356406447 WSZHSVSVZWABOB-ULGMGIKYSA-N 334.456 2.067 30 1 EEEF Cn1ncc(C#N)c1NC(=O)[C@H]1CC(c2ccccc2Cl)=NO1 4504953 OBMDODZBSHAYHD-CYBMUJFWSA-N 329.747 2.077 30 3 EEEF C(#Cc1ccccc1)CSc1nsnc1C12CN3C[C@H]1[C@@H]2C3 100829399 YRHXYFPBQSSIPM-KBPBESRZSA-N 325.462 2.495 30 1 EEEF COc1ccc(C(=O)N2Cc3cnnn3-c3ccccc3[C@@H]2C#N)cc1 61942556 SSHNWICKICVEKS-SFHVURJKSA-N 345.362 2.497 30 3 EEEF CC(C)[C@@H]1CC[C@]23C[C@@H]4[C@H](C)C(=O)[C@@H]5O[C@@]54[C@]2(C)C(=O)[C@@H](O)[C@@]13C 2356871569 YCAWNFYZBRTGCT-RXYCDUMSSA-N 332.440 2.371 30 1 EEEF N#CCNC(=O)[C@H](CCCc1ccccc1)NC(=O)c1ccccc1 82064521 MHIDKDIIXBZHSJ-SFHVURJKSA-N 335.407 2.448 30 1 EEEF CSCC/C(=N/Nc1ccc([N+](=O)[O-])cc1[N+](=O)[O-])C(=O)O 238770080 IRLXZFCUAWIZQW-LCYFTJDESA-N 328.306 2.109 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@H]([C@H](C=O)[N+](=O)[O-])N1 587747119 PDDFVXQYGACOIB-LKXWSVAYSA-N 331.141 2.008 30 1 EEEF C[C@@]1(c2nc3nc(C#N)c(C#N)nc3[nH]2)C=C(c2ccccc2F)NO1 587157079 SDWWSOYTBOMBAM-KRWDZBQOSA-N 347.313 2.026 30 1 EEEF O=C(CCCCCCNC(=O)c1cc(-c2ccc(F)cc2)[nH]n1)NO 1857757910 GLUNWMQGDQEBAS-UHFFFAOYSA-N 348.378 2.402 30 1 EEEF CC1(C)C(=O)c2ccc(C#N)cc2[C@@H](NC(=O)c2ccccn2)[C@@H]1O 3783957 KEZLFRWXEUCVSJ-WBVHZDCISA-N 335.363 2.008 30 1 EEEF C=C1C[C@@]23C[C@@]1(O)CC=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)OC 2356473034 QQZHQZNECSBZML-QVFZOTCZSA-N 344.407 2.289 30 1 EEEF C=C1[C@H]2C[C@H](O)[C@@]3(C(=O)C[C@@H]4C(C)(C)[C@H](O)CC[C@]4(C)[C@@H]3C2)[C@@H]1O 2356634479 FYHBINXIARYPCI-KSZJCDRGSA-N 334.456 2.067 30 1 EEEF CC1(C)CN(CCO)C(=O)[C@@H]1Oc1ccc(C#N)c(C(F)(F)F)c1 73199081 LGMVZCFSPAZMCM-ZDUSSCGKSA-N 342.317 2.185 30 1 EEEF Cc1cc(C)c(C)c(OCCCO/N=C(/N)NC(=N)NC(C)C)c1 27308808 DRCRDHNBAWMWHJ-UHFFFAOYSA-N 335.452 2.149 30 1 EEEF O=C(NO)[C@H](Cc1ccccc1)C(=O)NCc1ccc(Cl)cc1 28604498 MDFALTKCDXYVEX-OAHLLOKOSA-N 332.787 2.321 30 1 EEEF in-vivo CC(C)(C)C(=O)CN1C(=O)[C@H](CC(=O)NO)Sc2ccccc21 29247241 UKQILYFNJNVXDG-LBPRGKRZSA-N 336.413 2.005 30 1 EEEF C=C(C)[C@H]1[C@@H]2C[C@H](C)[C@H]3CC[C@H](C)[C@H]4C(=O)[C@]1(O)[C@@](C)(O)C(=O)[C@]234 137446581 MNSYHSSUTWIPGM-VPYUHVSESA-N 332.440 2.131 30 1 EEEF C[C@@H]1CC(=O)[C@H](Cc2nc3cc(Cl)nc(C#N)c3[nH]2)[C@H]1C[N+](=O)[O-] 587265994 YQSUHXZFPMTARU-HLTSFMKQSA-N 347.762 2.143 30 1 EEEF C[C@H]1C[C@@H]2O[C@H]2CC/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 105564233 XFALPAMSDFFXGY-WSQXNAIUSA-N 332.352 2.262 30 1 EEEF COc1ccc(S(=O)(=O)[C@H](CC(=O)NO)C2CCCCC2)cc1 29395925 NATAMMXFTCDJKF-OAHLLOKOSA-N 341.429 2.313 30 1 EEEF CCN(C)c1ncc(C#Cc2ccc(C[C@@H](C)NC(C)=O)cc2)cn1 113412500 IGGLVNBBXXXTDP-OAHLLOKOSA-N 336.439 2.400 30 1 EEEF N#Cc1ccc2c(c1)CC[C@@H]2N1C[C@H](N)[C@H](C(=O)[C@@H]2CCC[C@H]2C#N)C1 28955125 ZAWGLJVNJZBVID-VRCPBSEVSA-N 348.450 2.314 30 1 EEEF C[C@H](O)[C@@H]1C(O)=C(C(=O)[C@@H]2[C@H](C)C=C[C@H]3CCCC[C@H]32)C(=O)N1C 2356723588 NOYBJWXGAYWITN-NVWMEEMDSA-N 333.428 2.218 30 1 EEEF CCN/C(=N\S(=O)(=O)c1ccc(Cl)cc1)N1C[C@H](CC)C=N1 72123464 RMRMGNRTOXJZLL-LLVKDONJSA-N 342.852 2.322 30 1 EEEF CCC(=O)C[C@H](C)[C@@H]1O[C@]1(C)/C=C\C(=O)N[C@H](CO)[C@@H](C)CC 210913566 RDWBIAZAAVLQEC-IPYSNMQBSA-N 325.449 2.229 30 1 EEEF C=C1C[C@]23C[C@H]1[C@@H](O)C[C@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 70454928 IPHNMKITOREFLW-MTVNJVDJSA-N 332.396 2.136 30 1 EEEF biogenic,in-vitro C[C@@H]1Cc2ccc(F)c(Br)c2[C@]2(COC[C@H]2C#N)N1 587739117 FRFVAZZMRPQOFX-PJCOJXEDSA-N 325.181 2.488 30 1 EEEF C=C1[C@@H](O)C[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1C[C@H](O)[C@H]1CC(=O)NC1=O 166794629 PPQGMYUYEYHPEL-ZVZFHZCBSA-N 349.471 2.170 30 1 EEEF COc1c(C)c2c(c(OC)c1C/C=C(\C)CCC(=O)NO)C(=O)OC2 28870024 VEURGGSTVLSJTB-BJMVGYQFSA-N 349.383 2.457 30 1 EEEF COc1c(O)cc2c(c1O)C(=O)C(=Cc1ccc(O)c(O)c1)CO2 2356625369 KUIRIGZNHOTLPQ-UHFFFAOYSA-N 330.292 2.176 30 1 EEEF O=C(OCCOCCOCCOCCS)c1ccccc1S 82158217 PBXMRPFCIQVZIL-UHFFFAOYSA-N 346.470 2.112 30 1 EEEF C=C1C[C@H](OC(C)=O)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@@H](OC(C)=O)C[C@@H]12 238740503 BDUMUWUQRSWNQA-UXJCHEOYSA-N 346.379 2.100 30 1 EEEF C=C1C2=C(C(=O)N1OC)[C@H](O)[C@](C)(O)[C@H](CCCCCCC)O2 2356342528 FLJXRCWDXADIBL-YLQAJVPDSA-N 325.405 2.029 30 1 EEEF Fc1cc(F)cc(C#CCOc2nsnc2C23CN4C[C@H]2[C@@H]3C4)c1 100829320 RWIBKAGXMHMEFU-KBPBESRZSA-N 345.374 2.060 30 1 EEEF O=C(/C=C/c1ccc(NS(=O)(=O)Cc2ccccc2)cc1)NO 116083751 APAVEJNRRDVCGG-DHZHZOJOSA-N 332.381 2.147 30 1 EEEF C=C1C[C@]23C[C@@]4(O)CN5C[C@@]6(C)CCC[C@@]7([C@H]64)[C@H]2C(=O)[C@@H]1C[C@@H]3[C@@H]57 2356506554 MGEDPNBPAMLIHW-PUTNOJKFSA-N 325.452 2.393 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@@H]1CC(=O)[C@@H]2[C@]1(C)CCCC(C)(C)[C@@H]1[C@H](O)[C@H]3O 2356643668 AUVGEKXCVIHEPI-QVLSARIOSA-N 334.456 2.067 30 1 EEEF C=C[C@](C)(O)[C@H](O)C[C@@H]1C(=C)[C@H](O)C[C@H]2[C@]1(C)CCC[C@@]2(C)CO 2356651821 CYJDHAXSZJABJA-PDKYLHCFSA-N 338.488 2.416 30 1 EEEF COc1cc2c3c(c1OC)C1(C=CC(=O)C=C1)C[C@@H]3N(C=O)CC2 14679736 ZRWKJCKLHBPSBY-AWEZNQCLSA-N 325.364 2.096 30 1 EEEF biogenic C[C@]1(CO)CCC[C@@]2(C)C3=CC(=O)[C@@H]4C[C@]3(C[C@@H]4CO)[C@@H](O)C[C@H]12 238751788 YJMRIEXSUIQKDN-FLSQSPPCSA-N 334.456 2.070 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc2cc(C(=O)O)nn2c1 587912608 LNDUZWNKGISADE-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF CCNc1ncc2nc(-c3cccc(C#N)c3)c(=O)n(CCC#N)c2n1 4239076 VQVNCPSPZCGTCS-UHFFFAOYSA-N 345.366 2.071 30 1 EEEF Cc1nc2ccc(C#C[C@](C)(O)CC3CC3)cc2n1-c1ncnc(N)n1 103249632 QLGJIHXONUCKCU-IBGZPJMESA-N 348.410 2.004 30 1 EEEF CC=CC(=O)O[C@H]1[C@@H](O)[C@]2(C)[C@@]3(C)CCC(C)=C[C@H]3O[C@H]1[C@]21CO1 2356845518 OFRDWLCMCXXLSX-IXLDOGFXSA-N 334.412 2.138 30 1 EEEF CC(C)(O)C(C)(C)OB(OC(C)(C)C(C)(C)O)c1cccnc1F 221636395 TUOBLEREGFFHHU-UHFFFAOYSA-N 341.232 2.048 30 1 EEEF COC(=O)c1ccc(-c2c(C#N)n(O)c3cc(C)ccc3[n+]2=O)cc1 139308283 NSCNZEDHGIJBQG-UHFFFAOYSA-N 336.327 2.427 30 1 EEEF O=S(=O)(c1ccc(C#Cc2cccc(F)c2)cc1)N1CCOCC1 95560306 DIYDPHCIBOZKIZ-UHFFFAOYSA-N 345.395 2.246 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1cncnc1O 587880205 HBMVHOOFAURWQR-UHFFFAOYSA-N 336.178 2.199 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cn(CCC(=O)O)nc1[N+](=O)[O-] 587909491 SQSAFVUMOKMSEA-UHFFFAOYSA-N 349.730 2.328 30 1 EEEF N#Cc1ccc(N2C(=O)[C@@H]3[C@@H]4CC[C@H](O4)[C@@H]3C2=O)cc1C(F)(F)F 101488338 QZRQLVZGQQVBIK-ZDEQEGDKSA-N 336.269 2.244 30 1 EEEF O=C(C[C@H](S)C(F)(F)F)N[C@H](Cc1ccc(F)cc1)C(=O)O 43066215 PGJZLTNQRTXDPB-ZJUUUORDSA-N 339.310 2.188 30 1 EEEF COc1ccc(-n2cc(Cn3cc(/C=N/O)c4cccnc43)nn2)cc1 653716952 BPJOFDHMJSGOKY-AWQFTUOYSA-N 348.366 2.482 30 1 EEEF C=C(C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)C(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 5158262 ZGDWDAMVZDRRQA-NQLMQOPMSA-N 330.380 2.085 30 1 EEEF biogenic C=C1C(=O)[C@@]23[C@H](O)C[C@@H]4C(C)(C)CCC[C@]4(C(=O)O)[C@@H]2CC[C@H]1[C@H]3O 2356455478 VBQWGSKSQFBYOX-RJVMHIQOSA-N 348.439 2.161 30 1 EEEF CN1C[C@]23C[C@H](O)[C@H]4[C@@H](CCC5=CC(=O)C=C[C@@]54C)[C@@H]2CC[C@H]3C1=O 2356501573 GDWBXDLUQZIGKG-QMFSJDNRSA-N 341.451 2.333 30 1 EEEF COc1c2c(c(OC)c3c1C(=O)C1=C(C3=O)[C@@H](C)O[C@@H](C)C1)OCO2 14827940 FRYKBCAHLYVUDQ-JGVFFNPUSA-N 346.335 2.305 30 1 EEEF biogenic C=C1C(=O)O[C@H]2C[C@]3(C)C(=C(C)CC[C@H]3OC(C)=O)[C@@H](OC(C)=O)[C@H]12 238777572 DNNWITSSRUKCLW-DONWEKBKSA-N 348.395 2.468 30 1 EEEF C[C@H]1CCC(=NN(C)c2ccccc2)c2ncc(C(=O)O)c(=O)n21 253683903 DXCAOAFKYKPQRQ-NSHDSACASA-N 326.356 2.137 30 1 EEEF C[C@@](Cc1ccccc1)(C(=O)NO)C(=O)NCCCc1ccccc1 13528320 UTCZFYMAGMNXSW-FQEVSTJZSA-N 340.423 2.490 30 1 EEEF C[C@](O)(C#Cc1cn2nc(-c3ccco3)nc2c(N)n1)c1ccccc1 13978291 MUBQTNOOAXJJSD-IBGZPJMESA-N 345.362 2.226 30 1 EEEF CCN/C(=N\S(=O)(=O)c1cccc(Cl)c1)N1C[C@H](CC)C=N1 72122809 MKGZFKFZQDUADL-LLVKDONJSA-N 342.852 2.322 30 1 EEEF COc1ccc(CCC(=O)NC2(C(=O)NCC#N)CCCCC2)cc1 169329173 FPUMZGVACLYJFH-UHFFFAOYSA-N 343.427 2.087 30 1 EEEF CC1=C(N2[C@H](C)[C@H]2C)C(=O)C(Br)=C(N2[C@@H](C)[C@@H]2C)C1=O 169335121 RKTOSHDREXTIII-IMSYWVGJSA-N 339.233 2.204 30 1 EEEF Cc1c(O)cc(C[C@@H](C)O)c2cc(C3=CC(=O)C[C@H](C)O3)c(=O)oc12 14594761 QOKXUEDIOODDAI-ZJUUUORDSA-N 344.363 2.449 30 1 EEEF biogenic C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@H](C(=O)O)[C@H]1[C@@]2(C)CCC[C@@]31OC2=O 257480365 MBNDVMTZEKAWKP-AMAVCMRRSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C[C@H]1Cn2c(N=C(N)N)nc3cc(Cl)cc(c32)CN1CC1CC1 5890713 CJHRVDIZIMGJJA-VIFPVBQESA-N 332.839 2.209 30 1 EEEF CC#CCOc1ccc([S@@](=O)[C@@H](C(=O)NO)c2ccccc2)cc1 13585970 LMLJZJGMFKPKNY-OSPHWJPCSA-N 343.404 2.443 30 1 EEEF CCOC(=O)[C@H](C#N)[C@@H]1c2ccccc2OC(=N)[C@@H]1C(=O)OCC 169719787 KJGRHZCOMOPYTQ-KWCYVHTRSA-N 330.340 2.022 30 1 EEEF CN=C1NC(=Cc2c[nH]c3cc(Br)ccc23)C(=O)N1C 2356511059 WIJJEZADZQGDSE-UHFFFAOYSA-N 333.189 2.319 30 1 EEEF CC(=O)[C@@H](O)Cc1c(O)ccc(C(=O)C=Cc2ccc(O)cc2)c1O 2356784046 MZOMYVOGPUTEFR-SFHVURJKSA-N 342.347 2.192 30 1 EEEF CCSCC[C@H](NC(=O)OCc1ccccc1)C(=O)NCC#N 82064869 ZGKHJIRHVYSKEM-AWEZNQCLSA-N 335.429 2.064 30 1 EEEF Cc1ccc(C(=O)/C=C\c2nc3ccc(S(N)(=O)=O)cc3[nH]2)cc1 587965276 IZPOYDZNOLOYNG-HJWRWDBZSA-N 341.392 2.415 30 1 EEEF C=CC[C@@]1(OCc2ccccc2)C(=O)C(=O)O[C@H]1[C@@H]1COC(C)(C)O1 17259959 QUSJNYTVFAJGCT-URLQWDBASA-N 346.379 2.164 30 1 EEEF C#CCN(C)C[C@@H]1CN2CC[C@H]1C[C@H]2CNC(=O)Nc1ccsc1 2356298901 IYIDYUMTPGQBJD-UXLLHSPISA-N 346.500 2.145 30 1 EEEF C=CCN1CCN(CC(=O)[C@](O)(c2ccccc2)C2CCC2)CC1 22940322 ZMNUXXPBCFVUNL-FQEVSTJZSA-N 328.456 2.047 30 1 EEEF C=C1[C@@H]2C[C@H]3[C@]4(C)CCC(=O)C(C)(C)[C@H]4CC[C@]3(C(=O)[C@@H]2O)[C@H]1O 238753798 JSGKBZHXHVBDMU-MGPIMVJZSA-N 332.440 2.275 30 1 EEEF CC1(C)[C@H](C(=O)N=C(N)N)[C@H]1c1ccc(F)c(Br)c1 13864221 AOXSBTBCCUZZSC-ZJUUUORDSA-N 328.185 2.128 30 1 EEEF C=C(CO)[C@H]1CC2=CC[C@H]3[C@@](C)(CC[C@@H](O)[C@]3(C)CO)[C@@H]2C[C@@H]1O 207619220 VJVZOSZFDKSLNA-KSLKBLKXSA-N 336.472 2.028 30 1 EEEF O=C(/C=C/c1cccn1Cc1ccc(F)c(F)c1)CC(=O)C(=O)O 103295941 HKUAVJFTSBBMRW-SNAWJCMRSA-N 333.290 2.441 30 1 EEEF O=C(CCCCCCC(=O)Nc1ccc2c(c1)CCC(=O)N2)NO 222875508 HXDYRFDOQYZPBS-UHFFFAOYSA-N 333.388 2.356 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)(CC[C@@H](O)[C@@]4(C)CO)[C@H]2C[C@@H](O)[C@H]1C3 2356417363 YYNFNCPHITUVRP-TXRUPPPDSA-N 334.456 2.068 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@H]2[C@@]12CO[C@@H]4OC[C@@](C)(CC[C@@H]1OC3=O)[C@H]42 103109409 QRZAIOQXVJRCBS-CMKHACMRSA-N 344.407 2.243 30 1 EEEF N#Cc1cccc(CN2CC[C@@H]3CO[C@@H](CN4CCCC4)[C@@H]3C2)c1 107202355 JQPKVYRPIBQALQ-AQNXPRMDSA-N 325.456 2.491 30 1 EEEF C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@H](O)[C@@H]1C(=C)[C@H](C)CC[C@]21C 2356574597 GCVDFMXIDUYWBG-DBUDBLFLSA-N 344.407 2.167 30 1 EEEF CCOc1cccc(CCn2cccc(/C=C/C(=O)NO)c2=O)c1 143875064 KLXKWWDJEHNMKO-CMDGGOBGSA-N 328.368 2.008 30 1 EEEF C=C1C[C@]23CC[C@@H]4C(CO)(CO)CC(=O)C[C@]4(C)[C@@H]2[C@H](O)C[C@H]1C3 5843240 SRLVFQVUOGIQFP-IZGXTJEISA-N 334.456 2.070 30 1 EEEF C=C1[C@@H](O)CC[C@]2(C)[C@@H]1C[C@@H]1C[C@H](O)C(C)=C([C@@H](O)[C@@H]2O)C1(C)C 103586676 FMWULVIPGFAKFN-KYOGYUBWSA-N 336.472 2.169 30 1 EEEF biogenic,in-vitro C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@@]12CO[C@@H]4OC[C@@](C)(CC[C@@H]1OC3=O)[C@@H]42 103109413 QRZAIOQXVJRCBS-BZNVISFXSA-N 344.407 2.243 30 1 EEEF C[C@@H]1C[C@]23C(=O)[C@H](C)C[C@@H]4C(C)(C)[C@]45O[C@@](C)(C=C2C1=O)[C@H](O)[C@H]53 2356522876 XKHKWWYWWNXZDZ-VCXRVSLSSA-N 330.424 2.291 30 1 EEEF C=C(CC[C@@H](O)C(C)(C)O)[C@@H](O)COc1ccc2ccc(=O)oc2c1 14587283 GOOJJMAKBXRBIG-DOTOQJQBSA-N 348.395 2.001 30 1 EEEF biogenic C=C[C@]1(CO)CC[C@@H]2[C@H](CC[C@H]3[C@H]2CC[C@@H](O)[C@]3(C)C(=O)OC)O1 40845781 FUFHOMLKBCCTIV-ZONKCHNNSA-N 338.444 2.059 30 1 EEEF N#CCC[C@@]1(c2cccnc2)N[C@H](C(=O)O)Cc2cccc(F)c21 962898689 MFAIZCRLGMMKKH-YJBOKZPZSA-N 325.343 2.367 30 1 EEEF CS(=O)(=O)N1Cc2ccccc2C[C@@H]1/C(O)=N/Cc1ccco1 213576 FVMDWQCAHRVRNX-OAHLLOKOSA-N 334.397 2.123 30 1 EEEF N#Cc1ccc(-n2c(O)c3n(c2=O)CC[C@H]3O)cc1-c1ccccc1 169719903 ZSNYYLJANJNVRB-MRXNPFEDSA-N 333.347 2.320 30 1 EEEF O=C(C#Cc1ccc([N+](=O)[O-])cc1)c1cn(Cc2ccccc2)nn1 1857758278 FHWFKSRZNYTUMV-UHFFFAOYSA-N 332.319 2.469 30 1 EEEF C=C1[C@H]2CC[C@]3([C@H]1O)[C@H]1C[C@@H]4[C@]5(COC(=O)[C@]4(C)CC[C@H]5O1)[C@H]3C2 2356785280 SEUIPTLIXVTZIG-HPSVQNBCSA-N 330.424 2.450 30 1 EEEF NS(=O)(=O)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F 49780183 KKHMBQUHTGIUDQ-UHFFFAOYSA-N 327.168 2.133 30 1 EEEF CCC#CCOc1nc2oc(=O)cc(CCC3CCC3)c2c(=O)[nH]1 82158158 MGJXFBLDBRUPRX-UHFFFAOYSA-N 328.368 2.401 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O[C@H]([C@@H]21)[C@@H]3O 257506483 OSYJLXUUZYSFTC-QQPALEHNSA-N 332.440 2.432 30 1 EEEF endogenous,in-man COc1ccc(Cl)cc1C#Cc1cc(F)cc2[nH]c(=O)c(=O)[nH]c12 587917879 UZYUAYGYHZICDU-UHFFFAOYSA-N 344.729 2.417 30 1 EEEF Cc1cccc2c1NC(=O)[C@@H]2/C=N/c1ccc(S(N)(=O)=O)cc1 169727075 SKFOKDNXKMEDPH-UHPUNMKFSA-N 329.381 2.081 30 1 EEEF C=C(C)C(=O)O[C@@H]1CCC(=C)[C@@H]2[C@@H]3OC(=O)[C@H](C)[C@@H]3[C@H](O)C[C@@]21C 2356480135 QHTWVJOMDDBORA-LGJYOPEASA-N 334.412 2.389 30 1 EEEF O=C1C(F)=C(N2CCOCC2)C(=O)c2c(F)c(F)c(F)c(F)c21 66259091 MJFIPCNOPAUJCF-UHFFFAOYSA-N 333.212 2.135 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)[C@H](C)C[C@@H]2OC(=O)C(=C)[C@H]21 254133132 KYTKEOOPALLADL-AOMCHWLGSA-N 346.379 2.244 30 1 EEEF Cc1nc(C2CC(C(=O)/C=C/c3cnc4c(c3)CCC(=O)N4)C2)no1 169707514 LNJLBIXSZSNLLP-DUXPYHPUSA-N 338.367 2.434 30 1 EEEF COc1ccc(CN2CCN(c3ccc(C(=O)NO)cc3)C2=O)cc1 205704695 BHZBZYCRXWOUJU-UHFFFAOYSA-N 341.367 2.256 30 1 EEEF CCCCCC=CC1=C(CO)C(=O)[C@H]2O[C@@]2(CC=C(C)C(=O)O)C1=O 2356716672 UJNVMSXVUCFBMB-MJGOQNOKSA-N 348.395 2.122 30 1 EEEF COc1ccnc(NC2CCN(C(=O)c3ccc(C#N)nc3)CC2)c1 72107520 ITVKOVUYAWRKNF-UHFFFAOYSA-N 337.383 2.074 30 1 EEEF COc1ccc(/C=C/C(=O)c2c(O)cc(O)c(OC)c2O)cc1O 15274475 GYEZIQDCZWTBTP-HWKANZROSA-N 332.308 2.422 30 1 EEEF COC1=C(OC)C(=O)/C(=C2\NC=NC=C2c2csc(C)n2)C=C1 104002341 DNJBMNXUGGMXNG-UVTDQMKNSA-N 329.381 2.321 30 3 EEEF COc1ccc(/C=C/C(=O)/N=C(\N)N/N=C/c2ccc(F)cc2)cc1 49034243 GGWAKURQHXYUSC-NEHYNPCWSA-N 340.358 2.313 30 1 EEEF CC1=C[C@@]2(O)/C(=C\[C@@](C)(O)CC[C@H]3[C@@H](C[C@@H](C)[C@@H]2O)C3(C)C)C1=O 238749194 CZUBZNDQQZRXMB-NDWWEPFFSA-N 334.456 2.377 30 1 EEEF CC(C)[C@H]1CC[C@]23C[C@@H]4[C@H](C)C(=O)[C@H]5O[C@]54[C@@]2(C)[C@@H](O)C(=O)[C@]13C 1772654535 QRAOOADPSNNYON-GUMRYWFSSA-N 332.440 2.371 30 1 EEEF C=C[C@@H]1CN2[C@H]3C[C@]45c6ccccc6N[C@@]4(O3)[C@H]2C[C@H]1[C@H]5C(=O)OC 2356762802 VQQRVBOFQXPEAN-FGIZOLGGSA-N 338.407 2.102 30 1 EEEF CC(C)[C@@H]1CC[C@]23C[C@@H]4[C@H](C)C(=O)[C@@H]5O[C@@]54[C@]2(C)C(=O)[C@H](O)[C@@]13C 2356871568 YCAWNFYZBRTGCT-LAIDARAASA-N 332.440 2.371 30 1 EEEF CC1=C(OCCN2C(=O)C(=O)c3cc(C)ccc32)[C@H](C)SC1=O 71329923 ISOWPJUDFHSJBK-NSHDSACASA-N 331.393 2.477 30 1 EEEF CC1=CC(=O)C2=C(C)C[C@H](OC(C)(C)C)[C@@H]3[C@H](C)C(=O)O[C@H]3[C@@]12O 2356331207 GFSKBOWVEKODGN-JCELZLRTSA-N 334.412 2.328 30 1 EEEF CCn1c(C(=O)c2cc(C)cc(C#N)c2)c(C(C)(C)C)c(=O)[nH]c1=O 49036983 JPGSLVKOUHOFMK-UHFFFAOYSA-N 339.395 2.265 30 1 EEEF C[C@@H]1CC(=O)[C@@H](Cc2nc3cc(Cl)nc(C#N)c3[nH]2)[C@H]1C[N+](=O)[O-] 587266134 YQSUHXZFPMTARU-VGMNWLOBSA-N 347.762 2.143 30 1 EEEF Cc1nn(-c2ccc([N+](=O)[O-])cc2)c(O)c1/C=N/C[C@@H]1CCCO1 101888680 WDMAQOAAIYXHRE-FBJMNJBLSA-N 330.344 2.392 30 1 EEEF CC=CC=CC(=O)NCCC[C@@H]1NC(O)=C(C(=O)C=CC=CC)C1=O 2356700594 UOPXXWDGQCFNHZ-AWEZNQCLSA-N 344.411 2.027 30 1 EEEF N#Cc1ccnc(C(=O)Nc2ccc([C@@H]3CNCCO3)cc2F)c1 149862020 SIRAEEFSAZVTRZ-INIZCTEOSA-N 326.331 2.006 30 1 EEEF COc1ccc(S(=O)(=O)[C@@](C)(CC=C(C)C)C(=O)NO)cc1 13520767 COEXRWHXVMMHEF-HNNXBMFYSA-N 327.402 2.089 30 1 EEEF C=C1[C@@H]2CC[C@@H]3C[C@@]2(C[C@@H](O)[C@@]2(O)[C@@H]1C[C@H](O)C2(C)C)C[C@@]3(C)O 1857575896 AHMSDGIIEDDLQI-CSMKTOTHSA-N 336.472 2.003 30 1 EEEF NS(=O)(=O)c1ccc(C/N=C/c2coc3ccccc3c2=O)cc1 28525044 AEECELZBHQHFHH-VXLYETTFSA-N 342.376 2.060 30 1 EEEF CNC(=O)/C(=N/OC)c1ccccc1COc1cccc([N+](=O)[O-])c1 103184429 JQRHTBAWRJOLBC-KNTRCKAVSA-N 343.339 2.270 30 1 EEEF C=C1CC[C@H]2C[C@H](O)C3=C(C(=O)[C@@H](C(C)=C[C@@H](O)C1)[C@@H]3O)C2(C)C 2356605254 YZCJZJQRTRSJHJ-PQKJENKHSA-N 332.440 2.297 30 1 EEEF Cc1noc(C)c1COc1ccc(C(=O)N2CCOC[C@H]2C#N)cc1 76042350 VWDYGRPFQCZWMD-OAHLLOKOSA-N 341.367 2.235 30 1 EEEF CC(C)(O)C(C)(C)OB(OC(C)(C)C(C)(C)O)c1ccncc1F 221635178 KBRAJCNFHBYXDH-UHFFFAOYSA-N 341.232 2.048 30 1 EEEF C=CC(C)(C)[C@]1(C)OC=C[C@@]1(C)CC(=O)[C@@H](O)[C@H](OC)[C@@H](C)O 6494294 BSIAHHIPMGVHJM-ZVEIASASSA-N 326.433 2.223 30 1 EEEF in-vitro CC1=C2C=C3C(=O)C(O)=C([C@H](C)CO)[C@]3(C)CC[C@@]2(C)C[C@H](O)C1=O 2356521436 XUINLCMVOIWOKB-QXQMREQMSA-N 346.423 2.393 30 1 EEEF CC(C)(C)C(=O)CC1(NCC(=O)N2[C@H](C#N)CC[C@@H]2C#N)CCCC1 36310848 DXPKEVJIZJQCLD-GASCZTMLSA-N 344.459 2.301 30 1 EEEF C[C@]1(c2cccc(I)c2)OC(C(=O)O)=CC1=O 36377856 QJKQNKXFEZQYQP-GFCCVEGCSA-N 344.104 2.074 30 1 EEEF COc1c2c(c(OC)c3c1C(=O)C1=C(C3=O)[C@H](C)O[C@H](C)C1)OCO2 14827945 FRYKBCAHLYVUDQ-SFYZADRCSA-N 346.335 2.305 30 1 EEEF biogenic CC1=CC(=O)[C@@]2(CN1)N[C@H](C)Cc1ccc(F)c(Br)c12 587799464 XHIZTKJYJVNHTR-RFAUZJTJSA-N 339.208 2.394 30 1 EEEF COC1=C[C@@H]2[C@H]3Cc4ccc(C(C)=O)c(O)c4[C@@]2(CCN3C)CC1=O 2356347275 DWQIEUYIJNZWSH-SXGZJXTBSA-N 341.407 2.212 30 1 EEEF CC(N)=C1C(=O)[C@@H]2[C@H]3c4c[nH]c5cccc(c45)C[C@@H]3C(C)(C)N2C1=O 2356386933 AFOUSJMOYMLOPA-ZLIFDBKOSA-N 335.407 2.229 30 1 EEEF O=C1C(Br)=CC(Br)=C/C1=C\Nc1cn[nH]n1 103979741 IYZBAOMTANHFIE-HWKANZROSA-N 345.982 2.241 30 3 EEEF C=C1C(=O)O[C@H]2[C@@H](C(C)=O)[C@]3(C)[C@@H](C(C)=O)CC[C@@](C)(O)[C@H]3[C@@H](C)[C@H]12 2356678063 QRJWNJLDUSTASQ-CXAKLKPNSA-N 348.439 2.312 30 1 EEEF COc1cc(/C=C/C(=O)Nc2ccc(C(=O)NO)cc2)ccc1O 1857559624 NSHUUPAUTMDRSF-YCRREMRBSA-N 328.324 2.172 30 1 EEEF COC(=O)N1CCC2(CC1)CN(C(=O)Nc1cccc(C#N)c1)C2 3956391 MKMQUYMLDWOCHW-UHFFFAOYSA-N 328.372 2.254 30 1 EEEF C=C1[C@@H]2COC(=O)C(=CC=CC(C)(C)O)[C@@H]2C[C@@H]2C(C)=CC(=O)O[C@@H]12 2356470955 LUHDPMVWXCNPMF-CVYDXHPNSA-N 344.407 2.477 30 1 EEEF Cc1cc(C)nc(N2C[C@H]3CN(C(=O)c4ccccc4C#N)C[C@@H]3C2)n1 116825027 FEMHBRHDPBAADC-IAGOWNOFSA-N 347.422 2.174 30 1 EEEF C=C1C[C@@]23C[C@H]1CC(=O)[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1[C@H](O)[C@H]3O 2356684939 ZAPSETLSDTWUQE-OBZFQAFOSA-N 348.439 2.161 30 1 EEEF NC(=S)N/N=C(\c1ccc(Br)cc1)c1ccccn1 72116475 MOEVXWKJGXAIKY-SFQUDFHCSA-N 335.230 2.430 30 1 EEEF C=C1[C@H](O)CC[C@H](C)[C@@H](O)CC2=C(C)[C@@H]3[C@H]1CC[C@]3(C)[C@@H](O)[C@@H]2O 238766186 YAYNWFQJPHWSPY-HMFWARFCSA-N 336.472 2.169 30 1 EEEF CC1=C[C@]2(O)C(=O)[C@](C)(O)[C@@H]3[C@@H]4[C@H](CC[C@]3(C)C=C2C1=O)C4(C)C 2356419500 UZEAKOOBNZOXDE-WJGUIKCLSA-N 330.424 2.195 30 1 EEEF C=C1C[C@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@@H](O)CO)[C@H]2C[C@@H]1CC3 195411662 FYKIZBPSTADBEK-HGDKKCICSA-N 348.439 2.171 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3ccc(C(=O)OC)cc3[nH]2)C1=O 587038106 CUQNUQCVTJVDBS-LBPRGKRZSA-N 345.380 2.142 30 1 EEEF C=C[C@H]1CC[C@@H]2[C@@H]3CC(=O)[C@@]4(O)C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C 2356429459 VQFKUKMXFNCVKK-DHNRSMCVSA-N 348.483 2.457 30 1 EEEF Cc1ccc2c(n1)N(C)[C@@H](CO)CCN(Cc1ccc(C#N)cc1)C2 2356290064 IQPCJZUXYZQDIR-LJQANCHMSA-N 336.439 2.465 30 1 EEEF O=C1C2=CCCC3(Oc4cccc5cccc(c45)O3)[C@@H]2[C@H](O)[C@@H]2O[C@@H]12 2356793059 GZNZGNSOLGAMAJ-WNHJNPCNSA-N 336.343 2.355 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc(C(=O)O)cn2cnnc12 587912436 PADHJYHHVYYWFL-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF Cc1cnnc2c1/C(=N/N=C(N)N)C[C@H](c1ccccc1Cl)C2 13474681 LEJYYRQUAZFCLY-CONVLBPTSA-N 328.807 2.146 30 1 EEEF C=C(C)[C@@H](O)COc1cc(O)cc2c1-c1c(O)ccc(O)c1C2=O 2356393793 SVLCTBWISIZGTK-ZDUSSCGKSA-N 328.320 2.331 30 1 EEEF CC(C)N(C(=O)Cn1c(-c2cccnc2)ccc(C#N)c1=O)C(C)C 4931830 JIAJJYSKPAKDES-UHFFFAOYSA-N 338.411 2.427 30 3 EEEF C=C(C)C(=O)O[C@H]1[C@@H]2C(=C)[C@H](O)C[C@H]2C(=C)C[C@H]2OC(=O)C(=C)[C@@H]12 2356627897 ZQBZOPWDBPOXPR-WYJHLCISSA-N 330.380 2.085 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@@]1(C)CCC[C@]2(C)C(=O)O[C@H]([C@@H]3O)[C@@H]21 33698789 OSYJLXUUZYSFTC-UTASHEBBSA-N 332.440 2.432 30 1 EEEF in-man O=C1C=CCN(S(=O)(=O)c2ccccc2)[C@@H]1Cc1ccccc1 36175739 ATIRPKRDWOUCGZ-QGZVFWFLSA-N 327.405 2.428 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C(O)=C3C(C)(C)[C@@H](O)CC[C@]3(C)[C@@]2(O)[C@H](O)C1 238781640 PYMRQNNIAHSRKU-RBYDNREISA-N 348.439 2.183 30 1 EEEF N#Cc1ccc(-c2ccc(NC(=O)Cn3cnc([N+](=O)[O-])n3)cc2)cc1 299863800 LNEYOZORSQCSSN-UHFFFAOYSA-N 348.322 2.364 30 1 EEEF N#CCn1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cn1 587885098 BCIFRWVPZCEOAX-UHFFFAOYSA-N 347.205 2.424 30 1 EEEF CCOC(=O)[C@@H](C#N)[C@@]1(CC)Oc2cc(OC)cc3c2C(=O)[C@H]1C3 587428362 OAFVAGNNVDRDRW-VFVRVIDISA-N 329.352 2.294 30 1 EEEF C[C@H]1Cc2ccc(F)c(Br)c2[C@@]2(COC=CC2=O)N1 587835167 NUURRDCZWYFTPT-RTHLEPHNSA-N 326.165 2.431 30 1 EEEF CN1C(=O)C[C@@](C#N)(C(=O)NCc2ccccc2)[C@H]1c1ccccc1 203470003 OBHPTANUQXBDJR-QUCCMNQESA-N 333.391 2.416 30 3 EEEF CC(=O)Nc1nc(SCCO)c(C#N)c(-c2ccco2)c1C#N 1857572093 XUSDDLLNFIURBQ-UHFFFAOYSA-N 328.353 2.128 30 1 EEEF C=C1CCC=C(C)[C@]2(O)[C@@H]1[C@@H]1OC(=O)[C@H](C)[C@@H]1[C@H]2OC(=O)C(C)C 238781813 DAVDCPBTHVRYEI-OMDXXEBNSA-N 334.412 2.389 30 1 EEEF Cc1cc(=O)oc2cc(NC(=O)CNc3ncccc3C#N)ccc12 1772608709 YCTCNHVLPWRXQD-UHFFFAOYSA-N 334.335 2.419 30 1 EEEF CO[C@]1(C#C[C@@](O)(c2ccccn2)C2CCC2)CN2CCC1CC2 28563785 URXQXNPRSDVQNH-UXHICEINSA-N 326.440 2.184 30 1 EEEF C=C1C[C@@H](O)[C@H](O)C(=C)CC[C@@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@H]12 2356711543 DFVRPHGROBFFBS-VDHUWJSZSA-N 348.439 2.047 30 1 EEEF COC1=C[C@@]2(C=CC1=O)C[C@@H]1c3c(cc(OC)c(O)c32)CCN1C 14618490 RICRDZJWIPYDGM-CWTRNNRKSA-N 327.380 2.241 30 1 EEEF biogenic COc1ccc2c3c1O[C@H]1C=C(C(C)=O)C[C@@H]4[C@H](C2)N(C)CC[C@]314 195299922 FKNWJBZMTKZQMB-TXDAXLQXSA-N 325.408 2.490 30 1 EEEF CN[C@H]1CCN(c2nc(N(C)CCC#N)c3sccc3n2)C[C@H]1F 1911583866 HMVNYEPSKJGOHX-NEPJUHHUSA-N 348.451 2.177 30 1 EEEF O=C(OCCOCCOCCOCCS)c1ccc(S)cc1 82158215 CECANUAMTFBCSU-UHFFFAOYSA-N 346.470 2.112 30 1 EEEF C=C1[C@H](O)[C@@]23CC[C@@H]4C(C)(C)C[C@@H](O)C[C@@]4(C)[C@@H]2CC[C@]1(O)[C@H]3O 238749127 OUKQFTKNWPTKCZ-USKJMLCYSA-N 336.472 2.003 30 1 EEEF C=C1C(=O)O[C@@H]2/C=C(/C)C3=CC(=O)[C@](C)(C[C@@H](OC(=O)C(C)C)[C@@H]12)O3 238758205 WQQJRSDFQHYDRU-MENFSSKMSA-N 346.379 2.244 30 1 EEEF C=C1C[C@H](OC(=O)C(C)C)[C@H]2[C@H](C)C(=O)O[C@@H]2[C@H]2C(=C)[C@@H](O)C[C@@H]12 238776952 VKFKILXPTYWTRI-OGEQHFGCSA-N 334.412 2.245 30 1 EEEF Cc1c(O)ccc2c1[C@H](c1cc(C#N)cnc1Cl)N[C@H](C(=O)O)C2 963511064 SMZDONVMMJRILA-WFASDCNBSA-N 343.770 2.309 30 1 EEEF CN1C[C@]23C[C@@H](O)[C@H]4[C@@H](CCC5=CC(=O)C=C[C@@]54C)[C@@H]2CC[C@@H]3C1=O 152881820 GDWBXDLUQZIGKG-DXUNKFAKSA-N 341.451 2.333 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)[C@@H]4O[C@@H]4[C@]3(C)[C@@]1(C)[C@@]21CO1 2356419982 LAQCZBYXNRANFU-HGRQPHNRSA-N 332.396 2.154 30 1 EEEF COC(=O)/C=C/c1ccc2c(c1)C(=O)C(=O)N2Cc1ccc(C#N)cc1 103230053 GYTCVIGEOJKQQN-VQHVLOKHSA-N 346.342 2.474 30 1 EEEF COc1cc2c(cc1OC)C(c1ccc(C#N)cc1)=NN(C)C(=O)C2 28258305 LIHSWLIYDNOKPY-UHFFFAOYSA-N 335.363 2.342 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 257447097 IPHNMKITOREFLW-XUGKGZAYSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C[C@@H]1NC=CC(=O)[C@]12N[C@H](C)Cc1cc(Br)c(F)cc12 587792921 INJXIIPYPDFSAK-OLBFVZFUSA-N 339.208 2.392 30 1 EEEF N#Cc1nc2nc([C@H]3CS[C@@H](Cc4ccccc4)N3)[nH]c2nc1C#N 587040600 IHUXBNSHRYAUJR-KGLIPLIRSA-N 347.407 2.043 30 1 EEEF C#CCN(C(=O)/C=C/c1cc(OC)c(OC)c(OC)c1)C(=O)C(=C)C 1857756984 CGPHUUXPRBBFIN-CMDGGOBGSA-N 343.379 2.290 30 1 EEEF C=C[C@]1(C)C(=O)C=C2C(=CC[C@H]3C(C)(C)[C@H](O)[C@@H](O)C[C@]23C)[C@@H]1O 2356432457 AZNDIKGKUJHYJB-WUGYKTLSSA-N 332.440 2.153 30 1 EEEF C=C1[C@H](O)[C@@H]2O[C@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@]1(C)[C@@H](O)C(=O)[C@@]32C 2356479224 ILPXHKMIZLTLAS-HUGAXFDVSA-N 332.440 2.083 30 1 EEEF CC=C(C)C(=O)O[C@@H]1C[C@H](O)C2=CC(=O)C(C(C)(C)O)=C[C@@]2(C)[C@@H]1C 2356594908 LHZKEPWOCHFOLY-VWHWKWRLSA-N 348.439 2.478 30 1 EEEF C=CC1=CC(=O)[C@@H]2[C@@H](CC[C@@H]3C(C)(C)[C@H](O)[C@H](O)[C@H](O)[C@]23C)[C@H]1C 86007145 XFRCVLKGZMPUFQ-CELYEMQESA-N 334.456 2.089 30 1 EEEF in-man C[C@@H]1Cc2cc(Br)c(F)cc2[C@@H]([C@@H](C=O)[N+](=O)[O-])N1 587747118 PDDFVXQYGACOIB-KKIHLJRUSA-N 331.141 2.008 30 1 EEEF C#CCN(CC=C)C(=O)CCc1nnc(COc2ccccc2)o1 11815236 ZPJBWJKZNVDZJI-UHFFFAOYSA-N 325.368 2.229 30 3 EEEF CC1=C(O)C(=O)C[C@]2(C)[C@@H]3CCc4cocc4[C@@]3(CO)CC[C@]12O 2356337347 YJYCGDAWLMWZRS-NQYYFHDYSA-N 332.396 2.408 30 1 EEEF C=C(CO)[C@@H]1CC2=CC[C@H]3[C@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@@H]2C[C@@H]1O 2356464955 VJVZOSZFDKSLNA-MPIWTDJGSA-N 336.472 2.028 30 1 EEEF C=C1C2=C(O)[C@H](O)[C@H](C)C=C2C(=O)c2cc(OC)c(O)c(OC)c21 69482139 NCHXGWSVVROJJA-NXSYQRQQSA-N 330.336 2.368 30 1 EEEF biogenic,in-vitro C=C[C@@H]1CN2[C@H]3C[C@@]45c6ccccc6N[C@@]4(O3)[C@H]2C[C@H]1[C@@H]5C(=O)OC 2356762803 VQQRVBOFQXPEAN-UURLAPNRSA-N 338.407 2.102 30 1 EEEF C=CCN(C(=O)OC(C)(C)C)S(=O)(=O)NCc1ccccc1 36382994 WWUWIQUSDSYFRE-UHFFFAOYSA-N 326.418 2.444 30 3 EEEF CN(C)S(=O)(=O)c1cccc2nc(-c3cc(O)cc(C#N)c3)[nH]c12 587191963 VGVQYOBIOZCZKJ-UHFFFAOYSA-N 342.380 2.057 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(C(=O)NCCN)cc1 587905904 MKZKZXYFJSBXCR-UHFFFAOYSA-N 328.799 2.437 30 1 EEEF CS(=O)(=O)Nc1ccc(O)c(-c2nc3ccc(C#N)cc3[nH]2)c1 586947690 AQBRTNJEFQJZPV-UHFFFAOYSA-N 328.353 2.179 30 1 EEEF COc1ccc(OC)c(CCC(=O)/C=C2\NC(=O)[C@H](C(C)C)O2)c1 1857608266 CCGROBCBGOSSNB-KGZWWPETSA-N 333.384 2.218 30 1 EEEF CC(C)=C1NC(=O)[C@](CC=CC[C@H](C)O)([C@@H]2CC(=O)O[C@@H](C)C2)C1=O 2356490431 IIYKLCYWWXLYAF-WFTHSTBKSA-N 349.427 2.025 30 1 EEEF C=C(C)C(=O)O[C@H]1CC2=C[C@@H](C/C(C)=C\[C@H]3OC(=O)C(=C)[C@@H]13)OC2=O 34171874 JMUOPRSXUVOHFE-XFKDXUHGSA-N 344.363 2.164 30 1 EEEF C=C1C[C@]23C[C@]4(O)CN5C[C@]6(C)CCC[C@]7([C@H]5[C@H]2C[C@H]1C(=O)[C@H]37)[C@@H]64 238749799 MGEDPNBPAMLIHW-WVRIYPJASA-N 325.452 2.393 30 1 EEEF N#Cc1cnn2c(Nc3ccccc3)cc(N3CCC[C@H]3CO)nc12 1772640986 MESZQPQYLQBOST-HNNXBMFYSA-N 334.383 2.306 30 1 EEEF C[C@](O)(COc1ccccc1C#N)C(=O)N1CCc2c(C#N)cccc21 169313290 SKDVDQLYZLGNFP-FQEVSTJZSA-N 347.374 2.149 30 1 EEEF COc1ccc(N2C(=S)[C@@H](C#N)C(=O)N[C@H]2c2ccco2)cc1 169688085 PSLDKXQWVTXHEX-GXTWGEPZSA-N 327.365 2.390 30 1 EEEF C#CC[C@H](NC(=O)c1ccc(C(F)(F)F)cc1)C(=O)NCCC 36389139 XFGGFMUOUXGINT-ZDUSSCGKSA-N 326.318 2.353 30 3 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@@]2(COC=CC2=O)N1 587835164 NUURRDCZWYFTPT-CLAHSXSESA-N 326.165 2.431 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc(C#N)ccc1S(N)(=O)=O 587918573 XKONTLDYFJQILQ-UHFFFAOYSA-N 346.795 2.267 30 1 EEEF CC(C)C[C@H](NC(=O)[C@@H](CS)Cc1ccccc1)S(=O)(=O)O 13449695 IFOJNPIPERNZBH-ZIAGYGMSSA-N 345.486 2.151 30 1 EEEF N#Cc1ncn(-c2ccc(O)cc2)c1/N=C/c1ccc(O)c(O)c1O 169350307 ZFVFKTLQSQGNLG-UFWORHAWSA-N 336.307 2.317 30 1 EEEF N#Cc1cc[nH]c(=NCCCNC(=O)c2cc(-c3ccccc3)on2)c1 473089723 STRMAPMVQACSSG-UHFFFAOYSA-N 347.378 2.262 30 1 EEEF N#Cc1nc2nc([C@@H]3C=C(c4ccc(Cl)cc4)NO3)[nH]c2nc1C#N 587076706 NWEFMGOIXRZFFG-ZDUSSCGKSA-N 349.741 2.367 30 1 EEEF N#Cc1cccc(-c2coc(NC(=O)[C@@]3(F)CCCN(C#N)C3)n2)c1 1857558044 VOZPNGOVUPKNNO-QGZVFWFLSA-N 339.330 2.437 30 1 EEEF C=C1C(=O)[C@@]23[C@H](CC[C@H]1[C@H]2O)[C@@]1(C(=O)O)CCCC(C)(C)[C@H]1C[C@H]3O 2356455479 VBQWGSKSQFBYOX-UKGYBIBNSA-N 348.439 2.161 30 1 EEEF C(#Cc1ccccc1)CSc1nsnc1C12CN3C[C@@H]1[C@H]2C3 100829401 YRHXYFPBQSSIPM-ZIAGYGMSSA-N 325.462 2.495 30 1 EEEF CC1=C(O)c2ccccc2C(=O)/C1=N\CCCN1CCN(C)CC1 100872311 FALQLITXWZAKLX-JZJYNLBNSA-N 327.428 2.250 30 1 EEEF CC(C)[C@]12O[C@H]1C=C1[C@@]3(C)CCC4=C(COC4=O)[C@@H]3C[C@@H]3O[C@]13C2=O 64528441 NDBFYINIVHOHLP-JZEYQUPZSA-N 342.391 2.100 30 1 EEEF CCCCCCCCC[C@@H]1C[C@H](O)[C@H](O)C=C[C@@H](O)CC(=O)O1 2356721136 VKFBQLMPTJTKBZ-VQHPVUNQSA-N 328.449 2.472 30 1 EEEF C#CCOc1ccc2cc(Cn3ccc(=O)c(O)c3C)c(=O)oc2c1 1857600068 DENRXQVGAOBUQT-UHFFFAOYSA-N 337.331 2.029 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)/C(C)=C/[C@H]2OC(=O)C(=C)[C@@H]21 103578278 RYBHZNMPMHOBAR-NDYSYXOHSA-N 344.363 2.164 30 1 EEEF biogenic,in-vitro C=C1C(=O)O[C@@H]2[C@@H]1CCC(=C)[C@]1(O)C[C@H](OC(=O)C(C)C)C(=C)[C@H]21 2356650629 LUUJHRSUAVIZOX-PPLBCVRQSA-N 332.396 2.309 30 1 EEEF Cc1nnc(N/N=C\c2cc(C)n(-c3ccc(F)cc3)c2C)n1N 15973629 RYKQZEORMXVJNI-OCKHKDLRSA-N 327.367 2.293 30 1 EEEF C/C1=C\CC[C@@]2(C)O[C@@H]2[C@H]2OC(=O)[C@@H](Cn3cnc(CO)c3)[C@@H]2CC1 169308975 LEZDFUSTWQETNC-JDNHZJQCSA-N 346.427 2.211 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(CO)CC[C@]3(C)[C@@]1(C)[C@@]21CO1 2356551314 ZJTUORWHCGIUBM-QXRKFJRXSA-N 334.412 2.140 30 1 EEEF CO/N=C/c1cc(OC)c2c(c1)C(=O)c1cccc(OC)c1C2=O 473156642 TWTJFIYUFSFODW-DJKKODMXSA-N 325.320 2.460 30 1 EEEF CC1(C)CN(C(=O)CC#N)[C@@]12CCCN(c1ncnc3[nH]ccc13)C2 169698968 XOSMEQOCKMFFJZ-GOSISDBHSA-N 338.415 2.079 30 1 EEEF CCO[C@]12C[C@]3(C)[C@@H](CC1=C(C)C(=O)O2)C(C)=CC(=O)[C@H]3OC(C)=O 2356500634 YDUWTFHAUBSRIH-QVSURHGTSA-N 348.395 2.470 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)Nc2cccnc2)[C@@H]1O 15468 VOPFGEFCSPSJGG-CVEARBPZSA-N 338.367 2.348 30 1 EEEF COc1ncc2nc(-c3ccc(Cl)cc3)c(=O)n(CCC#N)c2n1 4239121 WFQSMEHDGLNNHE-UHFFFAOYSA-N 341.758 2.429 30 1 EEEF CC(C)(O)C1=CC2=C[C@H](O)[C@@H]3[C@](C)(C(=O)O)CCC[C@]3(C)[C@@H]2CC1=O 2356510903 QMSWKASVXHXIKB-ZOROFGBHSA-N 348.439 2.471 30 1 EEEF N#C[C@H]1C[C@@H](O)CC[C@@H]1n1cc(C(N)=O)c(Nc2ccc(F)cc2)n1 221213080 USZHEZVXLJZXEW-DGFSRKRXSA-N 343.362 2.090 30 1 EEEF Cc1ccccc1S(=O)(=O)N1[C@H](C#N)[C@H](c2ccccc2)[C@H]1CO 95897620 UKJFDLKEHROOFG-NUJGCVRESA-N 342.420 2.036 30 1 EEEF COc1ccc(Br)cc1-c1ccc(C(=O)N=C(N)N)o1 13642710 IZFBBJUCHTYXPY-UHFFFAOYSA-N 338.161 2.131 30 1 EEEF C=C1C(=O)[C@@]23C[C@H](O)[C@H]1C[C@@H]2[C@]1(C)CCC[C@](C)(CO)[C@@H]1C[C@H]3O 2356788035 WHNRXVKFGPGHAF-CRXBOGTJSA-N 334.456 2.068 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1CCC(COC(=O)C(C)C)=C1C[C@H](O)C(=C)[C@@H]12 238771273 INJHISWMTROACX-HJWJTTGWSA-N 332.396 2.311 30 1 EEEF C=C1[C@H]2C[C@@H]3C(=C)C(=O)O[C@@H]3C[C@@]2(C)[C@@H](O)C[C@H]1OC(=O)C(C)C 238749953 DEXDLEUFCATLMY-BJDQLAMTSA-N 334.412 2.389 30 1 EEEF CCc1nc2n(c(=O)c1C(N)=O)[C@@H](C)CCC2=NNc1ccccc1 253634368 ROUYGSNPBKRWQM-NSHDSACASA-N 339.399 2.076 30 1 EEEF N#Cc1cc([C@@H]2N[C@@H](C(=O)O)Cc3c2cnc2ccccc32)ccn1 963229370 KMSBPESAZVWSRQ-MSOLQXFVSA-N 330.347 2.190 30 1 EEEF CCNc1nonc1C(=Nc1ccc(F)c(Br)c1)NO 1772589389 KUNZKTGDJQRVGH-UHFFFAOYSA-N 344.144 2.460 30 1 EEEF CC(C)[C@]1(O)C=C2C(=O)C[C@H]3[C@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@H]2CC1 2356337243 TVHWXCUVXSEILO-KUIMHTBBSA-N 336.472 2.459 30 1 EEEF O=C1C=C2CC[C@@H]3[C@H]([C@H]4C[C@@]5(CO4)[C@H](C(=O)CO)CC[C@H]35)[C@H]2CC1 2356416616 ZQTXDFVYZQQLOY-FDMURRQVSA-N 330.424 2.295 30 1 EEEF CO[C@](C)(C(=O)O)C1=C[C@]2(C)C(=CC1=O)CC[C@@H](OC(C)=O)[C@@H]2C 2356656319 RDRVOBNXHXPXJL-MRIGJWEJSA-N 336.384 2.280 30 1 EEEF COC1=CC2=C3C[C@@H]4CC[C@H](OC)[C@H](OC)[C@@H]4CN3CCC2=CC1=O 2356845135 OBXUDMPYADNLEQ-RYQXPZQSSA-N 345.439 2.446 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@H](C1=O)[C@@]1(C(C)C)C=C[C@]2(C)CC1 45245119 SDJYQQCUHRGBAF-HLNSBACISA-N 347.484 2.165 30 1 EEEF C/C=C/C#CC#C/C=C/C(=O)OCCCC#CC#C/C=C/C(=O)OC 238767685 YZENRRRDZBYNCT-IBBUKNMVSA-N 334.371 2.185 30 1 EEEF C=C1C(=O)O[C@@H]2[C@H]1CC[C@H](C)[C@]1(O)[C@H](OCCCC)CC(=O)[C@@]21C 96902417 WGXFJMMDVGQYJR-ZLHXMRDPSA-N 336.428 2.410 30 1 EEEF Cc1ccc(S(=O)(=O)Nc2ccc(/C=C/C(=O)NO)cc2)cc1 13493377 PAOPWNUFHBHBRD-IZZDOVSWSA-N 332.381 2.314 30 1 EEEF CN1CCC[C@@H]1C(=O)[C@@H](C#N)C(=O)Nc1ccc(C(F)(F)F)cc1 169714939 USCQNAKKBRTMAX-CHWSQXEVSA-N 339.317 2.447 30 1 EEEF Cc1ccc(-c2c(C#N)cnn2-c2ccc(S(N)(=O)=O)cc2)cc1 3814716 PECOITPCKXVJMZ-UHFFFAOYSA-N 338.392 2.367 30 1 EEEF OC1C2CC3CC1CC(C2)C3(C#Cc1ccccc1)Cc1nnn[nH]1 103230749 GAGLGFSQMXZPHF-UHFFFAOYSA-N 334.423 2.207 30 1 EEEF O=S(=O)([C@@H]1O[C@@H]1c1ccc(Cl)c(Cl)c1)N1CCOCC1 26379618 VDROCDVBBSIMQF-NEPJUHHUSA-N 338.212 2.053 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)C(=O)C=C[C@](C)(O)C[C@@H](OCC(C)C)[C@H]12 2356653593 LUEQCEAVADXVIC-MTNOOBJLSA-N 334.412 2.352 30 1 EEEF CC(=O)CNC(=O)CC(=O)/C=C/C(C)=C/c1ccc2c(c1)OCO2 40392850 MBMHRCUEVIJOIU-PPRDQHCASA-N 329.352 2.039 30 1 EEEF CCc1ncnc(N2CCC[C@H](CO)C2)c1C#Cc1ccc(C)nc1 149279186 KDCLJCNAZYFCAB-KRWDZBQOSA-N 336.439 2.351 30 1 EEEF COCCN(Cc1ccc(C(=O)NO)cc1)C(=O)Nc1ccccc1 95578019 XXVRDVJZLCUGFB-UHFFFAOYSA-N 343.383 2.486 30 1 EEEF C[C@H]1C(=O)[C@]23C[C@H]1C[C@@H](O)[C@H]2[C@@]1(CCCC(C)(C)[C@H]1C=O)COC3=O 34287850 DLDPXPARISOLCS-TXHXOCHASA-N 348.439 2.147 30 1 EEEF biogenic,in-vitro CC(=O)/C=C/N1C(=O)[C@@H](C)[C@@H]2[C@@H]1CCN2C(=O)OCc1ccccc1 13471508 RPKPBMQJCVNPKB-WEUZOMIGSA-N 342.395 2.347 30 1 EEEF C[C@](Cc1ccccc1)(C(=O)NO)C(=O)NCCCc1ccccc1 13528323 UTCZFYMAGMNXSW-HXUWFJFHSA-N 340.423 2.490 30 1 EEEF CN(O)C(=O)c1cc2c(CO)cn(Cc3ccc(F)cc3)c2cn1 64559819 MEIYUWJOHPFCMU-UHFFFAOYSA-N 329.331 2.177 30 1 EEEF CCN/C(=N\S(=O)(=O)c1cccc(Cl)c1)N1CCC(C)=N1 72123373 PVXMBXSXTYCKQF-UHFFFAOYSA-N 328.825 2.076 30 1 EEEF COC(=O)C1=C2[C@](C)(C(=O)OC)[C@@H]3O[C@H]3C[C@]2(C)c2ccccc21 2356695942 CCCHYPOECSYCKC-PNYIKSMMSA-N 328.364 2.235 30 1 EEEF COC(=O)C1CCN(/C(=N\O)c2cccnc2OC2CCC2)CC1 72101032 IRHGJJKONYVSHZ-CYVLTUHYSA-N 333.388 2.034 30 1 EEEF CC1=C(N2[C@@H](C)[C@H]2C)C(=O)C(Br)=C(N2[C@H](C)[C@H]2C)C1=O 253712050 RKTOSHDREXTIII-QRBPWOLZSA-N 339.233 2.204 30 1 EEEF C=C1[C@@H]2C[C@@H](O)C(C)(C)[C@@]2(O)[C@H](O)C[C@@]23C[C@@H](CC[C@@H]12)[C@](C)(O)C3 15263779 AHMSDGIIEDDLQI-SVGNPDPRSA-N 336.472 2.003 30 1 EEEF Cc1cc(C)c2c(c1)[C@@H](/C=N/c1ccc(S(N)(=O)=O)cc1)C(=O)N2 169727358 SMEQORQWGKNBGU-VTNJTDAWSA-N 343.408 2.389 30 1 EEEF CCCCCCCCS(=O)(=O)N[C@H]1CCC[C@H](CC(=O)O)[C@@H]1O 58582919 DLLOIOSRSAHLCT-YCPHGPKFSA-N 349.493 2.271 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)(CCC[C@@]4(C)C=O)[C@@H]2C[C@@H](O)[C@H]1[C@@H]3O 2356672639 RNQLPXGROISTQX-DEEWQJAJSA-N 332.440 2.275 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@](C)(O)CC[C@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@H]12 2356677096 GUGYUSGXSKYCJD-BOXKXSMZSA-N 348.439 2.288 30 1 EEEF C[C@@](Cc1ccccc1)(C(=O)NO)S(=O)(=O)c1cccs1 13520936 UQRFKNRXERPSMG-CQSZACIVSA-N 325.411 2.029 30 1 EEEF NCc1ccc(C/N=C2/[C@@H]3[C@H]4C[C@@H]5[C@@H]3C3(OCCO3)[C@H]3[C@H]2[C@H]4[C@@H]53)cc1 1857586246 PNPIPQKWOXPTBU-PCSTXWRASA-N 336.435 2.217 30 1 EEEF COc1ccc(/C(=N/O)c2cccc(NS(=O)(=O)N(C)C)c2)cc1 101484106 MDMDCWBFLSBWHN-MSUUIHNZSA-N 349.412 2.140 30 1 EEEF CCCCCCCCC[C@H]1C[C@@H](O)[C@H](O)/C=C/[C@H](O)CC(=O)O1 84728682 VKFBQLMPTJTKBZ-ISHVXOLWSA-N 328.449 2.472 30 1 EEEF CC1(C)CN(C(=O)CC#N)[C@]12CCCN(c1ncnc3[nH]ccc13)C2 169698969 XOSMEQOCKMFFJZ-SFHVURJKSA-N 338.415 2.079 30 1 EEEF CC(=O)O[C@H](C)[C@H](C=C1C=C(C)C2=NCC[C@@H]3O[C@@]123)OC(=O)C(C)C 2356476658 MRUZXUQKRAPYFF-XXHPDZBISA-N 347.411 2.374 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccccc1OC[C@@H](O)CN 587902822 QDHWURQLXFMCPV-INIZCTEOSA-N 331.799 2.447 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12OC(=O)[C@@](C)(CC[C@@H]1O)[C@H]2[C@H]3C(=O)OC 2356559834 NZAMXUVSJOQDKJ-DGBRJAHKSA-N 346.423 2.225 30 1 EEEF CC(C)C[C@@H](C(=O)NO)C(=O)NCc1ccc(C(F)(F)F)cc1 35276512 DTDRBGDWVVJPEW-GFCCVEGCSA-N 332.322 2.489 30 1 EEEF C=C[C@@H]1C=C2C(=O)C=C3[C@@](C)([C@@H](O)CC[C@@]3(C)C(=O)O)[C@@]2(O)CC1 2356788684 CHLJNZOUECQLLK-XQOGOWKJSA-N 332.396 2.001 30 1 EEEF C=C1[C@@H]2CC[C@@H]3[C@@]45CCC[C@@](C)(C(=O)O4)[C@H]5[C@H](C(=O)OC)[C@]3(C2)[C@@H]1O 238768505 KVXQCEAWXGANQC-UJDYUOFOSA-N 346.423 2.225 30 1 EEEF C=CC[C@@]12CC(=O)[C@@H](O)[C@@H]([C@H](c3ccc4c(c3)OCO4)[C@H]1C)[C@H]2O 238752469 FBPLISOOTGTZGY-ZBQVZVFRSA-N 330.380 2.022 30 1 EEEF CC(C)(C)c1nc(-c2nccs2)c2c(N)c(C#N)c(N)nc2n1 263621116 VDKRFQKJPXSMOG-UHFFFAOYSA-N 325.401 2.482 30 1 EEEF in-vitro C=CC(C)(C)n1cc(C[C@@H]2NC(=O)[C@H](C)NC2=O)c2ccccc21 299864447 RGJOYRGQGOLRLW-WFASDCNBSA-N 325.412 2.108 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N(C)C)nc1C(=O)O 587903032 IIZXYAZLGJILAD-UHFFFAOYSA-N 331.759 2.303 30 1 EEEF C=CC[C@]1(CNC(=O)OCC)NCCc2ccc(C(=O)N(C)C)cc21 962921879 FNNQCQNSAYHPFV-LJQANCHMSA-N 345.443 2.052 30 1 EEEF O=C(/C=C/c1ccc2ccccc2c1)CCC(=O)N(CCO)CCO 64573637 WOJIUTKWJQPBIU-SOFGYWHQSA-N 341.407 2.016 30 1 EEEF C=C(C)[C@H](O)Cc1c(O)c(O)cc2oc3cc(O)cc(O)c3c(=O)c12 14763105 GONMHOQVFDWXLV-SNVBAGLBSA-N 344.319 2.248 30 1 EEEF biogenic,in-vitro N#Cc1ccc2c(C(=O)c3cccc(S(N)(=O)=O)c3)coc2c1 587279491 JQWSTHSANVYJHM-UHFFFAOYSA-N 326.333 2.183 30 1 EEEF C=C1C[C@H](OCC(C)C)[C@@H]2C(=C)C(=O)O[C@H]2C=C(C)[C@@H](O)CC1=O 2356483577 PJRAJKIGBHSJPR-XSLAGTTESA-N 334.412 2.352 30 1 EEEF CC(C)[C@H](C=O)c1c(O[C@H](O)C(C)(C)O)ccc2ccc(=O)oc12 2356496200 FOMXOHFJUKCTAU-SJCJKPOMSA-N 334.368 2.200 30 1 EEEF C=C(C)[C@@H]1CCC(=C)[C@@H]2C3=C(C(=O)C(C)=C[C@H]12)[C@@H](O)[C@](C)(O)C3=O 2356599880 PMTAKUZIYCHAID-GDVCNKKZSA-N 328.408 2.281 30 1 EEEF N/N=C1/c2cc(-c3ccncc3)ccc2-n2c1nc1ccccc1c2=O 1772586448 ZHMKBOWOTRPOAQ-MOHJPFBDSA-N 339.358 2.472 30 1 EEEF O=C(CCCCCCn1cc(-c2nc[nH]c3nccc2-3)cn1)NO 1772643058 YRRVLBINSXVLFM-UHFFFAOYSA-N 328.376 2.229 30 1 EEEF CCOC1=C/C(=C/NN2CCN(Cc3ccccc3)CC2)C=CC1=O 13130503 XSILCFGUPRWLMC-OBGWFSINSA-N 339.439 2.252 30 3 EEEF N#C[C@H](C(=O)Nc1ccc([S@@](=O)C(F)(F)F)cc1)C(=O)C1CC1 13760275 HWZMCOGRZDFBES-RULNZOCKSA-N 344.314 2.371 30 1 EEEF CCOc1nc(C(=O)NCc2cc(OC)ccc2OC)ccc1C#N 14960015 VEGKZYFYGCWXMN-UHFFFAOYSA-N 341.367 2.299 30 1 EEEF in-vivo C=C[C@]1(C)C=C2C(=O)C[C@@H]3C(C)(C)[C@H](O)C[C@H](O)[C@]3(C)[C@@]2(O)CC1 2356415872 ZTWPAGAVIFLSKK-CCEQCLNRSA-N 334.456 2.377 30 1 EEEF COC1=CC(=O)[C@@]2(C)c3c(O)c(C)c(O)c(C(C)=O)c3O[C@]2(OC)C1 2356835306 KQROSALZXGEZDK-ZWKOTPCHSA-N 348.351 2.105 30 1 EEEF O=S(=O)(/N=C(/NO)Nc1ccc(Cl)cc1)c1ccccc1 6010135 OHOCEEISGJSVIO-UHFFFAOYSA-N 325.777 2.476 30 1 EEEF NCc1ccc(C/N=C2\[C@H]3[C@@H]4[C@@H]5[C@@H]6C[C@H]([C@@H]2[C@@H]6C42OCCO2)[C@@H]35)cc1 1857586245 PNPIPQKWOXPTBU-HBXKVMJZSA-N 336.435 2.217 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)(CC[C@@H](O)[C@@]4(C)CO)[C@H]2C[C@H](O)[C@H]1C3 2356417361 YYNFNCPHITUVRP-FNXAETDFSA-N 334.456 2.068 30 1 EEEF C=C[C@]1(C)CCC2=C(C1)C(=O)C[C@@H]1[C@]2(C)C[C@H](O)[C@@H](O)[C@@]1(C)CO 2356466351 BTYISKOGKBBMDI-IOXPTURASA-N 334.456 2.379 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(C)[C@@H](O)CC[C@@](C)(C(=O)O)[C@H]1C[C@@H]3O 72120340 LRECIABFFPIQSO-BALPIQRXSA-N 348.439 2.161 30 3 EEEF COc1cccc(-n2c3nc(=O)[nH]c(=O)c-3cc3ccc(C#N)cc32)c1 96282700 LSNADVQDLSNQPZ-UHFFFAOYSA-N 344.330 2.059 30 1 EEEF CN(O)C(=O)C[C@H](CP(=O)(O)O)c1ccc(Cl)c(Cl)c1 299844580 HRVAZZLZVPKODL-MRVPVSSYSA-N 342.115 2.492 30 1 EEEF C=C[C@H]1CN2CC[C@H]1C[C@H]2CNC(=O)CC1(CC(=O)O)CCCC1 2356389561 ZGYUSGIGQDEQMQ-JYJNAYRXSA-N 334.460 2.424 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)C2=CC3=C(CO)C(=O)C=C[C@]3(C)CC[C@]21C 2356730454 IQSIJJOWDAYBIC-OUUBHVDSSA-N 332.440 2.155 30 1 EEEF Cc1cc(Nc2cnc(C#N)c(N[C@@H](C)c3ncc(F)cn3)n2)n[nH]1 45258096 PIRRYRRDDTYFPP-VIFPVBQESA-N 339.338 2.226 30 1 EEEF COc1ccc(Cl)cc1C#Cc1c([N+](=O)[O-])nn(C)c1C(=O)O 587902996 UHYMYZGVVOXWEQ-UHFFFAOYSA-N 335.703 2.088 30 1 EEEF O=C[C@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)CCCc1ccccc1 13738813 ATHGZTRCNIYYSU-MSOLQXFVSA-N 342.439 2.190 30 1 EEEF C=C(CC[C@H](O)C(C)(C)O)[C@@H](O)COc1ccc2ccc(=O)oc2c1 14587282 GOOJJMAKBXRBIG-RDJZCZTQSA-N 348.395 2.001 30 1 EEEF biogenic C[C@](O)(COc1cccc(F)c1)C(=O)N1CCc2c(C#N)cccc21 169313270 YCQHDOUCTPXMLD-IBGZPJMESA-N 340.354 2.416 30 1 EEEF C=CCN(C(=O)C=C)C(=O)/C=C/c1cc(OC)c(OC)c(OC)c1 1857650374 HVOVFHVWOYCNBZ-CMDGGOBGSA-N 331.368 2.453 30 1 EEEF CC[C@H](O)C[C@H](C)[C@@H]1O[C@]1(C)C=CC(=O)N[C@H](CO)[C@H](C)CC 2356421456 KQYIQWJQJFWGMP-IAEPDVJVSA-N 327.465 2.020 30 1 EEEF N#C[C@@H]1CCC[C@H]1C(=O)[C@@H]1CN([C@H]2CCOc3ccccc32)C[C@@H]1N 28955130 AXLLQKGXUYCBGM-QYKUSJBESA-N 339.439 2.278 30 1 EEEF C#C[C@@H]1CN2CC[C@H]1C[C@H]2CNC(=O)Nc1cc(OC)cc(OC)c1 2356300804 SDRGEMKIXHLRFZ-YCPHGPKFSA-N 343.427 2.169 30 1 EEEF C=C1[C@@H](O)C[C@@H]2[C@](C)(CO)C[C@@H](O)C[C@@]2(C)[C@@H]1CC/C(C)=C\CO 39158857 LCWHTWNKEOSQBZ-PLUVHVLOSA-N 338.488 2.418 30 1 EEEF C=CC1=CC(=O)[C@H]2[C@@H](CC[C@H]3C(C)(C)[C@@H](O)[C@@H](O)[C@@H](O)[C@]23C)[C@H]1C 38821388 XFRCVLKGZMPUFQ-ILKOOZTQSA-N 334.456 2.089 30 1 EEEF biogenic,in-vitro CC1=C(c2ccc3nc(-c4ccc(N)c(C#N)c4)[nH]c3c2)NNC(=O)C1 587250569 ZCQMRBGXTQNBSN-UHFFFAOYSA-N 344.378 2.439 30 1 EEEF C=C[C@@H](CCc1ccc(C(=O)OCC)cc1)c1c(N)nc(N)[nH]c1=O 5884292 FGBZUJXPLVUXJQ-LBPRGKRZSA-N 342.399 2.013 30 1 EEEF CC(C)(C)/N=C(\S)NCc1ccc(NS(C)(=O)=O)c(F)c1 13672855 FKMRRNRXEOSATM-UHFFFAOYSA-N 333.454 2.371 30 1 EEEF CC1(C)C=Cc2c(ccc3c2O[C@@H]2[C@H]3COC3=CC(=O)C=C[C@]32O)O1 14502672 XBSGPVUHRGTYRA-QMIHWGKISA-N 338.359 2.500 30 1 EEEF biogenic COc1cc(O)c2c3c(c(O)cc(C)c13)C1=C(C)C(=O)C[C@@]1(O)C2=O 1857647797 LLCALCWSGAGWQS-IBGZPJMESA-N 340.331 2.242 30 1 EEEF N#Cc1ccc2nc(CO[C@@H]3CN(C4CCOCC4)C[C@@H]3F)[nH]c2c1 2356299174 ANHAAGFWRVPBII-WMLDXEAASA-N 344.390 2.152 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@](CCC=O)(C(=O)O)N1 587825289 CNZBBDHJVSYJER-XLKFXECMSA-N 344.180 2.381 30 1 EEEF COc1cccc(C(=O)/C=C/c2cc(/C=C/C(=O)NO)n(C)c2)c1 13643594 RHXILNXFMGUMGY-CDJQDVQCSA-N 326.352 2.448 30 1 EEEF C=C[C@]1(C)C=C2C(=CC1)[C@]13C[C@@H]1CC[C@]1(C)C(=O)O[C@](O)([C@H]2O)[C@H]13 2356396830 XHJCBVNMOHCTOP-WILZEFGGSA-N 328.408 2.478 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)[C@H](O)C[C@]3(C)[C@@]1(C)[C@@]21CO1 2356610165 VRHZKNFFKJZHFD-ORHVNHJFSA-N 334.412 2.138 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H]1[C@@H](O)CC(=C)[C@@H]1C[C@@H](OC(=O)C(C)=CC)C(=C)[C@H]12 2356654403 UINWHHMWCJPCDZ-PVWHLQNVSA-N 344.407 2.475 30 1 EEEF C=CCNC(=O)Nc1ccc(OC[C@@H](O)CNC(C)C)c(Cl)c1 169317377 XCZZSQOOQIILSK-ZDUSSCGKSA-N 341.839 2.385 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnn(Cc2ncnn2C)c1 587908939 FQENWGKWQCEENZ-UHFFFAOYSA-N 327.775 2.122 30 1 EEEF COC1=CC(=O)c2c(c(COC(=O)c3ccccc3F)cn2C)C1=O 13557522 HGXPUZYJSVZLPU-UHFFFAOYSA-N 343.310 2.431 30 1 EEEF C=CC[C@@]1(OCc2ccccc2)C(=O)C(=O)O[C@@H]1[C@H]1COC(C)(C)O1 17259971 QUSJNYTVFAJGCT-IDHHARJASA-N 346.379 2.164 30 1 EEEF O=C(CCCCCCN1C(=O)/C(=N\O)c2cccc(Cl)c21)NO 103292929 KBQJCHJMAAJXLR-AQTBWJFISA-N 339.779 2.321 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@]12CCC[C@@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 104359187 ZCRLGANQNRMURE-FFRXTNJESA-N 346.423 2.384 30 1 EEEF in-man O=C1C=CC(O)=C/C1=C\NNC(=S)N[C@@H]1C[C@H]2C[C@H]1[C@H]1C=CC[C@H]21 104005511 NEWHOSFZGBPMPT-YQUMNZOZSA-N 343.452 2.021 30 3 EEEF CC(C)C[C@H](NC(=O)OCc1cccc2[nH]ccc12)C(=O)NCC#N 82065159 GNTWIINQXGPTCC-INIZCTEOSA-N 342.399 2.449 30 1 EEEF N#Cc1cc([C@H]2N[C@H](C(=O)O)Cc3c2cnc2ccccc32)ccn1 963229377 KMSBPESAZVWSRQ-ZWKOTPCHSA-N 330.347 2.190 30 1 EEEF C=CCN1[C@H](C#N)[C@@H](c2ccc(C#Cc3cccnc3)cc2)[C@H]1CO 203473498 BOVDGNHDIMDIJQ-NJDAHSKKSA-N 329.403 2.320 30 3 EEEF CO[C@@]1(C#C[C@](O)(c2ccccc2)c2cccnc2)CN2CCC1CC2 28563570 ZGBSEJYQXDWFRF-VXKWHMMOSA-N 348.446 2.432 30 1 EEEF CO/N=C(\C)c1cnc2nnn(Cc3ccc4ncccc4c3)c2n1 68248545 DXHVTERDNXZQNS-SSDVNMTOSA-N 333.355 2.188 30 1 EEEF O=C1C(N2CCN(c3ccccc3)CC2)=CC(=O)c2c(O)cccc21 71294446 SMWAKBOPLFIQQV-UHFFFAOYSA-N 334.375 2.477 30 1 EEEF COc1ccc(OC)c(/C=N/NC2=CS(=O)(=O)c3ccccc32)c1 43120377 UOQSVXFCKKZUKR-VCHYOVAHSA-N 344.392 2.413 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@H](C)C[C@@]2(O)C=C(C)[C@H](O2)[C@H]2OC(=O)C(=C)[C@H]12 525915107 RVJOETCQOOQGPR-FNPIUROLSA-N 348.395 2.036 30 1 EEEF biogenic C=CC1=CC(=O)[C@@H]2[C@H](CC[C@@H]3C(C)(C)[C@H](O)[C@H](O)[C@H](O)[C@@]23C)[C@@H]1C 257619957 XFRCVLKGZMPUFQ-SUIMNPQMSA-N 334.456 2.089 30 1 EEEF endogenous,in-man COc1ccccc1NC(=O)ONC(=N)c1ccc2nonc2c1 653778438 IVLBXKVDBXQBQY-UHFFFAOYSA-N 327.300 2.310 30 1 EEEF COC(=O)[C@H](C=O)[C@H]1N[C@@H](C)Cc2ccc(F)c(Br)c21 587803868 CCYWOEOSTLKZON-WIMUKIRHSA-N 344.180 2.152 30 1 EEEF CNS(=O)(=O)c1ccc(/N=C/[C@H]2C(=O)Nc3ccccc32)cc1 169685172 XTPZAFMBWDNWIW-YFEUJDIGSA-N 329.381 2.033 30 1 EEEF C#Cc1cc(Oc2cnc(NCCO)nc2N)c(C(C)C)cc1OC 166789749 OLSSCUJJAVUSNC-UHFFFAOYSA-N 342.399 2.369 30 1 EEEF CC1(C)O[C@@H]1CC(=O)Nc1cccnc1C(=O)Nc1nccs1 28333962 CZHUCHUJVPAVIN-SNVBAGLBSA-N 332.385 2.296 30 1 EEEF CO[C@]1(C#C[C@@](O)(c2ccccc2)c2cccnc2)CN2CCC1CC2 28563568 ZGBSEJYQXDWFRF-FGZHOGPDSA-N 348.446 2.432 30 1 EEEF C=CCN(C)C[C@H]1CN2CC[C@H]1C[C@H]2CNC(=O)c1cccs1 2356813808 BURJLYWVSNLLMI-JYJNAYRXSA-N 333.501 2.306 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cc(OC)cc(OC)c3[nH]2)C1=O 587038504 JXIVSGDKDIPFCW-GFCCVEGCSA-N 347.396 2.373 30 1 EEEF CO[C@@]1(C#C[C@@](O)(c2ccccc2)c2ccccn2)CN2CCC1CC2 28563811 LLHFDYRCKMNGML-FCHUYYIVSA-N 348.446 2.432 30 1 EEEF CC(C)=CC[C@@H](OCCO)C1=CC(=O)c2c(O)ccc(O)c2C1=O 72183183 FCNRLKXRVLWCCM-OAHLLOKOSA-N 332.352 2.137 30 1 EEEF COCCNC(=O)[C@@H]1CCCC[C@@H]1c1nc2cccc(C#N)c2[nH]1 587230108 FJLCJTIIYPNMKU-UONOGXRCSA-N 326.400 2.471 30 1 EEEF C=C1C2=C(C(=O)N1OC)[C@H](O)[C@](C)(O)[C@@H](CCCCCCC)O2 2356342525 FLJXRCWDXADIBL-ISTRZQFTSA-N 325.405 2.029 30 1 EEEF CC(=O)C1=CC[C@H]2[C@@H]3CC[C@H]4[C@H](O)[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@@]12C 2356512832 GKCFQKGBOYKBGP-HEXRHRPMSA-N 348.483 2.457 30 1 EEEF COc1ccc2c3c1O[C@@H]1C=C(C(C)=O)C[C@H]4[C@@H](C2)N(C)CC[C@]314 40511525 FKNWJBZMTKZQMB-DKYLXPRQSA-N 325.408 2.490 30 1 EEEF COCC(=O)N1[C@@H](C#N)[C@@H](c2ccccc2C2=CCCCC2)[C@@H]1CO 95866850 XJOIDJIXTAYCGR-CMKODMSKSA-N 340.423 2.469 30 1 EEEF NC(N)=Nc1nc(C(=O)Nc2nc3c(F)cccc3s2)cs1 29568209 KSYWNCGZGFKOOQ-UHFFFAOYSA-N 336.377 2.049 30 1 EEEF CC(C)[C@H](c1nc2ccccc2o1)n1cc(/C=C/C(=O)NO)nn1 84668939 IOAXCKZMCHPECI-MVGZEHJDSA-N 327.344 2.183 30 1 EEEF N#Cc1cccc(CN2C[C@@H](OCC3CCOCC3)[C@H]3COC[C@H]32)c1 299841705 CDMJYJZSAHFMEJ-XUVXKRRUSA-N 342.439 2.201 30 1 EEEF C=C1C2=C(O)[C@H](O)[C@@H](C)C=C2C(=O)c2cc(O)c(OC)c(OC)c21 2356329701 KMJOSWUIOOZDTP-JKYUHCHBSA-N 330.336 2.368 30 1 EEEF CC#CCOc1ccc(S(=O)(=O)N2CCC[C@@H](S)C2)cc1 28820433 NVJUVGMOOGFJLZ-CQSZACIVSA-N 325.455 2.172 30 1 EEEF C[C@]12C=CC(=O)C=C1[C@](O)(CO)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@H]12 2356460237 NQQZWPXWZWALLC-NJQZYEBPSA-N 330.424 2.197 30 1 EEEF COc1cccc(NC(=O)ONC(=N)c2ccc3nonc3c2)c1 653778443 KJLFGRUYXLZLFX-UHFFFAOYSA-N 327.300 2.310 30 1 EEEF CC1=C(N2[C@@H](C)[C@H]2C)C(=O)C(Br)=C(N2[C@@H](C)[C@@H]2C)C1=O 169335118 RKTOSHDREXTIII-HWYRKCJFSA-N 339.233 2.204 30 1 EEEF C[N+](C)(C)CCCCCC[N+](C)(C)CC#CCOC1=NOCC1 203290883 FIVIWXPWPBVVMB-UHFFFAOYSA-N 325.497 2.083 30 1 EEEF Cc1ccc(S(=O)(=O)ON/N=C2\[C@H]3CCCC[C@H]3[C@@H]3O[C@H]23)cc1 6487588 AVTXTHBQNZOKPF-LQEGNRCWSA-N 336.413 2.148 30 1 EEEF CO[C@@]1(C#C[C@](O)(c2ccccn2)C2CCC2)CN2CCC1CC2 28563779 URXQXNPRSDVQNH-VQTJNVASSA-N 326.440 2.184 30 1 EEEF Oc1ccc(O)c(C=NNC(=S)N[C@@H]2C[C@H]3C[C@H]2[C@@H]2C=CC[C@H]23)c1 254047232 OFXIRPMFRVBDKI-NFWSPEMXSA-N 343.452 2.497 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cc(F)cc(C(=O)O)c3[nH]2)C1=O 587039570 TUSCFNMYDIKZEB-JTQLQIEISA-N 349.343 2.193 30 1 EEEF C#CCNC(=O)C1=C[C@@H](C2CCCCC2)C[C@@H](OCCCCO)O1 13656435 XNMGFLPANXTEIP-AEFFLSMTSA-N 335.444 2.352 30 3 EEEF CO[C@@H](C)COC1CCC(c2nc3nc(C#N)c(C#N)nc3[nH]2)CC1 587952471 ROYBRFZTYSOJEZ-UNXYVOJBSA-N 340.387 2.174 30 1 EEEF C=C1C[C@H](OC(=O)/C(C)=C\C)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@@H](O)C[C@@H]12 13326321 SDRJABGPZHYDOV-WPSQCNNFSA-N 344.407 2.475 30 1 EEEF N#Cc1c(-c2ccc3ccn(Cc4ccc(O)nc4)c3c2)[nH][nH]c1=N 1857535392 NDUQGKFKKXIFLP-UHFFFAOYSA-N 330.351 2.465 30 1 EEEF C=C1[C@@H]2CC(=O)[C@@H]3[C@](C2)([C@H](O)[C@H](O)[C@@H]2C(C)(C)CCC[C@@]32C)[C@@H]1O 299850148 AUVGEKXCVIHEPI-WQUFKNEXSA-N 334.456 2.067 30 1 EEEF CC[C@@H](C)N1CC(=O)/C(=C(/O)c2cc(OC)c(OC)cc2OC)C1=O 103272110 LTFSRMGIRPJUCJ-ILIMUTSYSA-N 349.383 2.191 30 1 EEEF CC[C@H](O)c1cc(C#Cc2cc(C(N)=O)c(NC(N)=O)s2)cs1 28524067 YFEAUXQZZQNVTD-NSHDSACASA-N 349.437 2.242 30 1 EEEF CC=C(C)C(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@]2(C)[C@H]3C(=O)C=C(C)[C@H]2[C@H]3C1(C)C 2356496382 HOXNGFVTRBWUMU-TURUBQNYSA-N 348.439 2.024 30 1 EEEF O=C1C[C@H](O)C2(Oc3cccc4cccc(c34)O2)[C@H]2C1=CC=C[C@@H]2O 2356719694 FKPPHRSYMWPOAW-IXDGSTSKSA-N 336.343 2.114 30 1 EEEF N#Cc1ccc(-c2nc3sc(Cl)cn3c2/C=N/N=C(N)N)cc1 73140741 GGMBDYXEOHNEMP-KPSZGOFPSA-N 343.803 2.195 30 1 EEEF C=C1C[C@@H](OC(=O)/C(C)=C/CO)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(C)=CC[C@@H]12 238754497 IEGGJIUEFMTJED-VFHVBBQNSA-N 344.407 2.477 30 1 EEEF Oc1ccc(O)c(C=NNC(=S)N[C@@H]2C[C@H]3C[C@H]2[C@@H]2C=CC[C@@H]23)c1 254047236 OFXIRPMFRVBDKI-NPODOCJWSA-N 343.452 2.497 30 1 EEEF CS(=O)(=O)/C=C/c1nc2cc(C#N)cc(Br)c2[nH]1 586923294 JBWYKPXIIVHNKZ-NSCUHMNNSA-N 326.175 2.212 30 1 EEEF C[C@H](Oc1ccc(C#N)cc1)c1nc2cccc(S(N)(=O)=O)c2[nH]1 587189659 DYQIRJKFYTURMZ-JTQLQIEISA-N 342.380 2.222 30 1 EEEF C=C1C[C@@]23CC[C@H]1C[C@@H]2[C@@]12CCC[C@](C)(CO)[C@H]1[C@@H](OC2=O)[C@@H]3O 2356553116 OMDPLJPNOXTENE-XYHPRSMDSA-N 332.440 2.434 30 1 EEEF C=C1[C@H](O)[C@@]23C(=O)C[C@@H]4C(C)(C)[C@H](O)CC[C@]4(C)[C@@H]2C[C@@H]1C[C@@H]3O 2356634481 FYHBINXIARYPCI-MQDQQGSHSA-N 334.456 2.067 30 1 EEEF CCCCCCCCN(CCC)C(=O)CC(=O)N[C@H]1CCOC1=O 71316812 SRCVTRQICSVPEH-HNNXBMFYSA-N 340.464 2.407 30 1 EEEF N#Cc1ccc(-c2csc(NCC(=O)NC[C@H]3CCCO3)n2)cc1 82193683 PAPZSCMQLGRBLL-CQSZACIVSA-N 342.424 2.389 30 1 EEEF CC(C)C[C@H](NC(=O)c1ccccc1OC(F)F)C(=O)NCC#N 82110503 JIPKPILBUGUQTK-LBPRGKRZSA-N 339.342 2.072 30 1 EEEF CC1(C)OC(=O)C(/C=N/c2ccnc(-c3ccncc3)n2)=C(O)O1 100053313 HENCFVXMAIMRLP-DJKKODMXSA-N 326.312 2.320 30 1 EEEF O=C1Nc2ccc([N+](=O)[O-])cc2/C1=C1/Nc2ccc(O)cc2/C1=N/O 101342026 MDIDMHALYFMVFV-BRNLPKLHSA-N 338.279 2.268 30 1 EEEF C=C(CO)[C@@H]1CC[C@@H]2C(=CC[C@H]3[C@@]2(C)CC[C@@H](O)[C@]3(C)C=O)[C@@H]1O 38493276 XHPCBLBUWVTOMU-UFANPLCHSA-N 334.456 2.235 30 1 EEEF biogenic,in-vitro NNc1cccc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)n1 587890205 VLGSSNBIVHLBIQ-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF N#Cc1cc2nc(CCNC(=O)Cc3ccccc3)[nH]c2cc1C#N 587228877 SLTYMWMZBKZZEL-UHFFFAOYSA-N 329.363 2.208 30 1 EEEF C=CCNC(=O)C(C)(C)N(Cc1ccncc1)C(=O)c1cccnc1 28953361 UKRWTGLGOWKFQL-UHFFFAOYSA-N 338.411 2.200 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)C(=O)C[C@@]3(C)[C@@]1(C)[C@@]21CO1 2356501723 LJWZOKOFCBPNAG-OUPALVCYSA-N 332.396 2.346 30 1 EEEF CCOc1ccc(CCn2cccc(/C=C/C(=O)NO)c2=O)cc1 143877409 STSDFRLWJQHIML-JXMROGBWSA-N 328.368 2.008 30 1 EEEF CCC/C=C/[C@@H]1C(=O)[C@H]2O[C@@H]2C2(OCC(CC)(CC)CO2)[C@@H]1CO 102688526 TWGDZVIUZPIUAD-FDYUCGAKSA-N 338.444 2.467 30 1 EEEF C=C(C)[C@@H](O)Cc1c(OC)c2cc(OC)cc(OC)c2n(C)c1=O 14682495 BPIVYUXQDVOPES-AWEZNQCLSA-N 333.384 2.044 30 1 EEEF biogenic C=C1C(=O)O[C@@H]2C3=C(COC(C)=O)CC[C@@H](OC(C)=O)[C@]3(C)CC[C@@H]12 138566994 LLUIAKNHFIRVHK-HIRMHNASSA-N 348.395 2.470 30 1 EEEF C[C@]12C[C@H](O)[C@H]3[C@H](CCC4=CC(=O)CC[C@@]43C)[C@H]1CC[C@@H]2[C@H](O)CO 255205354 DCMCEXCRUWBAFV-OGZRJVFESA-N 348.483 2.459 30 1 EEEF COCCNC(=O)[C@@H]1CCCC[C@H]1c1nc2ccc(C#N)cc2[nH]1 587230249 GVQINTUAKQBKOC-ZIAGYGMSSA-N 326.400 2.471 30 1 EEEF C#CCN1CCC(CNS(=O)(=O)c2ccc3ccccc3c2)CC1 1772586824 NBWJADYFSHGGRO-UHFFFAOYSA-N 342.464 2.463 30 1 EEEF Cc1cnnc2c1/C(=N/N=C(N)N)C[C@@H](c1ccccc1Cl)C2 13474682 LEJYYRQUAZFCLY-ADUAYUHLSA-N 328.807 2.146 30 1 EEEF CC(C)C[C@H](NC(=O)O[C@H]1CCc2ccccc21)C(=O)NCC#N 82065140 SKEJDBDLGODXLH-HOTGVXAUSA-N 329.400 2.455 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 257754421 ZCRLGANQNRMURE-GVPCIHJDSA-N 346.423 2.384 30 1 EEEF endogenous,in-man COCC(=O)N1CCC2(CCCN(Cc3ccc(C#N)cc3)C2)CC1 3956085 VPJYWROPQZDYKZ-UHFFFAOYSA-N 341.455 2.409 30 1 EEEF CO[C@@](C)(C(=O)O)C1=C[C@@]2(C)C(=CC1=O)CC[C@H](OC(C)=O)[C@@H]2C 238737023 RDRVOBNXHXPXJL-XNHCUKIZSA-N 336.384 2.280 30 1 EEEF C=C(C)C(=O)O[C@@H]1CC(=C)[C@@H]2C(=O)C=C(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 155855805 JSJWMSSGVMTDCV-NQNKBUKLSA-N 328.364 2.293 30 1 EEEF biogenic C[C@H]1CCC[C@@H](NC(=O)COC(=O)COc2ccc(C#N)cc2)[C@@H]1C 4994209 AUBMZDATDBAYQC-JJRVBVJISA-N 344.411 2.421 30 1 EEEF C#CC=C[C@@H]1[C@@H]2[C@H]3C[C@@H]4O[C@](OC)([C@H]2[C@H]4O3)[C@@]1(Br)CC 2356795172 IKEWAOKGFUGNOH-NCIOPRAOSA-N 339.229 2.494 30 1 EEEF CNc1ncc(C(=O)OC)cc1C#Cc1cc(Cl)ccc1OC 587903434 QXQAOXYQGAWWRN-UHFFFAOYSA-N 330.771 2.972 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]3C(COC(C)=O)=CC[C@H](OC(C)=O)[C@@]3(C)CC[C@H]12 2356430895 VHZJGEKNJYFJNY-FSNPWBFUSA-N 348.395 2.325 30 1 EEEF NC(=S)N/N=C(\c1cccnc1)c1cccc(Br)c1 64513806 DPTPEKAUCAAQNG-ATVHPVEESA-N 335.230 2.430 30 1 EEEF in-vivo CC1=C[C@@H](O)CC(CO)=CC[C@H]2CCC3=C(C(=O)[C@H]1[C@@H]3O)C2(C)C 2356536672 PLSLPANFUZMMNZ-GARXJVFOSA-N 332.440 2.299 30 1 EEEF C=C1C[C@@]23C[C@H]1C(=O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)O 2356735010 PHYYFNCWOIYWTJ-ZDCKYFFZSA-N 330.380 2.344 30 1 EEEF Cc1ccc(/C(=N/O)N2CC[C@H](N(C)C)C2)c(Oc2cccnc2)n1 72101683 RFNNXGWSOILSGH-NNLSSIJJSA-N 341.415 2.349 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)[C@]1(C)C[C@@H](O)CC(C)(C)[C@H]1C[C@H]3O 238763576 XIGJIFFLTSZIKL-STEARHNWSA-N 334.456 2.067 30 1 EEEF CC(C)[C@@H](NC(=O)c1ccc(C#Cc2ccccc2)cc1)C(=O)NO 96910100 ZBZLOHPXIWQAKZ-GOSISDBHSA-N 336.391 2.346 30 1 EEEF C[C@@H]1NC=CC(=O)[C@@]12Oc1ccccc1C(=O)[C@H]2C(=O)c1ccco1 587597085 SBOAAVAUODSRDI-UTLVKMTRSA-N 337.331 2.167 30 1 EEEF CCN1C(=O)N(CC)[C@H]2[C@H]1NC(=O)N2/N=C/C=C/c1ccccc1 1857754174 NRUADQHKBGCFCV-XUMQJTEQSA-N 327.388 2.140 30 1 EEEF O=C(CCCCCCN1C(=O)/C(=N\O)c2cc(Cl)ccc21)NO 103294343 FBRYAWBKACNJBY-JXAWBTAJSA-N 339.779 2.321 30 1 EEEF O=[N+]([O-])c1ccc(N/N=C/c2ccc(O)c(O)c2O)c([N+](=O)[O-])c1 26264146 RCIQHRVWYPAVOJ-MKMNVTDBSA-N 334.244 2.066 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]12C[C@@H](O)C[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 197452874 HHDWSDSMWJQURA-MTVNJVDJSA-N 332.396 2.136 30 1 EEEF Nc1n[n+](CC(=O)c2ccccc2)c2sc(-c3ccccc3)nn12 17256256 TXRQFDXHHCUYGX-UHFFFAOYSA-N 336.400 2.210 30 1 EEEF COc1ccc2c(c1OC(C)=O)C1=CC(=O)CC[C@@]13CCN[C@H]3C2 1611737 ITOZXSNVASSYGQ-QFBILLFUSA-N 327.380 2.271 30 1 EEEF Cc1cccc2sc(NC(=O)c3csc(N=C(N)N)n3)nc12 29567785 BLEBIUCRUYMISV-UHFFFAOYSA-N 332.414 2.218 30 1 EEEF C=C1CC[C@@H](OC(C)=O)[C@]2(C)C[C@H](OC(C)=O)[C@H]3C(=C)C(=O)O[C@@H]3[C@@H]12 40394042 IDVKLEJKBPWDKI-DIIACTEISA-N 348.395 2.324 30 1 EEEF NC(=O)c1cccc2c1O/C(=C\c1ccc(OC[C@H]3CO3)cc1)C2=O 169348816 SHMSNUPWFZACTQ-TUTDSIAXSA-N 337.331 2.179 30 1 EEEF C=C1C(=O)O[C@@H]2[C@H]3C(C)=C(O)C(=O)C3=C(C)C[C@@H](OC(=O)C(C)C)[C@@H]12 156044673 NLXVFIOZASEMRL-CVGURMSBSA-N 346.379 2.403 30 1 EEEF C[C@@H]1C[C@@H]2O[C@@H]2CCC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 2356421047 XFALPAMSDFFXGY-GTTSAUCSSA-N 332.352 2.262 30 1 EEEF NC(=O)NC(=O)C[n+]1ccc(/C=C/c2cccc3ccccc23)cc1 28224222 SLDBJHRATTTWIW-CMDGGOBGSA-O 332.383 2.493 30 1 EEEF C=C[C@](C)(O)[C@H](O)C[C@@H]1C(=C)[C@H](O)C[C@@H]2[C@](C)(CO)CCC[C@@]12C 2356651822 CYJDHAXSZJABJA-PHJNVHRLSA-N 338.488 2.416 30 1 EEEF C=C(C)OC(=O)[C@H]1CCN2C[C@@H]3C[C@@H](CN4C(=O)CCC[C@H]34)[C@@H]2C1 40848025 KYNLTFRMKGZMBW-VIQHNZTISA-N 332.444 2.175 30 1 EEEF N#Cc1ccc(C(=O)N2CC[C@H]3[C@@H]2CCC(=O)N3c2cccnc2)cc1 96186471 QMCOCJXTBFRUPJ-ROUUACIJSA-N 346.390 2.363 30 1 EEEF COCCCNc1ncc(C#Cc2cc(Cl)ccc2OC)cn1 587908479 XLEMPLFBGMQNRW-UHFFFAOYSA-N 331.803 2.987 30 1 EEEF NC(N)=N/N=C1\c2ccccc2C[C@@H]1Sc1nc2ccccc2[nH]1 101277709 OLXDFULPBKAYAM-UGHXVNEISA-N 336.424 2.257 30 1 EEEF COc1ccc(S(=O)(=O)OCC[C@@H]2CC(C)(C)OC2=O)cc1 64634090 XRUVELZYLVNPFK-LLVKDONJSA-N 328.386 2.132 30 1 EEEF in-vitro C=C1C(=O)[C@]23C[C@H]1CC[C@@H]2[C@@]1(CCC[C@]2(C)[C@H]1CO[C@H]2O)COC3=O 238758643 COKCKHYUZSETSY-NIQJFZTPSA-N 346.423 2.226 30 1 EEEF O=C1O[C@H]2C=CCC=C2C(=O)[C@H]1Cc1c(O)c2ccccc2oc1=O 169692525 FMTPOCAUOVRPJN-HIFRSBDPSA-N 338.315 2.038 30 1 EEEF N#C[C@@H](C(=O)Nc1ccc(C(F)(F)F)cc1)C(=O)[C@@H]1CCCN1 169714920 AVJJSTSKKNYXAA-NEPJUHHUSA-N 325.290 2.105 30 1 EEEF CC=C1CN2CC[C@@]34C5=CC(=O)C=CC5=N[C@@]23CC[C@H]1[C@H]4C(=O)OC 2356616939 LKDWBLMHMZGRGJ-UDDICAGYSA-N 338.407 2.054 30 1 EEEF COc1ccc2c(c1)CCN1C(=O)/C(=C/C(=O)c3ccccc3)NC[C@@H]21 96934326 LIMMLFUDPNTOJP-OVCORXIESA-N 348.402 2.491 30 1 EEEF O=C(NO)[C@H](Cc1ccccc1)C(=O)NCCCc1ccccc1 13777239 CQGGQNFRJIAPHA-QGZVFWFLSA-N 326.396 2.100 30 1 EEEF in-vivo C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@H]12 2356435471 DHTWVKTXQLZELP-IWQSFCKSSA-N 348.439 2.288 30 1 EEEF CCCC(=O)C=CC1=C(O)c2c(cc(OC)c(OC)c2O)C(=O)C1=O 2356516216 PIMHFJPKESFSSO-UHFFFAOYSA-N 346.335 2.369 30 1 EEEF C=C[C@]12CNCC[C@@H]1[C@@](C(=O)OC)(c1cc3ccccc3[nH]1)CO2 14693448 KZLFAYYOKRWYDO-ZYSHUDEJSA-N 326.396 2.143 30 1 EEEF biogenic CC(=O)C1=C(C)N=C(SCCC(=O)O)N[C@H]1c1cccc(O)c1 98084775 LFVCHCWJLBIVBU-HNNXBMFYSA-N 334.397 2.463 30 1 EEEF C=C1C[C@]23CC(=O)[C@@H]4[C@]56CCC[C@@]4(C)C(=O)N(C)[C@@H]5[C@H]2C[C@H]1C(=O)[C@H]36 95910014 YLHNZWYZUIPWIF-LOMBHMDLSA-N 339.435 2.374 30 1 EEEF biogenic,in-vitro O=C(NO)C1(C(=O)NCCCc2ccccc2)Cc2ccccc2C1 13780636 YTRVZNHAMCBMCT-UHFFFAOYSA-N 338.407 2.026 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2C1=CC[C@H](O)[C@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O 2356424824 WFTRKYGVESACJS-OCWUILPPSA-N 332.396 2.462 30 1 EEEF CN(O)C(=O)CO[C@H](c1ccc(Cl)c(Cl)c1)P(=O)(O)O 95553957 BNXJAJGNFMLKQG-JTQLQIEISA-N 344.087 2.034 30 1 EEEF N#Cc1nc2nc([C@H]3C=C(c4ccc(Cl)cc4)NO3)[nH]c2nc1C#N 587076669 NWEFMGOIXRZFFG-CYBMUJFWSA-N 349.741 2.367 30 1 EEEF CCNC(=N)N/N=C/c1ccc(-c2cn3cc(C)ccc3[n+]2C)cc1 26824871 VAXBEVFWTKAMCQ-SSDVNMTOSA-N 335.435 2.207 30 1 EEEF C[C@H](N[C@H]1c2cc(C#N)ccc2OC(C)(C)[C@@H]1O)C(=O)OC(C)(C)C 96941748 HTQRBOPBRPMVKW-KNXALSJPSA-N 346.427 2.451 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C[C@H]3C(C)(C)[C@@H](O)C[C@@H](O)[C@]3(C)[C@@]2(O)CC1 96086185 ZTWPAGAVIFLSKK-LOBZHTCKSA-N 334.456 2.377 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@]2(N1)C(=O)C=CN[C@@H]2C 587792923 INJXIIPYPDFSAK-XWRVAKJBSA-N 339.208 2.392 30 1 EEEF C[C@@H]1NC=CC(=O)[C@]12Oc1ccccc1C(=O)[C@H]2C(=O)c1ccco1 587597086 SBOAAVAUODSRDI-WQFAYQGZSA-N 337.331 2.167 30 1 EEEF C=C[C@]1(C)C=C2C(=O)C(O)=C3C(C)(C)[C@H](O)CC[C@]3(C)[C@]2(O)[C@@H](O)C1 2356460945 PYMRQNNIAHSRKU-UTMKNSETSA-N 348.439 2.183 30 1 EEEF C=C1C[C@@]23C=CC(=O)[C@](C)(CCC(=O)OC[C@@H](O)CO)[C@H]2C[C@H]1CC3 2356712542 FYKIZBPSTADBEK-KMJHBWPFSA-N 348.439 2.171 30 1 EEEF O=C(CCC1=CCN(CCc2cccc(C(F)(F)F)c2)C1=O)NO 84759346 GHZMJMRXPALWAN-UHFFFAOYSA-N 342.317 2.302 30 1 EEEF CC(C)C[C@H](NC(=O)c1coc(-c2ccccc2)n1)C(=O)NCC#N 82065624 ONQCKBSYQICEIX-AWEZNQCLSA-N 340.383 2.126 30 1 EEEF C=CCOCn1c(Cc2cc(C)cc(C)c2)c(CC)c(=O)[nH]c1=O 1912793 LWZPIMCWSJKHHW-UHFFFAOYSA-N 328.412 2.467 30 1 EEEF OCC#CCN1CCN(C2c3ccccc3CCc3ccccc32)CC1 29565226 NSJLKINAZYWLPI-UHFFFAOYSA-N 346.474 2.488 30 1 EEEF C[C@@]1(CO)[C@H]2C[C@H](O)[C@@]34C[C@@H](CC[C@H]3[C@]2(C)CC[C@H]1O)[C@]1(C)O[C@@H]14 238750179 VCANOOFBKLBIKN-WABSZHGXSA-N 336.472 2.101 30 1 EEEF O=C(/C=C/c1cc(C(=O)c2cccc(F)c2)c[nH]1)CC(=O)C(=O)O 95920713 BSZJLJRYNPZJPB-SNAWJCMRSA-N 329.283 2.011 30 1 EEEF N#Cc1c(-c2ccccc2)[n+](=O)c2ccc(C3OCCO3)cc2n1O 1772578403 MFNGWGXHAFHUSL-UHFFFAOYSA-N 336.327 2.377 30 1 EEEF C[C@@](CCc1ccc(C2=CCCC2)cc1)(C(=O)NO)S(C)(=O)=O 169708238 JFOZMRZNNNYARO-QGZVFWFLSA-N 337.441 2.495 30 1 EEEF C[C@@]12CC[C@@](C)(O1)[C@@H]1C(=O)N(c3cnc(C#N)c(Cl)c3)C(=O)[C@@H]12 29126880 VKOUOBLCMIKWHV-CRJCFHLZSA-N 331.759 2.054 30 1 EEEF CC1=C(OCCN2C(=O)C(=O)c3cc(C)ccc32)[C@@H](C)SC1=O 71329922 ISOWPJUDFHSJBK-LLVKDONJSA-N 331.393 2.477 30 1 EEEF Cc1c(O)cc(C[C@H](C)O)c2cc(C3=CC(=O)C[C@H](C)O3)c(=O)oc12 14594762 QOKXUEDIOODDAI-UWVGGRQHSA-N 344.363 2.449 30 1 EEEF biogenic Cn1c(N)c(C#N)c2cc(Oc3ccc(NC(=O)CN)cc3)ccc21 299855909 BYFWRNNQCQLOCH-UHFFFAOYSA-N 335.367 2.322 30 1 EEEF COC(=O)/C=C/c1cccc(CNC2=CC(=O)c3ncccc3C2=O)c1 1857744672 WVMWPWPKVBYOLT-BQYQJAHWSA-N 348.358 2.321 30 1 EEEF C=C1CCC=C(C)CC[C@H]2C(=CC=CC(O)(CO)CO)COC(=O)[C@@H]12 2356427346 WVMYRDBAJSJKGW-ROUUACIJSA-N 348.439 2.050 30 1 EEEF C/C1=C\CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)[C@@H](CN3CCOCC3)[C@@H]2CC1 136918511 VHSZRNXTICCEKT-UGARAJBXSA-N 335.444 2.154 30 1 EEEF CC(C)C[C@@H](NC(=O)Nc1ccc2ncsc2c1)C(=O)NCC#N 82061203 OSCXONMVMFKLLT-CYBMUJFWSA-N 345.428 2.472 30 1 EEEF COC(=O)Cc1n[nH]c2c1[C@H](c1c[nH]c3ccccc13)[C@@H](C#N)C(=N)O2 169690876 REGVENFQJHUBDE-BMIGLBTASA-N 349.350 2.248 30 1 EEEF COc1ccc(C(=O)N2Cc3cnnn3-c3ccccc3[C@H]2C#N)cc1 61942558 SSHNWICKICVEKS-GOSISDBHSA-N 345.362 2.497 30 3 EEEF CCCn1c(C(=O)c2cc(C)cc(C#N)c2)c(C(C)C)c(=O)[nH]c1=O 49036965 ZXONPSZUOLSXSE-UHFFFAOYSA-N 339.395 2.481 30 1 EEEF in-vitro COc1ccc(/C(=N\O)C(=O)c2ccc(S(C)(=O)=O)cc2)cc1 261179621 VSHPTRZGMOXKEQ-BMRADRMJSA-N 333.365 2.160 30 1 EEEF O=C1C=C(NC(=O)c2ccccc2)C(=O)C=C1NCc1ccccc1 1772609440 MQKOAQLICYSLAD-UHFFFAOYSA-N 332.359 2.126 30 1 EEEF CCN1C(C)=C(C(=O)OC)[C@H](c2cccs2)N/C1=N\CCOC 15937426 YCYQWDDVLPVOQG-AWEZNQCLSA-N 337.445 2.164 30 3 EEEF C=CCNC(=O)Nc1ccc(OC[C@@H](O)CNC(C)(C)C)c(C)c1 169317391 QSPRBYWGLZPEGG-HNNXBMFYSA-N 335.448 2.430 30 1 EEEF COc1cc(C=C2Oc3cc(O)cc(O)c3C2=O)cc(OC)c1O 2356321067 LOVMOOUQHWMIHZ-UHFFFAOYSA-N 330.292 2.437 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(C)[C@H](O)CC[C@](C)(C(=O)O)[C@@H]1C[C@H]3O 2356410452 LRECIABFFPIQSO-VZQULZNPSA-N 348.439 2.161 30 1 EEEF N#C[C@@H]1CCCN1C(=O)CNC(=O)c1ccnc2ccc(Cl)cc12 96270278 KPLYEVMFCDTZKW-LBPRGKRZSA-N 342.786 2.133 30 1 EEEF C[C@@H](Oc1ccccc1)C(=O)NCc1nc2cc(C#N)c(C#N)cc2[nH]1 587225222 NSSUQHVIWOMGQJ-GFCCVEGCSA-N 345.362 2.390 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(NCCNC(C)=O)nc1 587907597 CKNVUHLXSFQGQH-UHFFFAOYSA-N 343.814 2.691 30 1 EEEF N#C[C@@H](c1ccc(Cl)cc1)c1c(O)nc2ccc(N)cc2[n+]1[O-] 17188007 BRRIKBOQJWSCHX-LBPRGKRZSA-N 326.743 2.465 30 1 EEEF C=C1C[C@@]23C[C@]1(O)CC[C@H]2[C@]12C=CC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100784060 UXLXLQYIDWLPKX-YLSSHGGHSA-N 330.380 2.056 30 1 EEEF endogenous,in-man CSCC[C@@H](NC(=O)[C@@H](CS)CCc1ccccc1)C(=O)O 26494900 XZJCTWVYKRGLQJ-ZIAGYGMSSA-N 341.498 2.488 30 1 EEEF CCCC[C@H]1CN(C(=O)c2ccccc2)CCN1C[C@@H](N)CS 22938318 XNUGRKDPRCDTJX-SJORKVTESA-N 335.517 2.260 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@@](C)(CO)CC[C@H](O)[C@@]4(C)[C@@H]2CC[C@@H]1[C@H]3O 96902271 IOLAXGYDTVZNNV-UGKKBRBKSA-N 334.456 2.068 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccnc(N2CCOCC2)n1 587910922 ZDZUWRSXCUTLQP-UHFFFAOYSA-N 329.787 2.375 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cc4cn[nH]c4cc3[nH]2)C1=O 587038473 JEGSZZBXJDPIAZ-GFCCVEGCSA-N 327.369 2.232 30 1 EEEF Cc1cc2c(cc1O)[C@@](CC#N)(c1cccc(C#N)c1)N[C@H](C(=O)O)C2 963511644 URBIROOJYLTIAR-FXAWDEMLSA-N 347.374 2.328 30 1 EEEF CC(=O)[C@@H](CCC#N)[C@@]1(C)N[C@H](C(=O)O)Cc2ccc(O)c(C)c21 963549977 JPUZFQIOUALAPC-QWQRMKEZSA-N 330.384 2.024 30 1 EEEF Cc1c(O)cc(C[C@H](C)O)c2cc(C3=CC(=O)C[C@@H](C)O3)c(=O)oc12 14594760 QOKXUEDIOODDAI-VHSXEESVSA-N 344.363 2.449 30 1 EEEF biogenic C[C@@H]1C[C@@H]2O[C@H]2C=CC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 2356447606 XTUZVEOWUSGCSV-VFVAKGGASA-N 330.336 2.038 30 1 EEEF O=C1C=CC=C/C1=C\NNC(=S)N[C@@H]1C[C@H]2C[C@H]1[C@@H]1C=CC[C@@H]12 104017610 WVNYYTSFNKWSKL-UGVALMBNSA-N 327.453 2.135 30 3 EEEF O=C(NO)c1ccc2c(c1)C[C@@H](NC(=O)c1ccc(Cl)cc1)CN2 113848244 DLHFOYKBAKTUQQ-CQSZACIVSA-N 345.786 2.226 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)C(=O)C[C@]3(C)[C@@]1(C)[C@]21CO1 2356501726 LJWZOKOFCBPNAG-WGBOWRHLSA-N 332.396 2.346 30 1 EEEF C=C(C)[C@@H]1CC(=O)[C@@H]2[C@H]3C(=O)C[C@@H](C=C3C(C)=O)[C@H](C(=O)O)[C@@H]2C1 2356807588 XWUMXWKSQYTAOG-ODWHLXGASA-N 330.380 2.209 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@@]3(C)[C@@H](O)C[C@@H](OC(=O)C(C)C)C(=C)[C@@H]3C[C@H]12 73141107 DEXDLEUFCATLMY-XPYFFNBCSA-N 334.412 2.389 30 1 EEEF C=C1[C@H]2CC[C@@]3([C@H]1O)[C@@H](C2)[C@@]12CCC[C@@](C)(C(=O)OC1)[C@H]2C[C@H]3O 15046709 YCDLVBJHTHGAOX-AFQJYMIFSA-N 332.440 2.434 30 1 EEEF biogenic COc1cc(O)c2c(c1)CC(=O)C=CC=C[C@H]1O[C@@H]1C[C@@H](C)OC2=O 299807383 BXYHHINRBKIWCZ-SSKCKEOISA-N 344.363 2.341 30 1 EEEF N#CC1(NC(=O)[C@H](Cc2ccccc2)NC(=O)c2ccccc2)CC1 1857563640 PIEOUSVKYUIHRE-KRWDZBQOSA-N 333.391 2.200 30 1 EEEF C[C@@H](Cc1ccc(NS(=O)(=O)c2ccccc2)cc1)C(=O)NO 26722533 RKDXFSHFQNWESJ-LBPRGKRZSA-N 334.397 2.171 30 1 EEEF C=C1[C@@H]2C(=C(COC(=O)C(C)C)CC[C@@H]3C(=C)C(=O)O[C@@H]23)C[C@H]1O 2356644495 INJHISWMTROACX-MWQQHZPXSA-N 332.396 2.311 30 1 EEEF Clc1ccc(C#Cc2nc3[nH]cnc3c(=N[C@@H]3CCOC3)[nH]2)s1 1857549375 URIYBOOXAWAEFR-SECBINFHSA-N 345.815 2.090 30 1 EEEF O=C(/C=C/c1ccc(CNC23C[C@H]4C[C@@H](CC(O)(C4)C2)C3)cc1)NO 103130954 HYWWJTQPMSDRJZ-YLNGWFENSA-N 342.439 2.379 30 1 EEEF C=CCn1c(O)cc(=O)nc1SCC(=O)Nc1ccccc1C 103870525 YPGLWEOOXNCOLQ-UHFFFAOYSA-N 331.397 2.174 30 3 EEEF N#Cc1cccc(C(=O)N[C@H]2CCC[C@@H](NC(=O)c3ccccn3)C2)c1 95587693 WSQGEPYGCDINHA-DLBZAZTESA-N 348.406 2.424 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cc(C(=O)O)c(F)cc3[nH]2)C1=O 587038108 CWGARMMSGGNKLW-LLVKDONJSA-N 349.343 2.193 30 1 EEEF C=C1C[C@H](OC(=O)C(C)C)[C@@H]2[C@H](C)C(=O)O[C@@H]2[C@@H]2[C@@H]1C[C@@H]1O[C@@]12C 2356557721 ZEIPBAWKAWZVOR-WGZJJBEDSA-N 334.412 2.485 30 1 EEEF C=CCNC[C@@H](O)COc1cccc2c(=O)c3ccccc3oc12 40936197 RNEPUWOVSZUZJP-CYBMUJFWSA-N 325.364 2.462 30 1 EEEF CNC(=S)N/N=C(/c1ccc(OC)c(OC)c1)c1cccc(C)n1 95589031 RYNRGNFTUYUNRA-SILNSSARSA-N 344.440 2.254 30 1 EEEF Cc1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)nc(N)n1 587890080 OIDDXYOWTZOJDV-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF C=C1C2=C(O)[C@H](O)[C@@H](C)C=C2C(=O)c2cc(OC)c(O)c(OC)c21 2356329854 NCHXGWSVVROJJA-JKYUHCHBSA-N 330.336 2.368 30 1 EEEF CC(=O)N[C@@H](C)Cc1ccc(C#Cc2ccnc(N3CCC3)n2)cc1 113413970 KYRXALZKHBSCEJ-HNNXBMFYSA-N 334.423 2.154 30 1 EEEF CC(=O)O[C@H](C)[C@H](C=C1C=C(C)C2=NCC[C@@H]3O[C@]123)OC(=O)C(C)C 2356476656 MRUZXUQKRAPYFF-OYWVLEMYSA-N 347.411 2.374 30 1 EEEF C=C1C(=O)O[C@@H]2C3=C(C)C(=O)C[C@@H]3[C@](C)(O)C[C@H](OCC(C)C)[C@H]12 2356491346 IDJQTNTZPPTSEU-NULVTLCPSA-N 334.412 2.186 30 1 EEEF C=C1C(=O)[C@@]23[C@H]4CC5=C(C(=O)CC5(C)C)[C@@](C)(O4)[C@@H]2CC[C@H]1[C@H]3O 2356621036 MJXXHOYVYOQSOU-SKHUJLECSA-N 328.408 2.356 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(CO)CCC[C@](C)(CO)[C@@H]1C[C@@H]3O 2356645365 NLKCAXRWGIRDDQ-GVUXFJDWSA-N 334.456 2.070 30 1 EEEF C=C1C(=O)[C@@]23C[C@H](O)[C@H]1C[C@@H]2[C@]1(C)CCC[C@](C)(CO)[C@@H]1C[C@@H]3O 2356788038 WHNRXVKFGPGHAF-YMEAULIBSA-N 334.456 2.068 30 1 EEEF CC1=C[C@]2(O)C(=O)[C@](C)(O)[C@@H]3[C@@H]4[C@@H](CC[C@]3(C)C=C2C1=O)C4(C)C 2356419498 UZEAKOOBNZOXDE-DTMOTUAUSA-N 330.424 2.195 30 1 EEEF CCNc1nc2cc(C#CCCO)c(Cl)cc2nc1C#CCCO 115764978 AMBKOSADBRJUPZ-UHFFFAOYSA-N 343.814 2.183 30 1 EEEF C=C[C@]1(C)CCC2=C([C@H](O)C(=O)[C@@H]3C(C)(C)CC[C@H](O)[C@@]23C)[C@H]1O 2356734935 KKWFUTJLCATXQH-XCJOJWPZSA-N 334.456 2.377 30 1 EEEF C=CCN(C)C[C@@H]1CN2CC[C@H]1C[C@@H]2CNC(=O)c1cccs1 2356813807 BURJLYWVSNLLMI-ARFHVFGLSA-N 333.501 2.306 30 1 EEEF CC(C)C[C@H](NC(=O)O[C@@H]1CCOc2ccccc21)C(=O)NCC#N 82065209 KIZVLCBYIBQTSN-GOEBONIOSA-N 345.399 2.291 30 1 EEEF C#C[C@@]12O[C@]1(C=O)[C@@H]1[C@@H](O)C[C@H]3C(C)(C)CCC[C@]3(C)[C@H]1CC2=O 95099111 RLCVKAJQPCOLQK-OJQPHWMWSA-N 330.424 2.129 30 1 EEEF biogenic,in-vitro C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@@H](C(=O)O)[C@H]1[C@@]2(C)CCC[C@@]31COC2=O 257483223 MJFVMFNFTCKAEV-BHMJSRMOSA-N 346.423 2.384 30 1 EEEF endogenous,in-man Nc1nccc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)c1N 587877622 CUUWLWARHQJQAE-UHFFFAOYSA-N 349.221 2.263 30 1 EEEF CN1CCN(c2ccc(-c3cccc(CC(=O)NCC#N)c3)cc2)CC1 13525723 FLKKEIPZPPWUDF-UHFFFAOYSA-N 348.450 2.288 30 1 EEEF CN=C1NCC#C[C@H]2C[C@H](C)[C@@]34CCC(C(=O)O)=C3C[C@H]2[C@@]4(C)CN1 2356353100 IDOIZYCKBKFALL-OYTSCLNUSA-N 341.455 2.012 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)C(=O)O[C@]2(O)C[C@]23O[C@@H]2CC[C@H](C)[C@@]13C 100266471 YQSCJMNPXRPKAC-OFDCVIAWSA-N 348.395 2.014 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@H]2[C@]12OC(=O)[C@](C)(CC[C@H]1O)[C@@H]2[C@H]3C(=O)O 100823411 JKQCGVABHHQYKQ-VIJSRRTDSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C=C(C)C(=O)O[C@@H]1C[C@](C)(O)C(=O)CCC(C)=C[C@H]2OC(=O)C(=C)[C@H]21 2356754584 AYLHAROHTWZRTO-UMHPPVOVSA-N 348.395 2.022 30 1 EEEF O=C1C=CCN(S(=O)(=O)c2ccccc2)[C@H]1Cc1ccccc1 36175743 ATIRPKRDWOUCGZ-KRWDZBQOSA-N 327.405 2.428 30 1 EEEF CC(C)C[C@H](NC(=O)c1ccc2cc(N)ccc2c1)C(=O)NCC#N 82065396 KNTNWHXSICHQGG-KRWDZBQOSA-N 338.411 2.206 30 1 EEEF CCC1(CC)C(=O)NC(=O)N/C1=N\CCc1ccc(OC)c(OC)c1 3107008 XLOOZBSJBIFDQQ-UHFFFAOYSA-N 347.415 2.291 30 1 EEEF biogenic COc1ccc(F)cc1[C@H]1C/C(=N\N=C(N)N)c2c(C)ccnc2C1 13474713 WHMSZUDKRHONNW-FYUXQQNOSA-N 341.390 2.245 30 1 EEEF COc1cc([C@H](C)C#Cc2c(C)nc(N)nc2N)cc(OC)c1OC 14968142 RUQVXLIOJPKNCM-SNVBAGLBSA-N 342.399 2.130 30 1 EEEF C=C(C#CC1=C[C@H](O)[C@H](O)[C@H](O)[C@H]1O)CCC=C(C)CCC=C(C)C 2356334235 CADYTUXNRNXAES-XSDIEEQYSA-N 346.467 2.403 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2C1=CC[C@H](O)[C@](C)(C(=O)O)[C@H]1[C@H]3C(=O)O 2356424823 WFTRKYGVESACJS-HWBSVCAYSA-N 332.396 2.462 30 1 EEEF CC(C)C1=C[C@H]2C[C@@]3(C=O)[C@@H]4CC[C@](C)(O)[C@@H]4C[C@@]2(CO)[C@@]13C(=O)O 2356465760 GEHSSDSUIBHHAH-HCKJENEASA-N 348.439 2.018 30 1 EEEF C[C@@H]1C[C@]23C(=O)[C@H](C)C[C@@H]4C(C)(C)[C@]45O[C@@](C)(C=C2C1=O)[C@@H](O)[C@H]53 2356522873 XKHKWWYWWNXZDZ-DPDFDLJHSA-N 330.424 2.291 30 1 EEEF C=C1C(=O)[C@@]23C[C@H](O)[C@@H]4C(C)(C)CCC[C@]4(C)[C@@H]2[C@@H](O)C[C@H]1[C@H]3O 2356638808 RFZAFMSAZOFRSM-PYJNLVAWSA-N 334.456 2.067 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CC[C@H](O)[C@@]2(C)C(=O)O[C@H]([C@@H]12)[C@@H]3O 138945603 RYFKIVZHGGVMBP-OTFYASLDSA-N 332.440 2.432 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(OC[C@@H](O)CO)cc1 587907114 DXYMDRFGMMTYKD-INIZCTEOSA-N 332.783 2.480 30 1 EEEF O=CCC[C@]1(C(=O)O)Oc2ccccc2C(=O)[C@@H]1C(=O)c1ccco1 587603581 NTVWIXHUYWRWHD-KDOFPFPSSA-N 342.303 2.156 30 1 EEEF CC1=C[C@@H]2[C@H](CCC3=C[C@@H](C[C@]4(C)O[C@@H]4[C@H](O)[C@H]1O)OC3=O)C2(C)C 2356815656 CUCOPNHAVGPVDH-JZVOWAHYSA-N 348.439 2.120 30 1 EEEF C[C@@H]1CC2=C(C1=O)[C@H](O)[C@]1(C)CC[C@@H]3[C@H]([C@@H](O)[C@]1(C)C2=O)C3(C)C 2356876549 ZLWDXUVVPOSFGG-DSQXZVENSA-N 332.440 2.275 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@]45CCC[C@](C)(C(=O)OC4)[C@H]5[C@H](C(=O)O)[C@@]3(C2)[C@H]1O 85799974 MJFVMFNFTCKAEV-KGEDESCYSA-N 346.423 2.384 30 1 EEEF in-man Cc1cc2c(F)c(Oc3ncnc(N)c3/C=N/OCCO)ccc2[nH]1 14949834 PMSUAYIHWVITQX-QPSGOUHRSA-N 345.334 2.123 30 1 EEEF CCO[C@]12C[C@]3(C)[C@@H](CC1=C(C)C(=O)O2)C(C)=CC(=O)[C@@H]3OC(C)=O 2356500630 YDUWTFHAUBSRIH-IVJVFBROSA-N 348.395 2.470 30 1 EEEF C=C1C[C@@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)OC 2356549655 CSOGGDRRRLWUTQ-LVZBVOIRSA-N 344.407 2.145 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cc(OC)c(OC)cc3[nH]2)C1=O 587038058 CDAQLRRPNWAIAU-CYBMUJFWSA-N 347.396 2.373 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2C1=C[C@H]2OC(=O)[C@@](C)([C@H]1[C@@H]3C(=O)OC)[C@H]2O 238767953 JWHHXJJTWYOOAO-KNTVBGGZSA-N 344.407 2.001 30 1 EEEF N#Cc1ccc(OCCn2ccc(=O)n(Cc3ccccc3)c2=O)cc1 95589646 IXIBRPNIUPBWGV-UHFFFAOYSA-N 347.374 2.009 30 1 EEEF O=C(CCCCCONC(=O)c1ccc(C(F)(F)F)cc1)NO 95595651 ARCXYEXWOYVSTQ-UHFFFAOYSA-N 334.294 2.433 30 1 EEEF C[C@@H](C(=O)N(C)O)c1ccc2c(c1O)C(=O)c1c(O)cccc1C2 13606217 FMWKENZICXRFGI-SECBINFHSA-N 327.336 2.184 30 1 EEEF COC1=C[C@]23CCc4cc(OC)c(OC)cc4[C@]2(CCN3C)CC1=O 169426636 XWTJDHWJXSZTLM-VQTJNVASSA-N 343.423 2.465 30 1 EEEF COC(=O)C1=C2Nc3ccccc3[C@]23CCN2CC[C@H]1[C@]1(O[C@@H]1C)[C@@H]23 2356381466 NYHQYHWNIWLUDO-DPGRLXAWSA-N 338.407 2.042 30 1 EEEF C=C1C[C@H](O)[C@@H]2O[C@]2(C)CC[C@@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@@H]12 2356435469 DHTWVKTXQLZELP-FHXVVSRQSA-N 348.439 2.288 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@]2(CC[C@H]3C(=CC=CC(C)(C)O)C(=O)OC[C@@H]13)CO2 2356803328 WZDCQTZIRFGNEC-ZZKADIETSA-N 346.423 2.306 30 1 EEEF O=C(O)C[C@H](SC1=C(Cl)C(=O)c2ccccc2C1=O)C(=O)O 49803436 SQYAJXDRTWJQHM-QMMMGPOBSA-N 340.740 2.177 30 1 EEEF N#Cc1c(-c2ccc(Br)cc2)nc(S)n2nnnc12 96932361 OCXNKJCABXHUKT-UHFFFAOYSA-N 333.174 2.109 30 1 EEEF COC1=C[C@]23CCN(C)[C@H](Cc4cc(O)c(OC)cc42)[C@H]3CC1=O 238755331 IXNZNQMODAROFN-PJIJBLCYSA-N 329.396 2.018 30 1 EEEF N#Cc1ccc(-c2ccc3c(c2)OC[C@@H]2[C@H](CO)SC(=O)N32)cn1 299869360 UMOJOKQCEXAYIR-ZBFHGGJFSA-N 339.376 2.415 30 1 EEEF CC(N)=C1C(=O)[C@@H]2[C@@H]3c4c[nH]c5cccc(c45)C[C@@H]3C(C)(C)N2C1=O 2356386932 AFOUSJMOYMLOPA-VUCTXSBTSA-N 335.407 2.229 30 1 EEEF COC(=O)c1cc(N/N=C2\SC(=N)N=C2C)cc(C(=O)OC)c1 103863049 CZZHZSAVTYGPLQ-RAWCXKLBSA-N 334.357 2.128 30 3 EEEF COc1ccc(/C(=N\O)c2cccc(NS(=O)(=O)N(C)C)c2)cc1 27422533 MDMDCWBFLSBWHN-WUKNDPDISA-N 349.412 2.140 30 1 EEEF C=C(F)CN(CC)C(=O)[C@@]1(c2ccc3c(c2)OCCO3)C[C@H]1CN 29047457 WYBWTBVGJJOVDM-KBXCAEBGSA-N 334.391 2.006 30 1 EEEF O=C(NCCS)/C(Cc1ccc(F)c(Br)c1)=N/O 44091364 VFTXFIQHRQEGIB-XNTDXEJSSA-N 335.198 2.007 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)C(=O)O[C@]2(O)C[C@@]23O[C@H]2CC[C@H](C)[C@@]13C 100266476 YQSCJMNPXRPKAC-CSPUSPOWSA-N 348.395 2.014 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@]12OC(=O)[C@@](C)(CC[C@@H]1O)[C@H]2[C@@H]3C(=O)O 104365527 JKQCGVABHHQYKQ-MKMQNPNCSA-N 332.396 2.136 30 1 EEEF in-man COc1ccc(C(=O)O[C@@H]2c3cocc3[C@@H](CC=O)[C@H]2O)cc1OC 2356737453 SFCCTINUDYTREN-SSKCKEOISA-N 346.335 2.242 30 1 EEEF N#Cc1cccc2nc(-c3ccc(C(C=O)C=O)c([N+](=O)[O-])c3)[nH]c12 587262354 SQPWWCZDNXVDKK-UHFFFAOYSA-N 334.291 2.491 30 1 EEEF C=CC/N=C(\O)c1cc(S(=O)(=O)N2CCCCC2)ccc1F 8661918 HRDOMRWESFEFSV-UHFFFAOYSA-N 326.393 2.491 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)([C@@H](O)CC[C@@]4(C)CO)[C@@H]2CC[C@H]1[C@@H]3O 2356695479 IOLAXGYDTVZNNV-DEEWQJAJSA-N 334.456 2.068 30 1 EEEF C=CCNC[C@@H](O)COc1ccc2oc3ccccc3c(=O)c2c1 40935497 QRNFFCPQVMWMRT-CYBMUJFWSA-N 325.364 2.462 30 1 EEEF Cc1ccc2c(n1)C(=O)C=C(N1CCN(c3ccccc3)CC1)C2=O 84710992 XAUDADXRYQHBHF-UHFFFAOYSA-N 333.391 2.475 30 1 EEEF CCOC(=O)CN1C(=O)N[C@@H](c2cccc(F)c2)C(C(C)=O)=C1C 13816601 UEHPYFCBPAJOQY-INIZCTEOSA-N 334.347 2.318 30 3 EEEF C=C(C)[C@@H]1Oc2cc(O)c(C(C)=O)cc2[C@@H]1OC(=O)/C(=C\C)CO 238768742 CLWSKSKCEVBFSD-DFRNLPNRSA-N 332.352 2.455 30 1 EEEF C=CCCC(=O)N1C[C@@H]([C@@H](C)OC(=O)CCCc2ccncc2)C1=O 95596938 YPWDXESMVDYVDT-ZBFHGGJFSA-N 344.411 2.287 30 1 EEEF CO[C@H](C)[C@]1(CC#N)N[C@H](C(=O)C(F)(F)F)Cc2ccccc21 962728251 DHTCGHMJWKFPMC-DGFSRKRXSA-N 326.318 2.476 30 1 EEEF C=C(C1=CC(=O)C(OC)=CC1=O)c1cc(OC)c(OC)c(OC)c1 1857603149 BWVUPRVAMLAZJQ-UHFFFAOYSA-N 330.336 2.334 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)[C@@H]4O[C@@H]4[C@@]3(C)[C@@]1(C)[C@@]21CO1 2356419984 LAQCZBYXNRANFU-XXRPLBTLSA-N 332.396 2.154 30 1 EEEF C[C@]12CC(=O)[C@@]3(F)[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@H]1C[C@H](O)C2=O 2356756465 IASWIBHERBRGSC-SWXRVVBXSA-N 334.387 2.329 30 1 EEEF CS(=O)(=O)/C=C\c1nc2cc(C#N)cc(Br)c2[nH]1 586923293 JBWYKPXIIVHNKZ-IHWYPQMZSA-N 326.175 2.212 30 1 EEEF O=C1O[C@@H]2C=CCC=C2C(=O)[C@H]1Cc1c(O)c2ccccc2oc1=O 169692523 FMTPOCAUOVRPJN-UKRRQHHQSA-N 338.315 2.038 30 1 EEEF C=C(C)C#C[C@](O)(C(=O)O[C@@H]1CN2CCC1CC2)c1ccccc1 1640778 GBTXSVZHHMYRNF-UYAOXDASSA-N 325.408 2.091 30 1 EEEF C=C(CO)[C@]1(O)C=C2C(=O)C[C@H](C(C)C)[C@]2(C)C[C@H]2OC(=O)C[C@@]21C 2356423706 CMFMNGXFTLTMOH-PPOOEBMNSA-N 348.439 2.169 30 1 EEEF C=C1C(=O)[C@@]23C(=O)[C@@H]4OC[C@]5(CCCC(C)(C)[C@@H]45)[C@@H]2CC[C@@H]1[C@H]3O 1911582444 LFJAHWPREGZWHX-SDDUFPNZSA-N 330.424 2.293 30 1 EEEF CCCN/C=N/c1cc(-c2csc(N=C(N)N)n2)cc([N+](=O)[O-])c1 45323210 QVRFHYOYSGKJHG-UHFFFAOYSA-N 347.404 2.283 30 1 EEEF Cc1oc(CNS(C)(=O)=O)cc1-c1nc2cccc(C#N)c2[nH]1 586945477 GLCLXZUWMPVCKZ-UHFFFAOYSA-N 330.369 2.052 30 1 EEEF COc1ccccc1CCC(=O)NC1(C(=O)NCC#N)CCCCC1 169329175 VUDHTNYHMGOJFS-UHFFFAOYSA-N 343.427 2.087 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2CC/C=C\C(=O)Cc2cc(O)cc(O)c2C(=O)O1 169363876 XFALPAMSDFFXGY-UDSOTQMCSA-N 332.352 2.262 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@H]2[C@]12OC(=O)[C@@](C)(CC[C@@H]1O)[C@@H]2[C@H]3C(=O)O 100823412 JKQCGVABHHQYKQ-WINNGDLPSA-N 332.396 2.136 30 1 EEEF endogenous,in-man N#Cc1cc([C@]23CO[C@@H](CF)C[C@H]2CSC(N)=N3)c(F)cc1F 147750169 LGJIPDMTLWEFJV-WMFXKJRFSA-N 341.358 2.468 30 1 EEEF N#Cc1ccc2cc3c(=O)[nH]c(=O)nc-3n(-c3cccc(F)c3)c2c1 96282697 VKJADGNTZGKQPY-UHFFFAOYSA-N 332.294 2.190 30 1 EEEF NNc1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)ccn1 587883911 DFWJQAXTLWCGBG-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]12CC[C@@H](O)[C@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 104365882 QYXZQZMPZUEEML-XMKYHCGJSA-N 346.423 2.384 30 1 EEEF in-man C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(C)(C)C)[C@@H]1[C@@]3(C)CC[C@@H](O3)[C@@]1(C)[C@H]2O 2356544663 XVJNAEOCXFSHRU-SWHLBYKQSA-N 336.428 2.216 30 1 EEEF CO[C@@H]1c2c(cc(O)c3c2C(=O)c2cccc(O)c2-3)C(=O)[C@@]2(C)O[C@@H]12 95555365 CDBWDMSUWPFBMG-NZSAHSFTSA-N 338.315 2.351 30 1 EEEF C=C1C[C@H](O)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@@H](OC(=O)C=C(C)C)C[C@@H]12 238759747 DDKWVHFIPPNJCX-PJLNZIFKSA-N 344.407 2.475 30 1 EEEF Cc1sc2nc(C)n(N/C=C3\C=CC(=O)C=C3O)c(=O)c2c1C 13124251 CCLWXVKVPMYPKQ-YRNVUSSQSA-N 329.381 2.391 30 3 EEEF COc1ccc2c(c1OC(C)=O)C1=CC(=O)CC[C@]13CCN[C@H]3C2 1611735 ITOZXSNVASSYGQ-LPHOPBHVSA-N 327.380 2.271 30 1 EEEF Cn1c(=O)ccc2cc(NS(=O)(=O)c3cccc(C#N)c3)ccc21 1772647360 COVNONZQYCHIJS-UHFFFAOYSA-N 339.376 2.211 30 1 EEEF COc1cc(O)c(C(=O)/C=C/c2cc(O)c(O)c(O)c2)c(OC)c1 28713584 DRHNIABZRBIPDY-ONEGZZNKSA-N 332.308 2.422 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)C(=O)C=C[C@](C)(O)C[C@H](OCC(C)C)[C@H]12 2356653594 LUEQCEAVADXVIC-NTDBWNAOSA-N 334.412 2.352 30 1 EEEF Cc1cc2c(c(=O)o1)[C@@]1(C(=O)N(C)c3ccccc31)C1=C(CCC1=O)O2 199741593 KJOWRIUWIRODNW-FQEVSTJZSA-N 349.342 2.220 30 3 EEEF C=CC[C@]12C[C@H](OC)[C@H](O)[C@H]([C@@H]1O)[C@H](c1ccc3c(c1)OCO3)[C@H]2C 2356606164 GGFOVZYLYBVWDX-BHXLZQPASA-N 346.423 2.468 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@H]1[C@H]2O)C(=C)[C@@H](C(C)(C)CCCO)C[C@H]3O 2356737579 FBXNWXLXYGRNOE-VDRAPBNHSA-N 334.456 2.235 30 1 EEEF COc1cc2c3c(c1OC)C1(C=CC(=O)C=C1)C[C@H]3N(C=O)CC2 14679734 ZRWKJCKLHBPSBY-CQSZACIVSA-N 325.364 2.096 30 1 EEEF biogenic O=C1O/C(=C\c2ccc(O)c(O)c2)C(=O)C(c2ccc(O)cc2)=C1O 105563916 MCSQVSPITLWUGY-ZSOIEALJSA-N 340.287 2.240 30 1 EEEF CNC(=O)/C(=N/OC)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 103184531 MOXDXMPHZQYMAR-OBGWFSINSA-N 329.312 2.484 30 1 EEEF CCc1ncnc(N2CCC(CO)CC2)c1C#Cc1ccc(C)nc1 149154046 STZYJVQIUDUSGL-UHFFFAOYSA-N 336.439 2.351 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)C(=O)O[C@@]2(O)C[C@@]23O[C@@H]2CC[C@H](C)[C@@]13C 238770505 YQSCJMNPXRPKAC-XBCTYBCVSA-N 348.395 2.014 30 1 EEEF C=CC(C)(C)c1nc2ccc(S(=O)(=O)N3CCOCC3)cc2[nH]1 587955956 XDHASILWFBMZSY-UHFFFAOYSA-N 335.429 2.047 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2C=CC=CC(=O)Cc2cc(O)cc(O)c2C(=O)O1 253686636 XTUZVEOWUSGCSV-UHNFBRDESA-N 330.336 2.038 30 1 EEEF CCOCCOC(=O)/C(O)=N/c1nc(-c2conc2C)cs1 27706522 FAJGIFJRLXGHIG-UHFFFAOYSA-N 325.346 2.274 30 1 EEEF CC(=O)N[C@@H](C)Cc1ccc(C#Cc2cnc(OCCF)nc2)cc1 113412335 LGXUCECBFQADPO-AWEZNQCLSA-N 341.386 2.292 30 1 EEEF C[C@@H]1CN2C[C@H]3CC[C@]4(O)CCC5=C4[C@@]4(CC5=O)[C@@]3(C)CC[C@@H]1[C@@]24O 2356678544 KLIOZQZXDDOEMZ-FFOBKANASA-N 343.467 2.247 30 1 EEEF C=C(C)[C@H]1CCC2=C[C@@H](C/C(C)=C/C(=O)[C@H](O)CC(=O)C1)OC2=O 49073206 NKBOMIIKMNCYIQ-XOYNJCORSA-N 332.396 2.440 30 1 EEEF COC1=C(O)C(=O)c2c(O)c3c(c(OC)c2C1=O)C[C@@H](C)O[C@@H]3C 40407143 UIBXAMHOHCDVSB-RNFRBKRXSA-N 334.324 2.218 30 1 EEEF biogenic CCOC1=C(OCC)[C@]2(Oc3cc(OC)cc4c3C(=O)[C@H]2C4)C1=O 587444859 WFKDCXMTFNPFBI-ADLMAVQZSA-N 330.336 2.049 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cc(OC)c(OC)cc3[nH]2)C1=O 587038062 CDAQLRRPNWAIAU-ZDUSSCGKSA-N 347.396 2.373 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1cc(=O)cc[nH]1 587889595 OPAURECZBCPEBU-UHFFFAOYSA-N 335.190 2.392 30 1 EEEF C/C(=N\OCC(=O)OCCN(C)C)c1ccc(Br)cc1 169344785 NKNCPVMMSFTUQH-LFIBNONCSA-N 343.221 2.295 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@]1(C)CCC[C@](C)(CO)[C@@H]1C[C@H]3O 2356404715 VFCKRZZDFUUVFU-YQMODDGXSA-N 334.456 2.068 30 1 EEEF C[C@]12C[C@H](O)[C@@H]3[C@@H]4CCC(=O)C=C4CC[C@@H]3[C@@H]1CC[C@H]2C(=O)CO 2356672856 ACHGZZCRIIPHAX-HLINPZDZSA-N 332.440 2.277 30 1 EEEF COc1cc(O)c2c(c1OC)OC/C(=C\c1ccc(O)c(O)c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c1cc2c(cc1/C=N/n1c(CO)nc3ccccc31)OCO2 13005194 OEVQTGRFXSTUPZ-REZTVBANSA-N 340.295 2.048 30 1 EEEF Cc1ccc(/N=C/C2=C3NC=C(C(=O)O)C(=O)N3[C@H](C)CC2)cc1 100770902 OAXWUPGGPFTBDN-DKSCHZSNSA-N 325.368 2.492 30 1 EEEF Cc1ccc2[nH]c(=O)c([C@H]3NC(=S)NC4=C3C(=O)CCC4)cc2c1 103285167 MLDAFGSUVHDXHC-MRXNPFEDSA-N 339.420 2.362 30 1 EEEF N#Cc1ccc(N2C(=O)[C@@H]3[C@H](O)CCN3C2=O)cc1-c1ccccc1 28704375 BVJKTMPXYNNOLA-SJORKVTESA-N 333.347 2.127 30 1 EEEF CC/N=C(\NC#N)NCCSCc1ncccc1Br 27526955 QSVQYESUCVTVDQ-UHFFFAOYSA-N 342.266 2.113 30 1 EEEF C=C[C@@H]1[C@](C)(CO)C(=O)[C@H]2C[C@@]1(C)[C@@H]1[C@@H]3OC(=O)C(=CC)[C@H]3O[C@]21C 2356677555 UAVHCHBOMMAUHU-VBZMSDRKSA-N 346.423 2.042 30 1 EEEF C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1C(=O)CC1=CC(=O)OC1 238761695 XBINLYXLOLWNSB-ZRSLWSEBSA-N 348.439 2.171 30 1 EEEF C=C1C[C@H](OCC(C)C)[C@H]2C(=C)C(=O)O[C@@H]2/C=C(\C)[C@H](O)C[C@H]1O 238736075 JDMDKFIKZIBCPI-NYAWVVEMSA-N 336.428 2.144 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@H](c2ccccc2-c2ccccc2)[C@H]1CO 95668342 RRMULCFNGGBUJN-GGPKGHCWSA-N 336.391 2.179 30 1 EEEF Nc1cncc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)n1 587890021 KVUBMBGUQDNSOY-UHFFFAOYSA-N 335.194 2.076 30 1 EEEF COC1=CC2=C3C[C@@H]4C[C@H](OC)[C@H](OC)C[C@@H]4CN3CCC2=CC1=O 2356847093 OTLSHWIHWKUYQL-VPCNSNALSA-N 345.439 2.446 30 1 EEEF C=CCN(C)CC[C@@H]1CC[C@@H](O)[C@@H](C(=O)N(C)Cc2ccccc2)O1 2356876135 ZHTXQABDTNBAGM-OTWHNJEPSA-N 346.471 2.061 30 1 EEEF C[C@@]1(c2cccc(I)c2)OC(C(=O)O)=CC1=O 36377855 QJKQNKXFEZQYQP-LBPRGKRZSA-N 344.104 2.074 30 1 EEEF CC(C)C[C@H](NC(=O)Nc1ccccc1Br)C(=O)NO 95590753 UMAQQBGVOXNMKJ-NSHDSACASA-N 344.209 2.491 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@@]2(CCNC[C@H]2C#N)N1 587792178 GZQSQLGJENUGLF-OSQNNJELSA-N 338.224 2.451 30 1 EEEF CC(C)C(=O)OC[C@@]1(c2ccc(CO)cc2OC(=O)C(C)C)CO1 238781479 RILHKBOOMVZSPB-SFHVURJKSA-N 336.384 2.165 30 1 EEEF Cc1ccnc2c1/C(=N/N=C(N)N)C[C@@H](c1cc(F)ccc1F)C2 13474715 NOQLJONWLKOHDI-KLRIFPEDSA-N 329.354 2.376 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2/C=C/C=C\C(=O)Cc2cc(O)cc(O)c2C(=O)O1 169354754 XTUZVEOWUSGCSV-KIGOGIEMSA-N 330.336 2.038 30 1 EEEF C=C1C(=O)O[C@@H]2C3=C(C)C(=O)C[C@@H]3[C@](C)(O)C[C@H](OCC(C)C)[C@@H]12 2356491348 IDJQTNTZPPTSEU-VCMJVYQGSA-N 334.412 2.186 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1CCC(COC(=O)C(C)C)=C1C[C@H](O)C(=C)[C@@H]12 2356644494 INJHISWMTROACX-BSWAZPDLSA-N 332.396 2.311 30 1 EEEF C=C1CC[C@@H]2[C@H](CO)[C@H](O)[C@H](O)C[C@@]2(C)[C@@H]1CC(=O)c1ccoc1 196392502 JWPAVAPOANDRMB-FYRXIQKBSA-N 334.412 2.175 30 1 EEEF C[C@@H]1CN2C[C@H]3CC[C@@]4(O)CC(=O)C5=C4[C@@]4(CC5)C(=O)[C@@H]1C[C@@H]2[C@@]34C 28973008 LSKAYCSMVNNFJC-QXLLIFFRSA-N 341.451 2.106 30 1 EEEF Cc1c[nH]c2c1[C@@]13C[C@@H]1CN(S(=O)(=O)c1ccccc1)C3=CC2=O 38243927 VRRYPFUNOZUDIK-XIKOKIGWSA-N 340.404 2.366 30 1 EEEF C[C@@H]1CC(=O)[C@]2(CO)[C@H]([C@@H](O)CC[C@]23CO3)[C@@]1(C)CCc1ccoc1 95910323 VGSNGCOAALEARN-TUKSYLFRSA-N 348.439 2.346 30 1 EEEF biogenic,in-vitro C[C@H](Sc1nc(N)cc(O)n1)c1nc2cc(Cl)nc(C#N)c2[nH]1 586963040 XIVCAWKQXXBTRP-YFKPBYRVSA-N 347.791 2.414 30 1 EEEF O=C1C=C2CC[C@@H]3[C@@H]([C@@H]2CC1)[C@H]1C[C@]2(CO1)[C@H]3CC[C@H]2C(=O)CO 2356416617 ZQTXDFVYZQQLOY-IHAQYFQTSA-N 330.424 2.295 30 1 EEEF C=C(C)C(=O)O[C@@H]1CCC(CO)=C2[C@@H]3OC(=O)C(=C)[C@@H]3CC[C@@]21C 2356470535 DXUUYKZZAJEBSQ-XWESNNAXSA-N 332.396 2.455 30 1 EEEF C=C(C)[C@@H]1CC[C@@]23O[C@@H]2[C@@H](CC(C)=C[C@]2(O)C=C(C)C(=O)[C@@H]12)OC3=O 2356529176 XCSMOAULMOLHGO-ARUNDJTASA-N 344.407 2.248 30 1 EEEF CCC(=O)C[C@H](C)[C@@H]1O[C@]1(C)C=CC(=O)N[C@@H](CO)[C@H](C)CC 2356596953 RDWBIAZAAVLQEC-VFOQYASISA-N 325.449 2.229 30 1 EEEF C[C@@H]1C[C@H]2O[C@H]2CC/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1 86047878 XFALPAMSDFFXGY-VDKLIIOFSA-N 332.352 2.262 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1[C@H](OC(=O)C(C)C)C=C(C)[C@]1(O)CC=C(C)[C@H]21 13325914 BRSFRASATUTFRS-GMKVZWAMSA-N 332.396 2.309 30 1 EEEF COc1ccnc2c1/C(=N/N=C(N)N)C[C@@H](c1ccccc1Cl)C2 13474677 UNUUDMGTESLXRG-ADUAYUHLSA-N 343.818 2.451 30 1 EEEF C=CCN1C(=O)C(=Cc2ccc(OC)cc2)C(=O)N(CC=C)C1=O 299865075 SPFGDHCSKKNXDY-UHFFFAOYSA-N 326.352 2.241 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(C(=O)N2CCNCC2)o1 587912716 WJUMAJVLICRCHC-UHFFFAOYSA-N 344.798 2.387 30 1 EEEF C=CCN(C)C[C@@H]1CN2CC[C@H]1C[C@H]2CNC(=O)c1ccccc1 2356301870 ZDVHQAKIGXBAMN-OTWHNJEPSA-N 327.472 2.245 30 1 EEEF CC(C)NC[C@@H](O)CO/N=C1/c2ccccc2[C@@H]2CCCC[C@]12O 26944081 RTKLMTIRQZCKHN-FBBNXHRRSA-N 332.444 2.169 30 1 EEEF CC(C)O[C@@H]1Oc2ccc(O)c3c2[C@]1(C)[C@H]1C(=O)C=C(CO)C1=C3 2356722740 ORBWSHDOOZYCPR-QRQLOZEOSA-N 328.364 2.308 30 1 EEEF C=C[C@@]12CCN3Cc4c([nH]c5ccccc45)[C@](C(=O)OC)(CO1)[C@H]2C3 2356726299 JWWNAZIXKUAPOM-VDGAXYAQSA-N 338.407 2.369 30 1 EEEF N#C[C@@H](c1ccnc(N2CCNCC2)n1)c1nc2ccccc2s1 33994032 JNNCXVPDTRKORE-LBPRGKRZSA-N 336.424 2.151 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]1(C)CCC[C@]2(CO)C(=O)O[C@H]([C@@H]3O)[C@@H]21 85932797 RDUNXXWNAKBVER-YTPDCUKSSA-N 332.440 2.434 30 1 EEEF in-man COC(=O)CC[C@H](N)c1nc2cc(C#N)cc(Br)c2[nH]1 587259029 VWBZDTYFAHTMIS-VIFPVBQESA-N 337.177 2.150 30 1 EEEF C[n+]1c(-c2ccc(/C=N/Nc3cc(N)[nH]n3)cc2)cn2ccccc21 26828693 IBLYLEWQNQKDQQ-RGVLZGJSSA-N 332.391 2.182 30 1 EEEF CCC(=O)C[C@H](C)[C@@H]1O[C@]1(C)C=CC(=O)N[C@H](CO)[C@@H](C)CC 2356596955 RDWBIAZAAVLQEC-VZKYEUNXSA-N 325.449 2.229 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(CO)CCC[C@](C)(CO)[C@@H]1C[C@H]3O 2356645367 NLKCAXRWGIRDDQ-KSYFULEYSA-N 334.456 2.070 30 1 EEEF C=C1[C@H](O)[C@H]2O[C@@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@@]1(C)C(=O)[C@H](O)[C@@]23C 238734386 WRVAOIVFDLSROQ-VVKOICGRSA-N 332.440 2.083 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@@H](C(=O)O)[C@H]1[C@@]2(C)CCC[C@@]31OC2=O 257480367 MBNDVMTZEKAWKP-RASPSGESSA-N 332.396 2.136 30 1 EEEF endogenous,in-man Cc1ccnc2c1CCN[C@]2(CC1OCCO1)c1cccc(C#N)c1 963068441 LBEVGECGAFHZAY-HXUWFJFHSA-N 335.407 2.414 30 1 EEEF CCCn1c(=O)c2[nH]c(-c3ccc(C#N)cc3)nc2n(CCC)c1=O 13821355 WKCIHNDSFNSXHM-UHFFFAOYSA-N 337.383 2.245 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)Nc2ccccn2)[C@@H]1O 15470 NJMBRYRDHWBNEQ-CVEARBPZSA-N 338.367 2.348 30 1 EEEF C=C1[C@H]2CC(=O)[C@@H]3[C@]4(C)CCCC(C)(C)[C@@H]4[C@H](O)[C@@H](O)[C@@]3(C2)[C@@H]1O 2356643667 AUVGEKXCVIHEPI-OIVWHDOQSA-N 334.456 2.067 30 1 EEEF N#C[C@H](c1ccnc(N2CCNCC2)n1)c1nc2ccccc2s1 33994033 JNNCXVPDTRKORE-GFCCVEGCSA-N 336.424 2.151 30 1 EEEF C=CCN(c1ccc(Br)cc1C(=O)OC)S(C)(=O)=O 36383001 XZPOGZLRAHNYFN-UHFFFAOYSA-N 348.218 2.188 30 3 EEEF CN1C(=N)N[C@@](c2cccc(-c3cncc(C#N)c3)c2)(C2CC2)C1=O 84616429 YNHHKAKPUCUXLP-LJQANCHMSA-N 331.379 2.222 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3ccc([C@H](N)N=O)cc3[nH]2)C1=O 587038487 JKUMDYFJBJYQDQ-DGCLKSJQSA-N 345.384 2.079 30 1 EEEF Cn1ncc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)c1N 587880975 DLBUXGIEZDAGGZ-UHFFFAOYSA-N 337.210 2.020 30 1 EEEF C#CCN(Cc1ccc2nc(N)[nH]c(=O)c2c1)c1ccc(C(C)=O)cc1 18169517 KWSUUWFDIXJBRS-UHFFFAOYSA-N 346.390 2.348 30 1 EEEF N#Cc1cnn(-c2ccccc2)c1NC(=O)C(=O)NC1CCCCC1 58538395 CJCKGBPIJULNRE-UHFFFAOYSA-N 337.383 2.131 30 1 EEEF CCOC(=O)CN1C(=O)N[C@@H](CCc2ccccc2)C(C(C)=O)=C1C 13816595 VVWGUEORRWHOLA-INIZCTEOSA-N 344.411 2.439 30 3 EEEF O=C1C=C[C@@]23C[C@@H](N=C4C(=O)c5[nH]cc6c5C(=NCC6)[C@@H]42)SC3=C1 169723179 OVHZMAJFIKTHFC-FNFWKMNBSA-N 335.388 2.099 30 1 EEEF CC1CCN(C2CCN(S(=O)(=O)c3ccc(C#N)cc3)CC2)CC1 1857597572 DRWWXANVUNRUTI-UHFFFAOYSA-N 347.484 2.443 30 1 EEEF CCOC(=O)c1c(/N=C/n2nc(N)cc2O)sc2c1CCCC2 1857637660 ROYVRAGRILOHIB-CAOOACKPSA-N 334.401 2.496 30 1 EEEF CCC#C[C@](O)(C(=O)O[C@H]1C2CCN(CC2)[C@H]1C)c1ccccc1 1641767 VOCRJOMVKAJZBC-QKYXUNIQSA-N 327.424 2.314 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@H]1CC[C@H]2[C@@]12CCC[C@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100778341 MBNDVMTZEKAWKP-MRCYDUEQSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(C)C(=O)CC[C@](C)(C(=O)O)[C@H]1C[C@@H]3O 2356487487 CLGOGJHVMHIUDO-AJFPODLTSA-N 346.423 2.369 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@@]45C=CCC(C)(C)[C@H]4[C@@H](O)O[C@H]5OC(=O)[C@@]3(C2)[C@@H]1O 2356678691 PMIAIQKUXKRZIR-GOHZNODWSA-N 346.423 2.140 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@]4(C)CC[C@H](O)[C@](C)(C(=O)O)[C@@H]4[C@H]4C(=O)O[C@H]1[C@]43C2 2356691281 CXVXNQFWGOEIMV-ZZOOONPDSA-N 346.423 2.382 30 1 EEEF COC(=O)CCn1cc(C#Cc2cc(Cl)ccc2OC)ccc1=O 587912646 MFCCXGUPBUGLJX-UHFFFAOYSA-N 345.782 2.473 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)C(=O)C[C@@]3(C)[C@@]1(C)[C@]21CO1 2356501725 LJWZOKOFCBPNAG-VYHSGFQXSA-N 332.396 2.346 30 1 EEEF COc1ccc2c(c1)CCN(CCC#Cc1nccs1)C[C@H]2O 1857567096 VWUUYLGPLYILTF-QGZVFWFLSA-N 328.437 2.485 30 1 EEEF N#Cc1ccc(O[C@@H]2[C@@H]3CCC(=O)[C@@H]3C[C@H]2N2CCC[C@@H](N)C2)cc1 1857638338 QSAZIXCMYAOKGL-JQLJIJSLSA-N 339.439 2.096 30 1 EEEF C[C@H](CO)C1=C2CC[C@H](CO)C3=C(C[C@]2(C)CC1)[C@H](C)[C@@H](O)C3=O 2356325649 QNDHAMGPYFFBHA-UYDONHODSA-N 334.456 2.380 30 1 EEEF N#Cc1cccc(CN2C[C@H]3OCC(=O)N(c4ccccc4)[C@@H]3C2)c1 2356388134 STXKMDYQBAQXPG-RTBURBONSA-N 333.391 2.174 30 1 EEEF CCOC(=O)C1=C(C(=O)OCC)N(CC2CCCCC2)CCC1=O 61942759 KWVAPHAMGRRYDN-UHFFFAOYSA-N 337.416 2.222 30 3 EEEF CCC(=O)NC[C@@H]1N[C@@H](CO)[C@H]1c1ccc(-c2cccc(C#N)c2)cc1 95895242 IZVWTPQWCZYKCV-ZJOUEHCJSA-N 349.434 2.168 30 1 EEEF COC1=C[C@H]2[C@H]3Cc4ccc(C(C)=O)c(O)c4[C@@]2(CCN3C)CC1=O 2356347273 DWQIEUYIJNZWSH-MDOVXXIYSA-N 341.407 2.212 30 1 EEEF COC(=O)c1ccc(Oc2ccc(NC(=O)[C@@H](N)CS)cc2)cc1 28764286 YBVSRAQJICYAEB-HNNXBMFYSA-N 346.408 2.461 30 1 EEEF O=C(CCCCSc1nc(Cc2ccccc2)cc(=O)[nH]1)NO 28528356 XSRFVMQICLPJTA-UHFFFAOYSA-N 333.413 2.129 30 1 EEEF C=C1[C@@H](O)C[C@H]2C(C)(C)[C@@H](O)CC[C@]2(C)[C@H]1C/C=C1/COC[C@@H]1O 73162252 PQJNKPQZAXZXLP-PMDVJSMPSA-N 336.472 2.434 30 1 EEEF O=C1CCC/C(=N/NS(=O)(=O)c2ccc(Br)cc2)C1 8379116 UOMJZAFZRMDTQP-UVTDQMKNSA-N 345.218 2.227 30 1 EEEF COc1cccc(/C=N\Nc2nn3cnnc3c3ccccc23)c1O 73241288 WDHBIANOOALAIX-NVMNQCDNSA-N 334.339 2.438 30 1 EEEF COC1=C[C@@]23CCN(C)[C@@H](Cc4cc(O)c(OC)cc42)[C@H]3CC1=O 86034072 IXNZNQMODAROFN-TYILLQQXSA-N 329.396 2.018 30 1 EEEF CCOc1nc(NC(=O)Cc2ccc(OC)cc2)cc(N)c1C#N 14960062 ABBHPRNOFIXTQU-UHFFFAOYSA-N 326.356 2.124 30 1 EEEF Cn1c(Oc2ccc(-c3ccc(C#N)cc3)cc2)cc(=O)n(O)c1=O 1857554929 VHLRLNURMITXFK-UHFFFAOYSA-N 335.319 2.115 30 1 EEEF N=C(N/N=C/c1ccc(-c2cn3ccccc3n2)cc1)N1CCOCC1 27438766 HMHGNZBLLFIVRD-FYJGNVAPSA-N 348.410 2.192 30 1 EEEF C=CCn1ncc(OC)c(C#Cc2cc(Cl)ccc2OC)c1=O 587912335 LTPCLVWSSHRKLK-UHFFFAOYSA-N 330.771 2.500 30 1 EEEF C=CCNC[C@H](O)COc1ccc2c(=O)c3ccccc3oc2c1 38691905 QUAWTSJEZZGHFW-ZDUSSCGKSA-N 325.364 2.462 30 1 EEEF C=C(C)[C@@H]1CC(=O)[C@H]2[C@H](C1)[C@@H](C(=O)O)[C@@H]1C=C(C(C)=O)[C@@H]2C(=O)C1 2356807587 XWUMXWKSQYTAOG-MKAUXFRKSA-N 330.380 2.209 30 1 EEEF C[C@@]12CCC[C@]3(OC1=O)[C@H]1CC[C@@H]4C[C@]1(C[C@@]41CO1)[C@@H](C(=O)O)[C@H]23 2356849788 PXYCXLNQKAEBRB-HFODAXOSSA-N 332.396 2.378 30 1 EEEF CN(C)c1ccc(/C=N/CCCc2ccc(S(N)(=O)=O)cc2)cc1 45496356 SCSBGYJUFCMRHQ-XSFVSMFZSA-N 345.468 2.452 30 1 EEEF C=CC[C@@H]1C(=O)N(C(C)=O)[C@H]2CCN(C(=O)OCc3ccccc3)[C@@H]12 26487912 PHAYEXZAKQRIHL-ULQDDVLXSA-N 342.395 2.347 30 1 EEEF C=C1CC[C@@H]2[C@](C)(CO)C(=O)CC[C@@]2(C)[C@]1(O)CCC1=CCOC1=O 73292269 UBVOQCPZUUBZIZ-NMLACTOBSA-N 348.439 2.315 30 1 EEEF C=CCNC1=C(NC(=O)c2ccccc2)C(=O)c2ccccc2C1=O 169304472 KKHXRNXDPBNDTO-UHFFFAOYSA-N 332.359 2.483 30 1 EEEF CCOC1=C(OCC)[C@@]2(Oc3cc(OC)cc4c3C(=O)[C@H]2C4)C1=O 587445061 WFKDCXMTFNPFBI-ZMZPIMSZSA-N 330.336 2.049 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3ccc(C(=O)O)cc3[nH]2)C1=O 587038455 IHMKVWZVBKMWQR-NSHDSACASA-N 331.353 2.054 30 1 EEEF C=CC[C@]1(OCc2ccccc2)C(=O)C(=O)O[C@@H]1[C@@H]1COC(C)(C)O1 5538966 QUSJNYTVFAJGCT-GMBSWORKSA-N 346.379 2.164 30 1 EEEF N#CCN1C(=O)N(Cc2ccccc2)S(=O)(=O)c2cscc21 6840 OXCBPKZYTDEQDL-UHFFFAOYSA-N 333.394 2.403 30 1 EEEF C=C1C[C@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100783025 BSBICXIQCTXPMN-FARKZYBSSA-N 330.380 2.056 30 1 EEEF endogenous,in-man O=C(NO)c1ccc2c(c1)C[C@@H](Nc1ccc([N+](=O)[O-])cn1)CC2 113845001 HZAZIEOZGMNOQZ-ZDUSSCGKSA-N 328.328 2.078 30 1 EEEF COc1cc2c3c(c1)O[C@]1(CCCC(=O)/C1=C/N(C)C)[C@@H](C2)C3=O 587427259 CTRDIESGJSGEEB-YWSSFWSKSA-N 327.380 2.380 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@H]2[C@@]12C[C@H](O)C[C@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100778336 HHDWSDSMWJQURA-PHDAHLEGSA-N 332.396 2.136 30 1 EEEF endogenous,in-man CC(=O)N[C@H](C)Cc1ccc(C#Cc2ccnc(N3CCC3)n2)cc1 113413973 KYRXALZKHBSCEJ-OAHLLOKOSA-N 334.423 2.154 30 1 EEEF CC#CCOc1ccc(S(=O)(=O)N2CCC[C@H](S)C2)cc1 28820435 NVJUVGMOOGFJLZ-AWEZNQCLSA-N 325.455 2.172 30 1 EEEF N#C[C@H]1C[C@@H](N)CC[C@H]1n1cc(C(N)=O)c(Nc2ccc(F)cc2)n1 221156468 CVGYTGPFEWIONX-IFUGULHKSA-N 342.378 2.057 30 1 EEEF COc1c(O)cc2c(c1O)C(=O)/C(=C/c1ccc(O)c(O)c1)CO2 238735231 KUIRIGZNHOTLPQ-RUDMXATFSA-N 330.292 2.176 30 1 EEEF CC[C@H](C)[C@@H](CO)NC(=O)/C=C\[C@@]1(C)O[C@@H]1[C@@H](C)C[C@H](O)CC 238787718 KQYIQWJQJFWGMP-YDNAIBAGSA-N 327.465 2.020 30 1 EEEF CN[C@@](C)(C#N)Cn1cc(C#Cc2cc(Cl)ccc2OC)cn1 587909104 JNMJLVCTLGPDPC-KRWDZBQOSA-N 328.803 2.447 30 1 EEEF CC(C)CCO[C@@H]1C=CC(=O)[C@@H](Cn2cc(-c3ccccn3)nn2)O1 169353709 ATRKWWRCXBDCOH-MSOLQXFVSA-N 342.399 2.253 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100778338 HHDWSDSMWJQURA-XAEKMEBYSA-N 332.396 2.136 30 1 EEEF endogenous,in-man CN(C)c1ccc([CH+]Nc2ccc(C(=O)NCC(=O)O)cc2)cc1 100005359 WUTICFNLYGRQNH-UHFFFAOYSA-O 326.376 2.189 30 1 EEEF Cc1ccc2n(c1)cc(-c1ccc(/C=N/NC(=N)N(C)C)cc1)[n+]2C 26827305 MUDVWIMAPBNIBD-SRZZPIQSSA-N 335.435 2.159 30 1 EEEF Cc1ccc(S(=O)(=O)N2CCC(CCCC(=O)NO)CC2)cc1 73129889 SREHNPGGMJPTSF-UHFFFAOYSA-N 340.445 2.071 30 1 EEEF C[C@H]([C@@H](NC(=O)OCc1ccccc1)C(=O)NCC#N)C(F)(F)F 82064908 DQUMJPBSYXBJLB-ZYHUDNBSSA-N 343.305 2.120 30 1 EEEF C=C(C)[C@@H]1CCC(=C)[C@@H]2C3=C(C(=O)C(C)=C[C@@H]12)[C@H](O)[C@](C)(O)C3=O 143177706 PMTAKUZIYCHAID-RDVHEEPHSA-N 328.408 2.281 30 1 EEEF C=C1C[C@H](OCC(C)C)[C@H]2C(=C)C(=O)O[C@@H]2/C=C(\C)[C@H](O)CC1=O 238731964 PJRAJKIGBHSJPR-KBAKMHEVSA-N 334.412 2.352 30 1 EEEF N#Cc1cccc2nc(-c3nccnc3I)[nH]c12 587186684 OSBVWPSVHSIDJD-UHFFFAOYSA-N 347.119 2.496 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)O 2356783745 MEGPPDNKNMAIJN-JUVNIICASA-N 330.380 2.056 30 1 EEEF COc1cc(O)c2c(c1)CC(=O)/C=C/C=C\[C@H]1O[C@@H]1C[C@@H](C)OC2=O 40423466 BXYHHINRBKIWCZ-LZYJLVINSA-N 344.363 2.341 30 1 EEEF CN1C(=O)[C@H](CN2CCCCC2)C[C@H]1C#Cc1ccc2c(c1)CCO2 96248474 BSAYMXGAHRLDCA-RBUKOAKNSA-N 338.451 2.306 30 1 EEEF CCCCN(CC)C[C@H](C(C)=O)[C@@H]1C(=O)O[C@@H]2C=CCC=C2C1=O 169717776 GLMLCOHRCVZCDT-ZACQAIPSSA-N 333.428 2.311 30 1 EEEF CC(=O)NC[C@H]1CC(c2ccc(-n3ccc(C#N)c3)c(F)c2)=NO1 3963826 IAEZEQWXXHOOGM-CQSZACIVSA-N 326.331 2.117 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 238774548 JTSAEZNOAXDDOQ-OAAKCHFYSA-N 346.423 2.225 30 1 EEEF C=C(C)C(=O)O[C@H]1/C=C(/C)C2=CC(=O)[C@@](C)(C[C@@H]3OC(=O)C(=C)[C@@H]13)O2 238785611 AERIPQYYSNTIDA-IWOODGOJSA-N 344.363 2.164 30 1 EEEF CCCC[C@H](NC(=O)c1ccc(CN=[N+]=[N-])cc1)C(=O)NCC#N 299820414 BHGWDQYMGNIUFJ-AWEZNQCLSA-N 328.376 2.425 30 1 EEEF N#Cc1cc(Cl)c2[nH]c([C@@H](N)Cc3cccc(C(N)=O)c3)nc2c1 587260333 VKGPVMHBTNJKOS-ZDUSSCGKSA-N 339.786 2.429 30 1 EEEF COC1=C(O)C(=O)c2c(OC)c3c(c(O)c2C1=O)[C@@H](C)O[C@H](C)C3 2356408894 RVZCNHHDKHVNPP-RNFRBKRXSA-N 334.324 2.218 30 1 EEEF COc1cc2c3c(c1OC)[C@]1(C=CC(=O)C[C@@H]1OC)C[C@@H]3NCC2 14715564 YUAGGKXKMLLGQC-ZUEVXXBESA-N 329.396 2.076 30 1 EEEF biogenic COc1ccc(Cl)cc1C#Cc1c(C)nn(-c2nn[nH]n2)c1C 587902515 GMTLAOMEJHKZFW-UHFFFAOYSA-N 328.763 2.064 30 1 EEEF C[C@@]12CC[C@H](O)[C@@H]3COC(=C31)C(=O)c1cc3c(cc12)C(=O)CC[C@@H]3O 14723533 LDBFCXDBDKSROL-DXJCSPRDSA-N 340.375 2.206 30 1 EEEF C=CCNC(=O)Nc1ccc(OC[C@H](O)CNC(C)(C)C)c(C)c1 169317393 QSPRBYWGLZPEGG-OAHLLOKOSA-N 335.448 2.430 30 1 EEEF C=CCCC(=O)NCCOc1ccc(Cc2sc(=O)[nH]c2O)cc1 169721742 ITEIPWYIGUENJY-UHFFFAOYSA-N 348.424 2.194 30 1 EEEF Cc1cc(C)c(=O)oc1-c1c(O)c(C)cc2c1C(=O)C=C(N)C2=O 1857566450 VVSSMZJMIIWNNG-UHFFFAOYSA-N 325.320 2.159 30 1 EEEF CSCCNC(=O)/C(Cc1ccc(O)c(Br)c1)=N/O 39635948 QCJPJGDJMUSMQL-XNTDXEJSSA-N 347.234 2.007 30 1 EEEF N#Cc1ccc(-c2cc(N3CCN(CC4CC4)CC3)nc(N)n2)cc1 40956493 DLMAFAFZHGZDTJ-UHFFFAOYSA-N 334.427 2.129 30 1 EEEF COC1=CC(=O)c2c(c(COC(=O)c3ccc(F)cc3)cn2C)C1=O 13557530 BTJPTZLZCBSTGK-UHFFFAOYSA-N 343.310 2.431 30 1 EEEF O=C(O)CC/N=C(\S)[C@]1(c2cccnc2)CCCC[S@]1=O 13651019 MBPYCZVDQXRZIJ-SZNDQCEHSA-N 326.443 2.013 30 1 EEEF O=C(/C=C/c1cccc(S(=O)(=O)n2ccc3ccccc32)c1)NO 169343719 IKMBILRCONHQHD-CMDGGOBGSA-N 342.376 2.397 30 1 EEEF C=C(C)Cn1cc(C(=O)OCC)c(=O)c2ccc3c(nnn3C)c21 66100708 ZJAYVQKOSQNADC-UHFFFAOYSA-N 326.356 2.036 30 1 EEEF CCOC(=O)Cn1cc(C#Cc2cc(Cl)ccc2OC)ccc1=O 587913099 WXJGISKCPNENEO-UHFFFAOYSA-N 345.782 2.473 30 1 EEEF C=C[C@@]1(C)C(=O)C=C2C(=CC[C@@H]3C(C)(C)[C@H](O)C(=O)C[C@@]23C)[C@H]1O 15114057 WNHOOXVMGONUHL-NQAGYIRISA-N 330.424 2.361 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@@H]2[C@@H](C1=O)[C@@]1(C)C=C[C@@]2(C(C)C)CC1 169302818 SDJYQQCUHRGBAF-LUVWLHFXSA-N 347.484 2.165 30 1 EEEF N#CCNC(=O)[C@H](Cc1ccc(Cl)cc1)NC(=O)c1ccccc1 82064520 FPROUROMFXHZHE-INIZCTEOSA-N 341.798 2.321 30 1 EEEF CCc1ncnc(-c2ccnc(OC)c2)c1C#Cc1ccc(N)nc1 148859709 BWHMPFNABWMVCV-UHFFFAOYSA-N 331.379 2.487 30 1 EEEF N#C[C@@H]1CCC[C@@H]1C(=O)[C@@H]1CN([C@H]2CCOc3ccccc32)C[C@@H]1N 253664333 AXLLQKGXUYCBGM-ABJHKEKUSA-N 339.439 2.278 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1ccc[n+]([O-])c1 587888561 OJBQXSOACHKDTE-UHFFFAOYSA-N 335.190 2.337 30 1 EEEF Cc1ccc(S(=O)(=O)ON/N=C2\[C@H]3CCCC[C@H]3[C@H]3O[C@H]23)cc1 102950937 AVTXTHBQNZOKPF-OPOVMFRXSA-N 336.413 2.148 30 1 EEEF COC1=CC(=O)/C(=C2\NNC(C)=C2c2ccc(OC)c(OC)c2)C=C1 104028581 PIFOANVKKBMEGF-RGEXLXHISA-N 340.379 2.466 30 3 EEEF C=C1C(=O)O[C@@H]2[C@@H]1CCC(=C)[C@@H]1C[C@H](OC(=O)C=C(C)CO)C(=C)[C@@H]12 2356462686 AZDMJQODBMILBW-NLPXPOPTSA-N 344.407 2.477 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)CC[C@@](C)(C(=O)O)[C@H]1C[C@@H]3O 72120338 LRECIABFFPIQSO-YCUASDIUSA-N 348.439 2.161 30 3 EEEF C=C1C(=O)O[C@@H]2[C@H]1CC[C@H](C)[C@]1(OC(=O)CCC)C=CC(=O)O[C@@]21C 72107897 WIFLOZIQWRWMOH-WTBCKCGFSA-N 348.395 2.468 30 1 EEEF N/N=C1/c2cc(Br)ccc2-n2c1nc1ccccc1c2=O 95593957 NRMSJXCDGXJCFM-UYRXBGFRSA-N 341.168 2.173 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N2CCN(C)CC2)nc1 587907607 CZWHSXZGPRKQIW-UHFFFAOYSA-N 342.830 2.290 30 1 EEEF C=C(C)C(=O)O[C@@H]1CC(C)=C2C(=O)C=C(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 13585430 KFNIILPAQWDAJK-XLNGHYISSA-N 328.364 2.438 30 1 EEEF biogenic C=C(C)[C@H](Cc1c(OC)c2ccc3c(c2n(C)c1=O)OCO3)OC 14682517 GHCVBXAYFUCEKZ-AWEZNQCLSA-N 331.368 2.409 30 1 EEEF biogenic CC(=O)OC[C@@H]1O[C@H](C#Cc2ccc(C)cc2C)C=C[C@@H]1OC(C)=O 7992536 FLENGSMTXSLATM-AABGKKOBSA-N 342.391 2.473 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H]1[C@@H](O)CC(=C)[C@@H]1C[C@H](OC(=O)C=C(C)C)C(=C)[C@H]12 2356441755 DDKWVHFIPPNJCX-DNRBAQKOSA-N 344.407 2.475 30 1 EEEF Cc1cc(B(OC(C)(C)C(C)(C)O)OC(C)(C)C(C)(C)O)ccn1 221634948 RCSZHNHECTXCAG-UHFFFAOYSA-N 337.269 2.217 30 1 EEEF CC#CC#C/C=C1\O[C@@]2(CC[C@H](OC(=O)CC(C)C)CO2)[C@H]2O[C@@H]12 238743814 IZOBIZVXEKNCNN-LZTGIUHVSA-N 330.380 2.159 30 1 EEEF C=C1C(=O)[C@]23[C@@H](O)[C@@H]1CC[C@@H]2[C@@]1(C(=O)O)CCCC(C)(C)[C@H]1C[C@H]3O 2356455480 VBQWGSKSQFBYOX-VAPKMSFNSA-N 348.439 2.161 30 1 EEEF COc1c2c(c(O)c3c1C(=O)C1=C(C3=O)[C@@H](C)O[C@@H](C)C1)OCO2 14827932 XMTMJWRDSFDUBF-NKWVEPMBSA-N 332.308 2.002 30 1 EEEF biogenic C=C[C@@]1(O)CN2CC[C@@H]1C[C@@H]2[C@@H](O)c1ccnc2ccc(OC)cc12 5141313 BSRUJCFCZKMFMB-NWTFUFRBSA-N 340.423 2.288 30 1 EEEF N=c1nc2c(ccn2-c2ccnc(C#CC3(O)CCCCC3)c2)c[nH]1 1857575115 XRYCZOXAGJIBSG-UHFFFAOYSA-N 333.395 2.275 30 1 EEEF CN(O)C(=O)CCc1ccc2c(c1O)C(=O)c1c(O)cccc1C2 6784 LVHDBGIIVFUCHR-UHFFFAOYSA-N 327.336 2.013 30 1 EEEF COc1ccc(Nc2nc(N)n(-c3cccc(C#N)c3)n2)cc1OC 72127851 LTHKWTSYBMPGMS-UHFFFAOYSA-N 336.355 2.482 30 1 EEEF O=C(/C=C(\O)C(=O)O)/C=C/c1cc(C(=O)c2cccc(F)c2)c[nH]1 103521901 WQEAOCAOIXLGFY-OQLOTXMNSA-N 329.283 2.494 30 1 EEEF in-vitro C=CCC1=C(O)C(=O)C2=C(C1=O)[C@H](O)[C@H](O)[C@H]1C(C)(C)CCC[C@]21C 2356480244 UXBITRKCDARMSM-TXJVSEOTSA-N 346.423 2.391 30 1 EEEF C=C1C[C@@]23C=CC(=O)[C@](C)(CCC(=O)OC[C@H](O)CO)[C@@H]2C[C@H]1CC3 2356712541 FYKIZBPSTADBEK-AOHSKODXSA-N 348.439 2.171 30 1 EEEF N#Cc1c([C@H]2C[C@@H]2CO)[nH]c(SCc2cccc(F)c2F)nc1=O 146720279 KPRILTSMLHRTJO-ZJUUUORDSA-N 349.362 2.308 30 1 EEEF C=C1C(=O)O[C@@H]2[C@H]3[C@H](C)C(=O)C[C@@H](O)[C@]3(C)C[C@@H](OCC(C)C)[C@@H]12 238733336 BQKSKQIZKSAQEI-JQLAPQIMSA-N 336.428 2.121 30 1 EEEF CN(C)CC/N=C(/C=C1\C=Cc2ccccc2N1C)NCCN(C)C 377605848 ZKHGZFKQTDKCAO-FBMGVBCBSA-N 341.503 2.145 30 1 EEEF CC1=CC(=O)[C@]2(CN1)Oc1ccccc1C(=O)[C@@H]2C(=O)c1ccco1 587595351 NGEPTUKSQJSQGP-APWZRJJASA-N 337.331 2.169 30 1 EEEF CC#CC#C/C=C1/O[C@]2(CCCCO2)[C@@H](O)[C@@H]1OC(=O)CC(C)C 15274162 LEOZNWWIPMVKHH-NFNYSAHWSA-N 332.396 2.143 30 1 EEEF N#C[C@@H]1CCCN1C(=O)CN(C(=O)c1ccnc2ccccc12)C1CC1 169310673 SZHQMQDOBHYIJA-HNNXBMFYSA-N 348.406 2.354 30 1 EEEF O=C(NO)[C@H]1CN(Cc2ccc(Oc3ccc(F)cc3)cc2)C(=O)N1 3817611 NBBPYGNNDFCNNP-OAHLLOKOSA-N 345.330 2.017 30 1 EEEF CC(C)NC(=N)N/C(N)=N\OCCCOc1cccc2ccccc12 27299153 ZVKJURGLPBQTFE-UHFFFAOYSA-N 343.431 2.377 30 1 EEEF O=C(/C=C/c1ccc2c(c1)C(=O)N(CCc1ccccc1)C2=O)NO 28527210 SGWCNBRCSSZHNQ-VQHVLOKHSA-N 336.347 2.044 30 1 EEEF CC1=C(CCCc2nnnn2CCC#N)C(=O)c2ccccc2C1=O 28461728 LGYOUVDSKCYMQT-UHFFFAOYSA-N 335.367 2.305 30 1 EEEF CN/C1=N/CC#C[C@@H]2C[C@@H](C)[C@@]34CCC(C(=O)O)=C3C[C@@H]2[C@@]4(C)CN1 85549055 IDOIZYCKBKFALL-HAPLINFISA-N 341.455 2.012 30 1 EEEF biogenic,in-vitro C=C(C)C(=O)O[C@H]1CC(=C)[C@H]2C(=O)C=C(C)[C@H]2[C@@H]2OC(=O)C(=C)[C@@H]12 238760450 JSJWMSSGVMTDCV-KSWRQPAISA-N 328.364 2.293 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccnc2c(C(=O)O)cnn12 587913180 YFTZTJGEJFZETM-UHFFFAOYSA-N 327.727 2.489 30 1 EEEF C=CCN1CC[C@@](O)(c2cc(C(=O)OCC)[nH]c2-c2cc(C)no2)C1 5849693 ZTNCVERONIXYMS-SFHVURJKSA-N 345.399 2.234 30 1 EEEF N#CC[C@H]1COc2ccccc2N1C(=O)c1ccc2c(c1)NC(=O)CO2 1857561899 PQCJJRGKGCAZGP-ZDUSSCGKSA-N 349.346 2.339 30 1 EEEF Cc1c(N2/C(=N/C#N)N3CC[C@H](O)[C@H]3[C@@H]2C)ccc(C#N)c1Cl 62233449 ODOFFRAKWRHDKK-JPJCTVKHSA-N 329.791 2.001 30 1 EEEF COc1ccccc1N/N=C1\C(O)=NN=C1c1cnccc1OC 49051532 IVQMASHJLRLJHO-UHFFFAOYSA-N 325.328 2.241 30 1 EEEF Cc1ccc(S(=O)(=O)ON2C(=O)c3ccc(C)cc3C2=O)cc1 40498130 BCECTVMOUWMKAP-UHFFFAOYSA-N 331.349 2.220 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc(C#N)cc(S(N)(=O)=O)c1 587918542 WAZDMETVBBWKOJ-UHFFFAOYSA-N 346.795 2.267 30 1 EEEF Cc1[nH]nc2c1C1(CCN(C(=O)c3ccccc3)CC1)[C@@H](C#N)C(=N)O2 169690846 PRQROVPVHTVCIS-AWEZNQCLSA-N 349.394 2.402 30 1 EEEF O/N=C/c1cc[n+](CCCCCC[n+]2ccc(/C=N/O)cc2)cc1 28572652 JJHFDINYNFZLOD-UHFFFAOYSA-P 328.416 2.138 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@](C)(CO)CCC[C@]4(C=O)[C@H]2CC[C@H]1[C@@H]3O 2356462314 NGMHJAMTHJNIJX-HXZUJCDCSA-N 332.440 2.277 30 1 EEEF CO[C@](C)(C(=O)O)C1=C[C@]2(C)C(=CC1=O)CC[C@H](OC(C)=O)[C@@H]2C 2356656318 RDRVOBNXHXPXJL-CGAVHFNPSA-N 336.384 2.280 30 1 EEEF C=C1C[C@@]23C[C@H]1C(=O)C[C@@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)O 2356735007 PHYYFNCWOIYWTJ-BYVPMXMMSA-N 330.380 2.344 30 1 EEEF C=C1C[C@@]23C=CC(=O)[C@@](C)(CCC(=O)OC[C@@H](O)CO)[C@@H]2C[C@@H]1CC3 96085985 FYKIZBPSTADBEK-IEYYFSCXSA-N 348.439 2.171 30 1 EEEF COc1ccc(Cl)cc1C#Cc1c(C)nn(CCC(N)=O)c1C 587902218 ALTPQPQMJCLEEG-UHFFFAOYSA-N 331.803 2.437 30 1 EEEF CCCCn1c(N)c(C#Cc2cc(Cl)ccc2OC)c(O)nc1=O 587912556 RYUHFPXODQFKAD-UHFFFAOYSA-N 347.802 2.393 30 1 EEEF CSC1=N[C@@H]2[C@@H](N(C)C(=O)N2C)N1/N=C/C=C/c1ccccc1 1857639634 WONCCEICUAEBNN-YCDJDXOFSA-N 329.429 2.370 30 1 EEEF C#Cc1ccc2c(c1)C(c1ccccn1)=NCc1c(C(=O)OC)ncn1-2 221122243 LWYYAGMSQFPJGP-UHFFFAOYSA-N 342.358 2.386 30 1 EEEF C=C1C2=C(O)[C@H](O)[C@H](C)C=C2C(=O)c2cc(O)c(OC)c(OC)c21 69482142 KMJOSWUIOOZDTP-NXSYQRQQSA-N 330.336 2.368 30 1 EEEF biogenic,in-vitro C=C1C(=O)O[C@@H]2C[C@@]3(C)OC(=CC3=O)C(C)=C[C@@H](OC(=O)C(C)C)[C@@H]12 2356539286 JHZYGPMGMMUUTG-NPNMTCQASA-N 346.379 2.244 30 1 EEEF CCOc1ccc(C#Cc2ccc(C[C@H](C)NC(=O)CN)cc2)cc1 113410790 SKPGZSWOVIGHGF-INIZCTEOSA-N 336.435 2.491 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cccc([N+](=O)[O-])c3[nH]2)C1=O 587039135 QEWKYRSZUCTWOB-JTQLQIEISA-N 332.341 2.264 30 1 EEEF CC(=O)[C@@H](CCC#N)[C@]1(C)N[C@H](C(=O)O)Cc2ccc(O)c(C)c21 963549975 JPUZFQIOUALAPC-GLJUWKHASA-N 330.384 2.024 30 1 EEEF COc1ccc(CCNc2nc3cc(C#N)ccc3c(=O)n2C)cc1 1772603328 NTKWKTAJWSZFIS-UHFFFAOYSA-N 334.379 2.468 30 1 EEEF C[C@@H](CO)C1=C(O)C(=O)C2=C(C1=O)[C@H](O)C[C@H]1C(C)(C)CCC[C@]21C 156754338 VGFOZVWPBCCFFJ-LCCANLFKSA-N 348.439 2.473 30 1 EEEF O=C(/C=C/c1cccc(NS(=O)(=O)Cc2ccccc2)c1)NO 29133833 OZUUMDZVFMUKLZ-MDZDMXLPSA-N 332.381 2.147 30 1 EEEF O=C(C1CC1)[C@H](c1ccccc1F)N1CC[C@@H]2C(=CC(=O)[S@@]2=O)C1 299851202 BGWGSGYBPUVHJJ-QEEIZYTISA-N 347.411 2.136 30 1 EEEF C[C@]1(c2nc3nc(C#N)c(C#N)nc3[nH]2)C=C(c2ccccc2F)NO1 587157080 SDWWSOYTBOMBAM-QGZVFWFLSA-N 347.313 2.026 30 1 EEEF C[C@H](Oc1ccccc1)C(=O)NCc1nc2cc(C#N)c(C#N)cc2[nH]1 587225223 NSSUQHVIWOMGQJ-LBPRGKRZSA-N 345.362 2.390 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@]2(COC=CC2=O)N1 587835169 NUURRDCZWYFTPT-XLKFXECMSA-N 326.165 2.431 30 1 EEEF CN1CCC[C@H]1C(=O)[C@@H](C#N)C(=O)Nc1ccc(C(F)(F)F)cc1 169714940 USCQNAKKBRTMAX-OLZOCXBDSA-N 339.317 2.447 30 1 EEEF C=C1C(=O)O[C@@H]2C3=C(COC(C)=O)CC[C@H](OC(C)=O)[C@]3(C)CC[C@H]12 2356410449 LLUIAKNHFIRVHK-YEWFCNIMSA-N 348.395 2.470 30 1 EEEF COc1ccc(C2=NO[C@@H](C(=O)N(C)O)C2)cc1OC1CCCC1 3812220 RMTPBROFMJKTND-MRXNPFEDSA-N 334.372 2.357 30 1 EEEF C=C1[C@@H]2[C@@H](C[C@H]1OC(=O)C=C(C)CO)C(=C)CC[C@@H]1C(=C)C(=O)O[C@@H]21 2356462685 AZDMJQODBMILBW-LMCLKVLCSA-N 344.407 2.477 30 1 EEEF COc1cc(/C=N/NC2=NCCc3ccccc32)cc(OC)c1O 78506148 FYVSGLJXNZBRRK-RGVLZGJSSA-N 325.368 2.336 30 1 EEEF CCc1ncnc(-c2ccc(OC)nc2)c1C#Cc1ccc(N)nc1 148328101 UGRYTNHMXIKZQP-UHFFFAOYSA-N 331.379 2.487 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3ccc(C(=O)OC)cc3[nH]2)C1=O 587038105 CUQNUQCVTJVDBS-GFCCVEGCSA-N 345.380 2.142 30 1 EEEF CCC/C=C/[C@H]1C(=O)[C@H]2O[C@H]2C2(OCC(CC)(CC)CO2)[C@H]1CO 13783071 TWGDZVIUZPIUAD-CFABOYIZSA-N 338.444 2.467 30 1 EEEF C#C[C@]1(O)[C@H](O)C[C@@H]2[C@@H]3CCc4cc(O)ccc4[C@@H]3[C@H](OC)C[C@@]21C 2356485659 OOMBHDXDTAYDBF-OHFNBNKZSA-N 342.435 2.208 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@@H](c2ccccc2C2=CCCCC2)[C@H]1CO 95866668 XJOIDJIXTAYCGR-QWFCFKBJSA-N 340.423 2.469 30 1 EEEF N#CCCCn1c(Cn2c(=O)[nH]c3cnccc32)nc2ccccc21 95563422 RREHTUHPSLFSHU-UHFFFAOYSA-N 332.367 2.426 30 1 EEEF CS(=O)(=O)N1CCC(C(=O)c2coc3cc(C#N)ccc23)CC1 587279889 SKRUFLQHNBACOH-UHFFFAOYSA-N 332.381 2.159 30 1 EEEF N#Cc1n[nH]cc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587880693 YMGRCQWHDAPQNP-UHFFFAOYSA-N 333.178 2.299 30 1 EEEF C[C@](Cc1ccccc1)(C(=O)NO)C(=O)N1CCc2ccccc2C1 13780634 BZDNZMAIXJGVGF-FQEVSTJZSA-N 338.407 2.326 30 1 EEEF CS(=O)(=O)Nc1ccc(/N=C/[C@@H]2C(=O)Nc3ccccc32)cc1 169726567 VSYGALGQXZUTRS-FBJMNJBLSA-N 329.381 2.496 30 1 EEEF CC1=C[C@@H]2[C@H](C[C@H](O)C(C)=C[C@@H]3C(=O)[C@@H](C)C[C@@]3(O)C1=O)C2(C)C 2356453085 NHOIUGORUWWMAP-MXSVDAKMSA-N 332.440 2.441 30 1 EEEF C#C[C@]1(O)CC[C@@H]2[C@@H]3C[C@H](O)c4cc(OC)ccc4[C@@H]3C[C@H](O)[C@@]21C 2356584248 YTRCAZOTWYOCGG-PUBOLSPZSA-N 342.435 2.377 30 1 EEEF C=C1C[C@H]2O[C@H]([C@@H]3[C@@H](C(C)C)CC=C(C)[C@H]23)[C@](C)(O)[C@@H](O)C[C@@H]1O 198521942 PMIONIXTNXHIOX-RNAQZQGESA-N 336.472 2.431 30 1 EEEF CCOC(=O)CCOCCCOCCc1nc2cccc(C#N)c2[nH]1 587570284 UWIRBCPDGUUXKG-UHFFFAOYSA-N 345.399 2.354 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cccc(C(=O)NCCO)c1 587904247 GIYHABFXMVEDOM-UHFFFAOYSA-N 329.783 2.471 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@@]2(CCNC[C@@H]2C#N)N1 587794326 MGFDYUSZRRNEOF-VPJDZLOFSA-N 338.224 2.451 30 1 EEEF Cc1cc(C)c(=O)oc1-c1c(O)c(C)cc2c1C(=O)C(N)=CC2=O 1857620655 YTJFRDVNUHPFEA-UHFFFAOYSA-N 325.320 2.159 30 1 EEEF C=CCN1[C@@H]2CC[C@@H]1[C@H](C(=O)OC)[C@@H](OC(=O)c1ccccc1)C2 100645134 OLKZDWYIZCZYLB-NCOADZHNSA-N 329.396 2.424 30 1 EEEF C=C[C@@]12C[N+](C)([O-])[C@H]3[C@H]4CO[C@H](C[C@@H]41)[C@@]1(C(=O)Nc4ccccc41)[C@H]32 103581062 LNBRLFDEFXKCAW-NTOLBQMHSA-N 338.407 2.040 30 1 EEEF biogenic,in-vitro C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@]1(C)CCC[C@@]2(CO)C(=O)O[C@H]([C@@H]3O)[C@H]12 85932788 RDUNXXWNAKBVER-AWLDRMOYSA-N 332.440 2.434 30 1 EEEF in-man N#Cc1nc2nc(-c3ncoc3CCC(F)(F)F)[nH]c2nc1C#N 587092609 SJTDDSZYKXPHCO-UHFFFAOYSA-N 333.233 2.246 30 1 EEEF CO[C@H](C)[C@@]1(CC#N)N[C@H](C(=O)C(F)(F)F)Cc2ccccc21 962728253 DHTCGHMJWKFPMC-RIEGTJTDSA-N 326.318 2.476 30 1 EEEF CC(=O)Nc1cccc(-n2nc3c(c(C#N)c2=N)CC(C)(C)OC3)c1 169730342 JBDNTMNVXFMRTO-UHFFFAOYSA-N 337.383 2.033 30 1 EEEF CCNC(=N)N/N=C/c1ccc(-c2cn3ccc(C)cc3[n+]2C)cc1 26828020 OQZJHNWMWMGJQY-WSDLNYQXSA-N 335.435 2.207 30 1 EEEF C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)C(CO)=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C 2356867881 WXBPWNNGZDXSDG-VDUMFTQRSA-N 346.467 2.379 30 1 EEEF C=C1C(=O)O[C@@H]2/C=C(/C)[C@]3(O)C=C[C@@](C)(C[C@@H](OC(=O)C(C)C)[C@@H]12)O3 38180634 XJUPOHKZSDZNBE-UMXFGWAOSA-N 348.395 2.036 30 1 EEEF C=C(C)[C@@H]1Oc2cc(O)c(C(C)=O)cc2[C@H]1OC(=O)/C(=C\C)CO 238780029 CLWSKSKCEVBFSD-VJVNXXCUSA-N 332.352 2.455 30 1 EEEF N#Cc1nc2nc([C@H]3CS[C@H](Cc4ccccc4)N3)[nH]c2nc1C#N 587040603 IHUXBNSHRYAUJR-ZIAGYGMSSA-N 347.407 2.043 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc2c(c1)C(=O)NCC(=O)N2 587909112 QPFDJRJKQGQLHH-UHFFFAOYSA-N 340.766 2.430 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(N2CCC[C@H](O)C2)nc1 587908288 PKHOMRZPOBXYFS-INIZCTEOSA-N 343.814 2.500 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cc(C#N)c(C#N)cc3[nH]2)C1=O 587038201 DTGRWODNXXWEQP-CYBMUJFWSA-N 337.364 2.099 30 1 EEEF C=C1[C@H](O)C[C@@H]2C(C)(C)[C@H](O)CC[C@]2(C)[C@H]1CC=C1COC[C@@H]1O 2356416314 PQJNKPQZAXZXLP-CKAYJIMUSA-N 336.472 2.434 30 1 EEEF O=C1C=CC(Br)=C/C1=C\NNc1ccc([N+](=O)[O-])cn1 104023506 SCEXDEDMFYCGEO-SOFGYWHQSA-N 337.133 2.208 30 3 EEEF CC(=O)CC1=C2C(=O)O[C@]3(C)CC[C@@H]4[C@H]([C@H]([C@H]23)[C@](C)(O)C1=O)C4(C)C 2356482936 BTLNQUGRPABJQH-MEFLNVJASA-N 346.423 2.210 30 1 EEEF C=C1[C@H](O)[C@@H]2O[C@]23[C@@H]1C[C@]12CC[C@H](C(C)C)[C@@]1(C)C(=O)C(=O)[C@@]32C 2356527238 ZVWIURNWTXCECX-CVGMCBACSA-N 330.424 2.291 30 1 EEEF COC(=O)c1cccc(Oc2ccc(NC(=O)[C@@H](N)CS)cc2)c1 28765772 IRPZTPVLQMMBTC-HNNXBMFYSA-N 346.408 2.461 30 1 EEEF C=C[C@H]1CC[C@H]2[C@@H]3CC(=O)[C@]4(O)C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@@]21C 215416706 VQFKUKMXFNCVKK-DGRCZTGZSA-N 348.483 2.457 30 1 EEEF CC(C)(C)NC[C@H](O)CO/N=C(\Cl)c1nc2ccccc2o1 42922688 WBYAJYDAQSGUMZ-XEVDPLJKSA-N 325.796 2.494 30 1 EEEF C=C[C@]1(C)C=C2[C@H](O)C[C@H]3C(C)(C)[C@@H](O)C[C@H](O)[C@]3(C)[C@H]2[C@H](O)C1 1857544712 JNDFPOMCRMNTHH-DVHHVVNSSA-N 336.472 2.025 30 1 EEEF COC(=O)c1cc2c([nH]1)C(=O)C=C1N(C(=O)OC(C)(C)C)C[C@H]3C[C@@]123 100866069 JVWWPRHIXMFAED-LZVRBXCZSA-N 344.367 2.390 30 1 EEEF C#C[C@@H]1CN2CC[C@H]1C[C@H]2CNC(=S)Nc1ccc(N(C)C)cc1 2356315204 DTTJJVZOCATUDS-VKJFTORMSA-N 342.512 2.383 30 1 EEEF C=C(C)C(=O)O[C@H]1[C@@H]2C(=C)[C@@H](O)C[C@H]2C(=C)C[C@H]2OC(=O)C(=C)[C@@H]12 2356627895 ZQBZOPWDBPOXPR-PFHJDOJBSA-N 330.380 2.085 30 1 EEEF Cc1ccc(CCC[C@H](CC(=O)N(C)O)CP(=O)(O)O)cc1 584905593 PCPXBXKPZNRAMA-CQSZACIVSA-N 329.333 2.349 30 1 EEEF in-vitro C=CC[C@@](C)(N)c1nc2ccc(S(=O)(=O)N(CC)CC)cc2[nH]1 587257600 HJYWFWJIRLRJOL-MRXNPFEDSA-N 336.461 2.343 30 1 EEEF C#CCO[C@H]1C=C2[C@H]3CN(Cc4cc5c(cc43)OCO5)[C@H]2C[C@@H]1OC 1857762506 WRLXHYHTGUIPNQ-DWRORGKVSA-N 339.391 2.060 30 1 EEEF CCCCCCCCS(=O)(=O)N[C@H]1CCC[C@H](CC(=O)O)[C@H]1O 58582920 DLLOIOSRSAHLCT-IJEWVQPXSA-N 349.493 2.271 30 1 EEEF C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@]2(C)[C@@H]1CC(=O)C1=CCOC1=O 2356711150 KPJIGLLMDBHXEB-YESPVIGUSA-N 348.439 2.171 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc2nc(CO)cc(=O)n2c1 587912103 AQJRJBDXHLKPSN-UHFFFAOYSA-N 340.766 2.249 30 1 EEEF Cc1ccc2c(c1)[C@]1(C)C=C(NC(=O)Cn3cccc3)C(=O)C[C@@H]1O2 169316321 VQCBOPJYVSCSCZ-ICSRJNTNSA-N 336.391 2.488 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 32270918 PVIQXTWXWOHHFV-ZTVWUKKDSA-N 344.407 2.001 30 1 EEEF CC(C)NC(=O)N1[C@H](CO)[C@@H](c2ccc(C#CC3CC3)cc2)[C@@H]1C#N 95897425 FGRJVUDIIQYRHF-OTWHNJEPSA-N 337.423 2.218 30 1 EEEF C=C1C[C@@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 257389677 BSBICXIQCTXPMN-TVUJFAMJSA-N 330.380 2.056 30 1 EEEF endogenous,in-man CC1=CCCC[C@@H]2O[C@]23CC(=O)O[C@@H]3c2c(O)ccc(O)c2[C@@H]1O 2356403622 PHCAOFZRCKAKBR-FCRVUTKVSA-N 332.352 2.387 30 1 EEEF N#Cc1cccc([C@H]2C3=C(CCCC3=O)NC3=C2S(=O)(=O)CC3)c1 103303683 HBFHAMGVEXDJCX-INIZCTEOSA-N 340.404 2.282 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12OC(=O)[C@@](C)(CC[C@@H]1O)[C@@H]2[C@@H]3C(=O)OC 2356559835 NZAMXUVSJOQDKJ-JRXPZBLKSA-N 346.423 2.225 30 1 EEEF C=C(Cc1c(OC)ccc(C(=O)O)c1O)[C@@H]1CC[C@](C)(O)[C@H](O)C1 27559302 JNPNGXWCEMBWHW-MZKGEVEHSA-N 336.384 2.110 30 1 EEEF Cc1c(C2=NN3CC[C@H](O)[C@H]3[C@@H]2OC(C)C)ccc(C#N)c1Cl 146595062 DFCZRPFNJWFTFF-RRQGHBQHSA-N 333.819 2.467 30 1 EEEF C=C1C[C@@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)O 257389675 BSBICXIQCTXPMN-BYVPMXMMSA-N 330.380 2.056 30 1 EEEF endogenous,in-man NCc1cc(Oc2cccc(C(=O)NO)c2)nc(C(F)(F)F)c1 1857554710 LLOOIRAXTRVTJW-UHFFFAOYSA-N 327.262 2.470 30 1 EEEF C=C1CCC=C(C)CC[C@@H]2C(=CC=CC(O)(CO)CO)COC(=O)[C@H]12 2356427345 WVMYRDBAJSJKGW-QZTJIDSGSA-N 348.439 2.050 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(CO)CCC[C@](C)(CO)[C@H]1C[C@H]3O 2356645368 NLKCAXRWGIRDDQ-NCLNHVEOSA-N 334.456 2.070 30 1 EEEF COc1cscc1C(=O)N[C@@H](CC1CCCCC1)C(=O)NCC#N 82064607 LZDUEXWCOMUDDN-AWEZNQCLSA-N 349.456 2.465 30 1 EEEF CC(C)C1=C[C@H]2[C@@H]3[C@@H](C(C(C)C)=CC(=O)[C@]3(C)O)[C@@H]1C(=O)[C@@]2(C)O 238765777 YNYHPBIGKWCFOA-DKUPAGJESA-N 332.440 2.297 30 1 EEEF CNS(=O)(=O)c1cc(-c2nc3c(Cl)cc(C#N)cc3[nH]2)n(C)c1 586947650 YAOHIAQMRGNDOS-UHFFFAOYSA-N 349.803 2.002 30 1 EEEF COc1ccc(C[C@H](C)c2nc3nc(C#N)c(C#N)nc3[nH]2)cc1OC 587926082 HZGRUUAMXABAPA-JTQLQIEISA-N 348.366 2.460 30 1 EEEF N#Cc1ccc2c(c1)O[C@@H](COc1ccc(F)c(C(N)=O)c1F)CO2 1772599462 CPBXVUMNRJTINE-SNVBAGLBSA-N 346.289 2.154 30 1 EEEF COC(=O)C/C(O)=N/[C@H](Cc1c[nH]c2cccc(Cl)c12)C(=O)O 13386792 ITVFBZXHWIFZDX-LLVKDONJSA-N 338.747 2.337 30 1 EEEF endogenous,in-man COc1ccc2c3c1O[C@@H]1C=C(C(C)=O)C[C@H]4[C@@H](C2)N(C)CC[C@@]314 101770809 FKNWJBZMTKZQMB-VZHLBOQGSA-N 325.408 2.490 30 1 EEEF CC(=O)NCCCCCCCC(=O)N(C)CC#CCN1CCCC1 27856143 VZNMIKAJDBRNBA-UHFFFAOYSA-N 335.492 2.021 30 1 EEEF CC(C)C[C@H](NC(=O)c1cccc(C(F)(F)F)c1)C(=O)NCC#N 82065018 YLGLXVDHNPHGMY-ZDUSSCGKSA-N 341.333 2.490 30 1 EEEF Cc1cc(C(=O)N[C@H](Cc2c[nH]c3ccccc23)C(=O)NO)c(C)o1 96269519 OIQWPJQECPFTCI-MRXNPFEDSA-N 341.367 2.224 30 1 EEEF COc1ccccc1C[C@@H]1S/C(=N/N=C/c2ccco2)NC1=O 5006072 JZGWNEGPTUVELP-FBJMNJBLSA-N 329.381 2.452 30 3 EEEF C/C(=N\c1ccc(S(N)(=O)=O)cc1)[C@H]1C(=O)Nc2ccccc21 169685123 DUGPEYYCVBKDIP-BFERYNQYSA-N 329.381 2.162 30 1 EEEF CCSC[C@@H](NC(=O)[C@H](CS)Cc1ccccc1)C(=O)O 26491784 DDZXMZMIRUSLFJ-QWHCGFSZSA-N 327.471 2.098 30 1 EEEF CC=C(C)C(=O)O[C@@H]1CCN2C[C@H]3C[C@@H](CN4C=CC(=O)C[C@H]34)[C@H]2C1 2356436103 ANLPQANGWMODSI-CSFFLVESSA-N 344.455 2.136 30 1 EEEF C[n+]1ccccc1COc1ccc(/C=N/NC(=N)N2CCCC2)cc1 26829945 RJNGIMSPQCKLQH-KGENOOAVSA-N 338.435 2.044 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(C)(C)C)[C@@H]1[C@@]3(C)CC[C@@H](O3)[C@@]1(C)[C@@H]2O 2356544661 XVJNAEOCXFSHRU-PTLGTOKSSA-N 336.428 2.216 30 1 EEEF CN1CC2=C(C(=O)c3ccccc3C2=O)[C@@]12C(=O)Nc1ccccc12 73298484 IBWUGLRRRIOIBF-FQEVSTJZSA-N 330.343 2.155 30 1 EEEF COC1=C(O)C(=O)c2c(cc3c(c2C)C(=O)C[C@H](O)C3(C)C)C1=O 85965613 BRNCENKARBVJTP-NSHDSACASA-N 330.336 2.015 30 1 EEEF C[C@@H]1CN2C[C@H]3CC[C@]4(O)CCC5=C4[C@]4(CC5=O)[C@@]3(C)CC[C@H]1[C@]24O 238746152 KLIOZQZXDDOEMZ-OTRRFDLGSA-N 343.467 2.247 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cccnc1-n1cnc(N)n1 587903564 UEVZTXMFKGQXHX-UHFFFAOYSA-N 325.759 2.306 30 1 EEEF N#Cc1cc2nc([C@@H]3CSCC(=O)N3)[nH]c2cc1C(F)(F)F 587042227 BDMPWYJTPWNGTN-JTQLQIEISA-N 326.303 2.357 30 1 EEEF Clc1ccc(C#CCOc2nsnc2C23CN4C[C@H]2[C@H]3C4)cc1 13798005 JVDFDVTZQWJMQV-VMZNBEPHSA-N 343.839 2.435 30 1 EEEF C[C@@H](O)CNC1=CC(=O)C(SC/C=C/c2ccccc2)=CC1=O 1857645796 URXSALGSXCHPPY-OQHXTRMZSA-N 329.421 2.323 30 1 EEEF C=CCN1CC[C@](O)(c2cc(C(=O)OCC)[nH]c2-c2cc(C)no2)C1 1653343 ZTNCVERONIXYMS-GOSISDBHSA-N 345.399 2.234 30 1 EEEF CCC#CCN1CCC[C@@H]1CNC(=O)c1ccc2c(c1)OCCO2 84729273 UMVKYXPRKGLPGN-MRXNPFEDSA-N 328.412 2.065 30 1 EEEF C=C1[C@H](O)[C@@]23CC[C@@H]4C(C)(C)C[C@@H](O)C[C@@]4(C)[C@H]2CC[C@]1(O)[C@H]3O 95914604 OUKQFTKNWPTKCZ-NLIBZLNVSA-N 336.472 2.003 30 1 EEEF biogenic,in-vitro COC(=O)c1cc2c([nH]1)[C@@]13C[C@@H]1CN(C(=O)OC(C)(C)C)C3=CC2=O 96902171 UAUAFLDBZMJDIS-LZVRBXCZSA-N 344.367 2.390 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@H](C)[C@@H]3[C@H](O)CC[C@]3(C)[C@@H](OC(=O)C=CC)[C@H]12 2356549662 HSXLCTYJIGXUOE-MDZJWTORSA-N 334.412 2.389 30 1 EEEF C[C@@H]1CN2C[C@H]3CC[C@]4(O)CCC5=C4[C@@]4(CC5=O)[C@@]3(C)CC[C@H]1[C@@]24O 2356678545 KLIOZQZXDDOEMZ-NJFAEZJKSA-N 343.467 2.247 30 1 EEEF COC1=CC(=O)c2c(cc3c4c(cc5c(c24)OCO5)CCN3C)C1=O 15216310 WDTZOTKRAGAZDC-UHFFFAOYSA-N 337.331 2.470 30 1 EEEF biogenic CCCCCCCCC[C@H]1C[C@@H](O)[C@H](O)C=C[C@H](O)CC(=O)O1 299815758 VKFBQLMPTJTKBZ-MWDXBVQZSA-N 328.449 2.472 30 1 EEEF CN1CCc2cn(C)c3c2C1=C/C(=N\CCc1ccc(O)cc1)C3=O 377811867 OLEMIURMTKKFSE-LTGZKZEYSA-N 335.407 2.440 30 1 EEEF CC(C)(C)OC(=O)N1CC[C@]2(NCCc3ccc(O)cc32)[C@H](C=O)C1 963351248 FUNVDCFOCWPYPX-LIRRHRJNSA-N 346.427 2.189 30 1 EEEF CC=C(C)C(=O)O[C@@H]1[C@H](O)[C@H](O)[C@@]2(C)[C@H]3C(=O)C=C(C)[C@H]2[C@H]3C1(C)C 2356496381 HOXNGFVTRBWUMU-SNCRXCSTSA-N 348.439 2.024 30 1 EEEF CSCC[C@@H](NC(=O)[C@H](CS)CCc1ccccc1)C(=O)O 26496208 XZJCTWVYKRGLQJ-UONOGXRCSA-N 341.498 2.488 30 1 EEEF COc1n[nH]cc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587889329 XULXOUDMCFLMOP-UHFFFAOYSA-N 338.194 2.436 30 1 EEEF C#CCNC(=O)C1=C[C@@H](c2ccccc2)[C@H](CCCO)[C@@H](OCC)O1 13656457 ZXKBQCCQOALWOU-ZWOKBUDYSA-N 343.423 2.185 30 3 EEEF N#Cc1cnc(N[C@H]2CC[C@@H](c3nnc4cnc5[nH]ccc5n34)C2)cn1 168771755 RSAXWGSYEWHTQB-MNOVXSKESA-N 345.370 2.015 30 1 EEEF C[C@H]1CC/C(=N\Nc2ccccc2)c2ncc(CC(=O)O)c(=O)n21 40791238 LBQDBYOUOYUTAL-BTNWAMHGSA-N 326.356 2.041 30 1 EEEF C=C1C[C@@H](O)[C@H]2O[C@]2(C)CC[C@@H]2/C(=C\C=C\C(C)(C)O)C(=O)OC[C@@H]12 238767285 DHTWVKTXQLZELP-NKDFVEDESA-N 348.439 2.288 30 1 EEEF CCOC(=O)[C@@H](/C=N/NC(N)=S)c1ccc(C(F)(F)F)cc1 653726139 JVTXUTBEGMHMES-DSSNYXJPSA-N 333.335 2.171 30 1 EEEF CN(C)S(=O)(=O)c1ccc2[nH]c(-c3ccc(F)cc3C#N)nc2c1 587159017 VGNKVFZOUODKCI-UHFFFAOYSA-N 344.371 2.491 30 1 EEEF Cc1ccnc2c1CCN[C@@]2(CC1OCCO1)c1cccc(C#N)c1 963068440 LBEVGECGAFHZAY-FQEVSTJZSA-N 335.407 2.414 30 1 EEEF O=C1C=C(NC2=C[C@H]3O[C@@H](c4ccccc4)OC[C@@H]3OC2=O)CCC1 19924575 WIDOMGFQDHPMIW-AOIWGVFYSA-N 341.363 2.136 30 1 EEEF COC(=O)c1ccc(Oc2cccc(NC(=O)[C@@H](N)CS)c2)cc1 28764288 JSDKOXJCEWMHPD-HNNXBMFYSA-N 346.408 2.461 30 1 EEEF Cc1ccc(CN(CC(=O)NO)Cc2cccc(C(=O)O)c2)cc1 1857754070 ICWSUXALMHGHSB-UHFFFAOYSA-N 328.368 2.201 30 1 EEEF CC[C@H](O)C[C@H](C)[C@@H]1O[C@]1(C)C=CC(=O)N[C@@H](CO)[C@@H](C)CC 2356421457 KQYIQWJQJFWGMP-OZINRZGZSA-N 327.465 2.020 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(COC3=O)C(=O)C=CC(C)(C)[C@H]1C=O 28708335 DEAIOAMNFATZQP-QUUXKOAQSA-N 342.391 2.051 30 1 EEEF C=C1C(=O)[C@@]23C[C@H](O)[C@@H]4C(C)(C)CCC[C@]4(C)[C@@H]2[C@@H](O)C[C@H]1[C@@H]3O 2356638807 RFZAFMSAZOFRSM-JCIZMHSVSA-N 334.456 2.067 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(COC(C)=O)CCC=C(C(=O)OC)CC[C@@H]12 2356738322 FELNAJVVBXSDQN-JKSUJKDBSA-N 334.368 2.247 30 1 EEEF N=C(NO)c1ccc(-c2ccc(-c3ccc(/C(N)=N/O)nc3)o2)cc1 27548774 LURIHRMJVRDYNA-UHFFFAOYSA-N 337.339 2.407 30 1 EEEF CCCCc1nc2cc(/C=C/C(=O)NO)ccc2n1[C@@H]1CCNC1 34987565 SNHWQAPINSMLNB-IZPAUZPXSA-N 328.416 2.432 30 1 EEEF O=C1c2ccccc2-c2cc(/C=N/N=C3NCCN3)nc3cccc1c23 49735143 DPEMAPDYBQZVSV-FOKLQQMPSA-N 341.374 2.329 30 1 EEEF C[C@]1(CO)CCC[C@]2(C)[C@@H]1C[C@@H](O)[C@@]13C[C@@H](CC[C@@H]21)[C@]1(CO)O[C@@H]13 238757377 SZQODOFRJMJMMC-NBWKEMLCSA-N 336.472 2.102 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc2nc(N)nc(O)c2c1 587909887 BTYXKXXOFDXRGY-UHFFFAOYSA-N 326.743 2.374 30 1 EEEF Cc1ccc(N2CC(=O)N(C)c3c(C#N)c4n(c3C2=O)CCC4)cc1 103276957 DSQISNIVVFUUNV-UHFFFAOYSA-N 334.379 2.238 30 1 EEEF C=CCC(=O)Nc1c2n(c(=O)n(C(C)C)c1=O)[C@@H]1CCCC[C@H]1N2 82206027 WUGDURPOQUGZTH-VXGBXAGGSA-N 332.404 2.015 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@]2(COC[C@H]2C#N)N1 587744416 ZUMGHCAWUGYXMG-PJCOJXEDSA-N 325.181 2.488 30 1 EEEF COc1ccc(Cl)cc1C#Cc1c([N+](=O)[O-])nn(CC(=O)O)c1C 587902907 RWKYTAUBVYCBRQ-UHFFFAOYSA-N 349.730 2.246 30 1 EEEF C[C@H](Cn1cc([N+](=O)[O-])cn1)c1nc2cc(Cl)nc(C#N)c2[nH]1 587276029 IAZWKBSKYADPDT-SSDOTTSWSA-N 331.723 2.391 30 1 EEEF C[C@]1(C=O)[C@H]2CC[C@@]3(C)O[C@@]14C(=O)c1ccc(O)cc1C(=O)C4=C[C@@H]23 5839739 NMLFNFAGOHGLMD-YJKZWKBDSA-N 338.359 2.470 30 1 EEEF biogenic,in-vitro N#Cc1cnn2c(NCCc3cnc[nH]3)nc(Nc3ccccc3)nc12 16052401 IWUUKHQIKFHWIW-UHFFFAOYSA-N 345.370 2.117 30 1 EEEF in-vivo COc1ccc(C[C@H](N=O)C(=O)NCCS)cc1Br 169727948 MRTTUMZFRRYWEL-JTQLQIEISA-N 347.234 2.181 30 1 EEEF N=C(NO)c1cccc(-c2ccc(-c3ccc(/C(N)=N\O)cn3)o2)c1 27547231 ZKRMPANPLWPDJE-UHFFFAOYSA-N 337.339 2.407 30 1 EEEF CC(=O)Nc1cccc(Nc2nc(NC3CC3)n3ncc(C#N)c3n2)c1 28707974 LNLGAIKWRXYMAM-UHFFFAOYSA-N 348.370 2.272 30 1 EEEF CC(C)[C@@H]1[C@H](O)[C@H](O)C2=CC3=C(CO)C(=O)C=C[C@]3(C)CC[C@@]21C 2356730453 IQSIJJOWDAYBIC-OBKDMQGPSA-N 332.440 2.155 30 1 EEEF C/N=C1/N/C(=C\c2c[nH]c3c(Br)cccc23)C(=O)N1C 84687771 BRWAMNLZPYODKK-WDZFZDKYSA-N 333.189 2.319 30 1 EEEF C[C@H]1CC/C(=N\Nc2ccc(F)cc2)c2ncc(C(=O)O)c(=O)n21 38153703 ZXPBEUXFWUEPIP-PQHMUEMWSA-N 330.319 2.252 30 1 EEEF N#Cc1cccc(-c2c[nH]c3ncnc(N4CCO[C@@H](C#N)C4)c23)c1 224858155 YDRMVAPJCHICGE-AWEZNQCLSA-N 330.351 2.225 30 1 EEEF N#Cc1ccc(-c2ccc3c(c2)OC[C@H]2[C@H](CO)SC(=O)N32)cn1 299869359 UMOJOKQCEXAYIR-HOCLYGCPSA-N 339.376 2.415 30 1 EEEF Nc1nnnn1N=Cc1cccc(OCc2ccccc2Cl)c1 8575283 MZIQYGXEYOZXSW-UHFFFAOYSA-N 328.763 2.370 30 1 EEEF aggregator CCCCCCCCS(=O)(=O)N[C@@H]1CCC[C@H](CC(=O)O)[C@H]1O 58582869 DLLOIOSRSAHLCT-IIAWOOMASA-N 349.493 2.271 30 1 EEEF C=CCOC(=O)[C@@H](NOS(=O)(=O)c1ccc(C)cc1)[C@@H](C)CC 58609386 OXOMMGYNRSYQRC-ZFWWWQNUSA-N 341.429 2.349 30 1 EEEF C=C(C)[C@@H]1C[C@H]2CC[C@H]1[C@@H]1[C@H](CC[C@@]1(O)CCNC(=N)NC)[C@@]2(C)O 2356521807 MKBHWZDZALSUAF-UIDCZCHTSA-N 349.519 2.251 30 1 EEEF C[C@@](O)(C#Cc1ccc2c(c1)-c1nc(C(N)=O)cn1C1CC2C1)CF 219438239 MNRGQBJVTUSAFH-PNQRNNEWSA-N 339.370 2.153 30 1 EEEF COCCNC(=O)[C@@H]1CCCC[C@H]1c1nc2cccc(C#N)c2[nH]1 587230109 FJLCJTIIYPNMKU-ZIAGYGMSSA-N 326.400 2.471 30 1 EEEF CC=C(C)C(=O)O[C@@H]1[C@H](O)[C@@H](O)[C@@]2(C)[C@H]3C(=O)C=C(C)[C@H]2[C@H]3C1(C)C 2356496379 HOXNGFVTRBWUMU-DKFSFIOTSA-N 348.439 2.024 30 1 EEEF C=C[C@H]1CC(=O)[C@@H]2Oc3c(OC)ccc4c3[C@@]23CCN(C)[C@@H](C4)[C@H]13 195202925 NTWGNEUJRLFCNI-AKTWKWODSA-N 325.408 2.345 30 1 EEEF CC(C)(C)C(=O)N[C@@H](C(=O)NO)c1ccc(Br)cc1 584905022 QSMFBPVNXFNEGF-SNVBAGLBSA-N 329.194 2.158 30 1 EEEF in-vitro C=CCN1C(=O)S[C@@H](Cc2nc3ccc([N+](=O)[O-])cc3[nH]2)C1=O 587040031 YYBXOTJLRGCPBT-NSHDSACASA-N 332.341 2.264 30 1 EEEF O=CCC[C@]1(C(=O)O)Oc2ccccc2C(=O)[C@H]1C(=O)c1ccco1 587603582 NTVWIXHUYWRWHD-KSSFIOAISA-N 342.303 2.156 30 1 EEEF CCCCOCC1(NCC(=O)N2[C@H](C#N)CC[C@@H]2C#N)CCCC1 13687450 MAPHXEDRFCDTJT-IYBDPMFKSA-N 332.448 2.112 30 1 EEEF C=C1[C@@H]2CC[C@@H]3[C@](C2)(C(=O)O[C@H]2CCC(C)(C)[C@H]4[C@H](O)OC[C@]234)[C@@H]1O 103239252 MSSXZZIDIPKYEB-YPDCMUIKSA-N 348.439 2.016 30 1 EEEF CCCCCCCCC[C@@H]1OC(=O)C[C@H](O)C[C@@H](O)C=C[C@H]1O 2356619468 HFGOXJHLMBNOHC-HZMVEIRTSA-N 328.449 2.472 30 1 EEEF C[C@]1(C=O)[C@H]2CC[C@@]3(C)O[C@@]14C(=O)c1cc(O)ccc1C(=O)C4=C[C@@H]23 31168268 XMDCRBHPCMHPQU-YJKZWKBDSA-N 338.359 2.470 30 1 EEEF Cc1nc(C(=O)NCCCCC(=O)NO)cc2c1[nH]c1ccccc12 210718095 FQKQZHDFSMIVFP-UHFFFAOYSA-N 340.383 2.430 30 1 EEEF Cc1ccc(CSC[C@H](NC(=O)[C@H](C)CS)C(=O)O)cc1 40865332 JACLNVPWBGMSHO-YPMHNXCESA-N 327.471 2.364 30 1 EEEF O=C1C(Cl)=C(Oc2cc(O)cc(O)c2)C(=O)c2c(O)ccc(O)c21 13652344 YEDBNIVGRALUGZ-UHFFFAOYSA-N 348.694 2.417 30 1 EEEF C=C1C[C@H](OC(=O)C(C)=CC)[C@@H]2C(=C)C(=O)O[C@@H]2[C@@H]2C(=C)[C@@H](O)C[C@H]12 2356486440 SDRJABGPZHYDOV-CMURFVSUSA-N 344.407 2.475 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(CO)CC[C@]3(C)[C@@]1(C)[C@]21CO1 2356551316 ZJTUORWHCGIUBM-WGBOWRHLSA-N 334.412 2.140 30 1 EEEF C=CC1=CC(=O)[C@@H]2[C@H](CC[C@@H]3C(C)(C)[C@H](O)[C@H](O)[C@H](O)[C@]23C)[C@@H]1C 86007152 XFRCVLKGZMPUFQ-HQQAYFDNSA-N 334.456 2.089 30 1 EEEF endogenous,in-man C#CCN(C)C[C@@H]1CN2CC[C@H]1C[C@@H]2CNC(=O)Nc1ccccc1 2356320497 MFSCSGBXHMMZNQ-YQVWRLOYSA-N 340.471 2.084 30 1 EEEF C=C1[C@H](O)[C@]23C[C@H]1CC[C@H]2[C@]12CO[C@H](CC1=O)C(C)(C)C2=C(O)C3=O 238788347 LRBFGRIVMPSVAV-OZMLQRHGSA-N 344.407 2.099 30 1 EEEF COc1ccc(C[C@@H](N=O)C(=O)NCCS)cc1Br 169727947 MRTTUMZFRRYWEL-SNVBAGLBSA-N 347.234 2.181 30 1 EEEF CN1CCN(/C(=N\c2ccc(F)cc2)NCCCCCCN)CC1 101719722 JDUCOFZALUDVQW-UHFFFAOYSA-N 335.471 2.169 30 1 EEEF CCCCN[C@H]1C2=C(OC(C)(C)[C@H]1O)C(=O)c1ccccc1C2=O 29134721 PWJHHLDOTFKWMM-KSSFIOAISA-N 329.396 2.248 30 1 EEEF COc1ccc2c(c1)[C@H]1CN/C(=C\C(=O)c3ccccc3)C(=O)N1CC2 96934352 YUWRQMRQVKNYSG-XLXASQRYSA-N 348.402 2.491 30 1 EEEF C=CCN1C(=O)c2cc3c(OC)c(OC)c(OC)cc3n2C1=S 13487555 ATFWTYPVOGVTBP-UHFFFAOYSA-N 332.381 2.442 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@@H]3C[C@@H](OCC(C)=CC)[C@@H]12 2356499443 DMVINTHATJOGFW-SISKNIMQSA-N 334.412 2.304 30 1 EEEF C=C[C@@H]1C=C2C(=O)C=C3[C@@](C)([C@@H](O)CC[C@@]3(C)C(=O)O)[C@]2(O)CC1 2356788683 CHLJNZOUECQLLK-SMGZUVQUSA-N 332.396 2.001 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)c2ccc(O)cc2)[C@@H]1O 40812375 GBKMQCYVHBYTGQ-SJORKVTESA-N 338.363 2.267 30 1 EEEF O=C(NO)c1ccc(CNCc2nc(-c3cccs3)no2)cc1 141907344 VENKYRVDNRMBJI-UHFFFAOYSA-N 330.369 2.207 30 1 EEEF CNC(=O)/C(=N/OC)c1ccccc1Oc1cccc(OCC#N)c1 103194495 YMRYZMGFYQPFMX-HEHNFIMWSA-N 339.351 2.478 30 1 EEEF C=C1C[C@H](OC(=O)C(C)=CC)[C@@H]2C(=C)C(=O)O[C@@H]2[C@@H]2C(=C)[C@H](O)C[C@H]12 2356486441 SDRJABGPZHYDOV-LVZMMCSGSA-N 344.407 2.475 30 1 EEEF O=C(NO)[C@@H](Cc1ccccc1)C(=O)NCCCCc1ccccc1 35270457 WBIXUIDQAJRMSZ-SFHVURJKSA-N 340.423 2.490 30 1 EEEF in-vivo C=C(CO)C(=O)O[C@@H]1CC(=C)[C@@H]2CCC(=C)[C@@H]2[C@@H]2OC(=O)C(=C)[C@H]21 14454386 PHJYCLCTXRJHJZ-QEOTZNIISA-N 330.380 2.087 30 1 EEEF biogenic C=CC[C@@]1(OCc2ccccc2)C(=O)C(=O)O[C@@H]1[C@@H]1COC(C)(C)O1 17259967 QUSJNYTVFAJGCT-ZSZQSSIHSA-N 346.379 2.164 30 1 EEEF C[C@H]1CO[C@H]2C(=O)C3=C4OC(=O)C5=C4[C@@](C)(CC[C@@H]5O)CC[C@]3(C)[C@@H]12 169657269 BEEKLPAFPKYOIZ-DYGWXWIKSA-N 344.407 2.289 30 1 EEEF C=C1C[C@@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)OC 2356549658 CSOGGDRRRLWUTQ-SWRUNGBXSA-N 344.407 2.145 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H]1[C@@H](O)CC(=C)[C@@H]1C[C@H](OC(=O)C(C)=CC)C(=C)[C@H]12 2356654404 UINWHHMWCJPCDZ-ZCVDQKGDSA-N 344.407 2.475 30 1 EEEF CCOC(=O)[C@@H](C#N)[C@@H]1c2cc(C)ccc2OC(=N)[C@@H]1C(=O)OCC 169719788 KQYZYWDUMYSEAD-AEGPPILISA-N 344.367 2.330 30 1 EEEF O=N[C@@H](Cc1ccc(F)c(Br)c1)C(=O)NCCS 169727920 XMEVZQFDGLJAGD-JTQLQIEISA-N 335.198 2.312 30 1 EEEF O=C1C[C@H](O)[C@H](O)[C@@H]2C1=CCCC21Oc2cccc3cccc(c23)O1 2356649601 QZXGWZACFKTEPU-JVPBZIDWSA-N 338.359 2.338 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@]2(C)C[C@@H]2C(=O)C=C(C)[C@@H](O)C1=O 2356671143 PCTOPLUNRDRIQE-SWQDORGXSA-N 344.407 2.296 30 1 EEEF C=C1C(=O)[C@@]23CC[C@H]4[C@](C)(CCC[C@@]4(C)C=O)[C@@H]2C[C@H](O)[C@H]1[C@@H]3O 2356672642 RNQLPXGROISTQX-IAOSKSRVSA-N 332.440 2.275 30 1 EEEF Cc1ccc(-n2c(N)c(C#N)c3c2C(=O)c2ncccc2C3=O)cc1 40420775 PLMAILCXOBVPFI-UHFFFAOYSA-N 328.331 2.410 30 1 EEEF C=C1C(=O)[C@]23[C@@H](CC[C@H]1[C@H]2O)[C@]1(C)C[C@@H](O)CC(C)(C)[C@H]1C[C@H]3O 238757823 XIGJIFFLTSZIKL-XJGNIKPNSA-N 334.456 2.067 30 1 EEEF CCNc1ncc2nc(CCc3ccccc3)c(=O)n(CCC#N)c2n1 4238626 MZTHCPHJPIHVBW-UHFFFAOYSA-N 348.410 2.317 30 1 EEEF Cc1ccc2c(n1)N(C)[C@@H](CO)CCN(Cc1cccc(C#N)c1)C2 2356295537 WITYMLYGFMEFLC-LJQANCHMSA-N 336.439 2.465 30 1 EEEF CC1=C(C(=O)O)C(=O)C[C@H]2CCC[C@@]3(C(=O)Nc4ccccc43)N12 2356516959 QQDWEMDBMCNRPU-ADLMAVQZSA-N 326.352 2.020 30 1 EEEF C=C(C)[C@H](O)Cc1c(OC)c2ccc(OC)c(OC)c2n(C)c1=O 14679261 NGOMVQJSMUMPNB-CYBMUJFWSA-N 333.384 2.044 30 1 EEEF biogenic NC(=O)/C(=C\c1ccc(/C=C/C(=O)NO)cc1)c1ccc(F)cc1 140643264 QSHKOYZBBMRZGY-BOHWWTNISA-N 326.327 2.370 30 1 EEEF O=C(NO)[C@H]1CCC[C@H]1S(=O)(=O)c1ccc(Cl)c(Cl)c1 1857586718 PAVNSONEORCDOC-GZMMTYOYSA-N 338.212 2.441 30 1 EEEF COc1cccc2c1O[C@@H]1C=C(OC[C@@]3(C)CO3)C=C(O)[C@@H]1C2=O 169368025 GLCNXGRTIKCJRG-VKJFTORMSA-N 330.336 2.400 30 1 EEEF C=CCNC(=S)N/N=C(\c1cccc([N+](=O)[O-])c1)c1ccccn1 28703773 YMSLWZQUSVQXCX-XDJHFCHBSA-N 341.396 2.392 30 1 EEEF O=C(CCC1=CCN(Cc2ccc(Br)cc2)C1=O)NO 36423072 RBDTUYJXXZIFKA-UHFFFAOYSA-N 339.189 2.003 30 1 EEEF C#CCn1nc(C)c2c(nc(C)n3nc(-c4ccccc4)cc23)c1=O 36476461 NHJWBSMROQXKRQ-UHFFFAOYSA-N 329.363 2.356 30 1 EEEF COC1=C[C@@]23CCN(C)[C@@H](Cc4cc(O)c(OC)cc42)[C@@H]3CC1=O 14636215 IXNZNQMODAROFN-NJSLBKSFSA-N 329.396 2.018 30 1 EEEF biogenic Cc1cccc(N/N=C2\CC[C@H](C)n3c2ncc(C(=O)O)c3=O)c1 40466751 WUHFIBQMXMWMIL-BTNWAMHGSA-N 326.356 2.421 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)C(C)=C[C@H]2OC(=O)C(=C)[C@H]12 1857637827 RYBHZNMPMHOBAR-PGSNGQOISA-N 344.363 2.164 30 1 EEEF O=S(=O)([C@@H]1O[C@H]1c1ccccc1)N1CCN(c2ccccc2)CC1 26291964 UPZFQDXXSQSJFN-ROUUACIJSA-N 344.436 2.236 30 1 EEEF CN(Cc1ccccc1)C(=O)/C=C/c1cc(Cl)cnc1N=C(N)N 13436530 HARQEJASRGXNTN-BQYQJAHWSA-N 343.818 2.312 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)[C@]1(C)CCC[C@](C)(C(=O)O)[C@H]1C[C@H]3O 40393668 ISUJIZPWBGOLMR-BTMJDVLPSA-N 348.439 2.161 30 1 EEEF C#CCCCC(=O)Nc1nc2nn(C)cc2c2nc(-c3ccco3)nn12 224289651 FUMIWYQFHWMBFT-UHFFFAOYSA-N 349.354 2.013 30 1 EEEF COC(=O)[C@H](C=O)[C@@H]1N[C@@H](C)Cc2ccc(F)c(Br)c21 587803836 CCYWOEOSTLKZON-HBSDOPKDSA-N 344.180 2.152 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@@]2(CCNC[C@H]2C#N)N1 587794325 MGFDYUSZRRNEOF-OSQNNJELSA-N 338.224 2.451 30 1 EEEF C=C1C(=O)[C@@]23[C@@H]([C@@H](O)C[C@@H]1[C@H]2O)[C@]1(C)CCCC(C)(C)[C@H]1C[C@H]3O 35032232 JHBXJYSJVIFEFY-FPARTEGVSA-N 334.456 2.067 30 1 EEEF N=C(N)N/N=C/c1cc([N+](=O)[O-])ccc1Sc1ccccc1CO 45195702 YXMQLRAQBWUKBW-QGMBQPNBSA-N 345.384 2.055 30 1 EEEF CO[C@H]1[C@H](/C(C)=N/OCc2ccccc2)[C@]2(CC[C@H]1OC(N)=O)CO2 13588334 QGWIAAHQFJYZGG-DLFRPCDNSA-N 348.399 2.237 30 1 EEEF CCNc1ncc2nc(-c3ccc(F)cc3)c(=O)n(CCC#N)c2n1 4238548 YFOKHUYMZVAYLA-UHFFFAOYSA-N 338.346 2.338 30 1 EEEF COc1ccc(NC(=S)N/N=C2\C(=O)N(C)c3ccccc32)cc1 7560647 WTMKZQPFCMHYEZ-CYVLTUHYSA-N 340.408 2.362 30 1 EEEF C[C@]12CC(=O)[C@@]3(F)[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@H]1C[C@@H](O)C2=O 2356756464 IASWIBHERBRGSC-RNHSOMGUSA-N 334.387 2.329 30 1 EEEF N#Cc1c(O)nc2nc(O)nc(O)c2c1-c1ccc(F)c(Cl)c1 1772590040 HVGBDQFMICGFEO-UHFFFAOYSA-N 332.678 2.473 30 1 EEEF N#C[C@@H]1CCCCN1C(=O)[C@@H](N)CCNCc1ccc(Cl)cc1 13561271 BVDDYIAHKIERDK-HOTGVXAUSA-N 334.851 2.052 30 1 EEEF CCOC1=CC(=O)/C(=C2\NNC=C2c2ccc(OC)c(OC)c2)C=C1 104028917 AHUORUIFHVJUKM-RGEXLXHISA-N 340.379 2.466 30 3 EEEF C#CCO[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1ccc(O)c(O)c1 1857647605 ABPXDXWODFWVEF-QZTJIDSGSA-N 328.320 2.204 30 1 EEEF N#Cc1ccc(C(=O)N2Cc3cnnn3-c3ccccc3[C@@H]2C#N)cc1 61942560 XGYLWYNKDWFNPN-SFHVURJKSA-N 340.346 2.360 30 3 EEEF C=C1C(=O)O[C@@H]2/C=C(/C)C(=O)/C=C/[C@](C)(O)C[C@@H](OCC(C)C)[C@@H]12 238746330 LUEQCEAVADXVIC-LLKXMLHGSA-N 334.412 2.352 30 1 EEEF COC(=O)[C@]1(C)CCC(=O)C(C)=C1C=CC(C)=C[C@H](O)C[C@H](C)O 2356377842 NGPTWMZMECMCMC-ZUEVXXBESA-N 336.428 2.479 30 1 EEEF O=C[C@@H]1CCCCN1C(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1 53242884 RCJMAACWTPHNIG-IRXDYDNUSA-N 344.411 2.368 30 1 EEEF C=C(CC[C@@H](O)C(C)(C)O)[C@H](O)COc1ccc2ccc(=O)oc2c1 14587285 GOOJJMAKBXRBIG-NVXWUHKLSA-N 348.395 2.001 30 1 EEEF biogenic CC1=CC(=O)C[C@H]2[C@@]1(C)C[C@H](O)[C@H]1C[C@@](C)([C@H](O)CO)CC[C@@]12C 238761387 OXXOSNYKIDCPQY-SXJNSPEGSA-N 336.472 2.459 30 1 EEEF COc1ccc(C2=C(C)NN/C2=C2\C=CC(=O)C=C2O)cc1OC 100496251 JKNIZTUPIAARQL-QGOAFFKASA-N 326.352 2.378 30 3 EEEF C#C[C@@H]1CN2CC[C@H]1C[C@@H]2CNC(=O)Nc1ccc(C(C)=O)cc1 2356641278 KRKGEQVUPUYJNG-UWWQBHOKSA-N 325.412 2.354 30 1 EEEF C[C@@H]1CCN(C(=O)CC#N)[C@@]12CCCN(c1ncnc3[nH]ccc13)C2 169699008 FDSLGXNJYBLDDV-FZKQIMNGSA-N 338.415 2.079 30 1 EEEF O=C(/C=C/c1cccn1Cc1cc(F)ccc1F)CC(=O)C(=O)O 103295934 JSBYVLSFHLMRGL-SNAWJCMRSA-N 333.290 2.441 30 1 EEEF C=C(C)C(=O)O[C@@H]1CCC(CO)=C2[C@@H]3OC(=O)C(=C)[C@H]3CC[C@]21C 2356470534 DXUUYKZZAJEBSQ-UMHPPVOVSA-N 332.396 2.455 30 1 EEEF Nc1ccc(-c2cc(C(=O)NCCCCCCC(=O)NO)no2)cc1 40880993 LPYYNHVPYNFJMU-UHFFFAOYSA-N 346.387 2.110 30 1 EEEF O=C(C[C@@H](S)C(F)(F)F)N[C@@H](Cc1ccc(F)cc1)C(=O)O 43066219 PGJZLTNQRTXDPB-VHSXEESVSA-N 339.310 2.188 30 1 EEEF C=C1COC(=O)[C@]12C[C@]1(C)[C@@H](C)CC[C@H](OC(=O)C(C)C)[C@@H]1[C@H]2O 144494431 DOYNORUEQQEQAA-ZUHYYECNSA-N 336.428 2.471 30 1 EEEF CC(C)=CCCc1ccc2c(c1)C(=O)C1=C(NCCS1(=O)=O)C2=O 34189801 WDWNYCNGMICAEA-UHFFFAOYSA-N 345.420 2.194 30 1 EEEF biogenic C=C(C)[C@H]1C[C@]2(O)[C@@H](C[C@@H]3C(=O)C(C(=O)C(C)C)=C(O)[C@@]32O)C1(C)C 1642676746 YQNMORSCDDSTCQ-CYWUSCJTSA-N 348.439 2.327 30 1 EEEF CCN(CC)CC/N=C(\NOC)c1cc(Cl)c(N)cc1OC 29339640 UEOPSCRGHLYAHM-UHFFFAOYSA-N 328.844 2.170 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(C)=O)C[C@]1(C)[C@@H](OC(C)=O)CCC(=C)[C@H]21 2356431880 IDVKLEJKBPWDKI-RFRLJHHNSA-N 348.395 2.324 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@@H](COC(C)=O)CCC=C(C(=O)OC)CC[C@H]12 2356493721 DRSUBRLQXQEHHE-NUEKZKHPSA-N 336.384 2.327 30 1 EEEF C=CCN1C(=O)N2C[C@@H](CC)N=C2c2[nH]c(-c3cc(C)nn3C)nc21 72110304 IDCILQLKRDAWDC-LLVKDONJSA-N 339.403 2.085 30 1 EEEF CC1(C)C(=O)c2ccc(C#N)cc2[C@@H](n2ccccc2=O)[C@@H]1OC=O 13832153 VGTAHIZZJBNXPY-AEFFLSMTSA-N 336.347 2.073 30 1 EEEF CCN1C(C)=C(C(=O)OC)[C@H](c2cccc(F)c2)N/C1=N\CCOC 15937429 IHKITIIRHZUGNU-INIZCTEOSA-N 349.406 2.241 30 3 EEEF CSCC[C@@H](NC(=O)[C@@H](CS)Cc1ccccc1)C(=O)O 26479174 HNZBQOSYCFLCAE-CHWSQXEVSA-N 327.471 2.098 30 1 EEEF C[C@H](/N=c1\c(O)c(O)\c1=N/CCc1ccc(C#N)cc1)C(C)(C)C 28227490 VMMSHUGXUNUKIS-FPIDZYJMSA-N 325.412 2.324 30 1 EEEF O=C1C[C@H](O)C2(Oc3cccc4cccc(c34)O2)[C@@H]2C1=CC=C[C@H]2O 2356719696 FKPPHRSYMWPOAW-XVGQJIODSA-N 336.343 2.114 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(OC[C@H](O)CO)cc1 587907117 DXYMDRFGMMTYKD-MRXNPFEDSA-N 332.783 2.480 30 1 EEEF N#Cc1ccc([C@@H]2N[C@H](C(=O)O)Cc3cccc(F)c32)c([N+](=O)[O-])c1 962891732 CNNZXQYEIVSGGQ-BBRMVZONSA-N 341.298 2.294 30 1 EEEF CN1c2ccccc2C(C#N)(C(=O)NCCC(=O)O)c2ccccc21 2047786 FRBAOMHMZCGBOJ-UHFFFAOYSA-N 335.363 2.168 30 1 EEEF in-vivo CC(C)(O)C1=CC2=C[C@H](O)[C@H]3[C@@](C)(CCC[C@@]3(C)C(=O)O)[C@@H]2CC1=O 2356510902 QMSWKASVXHXIKB-NGCRYJGJSA-N 348.439 2.471 30 1 EEEF C=C1CC[C@H]2C[C@H](O)C3=C(C(=O)[C@@H](C(C)=C[C@@H](O)C1)[C@H]3O)C2(C)C 2356605255 YZCJZJQRTRSJHJ-QHLBIMPKSA-N 332.440 2.297 30 1 EEEF C[C@@H]1CC/C(=N\Nc2ccc(F)cc2)c2ncc(C(=O)O)c(=O)n21 38153702 ZXPBEUXFWUEPIP-FLNUOUKISA-N 330.319 2.252 30 1 EEEF N#Cc1ccc(-c2csc(NCC(=O)NC[C@@H]3CCCO3)n2)cc1 82193680 PAPZSCMQLGRBLL-AWEZNQCLSA-N 342.424 2.389 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cc4cn[nH]c4cc3[nH]2)C1=O 587038474 JEGSZZBXJDPIAZ-LBPRGKRZSA-N 327.369 2.232 30 1 EEEF Cn1cc2c3c1C(=O)C(N/C=C/c1ccc(O)cc1)=CC3=[N+](C)CC2 14585420 YDNPKKWKDVMZTR-UHFFFAOYSA-O 334.399 2.059 30 1 EEEF N#CCC(=O)N1CCCC[C@@]12CCCN(c1ncnc3[nH]ccc13)C2 169699024 DHDGEXQRDYQYKP-SFHVURJKSA-N 338.415 2.223 30 1 EEEF C=C1C(=O)[C@@]23C[C@@H]1C[C@@H](O)[C@H]2[C@@]1(CCCC(C)(C)[C@H]1C=O)COC3=O 238765906 KIJKAQHLSSAHOL-JBUBPAQZSA-N 346.423 2.067 30 1 EEEF C=C1C(=O)[C@@]23CC(=O)[C@@H]4C(C)(C)CCC[C@]4(C)[C@@H]2[C@@H](O)C[C@H]1[C@@H]3O 2356397833 JLKBHAAAVQFJPZ-RDZPFAKASA-N 332.440 2.275 30 1 EEEF CC1=CCCC[C@@H]2O[C@]23CC(=O)O[C@H]3c2c(O)ccc(O)c2[C@H]1O 2356403623 PHCAOFZRCKAKBR-GYIHYUDTSA-N 332.352 2.387 30 1 EEEF CC(C)(O)C1=CC2=C[C@H](O)[C@H]3[C@@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1=O 2356510901 QMSWKASVXHXIKB-ILYSMZKRSA-N 348.439 2.471 30 1 EEEF CC(=O)C1=CC[C@@H]2[C@@H]3CC[C@H]4[C@H](O)[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@@]12C 2356512833 GKCFQKGBOYKBGP-KSVKSMJFSA-N 348.483 2.457 30 1 EEEF C=C(C)[C@@H]1CC(=O)[C@H]2[C@H](C1)[C@H](C(=O)O)[C@@H]1C=C(C(C)=O)[C@@H]2C(=O)C1 2356807589 XWUMXWKSQYTAOG-PMJCBJDISA-N 330.380 2.209 30 1 EEEF Cn1c(CNCc2ccccc2)nc2cc(/C=C/C(=O)NO)ccc21 139247725 OEDVYFRGPGFJIZ-CSKARUKUSA-N 336.395 2.382 30 1 EEEF C=CC(C)(C)[C@]1(C)OC=C[C@@]1(C)CC(=O)[C@@H](O)[C@H](OC)[C@H](C)O 6487501 BSIAHHIPMGVHJM-OZNHZTKRSA-N 326.433 2.223 30 1 EEEF in-vitro C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@]2(C)C[C@H]2C(=O)C=C(C)C(=O)[C@@H]1O 2356581520 YLQIJBIUALFEAE-PTCHYSAWSA-N 344.407 2.296 30 1 EEEF O=C1C=C(N2CCN(c3ccccc3)CC2)C(=O)c2c(O)cccc21 71295116 ADMCRKZCGGZRLA-UHFFFAOYSA-N 334.375 2.477 30 1 EEEF NNc1ncccc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587880667 WYIRRXOOUVBWPP-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF CC(=O)[C@H](CCC#N)[C@@]1(C)N[C@H](C(=O)O)Cc2ccc(O)c(C)c21 963549979 JPUZFQIOUALAPC-SUNYJGFJSA-N 330.384 2.024 30 1 EEEF C=CCCCSC[C@H](NC(=O)c1cc(O)cc(O)c1)C(=O)OC 1857540807 YXTRWRQINHZJTQ-AWEZNQCLSA-N 339.413 2.069 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@@]12C[C@H](O)C[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 104365798 HHDWSDSMWJQURA-JUQFQULXSA-N 332.396 2.136 30 1 EEEF in-man CNC1=CC(=O)c2c(OC)cc(C[C@@H]3CCOC(C)(C)O3)cc2C1=O 28342771 DTZWTWKQXGBKJU-LBPRGKRZSA-N 345.395 2.262 30 1 EEEF C[C@H](O)[C@H]1C(O)=C(C(=O)[C@@H]2[C@H](C)C=C[C@@H]3CCCC[C@H]32)C(=O)N1C 102967705 NOYBJWXGAYWITN-HHULCRSBSA-N 333.428 2.218 30 1 EEEF C=C[C@@]12CCN3Cc4c([nH]c5ccccc45)[C@@](C(=O)OC)(CO1)[C@H]2C3 2356726295 JWWNAZIXKUAPOM-FFZOFVMBSA-N 338.407 2.369 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)C(C)=C[C@@H]2OC(=O)C(=C)[C@H]21 2356740551 RYBHZNMPMHOBAR-XWESNNAXSA-N 344.363 2.164 30 1 EEEF N#CCNC(=O)[C@H](Cc1ccsc1)NC(=O)OCc1ccccc1 82064909 HJTLCMDZENYQON-HNNXBMFYSA-N 343.408 2.225 30 1 EEEF O=C(NO)c1ccc(N[C@@H]2CCN(Cc3ccccc3)C2=O)cc1 143726659 ALXBWSHZBQTFJJ-MRXNPFEDSA-N 325.368 2.019 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cnc(O[C@H]2CCNC2)nc1 587908076 LACGUCSPFCOQQH-HNNXBMFYSA-N 329.787 2.279 30 1 EEEF N/C(=N\S(=O)(=O)c1ccccc1)NCCc1ccc(Cl)cc1 13116726 LGYVDNDAOBWDFY-UHFFFAOYSA-N 337.832 2.176 30 3 EEEF C=C1C[C@H]2O[C@H]2[C@@](C)(O)CC[C@@H]2/C(=C/C=C/C(C)(C)O)C(=O)OC[C@@H]12 15119069 GUGYUSGXSKYCJD-VZDDEZTBSA-N 348.439 2.288 30 1 EEEF Cc1ccc(-n2c(O)c(/C=N/n3cnnc3)c3ccccc3c2=O)cc1 169689265 JWHQDOYFXRUZGM-LSHDLFTRSA-N 345.362 2.478 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@H]2C[C@@H](CC(C)=C[C@@H]3OC(=O)C(=C)[C@@H]31)OC2=O 2356536254 HOZUUHWHCWNMPV-LJIZCISZSA-N 346.379 2.244 30 1 EEEF CCCCCCCn1c(Br)nc2c(=O)[nH]c(N)nc21 43352722 BPPGHJVMKXMBNS-UHFFFAOYSA-N 328.214 2.435 30 1 EEEF COCC(=O)N1[C@H](CO)[C@@H](c2ccc(C3=CCCCC3)cc2)[C@@H]1C#N 95896165 NSZKTJJQZYFHQH-NSHGMRRFSA-N 340.423 2.469 30 1 EEEF O=C1Nc2ccc([N+](=O)[O-])cc2/C1=C1/Nc2ccc(O)cc2/C1=N\O 1857557807 MDIDMHALYFMVFV-BGBJRWHRSA-N 338.279 2.268 30 1 EEEF CC(=O)Nc1ccc(C(=O)NC2=CC(=O)C(=O)c3ccccc32)cc1 103193275 ZEDIHMXSKFVJJF-UHFFFAOYSA-N 334.331 2.181 30 1 EEEF CC(C)c1ccc(CC(=O)N2CC[C@]2(C)C(=O)NCCC#N)cc1 61929487 FYCDHWLTBVACJW-LJQANCHMSA-N 327.428 2.373 30 3 EEEF Cc1cc2c(cc1O)[C@]1(Cc3ccccc3[C@H]1C#N)N[C@H](C(=O)O)C2 963553103 RLECXGGYOMJNLF-UWVAXJGDSA-N 334.375 2.358 30 1 EEEF N#Cc1ccc([C@@H](O)C2=C3C=C[C@@H]4C[C@@]3(OC2=O)[C@H]2CCCCN42)cc1 1772599230 QFVVQFMCFLHDCD-WELBPKCISA-N 348.402 2.380 30 1 EEEF COC(=O)C[C@@]1([C@H](O)/C=C(\C)CCC=C(C)C)C[C@H](O)C=CC1=O 28566905 LRHXPNHCPURRDF-OROLVADBSA-N 336.428 2.479 30 1 EEEF CCCC[C@H](O)C#C[C@@H](O)C=CCCCCC[C@@H](O)CC(=O)O 2356516007 IRDUBXGVWQSMKQ-YESZJQIVSA-N 326.433 2.244 30 1 EEEF NC(N)=N/N=C/c1c(-c2ccc(F)cc2)nc2sc(Cl)cn12 73140737 SRPXUHSRAGHEKA-BLLMUTORSA-N 336.783 2.463 30 1 EEEF N#CCNC(=O)[C@H](Cc1ccccc1Cl)NC(=O)c1ccccc1 82064584 NUODGZIURLFRMZ-INIZCTEOSA-N 341.798 2.321 30 1 EEEF C=CCN(C[C@H]1Oc2cc(OC)cc3c2C(=O)[C@H]1C3)C(=O)OCC 587431042 YEUBKLJITZIBGN-DZGCQCFKSA-N 331.368 2.456 30 1 EEEF Cn1c(=O)ccc2cc(NS(=O)(=O)c3ccc(C#N)cc3)ccc21 1772640734 VXXXPCKZPJGNGK-UHFFFAOYSA-N 339.376 2.211 30 1 EEEF CCN1C(=O)N(CC)[C@H]2[C@@H]1NC(=S)N2/N=C/C=C/c1ccccc1 1857645995 ZKFBHJXHPXBJBI-SZTJSXAJSA-N 343.456 2.305 30 1 EEEF Cc1nc2n(c(=O)c1C(=O)O)[C@@H](C)CC/C2=N/Nc1ccccc1 101165691 PTMLSROVUJDKCJ-GKZQNMRQSA-N 326.356 2.421 30 1 EEEF CN1C[C@]23C[C@H](O)[C@H]4[C@@H](CCC5=CC(=O)C=C[C@@]54C)[C@H]2CC[C@H]3C1=O 2356501572 GDWBXDLUQZIGKG-OYMNSCGBSA-N 341.451 2.333 30 1 EEEF C=C1C[C@@]23C[C@H]1CC(=O)[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1[C@H](O)[C@@H]3O 2356684936 ZAPSETLSDTWUQE-BMJCULAASA-N 348.439 2.161 30 1 EEEF Cn1cc(N2C(=O)CC[C@@H]3[C@@H]2CCN3Cc2cccc(C#N)c2)cn1 299841870 APCRCLYBBAIEJT-MSOLQXFVSA-N 335.411 2.062 30 1 EEEF CCOC(=O)/C=C(/C)Nc1nc2c(c(C(=O)OC)c1C#N)CCCC2 5924130 XWIFDPIQTOKPPN-LUAWRHEFSA-N 343.383 2.497 30 1 EEEF C=CCc1cc(CNC(=O)CC)ccc1OC[C@H](O)CNC(C)C 169335426 QFFLOJZKMQLTQU-QGZVFWFLSA-N 334.460 2.179 30 1 EEEF C[C@H](O)[C@@H]1C(=O)C(=C(O)[C@@H]2[C@H](C)C=C[C@H]3CCCC[C@H]32)C(=O)N1C 2356417407 ACUUAFHILDALFB-NVWMEEMDSA-N 333.428 2.218 30 1 EEEF C=C[C@](C)(O)C=C[C@@H]1[C@](C)(O)[C@H](O)[C@H](O)[C@@H]2C(C)(C)CCC[C@@]12C 2356783861 MHBIPUOMMSRZKQ-PLOHHTLVSA-N 338.488 2.415 30 1 EEEF O=C(NO)[C@@H]1CCCN1S(=O)(=O)c1ccc(-c2ccccc2)cc1 73296049 XYGPNXMBVTVKDQ-INIZCTEOSA-N 346.408 2.012 30 1 EEEF CCCCCCCCC[C@H]1C[C@@H](O)[C@H](O)/C=C\[C@H](O)CC(=O)O1 169727818 VKFBQLMPTJTKBZ-PONYRBOISA-N 328.449 2.472 30 1 EEEF COc1ccc2c3c1O[C@H]1C=C(C(C)=O)C[C@H]4[C@@H](C2)N(C)CC[C@@]314 101770812 FKNWJBZMTKZQMB-MQJTVSLUSA-N 325.408 2.490 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)C(=O)C[C@]3(C)[C@@]1(C)[C@@]21CO1 2356501724 LJWZOKOFCBPNAG-QXRKFJRXSA-N 332.396 2.346 30 1 EEEF O=C(CC1=NCCc2cc3c(cc21)OCCCO3)C1=COCCO1 4090276 WKFQRRUIWUINIJ-UHFFFAOYSA-N 329.352 2.041 30 1 EEEF biogenic O=C(CCC1=CCN(Cc2cccc(C(F)(F)F)c2)C1=O)NO 84654924 OKWVWKAZWQAOKZ-UHFFFAOYSA-N 328.290 2.260 30 1 EEEF NNc1ccc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cn1 587887545 RDXZRNAAEXQCAW-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF COC(=O)/C=C/c1ccc(CNC2=CC(=O)c3cccnc3C2=O)cc1 1857749070 YYDNWQYQAUCOSM-CMDGGOBGSA-N 348.358 2.321 30 1 EEEF O=C(/C=C/c1ccc2c(c1)OCO2)Cc1nc2ccccc2[nH]c1=O 1864428 IGIYSIDROLFIRI-FNORWQNLSA-N 334.331 2.477 30 1 EEEF C=C1C[C@@]23C[C@@H]1[C@@H](O)C[C@@H]2[C@@]12CCC[C@](C)(C(=O)OC1)[C@H]2[C@@H]3C(=O)O 104359181 ZCRLGANQNRMURE-MVPLPQMZSA-N 346.423 2.384 30 1 EEEF in-man C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@@H](C(=O)O)[C@@H]1[C@]2(C)CCC[C@]13COC2=O 104371547 MJFVMFNFTCKAEV-ZQYFAWOVSA-N 346.423 2.384 30 1 EEEF in-man C=C1C2=C(O)[C@@H](O)[C@H](C)C=C2C(=O)c2cc(OC)c(O)c(OC)c21 2356329855 NCHXGWSVVROJJA-UOWDBTKRSA-N 330.336 2.368 30 1 EEEF COc1cccc2c1O[C@@H]1C=C(OC[C@]3(C)CO3)C=C(O)[C@H]1C2=O 64475220 GLCNXGRTIKCJRG-IIDMSEBBSA-N 330.336 2.400 30 1 EEEF CC(C)[C@@]1(O)C=C2C(=O)C[C@@H]3[C@@](C)(CO)[C@H](O)CC[C@@]3(C)[C@@H]2CC1 473093346 TVHWXCUVXSEILO-UFGPKIGGSA-N 336.472 2.459 30 1 EEEF COC(=O)[C@H](C=O)[C@@H]1N[C@H](C)Cc2ccc(F)c(Br)c21 587803867 CCYWOEOSTLKZON-JPVBRFOXSA-N 344.180 2.152 30 1 EEEF C[C@@H]1NC=CC(=O)[C@]12N[C@H](C)Cc1ccc(F)c(Br)c12 587799521 XROGJGIIBPMHKL-CEFVDNRUSA-N 339.208 2.392 30 1 EEEF COc1cccc(C[C@@H](CS)C(=O)Nc2c[nH]c(C(=O)O)c2)c1 19572 XRMVSIGVJPNKLV-NSHDSACASA-N 334.397 2.449 30 1 EEEF C=C1C2=C(O)[C@@H](O)[C@@H](C)C=C2C(=O)c2cc(O)c(OC)c(OC)c21 2356329703 KMJOSWUIOOZDTP-WJWGPLDTSA-N 330.336 2.368 30 1 EEEF C=C1[C@H](O)[C@]23CC(=O)[C@@H]4C(C)(C)[C@@H](O)CC[C@@]4(C)[C@H]2[C@@H](O)C[C@H]1C3 2356406448 WSZHSVSVZWABOB-VDIZICOCSA-N 334.456 2.067 30 1 EEEF C=CCCN1CCN(CC(=O)[C@](O)(c2ccccc2)C2CCC2)CC1 22940350 XYJZEMYDBLYKMK-NRFANRHFSA-N 342.483 2.437 30 1 EEEF C=C1[C@H]2C(=O)C[C@H]3[C@](CC[C@H]4C(C)(C)[C@@H](O)CC[C@]43C)([C@@H]1O)[C@@H]2O 2356522497 JGAWMQVJTGKMKT-PYBRPDLESA-N 334.456 2.067 30 1 EEEF C=C1[C@@H](C[C@H](O)[C@H]2CC(=O)NC2=O)[C@@]2(C)CCCC(C)(C)[C@H]2C[C@H]1O 2356380056 PPQGMYUYEYHPEL-HLROQWKMSA-N 349.471 2.170 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@H]1CC[C@H]2[C@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100778345 MBNDVMTZEKAWKP-OUYFYLLSSA-N 332.396 2.136 30 1 EEEF endogenous,in-man N#CCNC(=O)[C@H](CC1=CCCC1)NC(=O)OCc1ccccc1 82064862 UBZZYVLNRSNGDG-INIZCTEOSA-N 327.384 2.422 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@H]2C(=C)C[C@H](O)[C@@H]3[C@@H](C)C(=O)O[C@@H]3[C@H]2C1=C 238771819 ZNXKZMIVEDDWGE-LKCSHLFESA-N 332.396 2.165 30 1 EEEF COc1cc(O)c2c(c1O)OCC(=Cc1ccc(O)c(O)c1)C2=O 2356674199 ZCFXRZACTOEVGD-UHFFFAOYSA-N 330.292 2.176 30 1 EEEF CO/N=C/c1c(N)ncnc1Oc1ccc(NC(C)=O)cc1Cl 66079024 WBSFTWXRWKSZMN-KPSZGOFPSA-N 335.751 2.443 30 1 EEEF COc1cc(C(=O)C#Cc2ccc(S(C)(=O)=O)cc2)ccc1O 13683385 JTZACODMRDSWHQ-UHFFFAOYSA-N 330.361 2.039 30 1 EEEF CC1=C(C)C(=O)[C@@](C)(C2=C(O)[C@@H]([C@H](O)c3ccccc3)NC2=O)C1 154962591 CRAKOWUCMGTDDN-SPYBWZPUSA-N 327.380 2.346 30 1 EEEF C=C1C(=O)[C@]23[C@@H](O)[C@@H]1[C@H](O)C[C@H]2[C@@]1(C)CCCC(C)(C)[C@H]1C[C@H]3O 2356575635 UWJKFPFMTSZKRY-MQDQQGSHSA-N 334.456 2.067 30 1 EEEF CC(C)O[C@@H]1Oc2ccc(O)c3c2[C@@]1(C)[C@@H]1C(=O)C=C(CO)C1=C3 2356722741 ORBWSHDOOZYCPR-QXAKKESOSA-N 328.364 2.308 30 1 EEEF C=C1C[C@@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)O 257389678 BSBICXIQCTXPMN-ZDCKYFFZSA-N 330.380 2.056 30 1 EEEF endogenous,in-man COc1cc(C=O)c(Cl)cc1NC(=O)Nc1cnc(C#N)cn1 14956146 YTIZDTKSGSSUMG-UHFFFAOYSA-N 331.719 2.467 30 1 EEEF CC(=O)O[C@H](C)[C@H](C=C1C=C(C)C2=NCC[C@H]3O[C@@]123)OC(=O)C(C)C 2356476655 MRUZXUQKRAPYFF-BMHLXIAXSA-N 347.411 2.374 30 1 EEEF C[C@H](/N=c1/c(NC(=O)c2ccc(C#N)cc2)c(O)c1=O)C(C)(C)C 101179020 RYODQKBZBBAMKI-GKZQNMRQSA-N 325.368 2.087 30 1 EEEF C[C@@H]1C[C@]23C(=O)[C@H](C)C[C@@H]4C(C)(C)[C@@]45O[C@@](C)(C=C2C1=O)[C@H](O)[C@@H]35 2356522875 XKHKWWYWWNXZDZ-QPDUMXHESA-N 330.424 2.291 30 1 EEEF C[C@@H]1CC(=O)C2=C(CC[C@]34O[C@@]23C(=O)c2cccc(O)c2[C@H]4O)C1 2356796812 NNMGLXNJGVNRCH-PRGXFDKPSA-N 326.348 2.219 30 1 EEEF C=C(C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)/C(C)=C\[C@H]2OC(=O)C(=C)[C@H]12 34268477 RYBHZNMPMHOBAR-MFRWKCHVSA-N 344.363 2.164 30 1 EEEF biogenic COc1cccc2c1[C@H](O)[C@]1(O)CCC3=C(C(=O)C[C@H](C)C3)[C@H]1[C@@H]2O 13366639 GOUAMPBBOSYLQB-DXVDOYHPSA-N 344.407 2.212 30 1 EEEF biogenic C[C@H](C=O)NC(=O)[C@@H](Cc1ccccc1)NC(=O)Nc1ccccc1 82061186 IOBSHJKFMZWHDJ-RHSMWYFYSA-N 339.395 2.123 30 1 EEEF COc1ccc2c(c1OC)C(=O)C1=C(O[C@@H](C(C)=C(C)C)[C@H]1O)C2=O 40864256 HMDJOWAVRUNTOD-IRXDYDNUSA-N 344.363 2.453 30 1 EEEF O=C1/C(=C/c2ccc(O)c(O)c2)CNC/C1=C\c1ccc(O)c(O)c1 13781296 XXLSPXONMWOWKM-ACFHMISVSA-N 339.347 2.148 30 1 EEEF Cc1[nH]cnc1CSCC/N=C(\N)SCCCc1c[nH]cn1 29213087 PCGFXFCITUCLRK-UHFFFAOYSA-N 338.506 2.355 30 1 EEEF CC[C@H]1CN(C(=O)c2cccc(C)c2C)CCN1C[C@@H](N)CS 22938332 QHEJXFYXXWVDRL-CVEARBPZSA-N 335.517 2.097 30 1 EEEF S=C(N/N=C\c1ccccc1)N1CCN(c2ccccn2)CC1 40764075 GQZQMXBXOVEUPJ-RGEXLXHISA-N 325.441 2.112 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]12CO[C@@H]4OC[C@@](C)(CC[C@@H]1OC3=O)[C@@H]42 95884396 QRZAIOQXVJRCBS-BQKKUSDGSA-N 344.407 2.243 30 1 EEEF C=C1C(=O)[C@]23CC[C@H]4[C@@](C)(C(=O)O)CCC(=O)[C@]4(C)C2=C[C@H](O)[C@H]1C3 238782903 WEOFLALXTGKCTB-YLCPWTQVSA-N 344.407 2.289 30 1 EEEF O=Cc1n[nH]cc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587880705 YVVSCBFKYMZYCU-UHFFFAOYSA-N 336.178 2.239 30 1 EEEF C[C@]12C[C@H](O)[C@@H]3[C@@H]4CCC(=O)C=C4CC[C@@H]3[C@H]1CC[C@@H]2C(=O)CO 2356672855 ACHGZZCRIIPHAX-FRVYXANDSA-N 332.440 2.277 30 1 EEEF COc1ccc2c(c1)c(CCNC(C)=O)c1sc(CC#N)nn12 36433466 WBSMMFFFARHJCY-UHFFFAOYSA-N 328.397 2.302 30 1 EEEF CCn1ncc(/C=N/NS(=O)(=O)c2ccc(Cl)cc2)c1C 355970 LGDGAMCAHXRCNG-OVCLIPMQSA-N 326.809 2.177 30 3 EEEF CC1=C[C@H](OC=C2C(=O)O[C@H]3C4=C(C[C@H]23)C(=O)CCC4(C)C)OC1=O 2356498064 HZXNZCJZYALICU-QSGSBWRWSA-N 344.363 2.347 30 1 EEEF COc1cc2c(cc1OC)[C@]13C[C@@H](OC)C=C[C@@]14O[C@H]4CN3CCC2 31719784 JCKPCZAYDZJZIL-GAZPGATBSA-N 343.423 2.273 30 1 EEEF biogenic,in-vitro CN1C(=N)N[C@](c2cccc(-c3cncc(C#N)c3)c2)(C2CC2)C1=O 84616428 YNHHKAKPUCUXLP-IBGZPJMESA-N 331.379 2.222 30 1 EEEF C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)[C@]1(C)CC[C@H](O)C(C)(C)[C@H]1C[C@H]3O 84641199 BAXVJERFBZODKZ-BIGDWJEQSA-N 334.456 2.067 30 1 EEEF biogenic,in-vitro Cc1ccc(-c2nn(-c3ccc(S(N)(=O)=O)cc3)cc2C#N)cc1 59151504 JINQUNXXILDVNV-UHFFFAOYSA-N 338.392 2.367 30 1 EEEF CC/N=C(\NCC)N/N=C/c1ccc(-c2cn3ccccc3[n+]2C)cc1 26822500 RTRQHCFQNBUAPU-OEAKJJBVSA-N 349.462 2.340 30 1 EEEF CC(=O)O[C@@H](C)[C@H](/C=C1\C=C(C)C2=NCC[C@H]3O[C@]213)OC(=O)C(C)C 238733975 MRUZXUQKRAPYFF-MWNMZOINSA-N 347.411 2.374 30 1 EEEF C#CCNC(=O)C1=C[C@H](c2ccccc2)[C@@H](CCCO)[C@H](OCC)O1 13656465 ZXKBQCCQOALWOU-MBOZVWFJSA-N 343.423 2.185 30 3 EEEF CC=CC(=O)O[C@@H]1[C@H]2O[C@@H]3C=C(C)CC[C@]3(C)[C@@](C)([C@H]1O)[C@]21CO1 2356845521 OFRDWLCMCXXLSX-WZWMFVLASA-N 334.412 2.138 30 1 EEEF O=C(N[C@H](Cc1c[nH]c2ccccc12)C(=O)NO)c1ccc(F)cc1 96269526 ZGGUVSSJHHKVGJ-MRXNPFEDSA-N 341.342 2.154 30 1 EEEF C[C@H](O)[C@]1(c2ccc(C#N)cc2)NC[C@H]2CC(=O)N(C)c3cccc1c32 963017395 CMVJTQXTIAWOOQ-QDUSTFBWSA-N 347.418 2.236 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@]3(C)C[C@@H](OCC(C)C)[C@H]12 2356671226 RDYCVUNQBCWGOT-FEFVAOQBSA-N 336.428 2.384 30 1 EEEF O=C(CS)N[C@@H](Cc1ccc(OCc2ccccc2)cc1)C(=O)O 653717101 NQSSUVWWRFMHIE-INIZCTEOSA-N 345.420 2.307 30 1 EEEF N#Cc1cccc([C@@H](O)C2=C3C=C[C@@H]4C[C@@]3(OC2=O)[C@H]2CCCCN42)c1 1772654689 JGRCTRMFLQFCCH-WELBPKCISA-N 348.402 2.380 30 1 EEEF CO/N=C(/CCN1CCN(c2ccccn2)CC1)c1cccnc1 36216736 XSMJOXYQXGOXQV-FXBPSFAMSA-N 325.416 2.039 30 1 EEEF CC(C)(C)OC(=O)N1CC[C@@]2(NCCc3ccc(O)cc32)[C@H](C=O)C1 963351243 FUNVDCFOCWPYPX-IFXJQAMLSA-N 346.427 2.189 30 1 EEEF Cc1ccc(NS(=O)(=O)c2ccc(/C=C/C(=O)NO)cc2)cc1 13493384 DQBCBVSLJCVWJK-IZZDOVSWSA-N 332.381 2.314 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)C3=CC(=O)[C@@](C)(C[C@H](OC(=O)C(C)C)[C@@H]12)O3 1857535960 WQQJRSDFQHYDRU-PGSNGQOISA-N 346.379 2.244 30 1 EEEF C=C[C@]1(C)C=C2C(=CC1)[C@]13C[C@@H]1CC[C@]1(C)C(=O)O[C@](O)([C@@H]2O)[C@@H]13 2356396829 XHJCBVNMOHCTOP-RJFLNJOFSA-N 328.408 2.478 30 1 EEEF CC[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1 27619124 XPWASUHKKNPCDI-HOTGVXAUSA-N 334.416 2.421 30 1 EEEF CN(C)c1ccc(-c2cn(CCCCCCC(=O)NO)nn2)cc1 40409368 VCNZWJWQPRCWAL-UHFFFAOYSA-N 331.420 2.467 30 1 EEEF COc1cc2c(cc1OCCO)-c1[nH]nc(-c3ccc(C#N)nc3)c1C2 28951614 YPRVFEOFBUWCDZ-UHFFFAOYSA-N 348.362 2.294 30 1 EEEF CC(C)[C@]1(O)C=C2C(=O)C[C@@H]3C(C)(C)[C@H](O)CC[C@]3(C)[C@H]2C[C@@H]1O 2356336807 NHJLCDALTNPYBE-ZVQJROQZSA-N 336.472 2.457 30 1 EEEF CC(C)CNc1ccc2c(n1)C(=O)N([C@H](C)/C(O)=N/CCN(C)C)C2 82081752 BSBCXWQVZGIHCR-CYBMUJFWSA-N 347.463 2.012 30 3 EEEF C=C[C@@]1(C)C[C@@H](OC(=O)C(=C)CO)[C@@H]2[C@@H](OC(=O)[C@@H]2C)[C@@H]1C(=C)C 238743333 BQAVYYQJSBGQAO-ZZXBLFKASA-N 334.412 2.413 30 1 EEEF CCOC1=CC(=O)/C(=C2\NC(N)=NC=C2c2ccccc2OC)C=C1 100608838 NYDQVRGZSXUZFW-JXAWBTAJSA-N 337.379 2.267 30 3 EEEF C=CC[C@]12CC(=O)[C@H](O)[C@H]([C@@H]1O)[C@H](c1ccc3c(c1)OCO3)[C@@H]2C 2356536938 FBPLISOOTGTZGY-NGPWKISCSA-N 330.380 2.022 30 1 EEEF O=C1C[C@H](O)C2(Oc3cccc4cccc(c34)O2)[C@@H]2C1=CC=C[C@@H]2O 2356719695 FKPPHRSYMWPOAW-SOVGHPHASA-N 336.343 2.114 30 1 EEEF C[C@@H]1CC=CC(=O)CCCC(=O)Cc2cc(O)cc(O)c2C(=O)O1 1911573933 IMKPMBIEDVFFMM-LLVKDONJSA-N 332.352 2.454 30 1 EEEF Cc1cc(C#N)ncc1-c1ccc2c(c1)OC[C@H]1[C@H](CO)OC(=O)N21 95583408 XHILZVYEWCNOPA-RDJZCZTQSA-N 337.335 2.007 30 1 EEEF CCN(CC)CCNc1c(C#N)n(O)c2cc(Cl)ccc2[n+]1=O 377576689 VRYAIXPZBFSBIS-UHFFFAOYSA-N 336.803 2.072 30 1 EEEF O=C(CCCCCC(=O)NCc1ccc2cc(F)ccc2n1)NO 473087945 GUFAPZMEKCRUDE-UHFFFAOYSA-N 333.363 2.446 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc2c(c1)S(=O)(=O)NC2=O 587918845 LEJVQSWOSTVTSA-UHFFFAOYSA-N 347.779 2.181 30 1 EEEF N#C[C@H]1C(=N)NC(=S)[C@@H](C(N)=O)[C@@H]1c1ccc(Cl)cc1Cl 169689876 LCFKVZGBMDLSCI-SZEHBUNVSA-N 341.223 2.226 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@H]2[C@@]12CCC[C@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100776675 ZCRLGANQNRMURE-KMCKIRDCSA-N 346.423 2.384 30 1 EEEF endogenous,in-man N=C(N)N/N=C\c1cc([N+](=O)[O-])ccc1Sc1ccccc1CO 64608279 YXMQLRAQBWUKBW-LSCVHKIXSA-N 345.384 2.055 30 1 EEEF COc1ccc2c(c1)C[C@@H](c1nc3nc(C#N)c(C#N)nc3[nH]1)CC2 587945516 FWULXQJLTZZFPT-NSHDSACASA-N 330.351 2.377 30 1 EEEF O=CC(C=O)c1ccc(-c2nc3ccc(CO)cc3[nH]2)cc1[N+](=O)[O-] 587261678 FXDJBBVGRPMILZ-UHFFFAOYSA-N 339.307 2.112 30 1 EEEF Cc1cc(C)c([C@@H]2CN[C@H](C(=O)N3CCC[C@H]3C#N)C2)c(C)c1O 28714264 ZSEOLJMSNYIJFY-JYJNAYRXSA-N 327.428 2.278 30 1 EEEF C=C1C2=C(C(=O)N1OC)[C@H](O)[C@@](C)(O)[C@H](CCCCCCC)O2 2356342526 FLJXRCWDXADIBL-NUTKFTJISA-N 325.405 2.029 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)C(C)=C[C@H]2OC(=O)C(=C)[C@H]21 2356740549 RYBHZNMPMHOBAR-NPNMTCQASA-N 344.363 2.164 30 1 EEEF CN(c1ccccc1)S(=O)(=O)c1cccc(/C=C/C(=O)NO)c1 34280077 XDGZMSJUKYHOFR-ZHACJKMWSA-N 332.381 2.030 30 1 EEEF CCCCCCCCCCCNC(=O)CC(=O)N[C@H]1CCOC1=O 71316157 KKDXKPWXEHDJKB-HNNXBMFYSA-N 340.464 2.455 30 1 EEEF Cc1occ2c1CC[C@H]1[C@H]2C[C@@H]2O[C@@]23[C@H](O)[C@@]2(C(C)C)O[C@H]2[C@@H]2O[C@]213 71341445 QEVWRUKRUJZSCD-UATFJJIGSA-N 344.407 2.081 30 1 EEEF CCN(CC)C[C@H](O)CO/N=C(\Cl)c1nc2ccccc2o1 43025779 QHKFDFZJKZZLAR-WMEZLHQCSA-N 325.796 2.448 30 1 EEEF C[C@H]1CCCC[C@H]1Oc1nc(N)c2c(=O)ccn(CCC#N)c2n1 84653769 WRVHRTYWBDSUGJ-WCQYABFASA-N 327.388 2.245 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@]2(CCNC[C@@H]2C#N)N1 587792170 GZQSQLGJENUGLF-BPYAMOTFSA-N 338.224 2.451 30 1 EEEF O=C1N[C@@H](C(=O)NO)C[C@H]1c1ccc(Oc2ccc(F)cc2)cc1 13808789 TUIHSDQRXNNCLL-LSDHHAIUSA-N 330.315 2.096 30 1 EEEF CCOc1cc(C)nc(N[C@H]2CCc3ccc(C(=O)NO)cc3C2)n1 113846133 WBWFGMCELMVENS-HNNXBMFYSA-N 342.399 2.272 30 1 EEEF CO[C@]1(C#C[C@@](O)(c2ccccc2)c2ccncc2)CN2CCC1CC2 28563974 NSEVJPOKAGLQCK-FGZHOGPDSA-N 348.446 2.432 30 1 EEEF C=CCOC(=O)N1CCCc2c(c(=O)oc3c(C=O)c(O)ccc23)C1 169348338 VJQYOVRGTPQRNA-UHFFFAOYSA-N 343.335 2.382 30 1 EEEF C=C1C(=O)[C@@]23CC[C@@H]4[C@](C)(CO)CCC[C@]4(C=O)[C@@H]2CC[C@H]1[C@@H]3O 2356462315 NGMHJAMTHJNIJX-TXWGWWACSA-N 332.440 2.277 30 1 EEEF C=CC(C)(C)n1cc(C[C@H]2NC(=O)[C@H](C)NC2=O)c2ccccc21 2356800935 RGJOYRGQGOLRLW-SWLSCSKDSA-N 325.412 2.108 30 1 EEEF CN(C)/C=N/N1C(=O)[C@H]2C3c4ccccc4C(c4ccccc43)[C@@H]2C1=O 49053332 HDPDOFWCHBSNSP-SQEYXSAESA-N 345.402 2.384 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@]2(CCNC[C@H]2C#N)N1 587794327 MGFDYUSZRRNEOF-XDMRBOTDSA-N 338.224 2.451 30 1 EEEF C[C@@H](C(=O)N1CCC[C@H]1C#N)N(C)C(=O)CCCc1ccccc1 1857569158 GDNPDHOSCKVMAB-RDJZCZTQSA-N 327.428 2.371 30 1 EEEF C=C(C)C#C[C@](O)(C(=O)O[C@H]1CN2CCC1CC2)c1ccccc1 1640776 GBTXSVZHHMYRNF-AZUAARDMSA-N 325.408 2.091 30 1 EEEF C[C@H](O)C[C@@H]1O[C@@H]1C=CC=Cc1cc2cc(O)cc(O)c2c(=O)o1 2356744599 TYXXEQMKBIKKOL-JQAFLVLXSA-N 330.336 2.312 30 1 EEEF C=C1[C@@H]2CC[C@H]3[C@]4(C)CCC(=O)C(C)(C)[C@H]4C[C@@H](O)[C@@]3([C@H]1O)[C@@H]2O 95911661 NTFFIALEDUMPAM-OHMGPRHDSA-N 334.456 2.067 30 1 EEEF biogenic,in-vitro C=CCN1C(=O)S[C@@H](Cc2nc3cc(OC)cc(OC)c3[nH]2)C1=O 587038505 JXIVSGDKDIPFCW-LBPRGKRZSA-N 347.396 2.373 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)[C@H](C)C[C@H]2OC(=O)C(=C)[C@H]12 5662886 KYTKEOOPALLADL-VAQLCBBBSA-N 346.379 2.244 30 1 EEEF biogenic COC1=CC(=O)/C(=C(\C)NNC(=S)NCCc2ccccc2)C=C1 104005946 XOXSBYHADNQOBV-DTQAZKPQSA-N 343.452 2.141 30 3 EEEF C[C@@H]1O[C@@H]1C(=O)N[C@H](Cc1ccccc1)C(=O)OCc1ccccc1 28530233 XRLMLBLLFRZQEE-QGTPRVQTSA-N 339.391 2.245 30 1 EEEF C=C(C)[C@H]1CCC2=C[C@@H](CC(C)=CC(=O)[C@@H](O)CC(=O)C1)OC2=O 2356723587 NKBOMIIKMNCYIQ-XCRHUMRWSA-N 332.396 2.440 30 1 EEEF O=C(/C=C/c1ccc(CNCCc2ccc3c(c2)OCO3)cc1)NO 13528152 YEHLSQKPDJZXTB-SOFGYWHQSA-N 340.379 2.266 30 1 EEEF N#Cc1cc(C#N)c(NC2CCN(Cc3ccccc3)CC2)nc1N 84741004 CUQAAIMMMVTGCT-UHFFFAOYSA-N 332.411 2.484 30 1 EEEF CCOc1c(C(=O)OC)cc([N+](=O)[O-])c(/N=C(/C)O)c1[N+](=O)[O-] 40954425 JGADDMBLMHNPOK-UHFFFAOYSA-N 327.249 2.296 30 1 EEEF CC(C)C[C@H](NC(=O)O[C@@H]1CCc2ccccc21)C(=O)NCC#N 82065139 SKEJDBDLGODXLH-JKSUJKDBSA-N 329.400 2.455 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@@H]2[C@@H]3C(=O)O 257434381 HHDWSDSMWJQURA-XGOQZEQDSA-N 332.396 2.136 30 1 EEEF endogenous,in-man C=CCOc1ccc2c(c1)n1ncc(C(=O)c3ccco3)c1[nH][n+]2=O 377863586 FJLSLQXYCDLESR-UHFFFAOYSA-O 337.315 2.119 30 1 EEEF N#Cc1cccnc1NCc1cccc(-c2nc3c(N)ncnc3[nH]2)c1 587229964 NJRGWLLKYLORQS-UHFFFAOYSA-N 342.366 2.481 30 1 EEEF C=C1C[C@@]23C[C@H]1[C@H](O)C[C@H]2[C@@]12CCC[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100826193 IPHNMKITOREFLW-XAEKMEBYSA-N 332.396 2.136 30 1 EEEF endogenous,in-man CCO[C@]12C[C@@]3(C)[C@H](OC(C)=O)C(=O)C=C(C)[C@H]3CC1=C(C)C(=O)O2 2356500625 YDUWTFHAUBSRIH-AZFSHXRASA-N 348.395 2.470 30 1 EEEF CC1=C[C@]2(O)C(=O)C(C)=C[C@@H]3[C@H](C[C@@H](O)C(C)=C[C@H]2C1=O)C3(C)C 2356565158 QSTBGARAGIHHBB-KYNCSHIPSA-N 330.424 2.361 30 1 EEEF CC[C@@H]1O[C@]1(C)[C@H](OCOC)[C@H](C)C(=O)N1C(=O)OC[C@H]1C(C)C 2356700663 DMBYGHSIWBDJGS-CGEFAEBTSA-N 343.420 2.183 30 1 EEEF C[C@@H]1CC(=O)C2=C(CC[C@]34O[C@@]23C(=O)c2cccc(O)c2[C@@H]4O)C1 2356796810 NNMGLXNJGVNRCH-INFFMGMBSA-N 326.348 2.219 30 1 EEEF COC1=C(OC)C(=O)C(Cc2c(C)nc3sccn23)=C(C)C1=O 73351973 HWJSAFHRHOIXGQ-UHFFFAOYSA-N 332.381 2.219 30 1 EEEF Cn1c(C(N)=O)nc2c1C1CC(C1)c1ccc(C#CC(C)(C)O)cc1-2 215773351 UIXWWDHNXGMHLE-UHFFFAOYSA-N 335.407 2.283 30 1 EEEF Cn1cc[n+](COCCc2ccccc2C(F)(F)F)c1/C=N/O 27562360 QJQVUUMUYYLEQB-UHFFFAOYSA-O 328.314 2.356 30 1 EEEF C=C1C(=O)[C@@]23C[C@H](O)[C@@H]4C(C)(C)CCC[C@]4(C)[C@@H]2[C@H](O)C[C@H]1[C@@H]3O 2356638806 RFZAFMSAZOFRSM-HSSJFQGOSA-N 334.456 2.067 30 1 EEEF C[C@@](Cc1ccccc1)(C(=O)NO)C(=O)NCc1ccc(F)cc1 45283686 MTWFVXDQVQRQQS-SFHVURJKSA-N 330.359 2.196 30 1 EEEF CS(=O)(=O)c1ccc(/C=N/Nc2nncc3ccccc23)cc1 653890316 UYIOKQJJWYRDTL-LICLKQGHSA-N 326.381 2.479 30 1 EEEF COC(=O)c1cc2nc(C#Cc3ccc([N+](=O)[O-])c(C)c3)[nH]c2cn1 587262142 NTMMMAUIIZDRIO-UHFFFAOYSA-N 336.307 2.361 30 1 EEEF COc1ccc(/C=C/Cc2nc3nc(C#N)c(C#N)nc3[nH]2)c(OC)c1 587930873 WQDBDHIEJNHQCJ-ONEGZZNKSA-N 346.350 2.369 30 1 EEEF N#Cc1nc2nc(-c3ccnc(OCC(F)(F)F)c3)[nH]c2nc1C#N 587092066 RHZOBWBGHDVBAI-UHFFFAOYSA-N 345.244 2.099 30 1 EEEF CC(C)[C@H](C=O)c1c(O[C@@H](O)C(C)(C)O)ccc2ccc(=O)oc12 2356496202 FOMXOHFJUKCTAU-YVEFUNNKSA-N 334.368 2.200 30 1 EEEF C=C1C[C@]23C[C@H]1[C@@H](O)C[C@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O[C@H]([C@@H]12)[C@H]3O 100780472 OSYJLXUUZYSFTC-ADIGFXHLSA-N 332.440 2.432 30 1 EEEF endogenous,in-man N[C@@H](CS)C(=O)Nc1cccc(Oc2cccc(C(=O)O)c2)c1 28765295 FUQNHULOLHHNDO-AWEZNQCLSA-N 332.381 2.373 30 1 EEEF COC1=CC(=O)[C@]2(C)c3c(O)c(C)c(O)c(C(C)=O)c3O[C@@]2(OC)C1 2356835303 KQROSALZXGEZDK-MSOLQXFVSA-N 348.351 2.105 30 1 EEEF C=C1C(=O)[C@@]23C[C@@H]1C[C@H]1O[C@@H]4OC[C@]5([C@H](CCC(C)(C)[C@@H]45)OC2=O)[C@H]13 653721426 UXZDLIZHUBSGHR-FFRLOYEPSA-N 344.407 2.241 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@@H]3C[C@H](OCC(C)=CC)[C@@H]12 2356499445 DMVINTHATJOGFW-UCIFAOBLSA-N 334.412 2.304 30 1 EEEF C=C1[C@H]2CC[C@@]3([C@H]1O)[C@@H](C2)[C@]12COC(=O)[C@]4(C)CC[C@H]1O[C@@H]3C[C@H]24 2356785281 SEUIPTLIXVTZIG-HXEXAJMMSA-N 330.424 2.450 30 1 EEEF COCC/N=C1/Sc2ccccc2[C@@H]2C[C@H]3[C@H](CON3C)CN12 263590463 JEODAKNDZOTWMS-IHBNSJBNSA-N 333.457 2.403 30 3 EEEF N#Cc1cccc(C(=O)N2CC[C@H]3[C@@H]2CCN3CC2CCOCC2)c1 299842709 JBOOSJFMSXVGNZ-OALUTQOASA-N 339.439 2.274 30 1 EEEF O=C(NO)[C@@H]1CCCN1C(=O)c1ccc(C#Cc2ccccc2)cc1 1857577400 CRQADBHRPQHAIT-SFHVURJKSA-N 334.375 2.196 30 1 EEEF C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12CCC[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 100191680 SXJSUTBDMIRVGQ-QPLUWCFDSA-N 346.423 2.369 30 1 EEEF in-vitro CC[C@H](C)[C@H](NC(=O)C[C@@H]1CCC(=O)[C@@H]1CC=CCC=O)C(=O)O 2356812773 BLZRWMJJRGXFHK-ZJOBFFGXSA-N 337.416 2.123 30 1 EEEF CC(C)=CCc1cccc2c(C[C@H]3C(=O)N[C@@H](C)C(=O)N3O)c[nH]c12 45498542 UDQXPGDOXIBTDM-LRDDRELGSA-N 341.411 2.324 30 1 EEEF C=C1C(=O)O[C@H]2/C=C(/C)[C@@H](O)C[C@H]3O[C@H]3C[C@@H](OC/C(C)=C\C)[C@@H]12 238750131 DMVINTHATJOGFW-FBSCUJDBSA-N 334.412 2.304 30 1 EEEF C=C1C[C@@H](O)[C@H]2O[C@@]2(C)CC[C@@H]2/C(=C\C=C\C(C)(C)O)COC(=O)[C@H]12 238770119 CHWOLNBRUULGCY-WOKHDUKXSA-N 348.439 2.288 30 1 EEEF C=CC1=CC(=O)[C@@H]2[C@H](CC[C@@H]3C(C)(C)[C@H](O)[C@H](O)[C@H](O)[C@@]23C)[C@H]1C 257619956 XFRCVLKGZMPUFQ-KPHUCXPASA-N 334.456 2.089 30 1 EEEF endogenous,in-man C=C1[C@H]2C[C@H](O)[C@@H]3[C@]4(C)CC[C@H](O)C(C)(C)[C@@H]4C(=O)C[C@@]3(C2)[C@@H]1O 2356406449 WSZHSVSVZWABOB-WIADNQMXSA-N 334.456 2.067 30 1 EEEF C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12C[C@H](O)C[C@@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)OC 2356675177 JTSAEZNOAXDDOQ-NZRFLNHFSA-N 346.423 2.225 30 1 EEEF C=C1C[C@]23C[C@@]1(O)CC[C@@H]2[C@@]12CC=C[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 71757899 ZOWHLBOPCIHIHW-RNJLFBCHSA-N 330.380 2.056 30 1 EEEF N#C[C@@H]1CCCN1C(=O)[C@@H]1CC=C[C@H]2CN(Cc3ccccc3)C(=O)[C@@H]21 653873816 RSPHQZYIDJUMKI-OKYOBFRVSA-N 349.434 2.352 30 1 EEEF CC(C)(C)OC(=O)CN[C@H]1c2cc(C#N)ccc2OC(C)(C)[C@@H]1O 13652387 RKAFAAAUJGBZPI-JKSUJKDBSA-N 332.400 2.063 30 1 EEEF CC(C)NC[C@@H](O)CO/N=C1/c2ccccc2[C@@H]2CCCC[C@@]12O 58689917 RTKLMTIRQZCKHN-LODFXGECSA-N 332.444 2.169 30 1 EEEF C=C(C)[C@@H]1C(=O)[C@@]2(O)O[C@]3(C)O[C@]24[C@@H](C)CC[C@@H]2[C@@H](C)C[C@@H]1[C@@]24C3=O 39137768 POWMZEFVJLEORC-KTRZPMJESA-N 346.423 2.223 30 1 EEEF C=C1C[C@@]23C[C@H]1C(=O)C[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1[C@@H](O)[C@@H]3O 2356378093 VYSJMJOARWDSIN-NEEHOPHOSA-N 348.439 2.161 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@]4(C)CCC[C@](C)(CO)[C@@H]4CC(=O)[C@]3([C@H]2O)[C@@H]1O 2356407508 DBVNQUBNOIPPEM-YNXLXHAJSA-N 334.456 2.068 30 1 EEEF CNc1ccc(CN2C(=O)/C(=N\n3cnnc3)c3cc(C)ccc32)cc1 49116009 HHTJOIPGWNMMTE-NKFKGCMQSA-N 346.394 2.427 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@](CCC=O)(C(=O)O)N1 587828528 OZXIIBKYYJVMTP-XLKFXECMSA-N 344.180 2.381 30 1 EEEF CCC[C@@H](O)C1=C[C@@H](OC(C)C)O[C@H](COC(=O)C(C)(C)C)C1=O 28656166 JMRDPGIOVMXZAV-KFWWJZLASA-N 342.432 2.382 30 1 EEEF Cc1ccc(S(=O)(=O)ON/N=C2\[C@H]3CCCC[C@H]3[C@H]3O[C@@H]23)cc1 31841037 AVTXTHBQNZOKPF-VWTBPOSDSA-N 336.413 2.148 30 1 EEEF C=C1[C@@H](OC(C)=O)CC2=C(COC(C)=O)CC[C@@H]3C(=C)C(=O)O[C@H]3[C@H]12 2356674992 BRBKGYDAQMCZSA-BZZMCLGOSA-N 346.379 2.246 30 1 EEEF C=C1[C@@H]2CC[C@H]3[C@@]45CCC[C@@](C)(C(=O)OC4)[C@H]5[C@H](C(=O)O)[C@]3(C2)[C@@H]1O 238757193 MJFVMFNFTCKAEV-UJDYUOFOSA-N 346.423 2.384 30 1 EEEF N#CCCCn1cnc(N)c2nc(Sc3ccccc3CO)nc1-2 299859182 FJBSHTXTPZXCNA-UHFFFAOYSA-N 340.412 2.307 30 1 EEEF Fc1ccc(N2CCN(C(=S)N/N=C\c3ccccn3)CC2)cc1 1857580988 NDKUHPUSJGCESR-MOSHPQCFSA-N 343.431 2.251 30 1 EEEF C=C1C[C@H]2O[C@H]2[C@@](C)(O)CC[C@@H]2C3=C[C@@H]([C@H]4OC4(C)C)O[C@@H]3OC[C@@H]12 59779323 PVAIAJLEMKCLCA-VQWSFFERSA-N 348.439 2.336 30 1 EEEF COc1c2c(c(OC)c3c1C(=O)C1=C(C3=O)[C@@H](C)O[C@H](C)C1)OCO2 14827943 FRYKBCAHLYVUDQ-HTQZYQBOSA-N 346.335 2.305 30 1 EEEF biogenic CCCCCCCCCCC[C@H](O)C[C@H]1C[C@H](O)[C@@H](O)[C@@H](CO)N1 49881930 PEMMQZWMTJRCAR-OYSTVDSJSA-N 345.524 2.103 30 1 EEEF CCc1ncnc(N2CCC[C@@H](CO)C2)c1C#Cc1ccc(C)nc1 149278957 KDCLJCNAZYFCAB-QGZVFWFLSA-N 336.439 2.351 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)/C(C)=C\[C@@H]2OC(=O)C(=C)[C@@H]21 6613284 RYBHZNMPMHOBAR-XXWISIKXSA-N 344.363 2.164 30 1 EEEF C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@H]1CC[C@@]2(O)C(=O)O 2356744219 MCKJPJYRCPANCC-DNMCQFIDSA-N 346.423 2.081 30 1 EEEF COc1cccc(CNC(=O)c2nc(O)c3c(C#N)cccc3n2)c1 299824976 FFZPLZVSLOXRLU-UHFFFAOYSA-N 334.335 2.146 30 1 EEEF CNS(=O)(=O)c1ccc(CCc2nc3cccc(C#N)c3[nH]2)cc1 586946008 FNQVNHAJDWFODW-UHFFFAOYSA-N 340.408 2.128 30 1 EEEF N#Cc1ccc(Nc2nc(N3CCCC3)nc(N3CCCC3)n2)cn1 84688033 AMUPIXMKGVNZRL-UHFFFAOYSA-N 336.403 2.082 30 1 EEEF C/C=C\C(=O)O[C@@H]1C[C@@H]2OC[C@@]23O[C@@H]2C=C(C)C(=O)C[C@]2(C)[C@@]13C 238732604 GUTBYIDIQSFHLV-AWGBURACSA-N 332.396 2.346 30 1 EEEF O=C1N[C@@H](C(=O)NO)C[C@H]1c1cccc(Oc2ccc(F)cc2)c1 13808793 CNFIFPZUBUFKIB-LSDHHAIUSA-N 330.315 2.096 30 1 EEEF N#C[C@@H](C(=O)Nc1ccc(C(F)(F)F)cc1)C(=O)[C@H]1CCOC1 169714930 QRECZZCVBQCIIJ-JOYOIKCWSA-N 326.274 2.389 30 1 EEEF CCN(CCO)C[C@@H]1C(=O)O[C@H]2[C@H]1CCC(C)=CCC[C@@]1(C)O[C@H]21 1857612301 LTIJJNZVNHNQRV-YTGMWSOZSA-N 337.460 2.136 30 1 EEEF C[C@H](Cc1ccc(NS(=O)(=O)c2ccccc2)cc1)C(=O)NO 26722539 RKDXFSHFQNWESJ-GFCCVEGCSA-N 334.397 2.171 30 1 EEEF C=C1[C@H]2CC[C@@H]3[C@]4(C)CC[C@H](O)[C@](C)(C(=O)O)[C@@H]4[C@H]4C(=O)O[C@@H]1[C@]43C2 2356691279 CXVXNQFWGOEIMV-NGFBEOQASA-N 346.423 2.382 30 1 EEEF CCNC(=S)N/N=C(\c1cccc([N+](=O)[O-])c1)c1ccccn1 28703770 GAXZYHUDCNDPQX-NBVRZTHBSA-N 329.385 2.226 30 1 EEEF COC1=CC2=C3C[C@@H]4CC[C@H](OC)[C@H](OC)[C@H]4CN3CCC2=CC1=O 2356845136 OBXUDMPYADNLEQ-UBWHSECZSA-N 345.439 2.446 30 1 EEEF C=C(CO)[C@]12C=C3C(=O)C[C@H](C(C)C)[C@]3(C)C[C@H](O)[C@]1(C)CC(=O)O2 14769750 LAUXGJSHPLNZHD-FLYSZBIRSA-N 348.439 2.169 30 1 EEEF biogenic C[C@]12C[C@H](O)[C@@H]3[C@@H]4CCC(=O)C=C4CC[C@@H]3[C@H]1CC[C@H]2C(=O)CO 2356672857 ACHGZZCRIIPHAX-SKHRHGRFSA-N 332.440 2.277 30 1 EEEF N#Cc1c(NC(=O)c2cccs2)[n+](=O)c2cc(F)ccc2n1O 377845808 QLUSWJRRPMGSOE-UHFFFAOYSA-O 331.308 2.118 30 1 EEEF CC1=CC(=O)[C@@]2(CN1)Oc1ccccc1C(=O)[C@H]2C(=O)c1ccco1 587595354 NGEPTUKSQJSQGP-QFBILLFUSA-N 337.331 2.169 30 1 EEEF C=CC[C@H]1C(=O)N(C(C)=O)[C@H]2CCN(C(=O)OCc3ccccc3)[C@H]21 26487900 PHAYEXZAKQRIHL-IKGGRYGDSA-N 342.395 2.347 30 1 EEEF C=C(C)C(=O)O[C@@H]1C2=C(C)CC[C@H](O)[C@]2(C)C[C@@H]2OC(=O)C(=C)[C@@H]21 2356509315 LJFQOYCUYZGFOE-JCEDBOLHSA-N 332.396 2.453 30 1 EEEF C=C1C(=O)[C@@]23C[C@H](O)[C@H]1C[C@@H]2[C@]1(C)CCC[C@](C)(CO)[C@H]1C[C@H]3O 2356788036 WHNRXVKFGPGHAF-MIAYDVTISA-N 334.456 2.068 30 1 EEEF CO/N=C(/CN1CCN(c2ccccn2)CC1)c1ccc(F)cc1 36375049 FHPKNBFLJRFJBV-FXBPSFAMSA-N 328.391 2.393 30 1 EEEF C[C@@H]1Cc2ccc(F)c(Br)c2[C@@]2(COC[C@H]2C#N)N1 587739118 FRFVAZZMRPQOFX-PWZJLYFZSA-N 325.181 2.488 30 1 EEEF C=CCOC(=O)c1cccn1S(=O)(=O)c1cc(Cl)ccc1N 5852633 VPTUKIJZQGRZHS-UHFFFAOYSA-N 340.788 2.304 30 1 EEEF C=C[C@]1(C)C[C@H](OC(C)=O)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]1C(=C)COC(C)=O 15054218 GHCGLGLMFUFRDH-WAXPSYRMSA-N 348.395 2.347 30 1 EEEF COc1ccc(Oc2ncc3nc(C)c(=O)n(CCC#N)c3n2)cc1 4238333 SXNQEJNPHXRQAH-UHFFFAOYSA-N 337.339 2.210 30 1 EEEF COc1ccccc1N1C(=O)[C@H]2[C@@H]3C[C@@H]([C@H](S)[C@H]3S)[C@@H]2C1=O 4030502 LUMFAWHJRRAZQX-RTULDMFRSA-N 335.450 2.047 30 1 EEEF C=C[C@]1(C)C=C2[C@@H](O)[C@@]3(O)OC(=O)[C@@]4(CCCC(C)(C)[C@H]34)[C@@]2(O)CC1 73224419 XJXDJAQAAAVDCT-RHOFUAETSA-N 348.439 2.063 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cccc(C(=O)O)c3[nH]2)C1=O 587037921 AGSWTTBSUCRUJH-SNVBAGLBSA-N 331.353 2.054 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@]2(C)CC[C@@](O)(O2)/C(C)=C/[C@H]2OC(=O)C(=C)[C@@H]21 169349918 JCTQUEQSHOHEPW-XPBYCLLMSA-N 348.395 2.180 30 1 EEEF O=C1C[C@H](O)C2(Oc3cccc4cccc(c34)O2)[C@H]2C1=CC=C[C@H]2O 2356719693 FKPPHRSYMWPOAW-FMEYXAORSA-N 336.343 2.114 30 1 EEEF O=C(NO)c1ccc2c(c1)C[C@H](NC(=O)c1ccc(Cl)cc1)CN2 113848246 DLHFOYKBAKTUQQ-AWEZNQCLSA-N 345.786 2.226 30 1 EEEF COC1=CC(=CNNc2c(F)c(F)nc(F)c2F)C=C(OC)C1=O 38758284 WIRRBGPBIMWGHH-UHFFFAOYSA-N 345.252 2.082 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@@H](c2ccccc2C2=CCCCC2)[C@@H]1CO 95866857 XJOIDJIXTAYCGR-WSTZPKSXSA-N 340.423 2.469 30 1 EEEF N#Cc1cccnc1N1CCN(CC/C(=N\O)c2ccccc2)CC1 96316499 UQKXNFUEBSXDBC-RELWKKBWSA-N 335.411 2.344 30 1 EEEF O=C(C1=COCCO1)c1c(CO)oc2cc(Br)cnc12 587277055 XIHWMYAFGDCRFP-UHFFFAOYSA-N 340.129 2.154 30 1 EEEF CCC#C[C@](O)(C(=O)O[C@@H]1C2CCN(CC2)[C@@H]1C)c1ccccc1 17250320 VOCRJOMVKAJZBC-MOXGXCLJSA-N 327.424 2.314 30 1 EEEF C#Cc1cccc2c1[C@@]1(Oc3cc(OC)cc4c3C(=O)[C@H]1C4)C(=O)N2 587442838 YVUBPNZZQZOSMN-ZUOKHONESA-N 331.327 2.272 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1C[C@H]1O[C@@]1(CO)CCC=C(C)CCC=C(C)[C@H]2O 2356381447 MULWDJOXRRXULO-ILRSOXBSSA-N 348.439 2.432 30 1 EEEF C[C@@](O)(C#Cc1cn2nc(-c3ccco3)nc2c(N)n1)c1ccccc1 6717186 MUBQTNOOAXJJSD-LJQANCHMSA-N 345.362 2.226 30 1 EEEF C=C([C@H](O)C=C[C@](C)(O)CO)[C@@H]1CC(=O)[C@]2(C)[C@@H]3CC[C@H](C)[C@H]3[C@H]12 2356727545 PIQKTPMDCOQYRT-VFTTZHNOSA-N 334.456 2.090 30 1 EEEF CO[C@]1(C#C[C@](O)(c2ccccn2)C2CCC2)CN2CCC1CC2 28563781 URXQXNPRSDVQNH-WOJBJXKFSA-N 326.440 2.184 30 1 EEEF O=C(/C=C/c1ccc(CNCCc2c[nH]c3ccncc23)cc1)NO 72142874 GYVBOCYZRIRHIA-AATRIKPKSA-N 336.395 2.414 30 1 EEEF C=CCOC(=O)N1CCc2c(c(=O)oc3c(C=O)c(OC)ccc23)C1 169347631 JROXCWCPFHJREK-UHFFFAOYSA-N 343.335 2.295 30 1 EEEF C=C1CC[C@H]2[C@@](C)(CCC(=O)N[C@@]2(C)CO)[C@@H]1/C=C/C1=CCOC1=O 1857575188 KMWVVYHGNIPQHR-WHCBKWPTSA-N 345.439 2.276 30 1 EEEF CC1=C[C@H](OC=C2C(=O)O[C@H]3C4=C(C[C@@H]23)C(=O)CCC4(C)C)OC1=O 2356498061 HZXNZCJZYALICU-DRZCJDIDSA-N 344.363 2.347 30 1 EEEF O=C(/C=C/c1cccc(S(=O)(=O)Nc2cccc(F)c2)c1)NO 33993994 VCSWVYSDADYKCT-BQYQJAHWSA-N 336.344 2.145 30 1 EEEF CN[C@H]1CCN(c2nc(N(C)CCC#N)c3sccc3n2)C[C@@H]1F 1911570441 HMVNYEPSKJGOHX-RYUDHWBXSA-N 348.451 2.177 30 1 EEEF CNC(=O)c1ccc(-c2ccc(/C=C/C(=O)NO)c(Cl)c2)cn1 84668798 SRLHWHKOFGIPQO-FNORWQNLSA-N 331.759 2.280 30 1 EEEF CC(C)(C)C1=CC(=O)C=C(N[C@@H](Cc2ccccc2)C(=O)O)C1=O 473149141 HWJAKGIZEGEZRJ-INIZCTEOSA-N 327.380 2.280 30 1 EEEF C#CCNC(=O)C1=C[C@@H](C2CC2)C[C@@H](OCc2ccc(CO)cc2)O1 13656578 DMXZWWGOTYEDDK-MJGOQNOKSA-N 341.407 2.101 30 3 EEEF CCOc1ccccc1OC1=CNN/C1=C1\C=CC(OC)=CC1=O 104028408 CAJOVDJGHXWANZ-QGOAFFKASA-N 326.352 2.337 30 3 EEEF CO[C@@]1(C#C[C@@](O)(c2ccccn2)C2CCC2)CN2CCC1CC2 28563783 URXQXNPRSDVQNH-PMACEKPBSA-N 326.440 2.184 30 1 EEEF Cn1c2c(c3ccc(Cl)cc31)[C@@H](C#N)C1(CCNCC1)NC2=O 24980601 LPFQFJAOMCGYCP-GFCCVEGCSA-N 328.803 2.304 30 1 EEEF in-vivo Nc1ccc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)nc1N 587890212 VRXKRJHJZCBCRL-UHFFFAOYSA-N 349.221 2.263 30 1 EEEF COc1ccc(/C=C2\COc3cc(O)c(O)c(O)c3C2=O)cc1O 1772652656 FTCMDWAZGJAHKV-RUDMXATFSA-N 330.292 2.176 30 1 EEEF C#CCN(C)C(=O)c1c(-c2ccc(OC)c(OC)c2)noc1[C@@H](C)O 2356303588 YUDNMJKXXXMCCE-LLVKDONJSA-N 344.367 2.117 30 1 EEEF C[C@@]12CC[C@H](O)[C@@H]3COC(=C31)C(=O)c1cc3c(cc12)[C@@H](O)CCC3=O 40917800 QBIVTXOPBMJYTJ-NADSTKFWSA-N 340.375 2.206 30 1 EEEF O=C(O)Cc1cc(CC(=O)O)cc(-c2ccc(C#CCO)s2)c1 584905616 GUHLJLFVRKYNRL-UHFFFAOYSA-N 330.361 2.013 30 1 EEEF in-vitro CC(C)C[C@@H](NC(=O)[C@H](CS)Cc1ccccc1)S(=O)(=O)O 13449700 IFOJNPIPERNZBH-KBPBESRZSA-N 345.486 2.151 30 1 EEEF N#Cc1ccc(Cn2nnc(-c3ccc(N4CCOCC4)cc3)n2)cc1 203474424 AORNGONUNZFROH-UHFFFAOYSA-N 346.394 2.097 30 3 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](C)[C@@H]1[C@](C)(O)CC[C@H](C(C)=O)[C@]1(C)[C@H]2C(C)=O 2356678064 QRJWNJLDUSTASQ-MMJKIMDRSA-N 348.439 2.312 30 1 EEEF N#Cc1ccc(Nc2nn([C@H]3CCCC[C@@H]3C#N)cc2C(N)=O)cn1 221164894 OSITZTJOYPFOOX-ABAIWWIYSA-N 335.371 2.247 30 1 EEEF CCO[P@@]1(=O)C(C#N)=NN(CC)C12C(=O)c1ccccc1C2=O 40402823 SMDNSXNVNQEVHJ-QHCPKHFHSA-N 331.268 2.249 30 1 EEEF CN1CCN(c2ccc3nc(-c4ccc(N)c(C#N)c4)[nH]c3c2)CC1 587249508 MTCQUIARFWJTRG-UHFFFAOYSA-N 332.411 2.436 30 1 EEEF COc1ccc(/C=C\Cc2nc3nc(C#N)c(C#N)nc3[nH]2)c(OC)c1 587930870 WQDBDHIEJNHQCJ-ARJAWSKDSA-N 346.350 2.369 30 1 EEEF O=C1C=CC([N+](=O)[O-])=C/C1=C\Nn1c(-c2ccccc2)n[nH]c1=S 13126538 DHUYFHMJLYXQRD-PKNBQFBNSA-N 341.352 2.335 30 3 EEEF COc1cccc2[nH]c(C(=O)NCCCCCCC(=O)NO)cc12 13490060 WBWKROXBLJWTKY-UHFFFAOYSA-N 333.388 2.362 30 1 EEEF CCN1C(=O)N(CC)[C@@H]2[C@H]1NC(=O)N2/N=C/C=C/c1ccccc1 1857754171 NRUADQHKBGCFCV-QKJONGJWSA-N 327.388 2.140 30 1 EEEF Fc1cc(F)cc(C#CCOc2nsnc2C23CN4C[C@H]2[C@H]3C4)c1 3931556 RWIBKAGXMHMEFU-VMZNBEPHSA-N 345.374 2.060 30 1 EEEF C=C1CC[C@H](OC(C)=O)[C@@]2(C)C[C@@H]3OC(=O)C(=C)[C@H]3[C@H](OC(C)=O)[C@@H]12 40393586 JBGDRCNWJFVVLR-NHDVRJRVSA-N 348.395 2.324 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC=C2[C@@]12CC[C@@H](O)[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 104377876 BSBICXIQCTXPMN-SHTCDAFQSA-N 330.380 2.056 30 1 EEEF in-man CO[C@]1(C#C[C@](O)(c2ccccc2)c2ccccn2)CN2CCC1CC2 28563817 LLHFDYRCKMNGML-YADHBBJMSA-N 348.446 2.432 30 1 EEEF N#C[C@@H]1[C@H](c2ccc(-c3cncnc3)cc2)[C@H](CO)N1C(=O)C1CCC1 95897720 RYHHKKTZXOEYDH-QYZOEREBSA-N 348.406 2.123 30 1 EEEF O=C(/C=C/c1cccn(Cc2ccccc2Br)c1=O)NO 143793368 VJNNUHOKJNVWAW-BQYQJAHWSA-N 349.184 2.178 30 1 EEEF Nc1n2nc(-c3ccccc3)sc2n[n+]1CC(=O)c1ccccc1 1644507 QAGHQRMSFGVKDG-UHFFFAOYSA-O 336.400 2.210 30 1 EEEF C[C@@]12CC[C@@](C)(O1)[C@H]1C(=O)N(c3cnc(C#N)c(Cl)c3)C(=O)[C@H]12 29126879 VKOUOBLCMIKWHV-HMEQZMJYSA-N 331.759 2.054 30 1 EEEF C=C(Cc1c(OC)ccc(C(=O)O)c1O)[C@H]1CC[C@](C)(O)[C@H](O)C1 27559304 JNPNGXWCEMBWHW-POHZPAGDSA-N 336.384 2.110 30 1 EEEF O=C(NO)c1ccc(NC(=O)C2(c3ccccc3)CCNCC2)cc1 1911577670 TYTDNBZIYWDAGK-UHFFFAOYSA-N 339.395 2.066 30 1 EEEF CN(O)C(=O)[C@@H](Cc1ccccc1)C(=O)NCc1ccc(F)cc1 45299469 JZRIMQYBETYOBO-INIZCTEOSA-N 330.359 2.148 30 1 EEEF CCc1nc(N)nc(N)c1C#CCc1cccc(-c2cncnc2)c1 95921196 UEZKDWYIIOOENX-UHFFFAOYSA-N 330.395 2.255 30 1 EEEF in-vitro COC1=CC(=O)c2cc3c4c(cc(OC)c(O)c4c2C1=O)CCN3C 14711498 MEYYOKCMFDAQQU-UHFFFAOYSA-N 339.347 2.456 30 1 EEEF biogenic C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)C(=C)[C@@H](C(C)(C)CCCO)C[C@H]3O 144782570 FBXNWXLXYGRNOE-NHIRPJQQSA-N 334.456 2.235 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(COC3=O)[C@H]2CC[C@@]3(C)CO[C@H](O2)[C@@H]13 101692114 VGHUWBCJSRMGIQ-CLPWOPBYSA-N 344.407 2.243 30 1 EEEF C=C[C@@](C)(O)[C@H](O)C[C@@H]1C(=C)[C@H](O)C[C@@H]2[C@@](C)(CO)CCC[C@@]12C 238744269 CYJDHAXSZJABJA-AIFSHUDHSA-N 338.488 2.416 30 1 EEEF C#CCN(C)C[C@@H]1CN2CC[C@H]1C[C@H]2CNC(=O)Nc1ccccc1 2356320496 MFSCSGBXHMMZNQ-SCTDSRPQSA-N 340.471 2.084 30 1 EEEF COC(=O)c1cc2c([nH]1)C(=O)C=C1N(C(=O)OC(C)(C)C)C[C@H]3C[C@]123 26831862 JVWWPRHIXMFAED-DYBLOJMWSA-N 344.367 2.390 30 1 EEEF CCOC(=O)CCCn1cc(C#N)c2cc(OC)c(OC)cc2c1=O 13800922 INZYIXXPHQCEJL-UHFFFAOYSA-N 344.367 2.234 30 1 EEEF C=C(C#CC1=C[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O)CCC=C(C)CCC=C(C)C 2356334234 CADYTUXNRNXAES-WOZUAGRISA-N 346.467 2.403 30 1 EEEF CC1(C)CCC[C@@]2(C)O[C@@]12/C=C/c1cc(S(C)(=O)=O)nc(N)n1 28712574 SKULGIFBFWXBLY-GRLYAWNKSA-N 337.445 2.213 30 1 EEEF CN(C)CCCN(C)c1nc(N(C)CCC#N)c2ccccc2n1 1911584546 CLSXWCBPTVVJNU-UHFFFAOYSA-N 326.448 2.368 30 1 EEEF CN(O)C(=O)C[C@@H](CCCCc1ccccc1)CP(=O)(O)O 230570880 FWCPRMVLUHPTMF-CQSZACIVSA-N 329.333 2.431 30 1 EEEF in-vitro Nc1cc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cc(N)n1 587882276 SDGSLWXPJSUBMY-UHFFFAOYSA-N 349.221 2.263 30 1 EEEF CC=CC(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)[C@@H]4O[C@@H]4[C@]3(C)[C@@]1(C)[C@]21CO1 2356419983 LAQCZBYXNRANFU-QHGGPOTCSA-N 332.396 2.154 30 1 EEEF C=C(C)C(=O)O[C@@H]1C[C@H]2C[C@@H](CC(C)=C[C@@H]3OC(=O)C(=C)[C@H]31)OC2=O 2356536252 HOZUUHWHCWNMPV-IBEHDNSVSA-N 346.379 2.244 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@@]3(O)C=C[C@@](C)(C[C@H](OC(=O)C(C)C)[C@H]12)O3 2356625028 XJUPOHKZSDZNBE-WCVDCBDPSA-N 348.395 2.036 30 1 EEEF CC=CC1=CC(=O)C([C@@H]2OC(=O)c3cc(OC)cc(OC)c32)=CC1=O 2356725650 JDJRBGGOYNOXOV-SFHVURJKSA-N 340.331 2.496 30 1 EEEF Cc1nc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cnc1N 587890238 WWBNEXPUEOJTQJ-UHFFFAOYSA-N 349.221 2.384 30 1 EEEF CC(C)(Cc1ccc(F)cc1)NCC(=O)N1[C@H](C#N)CC[C@@H]1C#N 13687392 ZMZYFCSCMQSYSZ-IYBDPMFKSA-N 328.391 2.143 30 1 EEEF O=C1C=CC=C/C1=C\NNC1=NC(=O)[C@@H](Cc2ccc(F)cc2)S1 15952886 HPUMHJYDWOJHJM-HBIYDYFMSA-N 343.383 2.039 30 3 EEEF COC(=O)N1CCC2(CC1)C[C@@](O)(C#Cc1cccc(C)c1)CO2 103273452 SCOTVKYJDVTBLI-SFHVURJKSA-N 329.396 2.099 30 1 EEEF CC1(C)Oc2ccc(C#N)cc2[C@@H](n2cc(Cl)ccc2=O)[C@@H]1O 27557999 AVWKEPBNSDFJOF-CVEARBPZSA-N 330.771 2.495 30 1 EEEF C[C@]12C3=C(C(=O)c4occ(c41)[C@H](O)[C@@H]1O[C@H]12)[C@@H]1CC[C@@H](O)[C@]1(C)CC3 2356449775 XPAHMBAVRBKIJS-ONKBVOLYSA-N 342.391 2.416 30 1 EEEF C=C(C)C(=O)O[C@@H]1C=C(C)C2=CC(=O)[C@@](C)(C[C@@H]3OC(=O)C(=C)[C@H]31)O2 2356686320 AERIPQYYSNTIDA-PGSNGQOISA-N 344.363 2.164 30 1 EEEF C#CC[C@@H](NC(=O)c1ccc(C(F)(F)F)cc1)C(=O)NCCC 36389138 XFGGFMUOUXGINT-CYBMUJFWSA-N 326.318 2.353 30 3 EEEF C#Cc1ncn2c1Cn1cnnc1-c1cc(Br)ccc1-2 45299091 VKXPNHVCRUUHMO-UHFFFAOYSA-N 326.157 2.236 30 1 EEEF CCC#CCOC(=O)CNC(=O)c1coc(-c2ccc(C)cc2)n1 82072262 ZRVOEPJBOKCRIO-UHFFFAOYSA-N 326.352 2.336 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1CCC(=C)[C@@H]1C[C@@H](OC(=O)/C=C(\C)CO)C(=C)[C@H]21 238761571 AZDMJQODBMILBW-ZNSUXFFOSA-N 344.407 2.477 30 1 EEEF CC(C)C1=C2[C@@H]3C[C@@H](O)C(CO)=CC(=O)[C@]3(C)CC[C@@]2(C)[C@H](O)C1 238765034 YEHJDRIYGMBBHB-DBSUQTKJSA-N 334.456 2.379 30 1 EEEF C=CCc1cc(CCC(=O)O)ccc1C#C[C@]1(O)CN2CCC1CC2 3809413 KRZHVWPIUYVUQH-NRFANRHFSA-N 339.435 2.241 30 1 EEEF CC(C)S(=O)(=O)N[C@H]1Cc2ccc(-c3cncc(C#N)c3)cc2C1 58540903 KGEABTFMCTZXTF-SFHVURJKSA-N 341.436 2.415 30 1 EEEF COCC(=O)N1[C@H](C#N)[C@H](c2ccc(C3=CCCC3)cc2)[C@@H]1CO 95897808 SMEVBYXHWQHXGK-AOIWGVFYSA-N 326.396 2.079 30 1 EEEF COC(=O)[C@@H](C#N)c1ncc(C#Cc2cc(Cl)ccc2OC)cn1 587908116 LWKQOGNDMWRIMP-AWEZNQCLSA-N 341.754 2.319 30 1 EEEF C=C1[C@@H]2CC(=O)C(C)(C)[C@@]2(O)[C@H](O)C[C@@]23C[C@@H](CC[C@@H]12)[C@](C)(O)C3 1857565422 YAORPCCQMOCHAF-UANYPFSNSA-N 334.456 2.211 30 1 EEEF C[C@H](O)[C@@H]1C(=O)C(=C(O)[C@@H]2[C@H](C)C=C[C@@H]3CCCC[C@H]32)C(=O)N1C 2356417406 ACUUAFHILDALFB-FHBCKGOSSA-N 333.428 2.218 30 1 EEEF COc1ccc(S(=O)(=O)[C@@H](CC(=O)NO)c2ccccc2)cc1 29391814 SZVMBGCUMABOMY-HNNXBMFYSA-N 335.381 2.106 30 1 EEEF C=C1C[C@@]23C[C@H]1CC=C2[C@@]12CC[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 2356549657 CSOGGDRRRLWUTQ-SLCZYMEHSA-N 344.407 2.145 30 1 EEEF O=C1C=CC=C/C1=C\NNC(=S)N[C@@H]1C[C@H]2C[C@H]1[C@@H]1C=CC[C@H]12 104017598 WVNYYTSFNKWSKL-IULKGGAYSA-N 327.453 2.135 30 3 EEEF COC(=O)C[C@]1([C@H](O)C=C(C)CCC=C(C)C)C[C@@H](O)C=CC1=O 2356635823 LRHXPNHCPURRDF-KVSKMBFKSA-N 336.428 2.479 30 1 EEEF Nc1ccc(S(=O)(=O)NN=C/C=C/c2ccccc2[N+](=O)[O-])cc1 253908046 WVEMQFVVHNUQTB-OWJSUJKRSA-N 346.368 2.155 30 3 EEEF N#Cc1nc2nc(C3(O)CCC(C(F)(F)F)CC3)[nH]c2nc1C#N 587124847 CQRVBMNPHICQBL-UHFFFAOYSA-N 336.277 2.036 30 1 EEEF CC(=O)N[C@H](C(=O)NO)c1ccc(-c2cc(F)c(F)c(F)c2)cc1 1857566877 JTKRAFAIGNTUQA-HNNXBMFYSA-N 338.285 2.454 30 1 EEEF CCNC(=O)Nc1ccc(Oc2ncnc(N)c2/C=N/OC)c(C)c1 66076378 JBVKSPDGOVJWPS-ODCIPOBUSA-N 344.375 2.281 30 1 EEEF COc1c(O)cc2c(c1OC)[C@@]13C=CC(=O)C=C1[C@@H](CC2)N(C)CC3 238783705 HQSBYMLNJWZFJC-FOIQADDNSA-N 341.407 2.363 30 1 EEEF C[C@](O)(COc1ccc(C#N)cc1)C(=O)N1CCc2c(C#N)cccc21 169313288 VHLMFSNVTYEYOE-FQEVSTJZSA-N 347.374 2.149 30 1 EEEF CN1CCN(c2ccc(NC3=CC(=O)c4ncccc4C3=O)cc2)CC1 1857635205 YUXUZSKTTBNYAH-UHFFFAOYSA-N 348.406 2.208 30 1 EEEF N=C(N/N=C/c1cnccc1Cl)N/N=C/c1cnccc1Cl 653729308 IFHJIQILAOFZND-OKXCLTPOSA-N 336.186 2.265 30 1 EEEF N#Cc1c(-c2ccc([N+](=O)[O-])cc2)nc(S)nc1N1CCOCC1 96910382 NNRQQTJPCXMIBT-UHFFFAOYSA-N 343.368 2.049 30 1 EEEF CCOC(=O)N(OC(=O)N(CC)CC)S(=O)(=O)c1ccccc1 13533371 LEQFLKRJHTWBOZ-UHFFFAOYSA-N 344.389 2.227 30 1 EEEF C=C1[C@@H](CC=C2COC[C@H]2O)[C@@]2(C)CC[C@@H](O)C(C)(C)[C@H]2C[C@H]1O 2356416315 PQJNKPQZAXZXLP-GGPCPXQKSA-N 336.472 2.434 30 1 EEEF Cc1nn(-c2ccccc2)nc1C(=O)Nc1ccc(C#N)cc1C(=O)O 28887099 PHWULYHAFYPALU-UHFFFAOYSA-N 347.334 2.398 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)C3=CC(=O)[C@@](C)(C[C@@H](OC(=O)C(C)C)[C@H]12)O3 2356531366 WQQJRSDFQHYDRU-NPNMTCQASA-N 346.379 2.244 30 1 EEEF N#Cc1ccc2cnn(-c3cncc(-n4ccc(CC(=O)O)c4)n3)c2c1 84669163 NMQVKKSZWZUZOB-UHFFFAOYSA-N 344.334 2.105 30 1 EEEF CCOC(=O)Cc1cc(O)cc(O)c1C(=O)/C=C/C=C/CCCO 141246598 DOCDDNYMBXDQJE-PBOULFJWSA-N 334.368 2.271 30 1 EEEF O=C(O)[C@@H](CS)NCc1c2ccccc2[n+]([O-])c2ccccc12 5614369 KMURGFIZSJATNI-CQSZACIVSA-N 328.393 2.099 30 1 EEEF CCCCN/C(N)=N/c1nc(-c2cccc(CNC(C)=O)n2)cs1 13558599 MBPIPLSKFRPYPI-UHFFFAOYSA-N 346.460 2.177 30 1 EEEF CCC#C[C@](O)(C(=O)OC1C[C@@H]2CC[C@@H](C1)N2C)c1ccccc1 101161040 CPSOCUUSNHHZOV-ABSDTBQOSA-N 327.424 2.456 30 1 EEEF O=C1[C@@H]2[C@@H](C(=O)N1/N=C\c1cccc([N+](=O)[O-])c1)[C@@H]1C=C[C@@H]2C12CC2 100556879 BAOWMYTUKUMZDC-OUDYMHSDSA-N 337.335 2.126 30 1 EEEF C[C@@H](C=O)NC(=O)[C@@H](Cc1ccccc1)NC(=O)Nc1ccccc1 82061184 IOBSHJKFMZWHDJ-WMLDXEAASA-N 339.395 2.123 30 1 EEEF C=CCn1c(=O)c(-c2ccc(OC)nc2)cc2c(C)nc(NC)nc21 140043301 NQCOXRGXUZZWFA-UHFFFAOYSA-N 337.383 2.398 30 1 EEEF C/C(=C\c1ccc(NS(=O)(=O)c2ccccc2)cc1)C(=O)NO 26736167 RCHSCTGFXSOIJV-VAWYXSNFSA-N 332.381 2.396 30 1 EEEF CCOC1=CC(=O)/C(=C2\NNC=C2Oc2ccccc2OC)C=C1 104028600 FZARZHBGIKZJLY-AQTBWJFISA-N 326.352 2.337 30 3 EEEF COc1cc2nc(-c3ccc(C(C=O)C=O)c([N+](=O)[O-])c3)[nH]c2cn1 587262370 SUGFFSOCQIHLLR-UHFFFAOYSA-N 340.295 2.023 30 1 EEEF Cc1ccc(S(=O)(=O)N/N=C2\CCCC[C@]23CCC(=O)NC3)cc1 5809817 XYCWNNPFZKUTNG-VXNZKSKFSA-N 349.456 2.100 30 1 EEEF CC(=O)N[C@@H](C(=O)NO)c1ccc(-c2cc(F)c(F)c(F)c2)cc1 1857566878 JTKRAFAIGNTUQA-OAHLLOKOSA-N 338.285 2.454 30 1 EEEF NC(=O)c1cn2c(n1)-c1cc(C#CC3(O)CCC3)ccc1C1CC2C1 219546005 SAUQZLRKWZCHQX-UHFFFAOYSA-N 333.391 2.348 30 1 EEEF N#Cc1nc2nc(-c3cccc(-c4csc(N)n4)c3)[nH]c2nc1C#N 587020489 AKZOPEMRQFZXKC-UHFFFAOYSA-N 344.363 2.469 30 1 EEEF C#CCN(C)C(=O)c1c(C)c(N2CCN(C)CC2)nc2ccccc12 13644293 UKRQFMMGNWQTFI-UHFFFAOYSA-N 336.439 2.000 30 1 EEEF COc1ccc(Oc2nc(C)ccc2/C(=N/O)NCCN(C)C)cc1 72183981 XNDUBQPTZMSTQY-UHFFFAOYSA-N 344.415 2.478 30 1 EEEF CC1=C[C@]2(O)C(=C[C@](C)(O)CC[C@@H]3[C@H](C[C@H](C)[C@@H]2O)C3(C)C)C1=O 2356515849 CZUBZNDQQZRXMB-VYYXDTIASA-N 334.456 2.377 30 1 EEEF CNC(=O)/C(=N/OC)c1ccccc1COc1cccc(Cl)n1 103195006 RRJBTQBSZKXYJL-HMMYKYKNSA-N 333.775 2.411 30 1 EEEF N[C@@H](CS)C(=O)Nc1cccc(Oc2ccc(C(=O)O)cc2)c1 28765067 OFPKPESTKYNWQZ-AWEZNQCLSA-N 332.381 2.373 30 1 EEEF Cc1cc(CN2C[C@H](N)[C@H](C(=O)[C@@H]3CCC[C@H]3C#N)C2)ccc1C#N 28955145 FWKUWRLCCHFYDK-MANSERQUSA-N 336.439 2.135 30 1 EEEF C=CCSc1nnc(-c2ccc(NC(=S)NCCO)cc2)o1 73169779 NVTRYWRDQFQLGY-UHFFFAOYSA-N 336.442 2.293 30 1 EEEF O=C(/C=C/c1ccccn1)c1ccc(O)c(CN2CCOCC2)c1O 40918618 PFYYEEIZTITCTE-GQCTYLIASA-N 340.379 2.221 30 1 EEEF CN(C)/C=N/N1C(=O)[C@H]2C3c4ccccc4C(c4ccccc43)[C@H]2C1=O 49053329 HDPDOFWCHBSNSP-UADDHJFWSA-N 345.402 2.384 30 1 EEEF CC(C)C[C@@H](NC(=O)c1ccccc1C(F)(F)F)C(=O)NCC#N 82064977 MIZGLZUZKGZYDY-CYBMUJFWSA-N 341.333 2.490 30 1 EEEF N#C[C@@H]1[C@H](c2ccc(-c3cccnc3)cc2)[C@H](CO)N1C(=O)C1CC1 95896229 FYALJDMLJJPLTL-QYZOEREBSA-N 333.391 2.337 30 1 EEEF C#C[C@]1(O)C[C@H](O)[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3[C@@H](OC)C[C@@]21C 238738043 TYTYJGWQMLLBDD-OUZKAEIWSA-N 342.435 2.208 30 1 EEEF COc1ccc(Cl)cc1C#CC1=CN2C(=O)CC(=O)N=C2C=C1 587912062 ACDSWAXUDXWWLL-UHFFFAOYSA-N 326.739 2.311 30 1 EEEF CCOC(=O)c1cn(C[C@@H]2CO2)c2cc(Cl)c(F)cc2c1=O 207914428 DTISBMDFRLIPKN-MRVPVSSYSA-N 325.723 2.370 30 1 EEEF O=C(O)[C@H]1CCCN(CCO/N=C/c2ccnc3ccccc23)C1 1857565879 FOTJDUOZGJMMPX-SLDJAQPHSA-N 327.384 2.382 30 1 EEEF NC(=O)/C(=C/c1ccc(/C=C/C(=O)NO)cc1)c1ccc(F)cc1 59278091 QSHKOYZBBMRZGY-JLLAUFTHSA-N 326.327 2.370 30 1 EEEF C=C1C(=O)OC2=C(C)[C@@]3(O)C=C[C@@](C)(C[C@@H](OC(=O)C(C)C)[C@H]1C2)O3 2356534613 NQTBGYYRPIDDKV-ARKSPBFVSA-N 348.395 2.385 30 1 EEEF C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1cc(=O)[nH]c2ccc(OC)cc12 33986450 FRZGROVVMXMITN-GEDLKBKPSA-N 340.423 2.467 30 1 EEEF CCCCCCCCCCC[C@@H](O)C[C@H]1C[C@H](O)[C@@H](O)[C@@H](CO)N1 49881931 PEMMQZWMTJRCAR-JKEDJMADSA-N 345.524 2.103 30 1 EEEF CC(C)(C)C(=O)N[C@H](Cc1ccc(Br)cc1)C(=O)NO 653801243 CMKKIEWVWXTANS-LLVKDONJSA-N 343.221 2.028 30 1 EEEF CCOc1nc(NC(=O)Cc2ccccc2OC)cc(N)c1C#N 14960055 PBKYQJDUQYHRCL-UHFFFAOYSA-N 326.356 2.124 30 1 EEEF CCNc1ncc2nc(-c3cccs3)c(=O)n(CCC#N)c2n1 4239054 LSVGMBFOSQBBSG-UHFFFAOYSA-N 326.385 2.260 30 1 EEEF CC[C@H](O)C[C@H](C)[C@@H]1O[C@]1(C)C=CC(=O)N[C@H](CO)[C@@H](C)CC 2356421458 KQYIQWJQJFWGMP-RIMFYDMWSA-N 327.465 2.020 30 1 EEEF CN1C(=O)/C(=C/c2ccc3c(c2)OCO3)N/C1=N\c1ccc(O)cc1 72110297 MMWGSUYGZVUNCC-ZSOIEALJSA-N 337.335 2.211 30 1 EEEF Cc1cc(=O)oc2cc(NC(=O)CNc3ccc(C#N)cn3)ccc12 1772656321 SCUIBFIHLNGCGN-UHFFFAOYSA-N 334.335 2.419 30 1 EEEF Cc1cc2c(cc1O)/C(=C\c1cccc(/C=N/NC(=N)N)c1)C(=O)N2 1857588506 CNMNSATYMWHUSQ-ZMLRYCRHSA-N 335.367 2.010 30 1 EEEF C=C1C[C@]23C[C@H]1[C@@H](O)C[C@H]2[C@@]1(C)CCC[C@]2(C)C(=O)O[C@H]([C@H]21)[C@H]3O 100780470 OSYJLXUUZYSFTC-GLMNFNDASA-N 332.440 2.432 30 1 EEEF endogenous,in-man C=CCNC(=S)NN1C(=O)[C@H]2[C@H](C1=O)[C@@]1(C)C=C[C@@]2(C(C)C)CC1 101869779 SDJYQQCUHRGBAF-OSLDLMBLSA-N 347.484 2.165 30 1 EEEF CCCCCCCCC[C@@H]1OC(=O)C[C@H](O)C[C@H](O)C=C[C@@H]1O 2356619469 HFGOXJHLMBNOHC-NCOADZHNSA-N 328.449 2.472 30 1 EEEF C=C1C(=O)O[C@H]2/C=C(/C)[C@@H](O)C[C@H]3O[C@H]3C[C@@H](OC[C@@H](C)CC)[C@@H]12 238765519 WULWDKXUHKIGSZ-CQZKYOERSA-N 336.428 2.384 30 1 EEEF C=CCc1cc(CCC(=O)O)ccc1C#C[C@@]1(O)CN2CCC1CC2 13905956 KRZHVWPIUYVUQH-OAQYLSRUSA-N 339.435 2.241 30 1 EEEF CN(C)c1ccc(C(=O)NCc2ccc(/C=C/C(=O)NO)cc2)cc1 3818748 WWMASNYTEATYTC-KPKJPENVSA-N 339.395 2.201 30 1 EEEF CC(C)[C@]1(O)C=C2C(=O)C[C@@H]3C(C)(C)[C@H](O)CC[C@]3(C)[C@@H]2C[C@@H]1O 2356336806 NHJLCDALTNPYBE-VIDQEAKSSA-N 336.472 2.457 30 1 EEEF C=C1C(=O)O[C@@H]2[C@@H]1[C@H](OC(C)=O)C[C@@]1(C)[C@@H]2C(=C)CC[C@H]1OC(C)=O 2356431879 IDVKLEJKBPWDKI-JCIRTYSKSA-N 348.395 2.324 30 1 EEEF CCOC(=O)C(/C=N\Nc1ccsc1C(=O)OC)=C(/O)OCC 102717644 KOXPRXZNRHMWLT-HZUQNYIRSA-N 342.373 2.302 30 1 EEEF C=C1C[C@@]23C[C@]1(O)CC[C@H]2[C@]12C=CC[C@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100784058 UXLXLQYIDWLPKX-NHJQEKMRSA-N 330.380 2.056 30 1 EEEF endogenous,in-man N#Cc1ccnc(C(=O)Nc2ccc([C@H]3CNCCO3)cc2F)c1 149861810 SIRAEEFSAZVTRZ-MRXNPFEDSA-N 326.331 2.006 30 1 EEEF CO[C@H]1[C@H](/C(C)=N\OCc2ccccc2)[C@]2(CC[C@H]1OC(N)=O)CO2 13588335 QGWIAAHQFJYZGG-WLQAGAIGSA-N 348.399 2.237 30 1 EEEF CCCOC[C@@H](O)COc1ccc(NC(=O)CC[S+](C)C)cc1 26994356 VYCPJZZIISAKJX-OAHLLOKOSA-O 342.481 2.059 30 1 EEEF CN1CCN(/C(=N\O)c2ccnc(Oc3cccc(F)c3)c2)CC1 72184084 DKRBRIWAPQGXOW-JZJYNLBNSA-N 330.363 2.396 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@@H]2C1=CC[C@H](O)[C@@](C)(C(=O)O)[C@H]1[C@@H]3C(=O)O 238772127 WFTRKYGVESACJS-HXGOOWQJSA-N 332.396 2.462 30 1 EEEF CC[C@H](C)[C@@H](CO)NC(=O)/C=C/[C@@]1(C)O[C@@H]1[C@@H](C)C[C@H](O)CC 206227175 KQYIQWJQJFWGMP-SRHRVUKGSA-N 327.465 2.020 30 1 EEEF COc1ccc(C(=O)O[C@@H]2c3cocc3[C@H](CC=O)[C@@H]2O)cc1OC 2356737452 SFCCTINUDYTREN-MZPVMMEZSA-N 346.335 2.242 30 1 EEEF C=C1C(=O)[C@@]23C[C@H](O)[C@H]1C[C@@H]2[C@]1(C)CCC[C@](C)(CO)[C@H]1C[C@@H]3O 2356788037 WHNRXVKFGPGHAF-XFFLZRQOSA-N 334.456 2.068 30 1 EEEF NC(N)=Nc1ccc(CNC(=O)NC23CC4CC(CC(C4)C2)C3)cc1 3874320 YQPLKJCBEOVDBS-UHFFFAOYSA-N 341.459 2.360 30 1 EEEF biogenic,in-vivo CC(C)(O)C(C)(C)OB(OC(C)(C)C(C)(C)O)c1ccnc(F)c1 221634867 KEGTYNDTDFWJQZ-UHFFFAOYSA-N 341.232 2.048 30 1 EEEF C=C1[C@@H]2C(=O)C[C@@H]3[C@](CC[C@@H]4C(C)(C)[C@@H](O)CC[C@]43C)([C@@H]1O)[C@@H]2O 144208425 JGAWMQVJTGKMKT-NQTJCWRASA-N 334.456 2.067 30 1 EEEF COC(=O)[C@@]1(CC(=O)c2ccc(C#N)cc2)NCCc2c(C)ccnc21 963072818 OEPWJBWNTBPHER-FQEVSTJZSA-N 349.390 2.049 30 1 EEEF C#Cc1cccc(Nc2ncnn3ccc(CN4CCC(N)CC4)c23)c1 66252028 RKUHGVDFHLNNLT-UHFFFAOYSA-N 346.438 2.377 30 1 EEEF C=C(C)[C@@H]1C[C@H]2[C@H](CC[C@@]2(O)CCNC(=N)NC)[C@@]2(O)CC=C[C@@H]1C2 85549844 SYAVXIORAFJRNU-QRNRZKQXSA-N 347.503 2.171 30 1 EEEF biogenic,in-vitro CC(C)C[C@H](NC(=O)c1cc(Cl)nc(Cl)c1)C(=O)NCC#N 82065369 HCPTXGLLRHGRBI-JTQLQIEISA-N 343.214 2.173 30 1 EEEF Cc1ccc(-c2noc(CNCc3ccc(C(=O)NO)cc3)n2)cc1 141906745 UQQNVHLKGVLXKE-UHFFFAOYSA-N 338.367 2.454 30 1 EEEF CCCC(=O)CCC1=C(O)C(=O)c2cc(O)c(OC)c(O)c2C1=O 40861868 GGNMTYGXUUGJFT-UHFFFAOYSA-N 334.324 2.447 30 1 EEEF biogenic CC1=C(N2[C@@H](C)[C@@H]2C)C(=O)C(Br)=C(N2[C@@H](C)[C@@H]2C)C1=O 169335115 RKTOSHDREXTIII-XKNYDFJKSA-N 339.233 2.204 30 1 EEEF COc1cccc2c1O[C@@H]1C=C(OC[C@]3(C)CO3)C=C(O)[C@@H]1C2=O 169368027 GLCNXGRTIKCJRG-RVKKMQEKSA-N 330.336 2.400 30 1 EEEF C#C[C@@H]1CN2CC[C@H]1C[C@@H]2COC(=O)Nc1ccccc1C(=O)OC 2356837727 LMLYDZBSOPFRQG-QLFBSQMISA-N 342.395 2.365 30 1 EEEF O=C(O)[C@@H]1CCCN(CCO/N=C/c2ccc3ccccc3n2)C1 1857555747 RAYNQXJPOQHGHK-IYSPOMMRSA-N 327.384 2.382 30 1 EEEF C=C(C#CC1=C[C@H](O)[C@H](O)[C@H](O)[C@@H]1O)CCC=C(C)CCC=C(C)C 2356334232 CADYTUXNRNXAES-JSXRDJHFSA-N 346.467 2.403 30 1 EEEF C=C1CC[C@@H]2CCC3=C(C(=O)[C@@H](/C(C)=C/[C@@H](O)[C@H]1O)[C@H]3O)C2(C)C 238772087 SMYOLHGQHZBFAQ-NKFDCMGOSA-N 332.440 2.297 30 1 EEEF Cc1nc2cc(/C=C/C(=O)NO)ccc2c(=O)n1CCc1ccccc1 96283755 NVEBAMFLYZFKKW-CSKARUKUSA-N 349.390 2.466 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(C)C(=O)CC[C@@](C)(C(=O)O)[C@@H]1C[C@@H]3O 72104717 CLGOGJHVMHIUDO-FQUJQCDKSA-N 346.423 2.369 30 3 EEEF C#CCNc1nc2c(cc1F)c(=O)c(C(=O)OCC)cn2C1CC1 84615796 SUWVVBFHBFVXRF-UHFFFAOYSA-N 329.331 2.092 30 1 EEEF COCCNC(=O)[C@H]1CCCC[C@H]1c1nc2ccc(C#N)cc2[nH]1 587230246 GVQINTUAKQBKOC-KGLIPLIRSA-N 326.400 2.471 30 1 EEEF C#Cc1ccc2c(c1)O[C@@H](COc1ccc(F)c(C(N)=O)c1F)CO2 1772577397 DTERGCNTHRPYJW-LLVKDONJSA-N 345.301 2.264 30 1 EEEF COC(=O)/C=C\C(C#N)(C#N)/N=C/c1ccc(Br)cc1 5924699 JXZLSCJGRCXWFF-FWNKGETMSA-N 332.157 2.383 30 1 EEEF COc1ccc(/C=N/n2c(Cc3ccccc3)n[nH]c2=O)c(OC)c1 1654980 LHLZYHGLORSCDQ-XDHOZWIPSA-N 338.367 2.062 30 1 EEEF CCN(CC)CCC[C@H](C)Nc1ncnc2c1C(=O)C(OC)=CC2=O 27523141 CENAUQJRBYLTJY-LBPRGKRZSA-N 346.431 2.308 30 1 EEEF C=C1CO[C@H]2C(=O)N(Cc3ccccc3)[C@@H]1C(=O)N2Cc1ccccc1 27862839 PMMTVBPXYUFOBA-RXVVDRJESA-N 348.402 2.339 30 1 EEEF CC(=O)O[C@@H]1O[C@H](OC(C)=O)[C@H]2CC[C@@H]3C(C)(C)[C@H]4C[C@@]23C1=CC4=O 2356696889 YUEBDHFRUOFFJT-PDFIYWEVSA-N 348.395 2.363 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@H]1O)[C@@H](C(=O)O)[C@@H]1[C@@]2(C)CCC[C@@]31OC2=O 85800285 MBNDVMTZEKAWKP-LDVUWJDQSA-N 332.396 2.136 30 1 EEEF in-man CS(=O)(=O)Nc1ccccc1Cc1nc2cccc(C#N)c2[nH]1 586948620 KMHQBQHZYLROKM-UHFFFAOYSA-N 326.381 2.397 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc(S(=O)(=O)CCN)cc1 587917857 UXSGKLUGJCDUNP-UHFFFAOYSA-N 349.839 2.481 30 1 EEEF N#C[C@@H](C(=O)Nc1ccc([S@@](=O)C(F)(F)F)cc1)C(=O)C1CC1 169714952 HWZMCOGRZDFBES-QVQLBTGDSA-N 344.314 2.371 30 1 EEEF C=C1C(=O)O[C@@H]2C[C@@H](COC(C)=O)CCC=C(C(=O)OC)CC[C@@H]12 2356493719 DRSUBRLQXQEHHE-CWRNSKLLSA-N 336.384 2.327 30 1 EEEF COc1ccccc1N/N=C1\CC[C@@H](C)n2c1ncc(C(=O)O)c2=O 40466639 VOSMIVRLZSSJJP-MDSXTQFQSA-N 342.355 2.121 30 1 EEEF O=C(/C=C/c1cccc2ccn(S(=O)(=O)c3ccccc3)c12)NO 84668670 RSEZOFMXXNCCPB-MDZDMXLPSA-N 342.376 2.397 30 1 EEEF Nc1nccnc1C#CCNC(=O)Cc1ccc(Cl)cc1Cl 587889663 RRRIVZGRYVDLKN-UHFFFAOYSA-N 335.194 2.076 30 1 EEEF C#CCN(C)C[C@@H]1CN2CC[C@H]1C[C@@H]2CNC(=O)Nc1ccsc1 2356298902 IYIDYUMTPGQBJD-ZMSDIMECSA-N 346.500 2.145 30 1 EEEF CCCCCCCCn1cc(CO[C@H]2CC(=O)[C@@H]3OC[C@H]2O3)nn1 1911582585 IPLWXHVSPCOUBU-GVDBMIGSSA-N 337.420 2.238 30 1 EEEF C=CC[C@]12CC(=O)[C@@H](O)[C@H]([C@@H](c3ccc(OC)c(OC)c3)[C@@H]1C)[C@H]2O 238744610 FWKAJIVKMLFWPD-DHWHARPESA-N 346.423 2.310 30 1 EEEF CCc1ccc(C(=O)CCc2nc3nc(C#N)c(C#N)nc3[nH]2)cc1 587957210 SWQLVAWDGIQIKY-UHFFFAOYSA-N 330.351 2.474 30 1 EEEF Cc1[nH]nc2c1C1(CCN(C(=O)c3ccccc3)CC1)[C@H](C#N)C(=N)O2 169690847 PRQROVPVHTVCIS-CQSZACIVSA-N 349.394 2.402 30 1 EEEF N#Cc1nccc(N2CC[C@H](S(=O)(=O)c3ccccc3Cl)C2)n1 168355103 WUVOZILMFRHSIU-NSHDSACASA-N 348.815 2.054 30 1 EEEF O=C1C=Cc2ccccc2/C1=C/NN1C(=O)[C@@H]2[C@H]3C=C[C@@H](CC3)[C@H]2C1=O 104011812 CXENGHZKMYPUDO-CHDXDLIUSA-N 346.386 2.325 30 3 EEEF C=C1C(=O)O[C@H]2C[C@]3(C=O)C=COC=C(COC(=O)C(C)C)[C@@H]3C[C@H]12 238746269 WEJGAPVLRYMYJQ-DRMAHVMPSA-N 346.379 2.307 30 1 EEEF C=C(CN(C)C)c1nc2ccc(S(=O)(=O)N(CC)CC)cc2[nH]1 587190755 NIIALYULXQHFQP-UHFFFAOYSA-N 336.461 2.168 30 1 EEEF CCSc1nc(N/N=C/c2cccs2)c2cnn(CO)c2n1 6411570 ZGLGROHLZGHDDU-MKMNVTDBSA-N 334.430 2.396 30 1 EEEF C=C1C(=O)O[C@@H]2[C@H](O)C(C)=CCCC(C)=CCC[C@]3(CO)O[C@H]3C[C@H]12 2356381446 MULWDJOXRRXULO-IHEQNBGGSA-N 348.439 2.432 30 1 EEEF C=CCNC(=O)c1cnc2c(cnn2CCC#CC)c1NC(=O)CC 26573664 NLXQWPVZXCXJDZ-UHFFFAOYSA-N 339.399 2.109 30 1 EEEF CCOC(=O)[C@@H](C#N)[C@@H]1c2ccccc2OC(=N)[C@@H]1C(=O)OCC 169719786 KJGRHZCOMOPYTQ-FPMFFAJLSA-N 330.340 2.022 30 1 EEEF O=S(=O)([C@@H]1O[C@H]1c1ccc(Cl)c(Cl)c1)N1CCOCC1 26379615 VDROCDVBBSIMQF-RYUDHWBXSA-N 338.212 2.053 30 1 EEEF C[C@H]1O[C@H]1C(=O)N[C@H](Cc1ccccc1)C(=O)OCc1ccccc1 28530221 XRLMLBLLFRZQEE-ZTFGCOKTSA-N 339.391 2.245 30 1 EEEF CC(C)C1=C[C@H]2C[C@@]3(C=O)[C@@H]4CC[C@](C)(O)[C@H]4C[C@@]2(CO)[C@@]13C(=O)O 2356465762 GEHSSDSUIBHHAH-XFYBACDRSA-N 348.439 2.018 30 1 EEEF CC1=C[C@]2(O)C(=O)C(C)=C[C@@H]3[C@H](C[C@H](O)C(C)=C[C@@H]2C1=O)C3(C)C 2356565157 QSTBGARAGIHHBB-HWEQFAERSA-N 330.424 2.361 30 1 EEEF C=CCN1CCN(CC(=O)[C@@](O)(c2ccccc2)C2CCC2)CC1 22940325 ZMNUXXPBCFVUNL-HXUWFJFHSA-N 328.456 2.047 30 1 EEEF O=C(C[C@H](S)C(F)(F)F)N[C@@H](Cc1ccc(F)cc1)C(=O)O 43066211 PGJZLTNQRTXDPB-UWVGGRQHSA-N 339.310 2.188 30 1 EEEF COC1=CC(=O)c2c(c(COC(=O)c3ccccc3)cn2C)C1=O 13557528 LRAWZIZHBZOJJF-UHFFFAOYSA-N 325.320 2.291 30 1 EEEF COCc1n[nH]c2c1[C@@H](c1ccc(OC)c(OC)c1)[C@@H](C#N)C(=N)O2 169690866 GUBJGLORYWMXBN-YGRLFVJLSA-N 342.355 2.215 30 1 EEEF O=S(=O)([C@H]1O[C@@H]1c1ccc(Cl)c(Cl)c1)N1CCOCC1 26379612 VDROCDVBBSIMQF-VXGBXAGGSA-N 338.212 2.053 30 1 EEEF CCOC1=CC(=O)/C(=C2\NNC=C2Oc2cccc(OC)c2)C=C1 100563391 YDAZVQJNHKWMTP-SDXDJHTJSA-N 326.352 2.337 30 3 EEEF C=C(CO)C(=O)O[C@H]1CC(=C)[C@@H]2CCC(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 238769581 PHJYCLCTXRJHJZ-SMLCLMEVSA-N 330.380 2.087 30 1 EEEF CN(O)C(=O)C[C@H](CCCCc1ccccc1)CP(=O)(O)O 299844558 FWCPRMVLUHPTMF-AWEZNQCLSA-N 329.333 2.431 30 1 EEEF O=Cc1ncc(C#CCNC(=O)Cc2ccc(Cl)cc2Cl)cn1 587887399 LZOIHGFTPQUMSR-UHFFFAOYSA-N 348.189 2.306 30 1 EEEF CC1=CC(=O)CC(C)(C)[C@]12N[C@H](C(=O)O)Cc1ccc(O)c(C)c12 963475070 ZWHPICJKNPIVQY-LIRRHRJNSA-N 329.396 2.440 30 1 EEEF O=C1/C(=C\c2ccco2)[C@H](CO)[n+]2cc(O)c(Cc3ccco3)cc21 1642676566 NCBGWRSEHNWMNA-KAKTVLCNSA-O 338.339 2.270 30 1 EEEF NCc1ccc(C/N=C2/[C@@H]3[C@H]4C[C@H]5[C@@H]6[C@@H]4[C@@H]2[C@@H]6C2(OCCO2)[C@H]53)cc1 1857586248 PNPIPQKWOXPTBU-ZUDPXVCLSA-N 336.435 2.217 30 1 EEEF C=C1CC[C@@H]2[C@H]([C@@H]3[C@@H]1C1=C(C[C@](C)(O)C1=O)C(=O)[C@@]3(C)O)C2(C)C 2356415982 DGXURLBVVBVHIO-TUGLXBCFSA-N 330.424 2.195 30 1 EEEF C[C@H]1Cc2ccc(F)c(Br)c2[C@](CCC=O)(C(=O)O)N1 587825287 CNZBBDHJVSYJER-RMLUDKJBSA-N 344.180 2.381 30 1 EEEF O=C(O)[C@@H]1Cc2cccc(F)c2[C@@H](c2cccc(OC[C@@H]3CO3)c2)N1 962903172 VSHFMNJQRIDHIY-UWWQBHOKSA-N 343.354 2.292 30 1 EEEF Clc1ccc(C#CCOc2nsnc2C23CN4C[C@H]2[C@@H]3C4)cc1 100829308 JVDFDVTZQWJMQV-KBPBESRZSA-N 343.839 2.435 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](CC(C)=CC(=O)[C@H](O)CC(=O)C1)OC2=O 2356723585 NKBOMIIKMNCYIQ-MZMPZRCHSA-N 332.396 2.440 30 1 EEEF CN(O)C(=O)[C@H](Cc1ccccc1)C(=O)NCc1ccc(F)cc1 45299471 JZRIMQYBETYOBO-MRXNPFEDSA-N 330.359 2.148 30 1 EEEF CC(C)C1=C[C@@H]2[C@@H]3[C@@H](C(C(C)C)=CC(=O)[C@]3(C)O)[C@H]1C(=O)[C@]2(C)O 238779531 YNYHPBIGKWCFOA-QODIPIJNSA-N 332.440 2.297 30 1 EEEF COc1ccc(Cl)cc1C#Cc1cc(C(=O)O)c(=O)n(C)c1C 587912481 PLSYCZNKISQDBM-UHFFFAOYSA-N 331.755 2.454 30 1 EEEF CC=C1CN2CC[C@@]34C5=CC(=O)C=CC5=N[C@@]23CC[C@H]1[C@@H]4C(=O)OC 2356616938 LKDWBLMHMZGRGJ-JBCDFXQESA-N 338.407 2.054 30 1 EEEF C=C(Cc1ccc(O)cc1)[C@@](O)(CO)Cc1ccc(OC)cc1O 6484005 UICXJFXGPMLFAQ-IBGZPJMESA-N 330.380 2.171 30 1 EEEF biogenic Cc1ccc2c(c1)[C@]1(C(=O)N2)C2=C(CN1C)C(=O)c1ccccc1C2=O 73298486 XNYBKQLDFJSITF-OAQYLSRUSA-N 344.370 2.464 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@]12OC(=O)[C@](C)(CC[C@@H]1O)[C@H]2[C@@H]3C(=O)O 70454941 JKQCGVABHHQYKQ-XZXFKYPMSA-N 332.396 2.136 30 1 EEEF biogenic,in-vitro Cc1nc2cc(/C=C/C(=O)NO)ccc2c(=O)n1Cc1ccccc1 96934288 DROCPQHWNIUOQA-CSKARUKUSA-N 335.363 2.272 30 1 EEEF C=C1[C@@H]2C[C@H](O)[C@H]3[C@]4(C)CC[C@H](O)C(C)(C)[C@H]4C(=O)C[C@]3(C2)[C@@H]1O 95591458 WSZHSVSVZWABOB-ANWSMTEOSA-N 334.456 2.067 30 1 EEEF C=CCc1cc(CNC(=O)CC)ccc1OC[C@@H](O)CNC(C)C 169335425 QFFLOJZKMQLTQU-KRWDZBQOSA-N 334.460 2.179 30 1 EEEF CC(C)[C@H]1[C@H](O)C(=O)C2=CC3=C(CO)[C@@H](O)CC[C@@]3(C)CC[C@@]21C 100156682 RVRMCOSMMOFDAU-LPBINRMYSA-N 334.456 2.379 30 1 EEEF C=C1C(=O)[C@@]23[C@H](O)C[C@@H]4C(C)(C)[C@@H](O)CC[C@@]4(C)[C@H]2CC[C@@H]1[C@H]3O 84641195 BAXVJERFBZODKZ-OEVGAXCVSA-N 334.456 2.067 30 1 EEEF Cc1nc2n(c(=O)c1C(=O)O)[C@@H](C)CC/C2=N\Nc1ccccc1 40631430 PTMLSROVUJDKCJ-JGASNLTESA-N 326.356 2.421 30 1 EEEF C=C1C[C@]23C[C@H]1[C@@H](O)C=C2[C@@]12CCC[C@@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)OC 238740225 USCAZUMBTXSGPI-JWHLHCCSSA-N 344.407 2.145 30 1 EEEF CS(=O)(=O)c1ccc(C(O)=C2C(=O)CCCC2=O)c(Cl)c1 96341899 NNRKAHNGSFUZKF-UHFFFAOYSA-N 328.773 2.335 30 1 EEEF COC(=O)C/C(O)=N/[C@@H](Cc1c[nH]c2cccc(Cl)c12)C(=O)O 13386791 ITVFBZXHWIFZDX-NSHDSACASA-N 338.747 2.337 30 1 EEEF endogenous,in-man COC1=CC2=C3C[C@@H]4C[C@H](OC)[C@@H](OC)C[C@@H]4CN3CCC2=CC1=O 2356847092 OTLSHWIHWKUYQL-NSMLZSOPSA-N 345.439 2.446 30 1 EEEF N#Cc1ccc(-c2ccc3c(c2)SC[C@H]2[C@H](CO)OC(=O)N32)cn1 299858248 DMXDWSQMJRNHJK-GJZGRUSLSA-N 339.376 2.412 30 1 EEEF COc1ccc(Cl)cc1C#Cc1ccc2c(c1)C(=O)NS2(=O)=O 587918763 HZMPJIBAUXKXJO-UHFFFAOYSA-N 347.779 2.181 30 1 EEEF COc1ccc(C2(C#N)CCN(CC(=O)O)CC2)cc1OCC1CC1 13588522 LFXWMJVJHWGJBK-UHFFFAOYSA-N 344.411 2.426 30 1 EEEF O=C(O)CSC1=NN/C(=C2/C=CC=CC2=O)N1Cc1ccccc1 104008735 RIMUMEXNBVONTA-DTQAZKPQSA-N 341.392 2.087 30 3 EEEF C=C[C@]1(C)C=C2C(=O)C=C3[C@@](C)([C@@H](O)CC[C@@]3(C)C(=O)O)[C@@]2(O)CC1 2356436783 ZQZVXOUQMKWMED-MVBLQPKNSA-N 346.423 2.391 30 1 EEEF COc1c(O)cc(O)c2c1OCC(=Cc1ccc(O)c(O)c1)C2=O 2356494917 XAVKZGJWLZVXHI-UHFFFAOYSA-N 330.292 2.176 30 1 EEEF Cc1ccccc1N/N=C1\CC[C@@H](C)n2c1ncc(C(=O)O)c2=O 39305379 XPILBRCHOIPYSA-OHARDZCESA-N 326.356 2.421 30 1 EEEF COCC(=O)N1[C@H](CO)[C@H](c2ccc(C3=CCCCC3)cc2)[C@@H]1C#N 95896169 NSZKTJJQZYFHQH-NLWGTHIKSA-N 340.423 2.469 30 1 EEEF O=CC(C=O)c1ccc(-c2nc3cnc(Cl)[nH]c-3n2)cc1[N+](=O)[O-] 587261405 AZGFKERDXHFICF-UHFFFAOYSA-N 345.702 2.015 30 1 EEEF C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@@]1(CCC[C@@]2(C)[C@@H](O)OC[C@H]21)COC3=O 15166330 COKCKHYUZSETSY-WCOWFJNTSA-N 346.423 2.226 30 1 EEEF C=C(C)[C@H]1C[C@H]2CC[C@@H]1[C@H]1[C@H](CC[C@@]1(O)CCNC(=N)NC)[C@]2(C)O 85549817 MKBHWZDZALSUAF-KUQQVBAHSA-N 349.519 2.251 30 1 EEEF biogenic,in-vitro C=C1C(=O)[C@@]23[C@@H](CC[C@@H]1[C@H]2O)[C@]1(C)CCC[C@](C)(CO)[C@H]1C[C@H]3O 28972758 NAXAHKFDLHFVHY-YNDYFHGHSA-N 334.456 2.068 30 1 EEEF biogenic,in-vitro C=C[C@]1(C)CCC2=C(C1)C(=O)C[C@@H]1[C@]2(C)C[C@H](O)[C@@H](O)[C@]1(C)CO 2356466352 BTYISKOGKBBMDI-RFVXBFLTSA-N 334.456 2.379 30 1 EEEF O=C(/C=C/c1cccn(Cc2cccc(Br)c2)c1=O)NO 143795148 JZRDLVKIVSVQNC-VOTSOKGWSA-N 349.184 2.178 30 1 EEEF COc1cc(/C=C/C(=O)O/N=C/c2ccccn2)cc2c1OCO2 473121162 FTUWFJNNORJMHA-NHDAZHRASA-N 326.308 2.409 30 1 EEEF C=C1C[C@H](OCC(C)C)[C@@H]2C(=C)C(=O)O[C@H]2C=C(C)[C@H](O)CC1=O 2356483575 PJRAJKIGBHSJPR-OWSLCNJRSA-N 334.412 2.352 30 1 EEEF C#C[C@]1(O)[C@H](O)C[C@@H]2[C@@H]3CCc4cc(O)ccc4[C@@H]3[C@H](OC)C[C@]21C 2356485660 OOMBHDXDTAYDBF-YMJVXHRNSA-N 342.435 2.208 30 1 EEEF C=CC[C@@]12CC(=O)[C@H](O)[C@@H]([C@H](c3ccc(OC)c(OC)c3)[C@H]1C)[C@H]2O 2356602595 FWKAJIVKMLFWPD-NJBWUTIFSA-N 346.423 2.310 30 1 EEEF Cc1ccccc1N/N=C1\CC[C@H](C)n2c1ncc(C(=O)O)c2=O 39305377 XPILBRCHOIPYSA-BTNWAMHGSA-N 326.356 2.421 30 1 EEEF COCCCCn1c(=O)cc(Nc2ccc(C)c(CC#N)c2)[nH]c1=O 13522360 PMTTVNSNTYBVTM-UHFFFAOYSA-N 342.399 2.081 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@@]1(C)CCC[C@]2(CO)C(=O)O[C@@H]([C@H]3O)[C@@H]21 14812352 RDUNXXWNAKBVER-ZMFRAZPKSA-N 332.440 2.434 30 1 EEEF endogenous,in-man C=C(CO)[C@H]1CC2=CC[C@@H]3[C@@](C)(CO)[C@H](O)CC[C@@]3(C)[C@@H]2[C@@H](O)C1 207619284 FISRUIAPOPDKNG-TUFIBKJQSA-N 336.472 2.028 30 1 EEEF C=CCNC(=O)Cn1nnc(-c2ccc(-c3ccc(OC)cc3)cc2)n1 4860080 MRVYLLLLTIOEDV-UHFFFAOYSA-N 349.394 2.318 30 3 EEEF C=C1C[C@@]23C[C@@H]1CC[C@@H]2[C@]12OC(=O)[C@@](C)(CC[C@H]1O)[C@H]2[C@@H]3C(=O)O 104365536 JKQCGVABHHQYKQ-NYKQURABSA-N 332.396 2.136 30 1 EEEF in-man C=C1C(=O)[C@@]23C[C@H]1C[C@H](O)[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@H]1C[C@H]3O 2356613907 BSPNTRYRRCCKFJ-KENGMEBKSA-N 348.439 2.161 30 1 EEEF O=C(CN1C(=O)S/C(=C\c2cccc3ccccc23)C1=O)NO 45497533 KGTWEQFPQUGRSO-JYRVWZFOSA-N 328.349 2.382 30 1 EEEF O=C(NO)c1ccc(N[C@H]2CCN(CCc3ccccc3)C2=O)cc1 169223270 OEOIWMTTYKVUJA-KRWDZBQOSA-N 339.395 2.061 30 1 EEEF COc1cc(/C=C/C(=O)Nc2ccc(CC(=O)NO)cc2)ccc1O 1857555109 WHIYSZYGQFLNPC-WEVVVXLNSA-N 342.351 2.101 30 1 EEEF C=C1C(=O)O[C@@H]2C=C(C)[C@H](O)C[C@@H]3O[C@]3(C)C[C@H](OCC(C)C)[C@@H]12 2356671229 RDYCVUNQBCWGOT-YNNDZGMISA-N 336.428 2.384 30 1 EEEF CNc1nc(Nc2ccc(C(=O)NC(C)C)cc2OC)ncc1C#N 169705120 WFQHGAPAKZMNFQ-UHFFFAOYSA-N 340.387 2.280 30 1 EEEF C=C(C)C#C[C@@](O)(C(=O)O[C@H]1CN2CCC1CC2)c1ccccc1 1640777 GBTXSVZHHMYRNF-ICSRJNTNSA-N 325.408 2.091 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@@H]2[C@@]12CC[C@H](O)[C@@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100778376 QYXZQZMPZUEEML-TZGNGTQESA-N 346.423 2.384 30 1 EEEF endogenous,in-man C=C1C[C@@]23C[C@H]1[C@H](O)C[C@H]2[C@]12CCC[C@@](C)(C(=O)OC1)[C@@H]2[C@H]3C(=O)O 100776682 ZCRLGANQNRMURE-CZGCYONISA-N 346.423 2.384 30 1 EEEF endogenous,in-man C=C1C(=O)[C@]23C[C@H]1CC[C@H]2[C@]1(C)[C@@H](O)CC[C@@](C)(C(=O)O)[C@@H]1C[C@@H]3O 72120341 LRECIABFFPIQSO-VQHPJEMPSA-N 348.439 2.161 30 3 EEEF C=C1[C@H]2C[C@@H]3[C@@H]4C[C@@H](C)[C@@]5(CC[C@](CO)(CC[C@H]1O)[C@H]2[C@H]35)C(=O)O4 1857641028 AVNWGGNJKGTWGP-MRXVPZOFSA-N 332.440 2.290 30 1 EEEF NC1=C(c2ccccc2)C(=O)CN1c1ccccc1N1CCOCC1 3183630 UNXINBSXPNGWQR-UHFFFAOYSA-N 335.407 2.240 30 3 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@H]3C=C(C)[C@@H](C[C@H]3C(C)C)[C@H]2C1=O 169304349 PBDZFTMSQJXALQ-ZQNQSHIBSA-N 347.484 2.021 30 1 EEEF C=C[C@@]1(C)CCC2=C([C@H]1O)[C@@H](O)C(=O)[C@H]1C(C)(C)CC[C@@H](O)[C@]21C 199894508 KKWFUTJLCATXQH-QTJPKYNYSA-N 334.456 2.377 30 1 EEEF COc1cc2c(cc1OC)[C@]13C[C@@H](OC)CC[C@@]14O[C@H]4CN3CCC2 238771364 HRLNMOQNWVDXBD-GAZPGATBSA-N 345.439 2.497 30 1 EEEF O=C(NO)/C(=C\c1ccc(F)cc1)C(=O)NCc1ccc(F)cc1 95572743 AFTNYQQEGYCLRW-DHDCSXOGSA-N 332.306 2.170 30 1 EEEF C=C(C)C(=O)O[C@H]1CC(=C)C2=C([C@H]3OC(=O)C(=C)[C@H]13)[C@H](C)CC2=O 14498916 YHDIZVVHFZZTPO-DCLMNAJPSA-N 328.364 2.438 30 1 EEEF C[C@@H]1C[C@H]2O[C@@H]2CCCCC(=O)Cc2cc(O)cc(O)c2C(=O)O1 101510547 YXPSTSCHAVSCKS-UHNFBRDESA-N 334.368 2.486 30 1 EEEF CC1=C[C@]2(O)C(=C[C@](C)(O)CC[C@@H]3[C@H](C[C@@H](C)[C@@H]2O)C3(C)C)C1=O 2356515847 CZUBZNDQQZRXMB-GSRMNPCBSA-N 334.456 2.377 30 1 EEEF C=C1[C@@H](OC(=O)C(C)C)C[C@@]2(O)C(=C)CC[C@@H]3C(=C)C(=O)O[C@H]3[C@H]12 2356650628 LUUJHRSUAVIZOX-LAIHZFQQSA-N 332.396 2.309 30 1 EEEF C=C1CC[C@@H]2C(=CC=CC(C)(C)O)C(=O)OC[C@@H]2C(=C)C[C@H](O)[C@H]1O 2356711540 DFVRPHGROBFFBS-BGTYHANMSA-N 348.439 2.047 30 1 EEEF CC(C)C[C@H](C(=O)NO)C(=O)NCc1ccc(C(F)(F)F)cc1 35276507 DTDRBGDWVVJPEW-LBPRGKRZSA-N 332.322 2.489 30 1 EEEF CCCCCCCC[S@@+](C)CC(P(=O)(O)O)P(=O)(O)O 34803952 HJUIIHFOXRYVDU-FQEVSTJZSA-O 349.346 2.277 30 1 EEEF C=C1C(=O)O[C@H]2C[C@]3(CO)C=COC=C(COC(=O)C(C)C)[C@@H]3C[C@H]12 238735173 IWDVYGYZNDTSSN-DRMAHVMPSA-N 348.395 2.100 30 1 EEEF O=C1C=C/C(=C\NN2C(=O)c3cccc4cccc(c34)C2=O)C(O)=C1 13126399 HARJVSQBPXKKME-ZRDIBKRKSA-N 332.315 2.405 30 3 EEEF C=CCNC(=O)c1cc(S(=O)(=O)N2CCC[C@@H](C)C2)ccc1F 3020442 HSDQTTDKCDZKIL-GFCCVEGCSA-N 340.420 2.162 30 1 EEEF CCCNC(=N)N/N=C/c1ccc(-c2cn3ccccc3[n+]2C)cc1 26818470 GOMRSTXVMUTEGP-LPYMAVHISA-N 335.435 2.289 30 1 EEEF C[C@@H]1CCC(/C=N/c2ccccc2F)=C2NC=C(C(=O)O)C(=O)N21 100771965 KCAUDGFTUAZJFX-OQOREVAYSA-N 329.331 2.322 30 1 EEEF N#C[C@@H]1C[C@H](F)CN1C(=O)[C@@H](N)Cc1csc(-c2ccccc2)n1 103248363 FXZKDUJFTODIHQ-QEJZJMRPSA-N 344.415 2.142 30 1 EEEF CC(=O)CC1=C2C(=O)O[C@]3(C)CC[C@@H]4[C@H]([C@H]([C@@H]23)[C@@](C)(O)C1=O)C4(C)C 2356482935 BTLNQUGRPABJQH-DCAULJKXSA-N 346.423 2.210 30 1 EEEF CC1=C[C@H](OC=C2C(=O)O[C@@H]3C4=C(C[C@@H]23)C(=O)CCC4(C)C)OC1=O 2356498063 HZXNZCJZYALICU-JJMVLAAESA-N 344.363 2.347 30 1 EEEF C=C1C(=O)[C@]23[C@@H](O)[C@@H]1CC[C@@H]2C(=C)[C@@H](C(C)(C)CCCO)C[C@H]3O 2356737580 FBXNWXLXYGRNOE-ZZWCWMLESA-N 334.456 2.235 30 1 EEEF CCN/C(=N\S(=O)(=O)c1ccc(Cl)cc1)N1C[C@@H](CC)C=N1 72123463 RMRMGNRTOXJZLL-NSHDSACASA-N 342.852 2.322 30 1 EEEF Cc1ccccc1N/N=C1/C(=O)Nc2ccc(S(=O)(=O)O)cc21 146044511 ZUESAPXTNJTTAU-UHFFFAOYSA-N 331.353 2.010 30 1 EEEF CCOC(=O)C1=C(Nc2cccc(Br)c2)OCC1=O 1857570053 AMJDVTFCSNEBPL-UHFFFAOYSA-N 326.146 2.235 30 1 EEEF CC=C(C)C(=O)O[C@@H]1[C@@H](O)[C@@H](O)[C@@]2(C)[C@H]3C(=O)C=C(C)[C@H]2[C@H]3C1(C)C 2356496380 HOXNGFVTRBWUMU-MLBSSRPKSA-N 348.439 2.024 30 1 EEEF C#C[C@]1(O)C[C@H](O)[C@@H]2[C@@H]3CCc4cc(O)ccc4[C@@H]3[C@H](OC)C[C@]21C 2356613657 TYTYJGWQMLLBDD-FVCOPRDSSA-N 342.435 2.208 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1C[C@H](O)[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@H]1C[C@@H]3O 2356613908 BSPNTRYRRCCKFJ-KUXGFGIDSA-N 348.439 2.161 30 1 EEEF C[C@H]1CC/C(=N\N(C)c2ccccc2)c2ncc(C(=O)O)c(=O)n21 40641080 DXCAOAFKYKPQRQ-FXONDUCNSA-N 326.356 2.137 30 1 EEEF N#CCNC(=O)[C@H](NC(=O)c1ccccc1)SC1CCCCC1 82064733 HLAIIAJZJGMXPW-QGZVFWFLSA-N 331.441 2.448 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1CC[C@@H]2[C@]1(C)[C@H](O)CC[C@](C)(C(=O)O)[C@@H]1C[C@@H]3O 2356410450 LRECIABFFPIQSO-JFVSWMOOSA-N 348.439 2.161 30 1 EEEF C=CC[C@]12CC(=O)[C@H](O)[C@H]([C@@H]1O)[C@H](c1ccc(OC)c(OC)c1)[C@H]2C 2356602594 FWKAJIVKMLFWPD-KHDXPSLXSA-N 346.423 2.310 30 1 EEEF COC(=O)C[C@@H]1C(=O)C=CN(Cc2cccc(C(F)(F)F)c2)C1=O 957624379 NDWZIJCCDQUZRN-GFCCVEGCSA-N 341.285 2.310 30 1 EEEF O=C(NO)[C@H](CCc1ccccc1)C(=O)NCCCc1ccccc1 13777240 XKSDROXJWZNHOT-GOSISDBHSA-N 340.423 2.490 30 1 EEEF O=C(O)[C@H](CS)NCc1c2ccccc2[n+]([O-])c2ccccc12 17193666 KMURGFIZSJATNI-AWEZNQCLSA-N 328.393 2.099 30 1 EEEF N#CCCn1c(SCC(=O)NC[C@@H]2CCCO2)nc2ccccc21 3504289 HYEGCIFIULAWCR-ZDUSSCGKSA-N 344.440 2.337 30 3 EEEF C=C(C)C(=O)O[C@@H]1C[C@@H]2C(=C)C[C@H](O)[C@@H]3[C@H](C)C(=O)O[C@H]3[C@@H]2C1=C 2356488762 ZNXKZMIVEDDWGE-XHMLNNKLSA-N 332.396 2.165 30 1 EEEF C#CCN1C[C@H](COCCCC)Oc2cccc(F)c2S1(=O)=O 96021259 DNNYIMBJLOXRDM-CYBMUJFWSA-N 341.404 2.027 30 3 EEEF N#Cc1cnc(NC(=O)N2CCCc3ccc(C=O)nc32)cc1C#N 1772613394 QSEXTDMSEJBZCD-UHFFFAOYSA-N 332.323 2.017 30 1 EEEF C[C@H]1CCC[C@H](NC(=O)COC(=O)COc2ccc(C#N)cc2)[C@@H]1C 4994198 AUBMZDATDBAYQC-VBQJREDUSA-N 344.411 2.421 30 1 EEEF Cc1nc(C(=O)NCCCC(=O)NO)cc2c1[nH]c1ccccc12 210717997 CEOCISGEFDKIGI-UHFFFAOYSA-N 326.356 2.040 30 1 EEEF C=C1C(=O)O[C@@H]2[C@H]3[C@@H](C)C(=O)C[C@@H](O)[C@]3(C)C[C@@H](OCC(C)C)[C@@H]12 238752842 BQKSKQIZKSAQEI-PENRQTSMSA-N 336.428 2.121 30 1 EEEF N#CCC(=O)N1CCCC[C@]12CCCN(c1ncnc3[nH]ccc13)C2 169699025 DHDGEXQRDYQYKP-GOSISDBHSA-N 338.415 2.223 30 1 EEEF COc1cccc(Nc2ncc3nc(C)c(=O)n(CCC#N)c3n2)c1 4238446 CHYCPHNXHGMPBZ-UHFFFAOYSA-N 336.355 2.161 30 1 EEEF CCc1nc2n(c(=O)c1C(N)=O)[C@H](C)CC/C2=N/Nc1ccccc1 100760743 ROUYGSNPBKRWQM-COQKLVBISA-N 339.399 2.076 30 1 EEEF C[C@](COc1ccc(-c2ccccc2)cc1)(C(=O)NO)S(C)(=O)=O 73310071 PBUOBWNMBHSRIY-KRWDZBQOSA-N 349.408 2.041 30 1 EEEF C=C1C[C@]23C[C@H]1CC[C@H]2[C@]12OC(=O)[C@](C)(CC[C@H]1O)[C@H]2[C@@H]3C(=O)O 70454931 JKQCGVABHHQYKQ-YZVDRFENSA-N 332.396 2.136 30 1 EEEF biogenic,in-vitro C=C1[C@H]2CC[C@@H]3C[C@@]2(C[C@H](O)[C@]2(O)[C@@H]1C[C@H](O)C2(C)C)C[C@@]3(C)O 238782694 AHMSDGIIEDDLQI-NLIBZLNVSA-N 336.472 2.003 30 1 EEEF C=C1[C@H]2C[C@@H]3[C@](C(=O)C[C@@H]4C(C)(C)[C@H](O)CC[C@]43C)([C@H](O)C2)[C@@H]1O 238785729 FYHBINXIARYPCI-CGKVIXHESA-N 334.456 2.067 30 1 EEEF C[C@@H]1NC=CC(=O)[C@@]12N[C@H](C)Cc1cc(Br)c(F)cc12 587792916 INJXIIPYPDFSAK-CEFVDNRUSA-N 339.208 2.392 30 1 EEEF C[C@@H](Sc1nc(N)cc(O)n1)c1nc2cc(Cl)nc(C#N)c2[nH]1 586963039 XIVCAWKQXXBTRP-RXMQYKEDSA-N 347.791 2.414 30 1 EEEF Cn1c(=O)ccc2cc(S(=O)(=O)Nc3cccc(C#N)c3)ccc21 1772646177 PVTLXVQZRVHRSH-UHFFFAOYSA-N 339.376 2.211 30 1 EEEF C#Cc1ccc2c(c1)O[C@H](COc1ccc(F)c(C(N)=O)c1F)CO2 1772577399 DTERGCNTHRPYJW-NSHDSACASA-N 345.301 2.264 30 1 EEEF CC1=C(CCCC(=O)N2CCN(C)CC2)C(=O)c2ccccc2C1=O 13861888 GGEHMURTRHZARM-UHFFFAOYSA-N 340.423 2.326 30 1 EEEF CCC#C[C@](O)(C(=O)OC1C[C@@H]2CC[C@H](C1)N2C)c1ccccc1 1641766 CPSOCUUSNHHZOV-NHJHPMQKSA-N 327.424 2.456 30 1 EEEF N#Cc1cccc(CN2C[C@H]3[C@@H](C2)OCC(=O)N3c2ccccc2)c1 2356388133 STXKMDYQBAQXPG-RBUKOAKNSA-N 333.391 2.174 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@@H]2[C@@H]3C=C(C)[C@H](C[C@H]3C(C)C)[C@H]2C1=O 101880726 PBDZFTMSQJXALQ-VQJWOFKYSA-N 347.484 2.021 30 1 EEEF C[C@@H](/N=c1\c(O)c(O)\c1=N/CCc1ccc(C#N)cc1)C(C)(C)C 28227487 VMMSHUGXUNUKIS-POHHHJJASA-N 325.412 2.324 30 1 EEEF C=C1C[C@@H]2O[C@@H]2[C@](C)(O)CC[C@@H]2C3=C[C@H]([C@@H]4OC4(C)C)O[C@H]3OC[C@H]12 2356515464 PVAIAJLEMKCLCA-OGYOJLTKSA-N 348.439 2.336 30 1 EEEF O/N=C(/c1cccnc1Oc1ccc(-n2cncn2)cc1)N1CC=CC1 72180284 SIVWDUUMKKCDNE-XLNRJJMWSA-N 348.366 2.462 30 1 EEEF C=CCN1C(=O)S[C@@H](Cc2nc3cc(Cl)nc(C#N)c3[nH]2)C1=O 587038423 HPEOYMAWPNIRIQ-VIFPVBQESA-N 347.787 2.275 30 1 EEEF C=C1C(=O)O[C@H]2[C@@H]1[C@@H](OC(=O)C(O)=CCO)CC(C)=C1CC=C(C)[C@H]12 2356493433 SWIFBBRXRXNLBH-VVLHAWIVSA-N 346.379 2.117 30 1 EEEF C=C1C(=O)O[C@@H]2CC(=C)[C@H]3[C@H](C[C@H]12)[C@@](C)(O)C[C@H]3OC(=O)C(C)C 2356693949 RPFZMZXPFLBITO-OJOYRBBKSA-N 334.412 2.389 30 1 EEEF C=C1C(=O)O[C@@H]2/C=C(/C)[C@@H](O)C[C@H]3O[C@]3(C)C[C@@H](OCC(C)C)[C@@H]12 238774489 RDYCVUNQBCWGOT-MGZBKCODSA-N 336.428 2.384 30 1 EEEF C[C@@H]1CCN(C(=O)CC#N)[C@]12CCCN(c1ncnc3[nH]ccc13)C2 169699010 FDSLGXNJYBLDDV-ACJLOTCBSA-N 338.415 2.079 30 1 EEEF COC(=O)c1ccc(-c2c(C#N)[n+]([O-])c3cc(C)c(C)cc3[n+]2[O-])cc1 40877759 DWXOYSAILRYDCW-UHFFFAOYSA-N 349.346 2.049 30 1 EEEF N#C[C@@H]1CCCN1C(=O)CNC(=O)c1ccnc2c(Cl)cccc12 96270272 GVEVKFYZSMHFEB-NSHDSACASA-N 342.786 2.133 30 1 EEEF Cc1nc(C#Cc2ccc(C(=O)N[C@H](C)C(C)(C)O)nc2)cs1 96933593 JZOIIWOBUPBBCB-LLVKDONJSA-N 329.425 2.136 30 1 EEEF C[C@H]1Cc2cc(Br)c(F)cc2[C@@]2(COC=CC2=O)N1 587836680 XGVUTVUEYPXGQD-RMLUDKJBSA-N 326.165 2.431 30 1 EEEF CNC(=O)/C(=N/OC)c1ccccc1COc1ccc(Cl)cn1 103193396 OXORIZFZEKALDU-HMMYKYKNSA-N 333.775 2.411 30 1 EEEF N#Cc1c(N)nc(N2CCSCC2)c(C#N)c1-c1ccc(O)cc1 28875598 ROYOEKXTTUODAA-UHFFFAOYSA-N 337.408 2.333 30 1 EEEF C=C1C[C@@]23C[C@@]1(C)CC[C@@H]2[C@@]12C=C[C@H](O)[C@@](C)(C(=O)O1)[C@H]2[C@H]3C(=O)O 2356832911 JXHBGFBFCVSITH-AYHYJEAPSA-N 344.407 2.302 30 1 EEEF C[C@@H](Oc1ccc(C#N)cc1)c1nc2cccc(S(N)(=O)=O)c2[nH]1 587189661 DYQIRJKFYTURMZ-SNVBAGLBSA-N 342.380 2.222 30 1 EEEF C#CCN(Cc1ccc2nc(N)nc(N)c2n1)c1ccc(C(C)=O)cc1 5833592 SSWYRLKEHKZJPV-UHFFFAOYSA-N 346.394 2.032 30 1 EEEF CN(CCCC[C@@H](C=O)NC(=O)OC(C)(C)C)C(=O)C(F)(F)F 13588608 HPGFTHGEURVKTK-JTQLQIEISA-N 340.342 2.270 30 1 EEEF N#CCC(=O)N1CCC[C@@]12CCN(c1c(Cl)cnc3[nH]ncc13)C2 169699028 UPPRBFBTNAYEJK-INIZCTEOSA-N 344.806 2.096 30 1 EEEF C=C1[C@@H](CC=C2COC[C@@H]2O)[C@@]2(C)CC[C@@H](O)C(C)(C)[C@H]2C[C@H]1O 2356416316 PQJNKPQZAXZXLP-KMBCLYMLSA-N 336.472 2.434 30 1 EEEF C=C1C[C@@]23C[C@H]1C(=O)C[C@@H]2[C@]1(C)CCC[C@](C)(C(=O)O)[C@@H]1[C@H](O)[C@@H]3O 2356378091 VYSJMJOARWDSIN-IVHSOPPWSA-N 348.439 2.161 30 1 EEEF C[C@H](O)C[C@@H]1O[C@H]1C=CC=Cc1cc2cc(O)cc(O)c2c(=O)o1 2356744598 TYXXEQMKBIKKOL-HNHYXYPQSA-N 330.336 2.312 30 1 EEEF C=CCOc1cc(-n2nnc3c(c(C)nn3C)c2=O)c(F)cc1Cl 98082560 WDHXQQYVMZJJTB-UHFFFAOYSA-N 349.753 2.180 30 1 EEEF C=CCc1cccc2nc([C@@H](CC(N)=O)NC(=O)CC(C)C)[nH]c12 587202865 HFPYZOCZEUVCES-CQSZACIVSA-N 328.416 2.370 30 1 EEEF COC(=O)c1nc(OC)ncc1C#Cc1cc(Cl)ccc1OC 587903121 KPIXDIRKSGSKLT-UHFFFAOYSA-N 332.743 2.334 30 1 EEEF C[C@H](CO)C1=C(O)C(=O)C2=C(C[C@H](O)[C@@H]3C(C)(C)CCC[C@@]23C)C1=O 504703446 KSXQZHNLPHBARZ-NVEIYHCCSA-N 348.439 2.473 30 1 EEEF biogenic C=C1CC[C@H]2[C@@H]([C@H]3C(COC(C)=O)=CO[C@H](OC(C)=O)[C@@H]13)[C@]2(C)C=O 238748993 BUPSRZRAPQPIRE-XREYTECCSA-N 348.395 2.386 30 1 EEEF O=C(C1CC1)[C@H](c1ccccc1F)N1CC[C@H]2C(=CC(=O)[S@@]2=O)C1 299851199 BGWGSGYBPUVHJJ-OWWADGOUSA-N 347.411 2.136 30 1 EEEF C/C1=C\[C@@H](O)C/C(CO)=C/C[C@@H]2CCC3=C(C(=O)[C@@H]1[C@H]3O)C2(C)C 238775738 PLSLPANFUZMMNZ-DNLMZOLDSA-N 332.440 2.299 30 1 EEEF C[C@@H]1Cc2cc(Br)c(F)cc2[C@@]2(COC[C@@H]2C#N)N1 587744418 ZUMGHCAWUGYXMG-YACGNSKGSA-N 325.181 2.488 30 1 EEEF C=C(C)C(=O)O[C@H]1CC(C)=C2C(=O)C=C(C)[C@H]2[C@@H]2OC(=O)C(=C)[C@@H]12 14499038 KFNIILPAQWDAJK-ORQFMDKSSA-N 328.364 2.438 30 1 EEEF C=C1[C@H](O)[C@@]23C(=O)C[C@H]4[C@@](C)(CO)CCC[C@@]4(C)[C@H]2CC[C@H]1[C@@H]3O 2356407507 DBVNQUBNOIPPEM-SUQCKXMHSA-N 334.456 2.068 30 1 EEEF CCN/C(=N\S(=O)(=O)c1ccc(Cl)s1)N1C[C@@H](CC)C=N1 72124407 SBCKDJZRMMRMDJ-VIFPVBQESA-N 348.881 2.383 30 1 EEEF C=C1C(=O)O[C@H]2C[C@@H](C)[C@H]3[C@@H](O)CC[C@@]3(C)[C@@H](OC(=O)/C=C/C)[C@@H]12 238766835 HSXLCTYJIGXUOE-GKLIPXAUSA-N 334.412 2.389 30 1 EEEF CS(=O)(=O)Nc1ccccc1Cc1nc2ccc(C#N)cc2[nH]1 586950031 NCICXVWKXQGELE-UHFFFAOYSA-N 326.381 2.397 30 1 EEEF C=C1C(=O)OC2=C(C)[C@@]3(O)C=C[C@@](C)(C[C@H](OC(=O)C(C)C)[C@H]1C2)O3 2356534615 NQTBGYYRPIDDKV-KNEBKQPDSA-N 348.395 2.385 30 1 EEEF O=C(NO)[C@H]1CN(Cc2cccc(Oc3ccc(F)cc3)c2)C(=O)N1 28227690 XYJDYCVPZSFGLI-OAHLLOKOSA-N 345.330 2.017 30 1 EEEF CCCC[C@H](O)C#C[C@@H](O)/C=C\CCCCC[C@H](O)CC(=O)O 138652407 IRDUBXGVWQSMKQ-AXGJCRNTSA-N 326.433 2.244 30 1 EEEF N#C[C@@H]1CCCN1C(=O)CNC(=O)c1ccnc2cccc(Cl)c12 96270280 ALYYADQHQGUFHD-NSHDSACASA-N 342.786 2.133 30 1 EEEF N#Cc1cnc2ccc(-c3c(-c4ccc(F)cc4)ncn3CCO)nn12 1857552084 AIQZOKCURJAIIL-UHFFFAOYSA-N 348.341 2.263 30 1 EEEF COc1cc(/N=C2\NCc3ccnc(OC4CCOCC4)c32)ccn1 96176046 KSRRWGICBHQQCA-UHFFFAOYSA-N 340.383 2.225 30 1 EEEF N=c1[nH]cc2nc(CCCCCC#CCO[C@H]3CCCCO3)nc-2[nH]1 586910065 LDKJPNOJZAEHMT-MRXNPFEDSA-N 343.431 2.367 30 1 EEEF Cc1c(O)cc(C[C@@H](C)O)c2cc(C3=CC(=O)C[C@@H](C)O3)c(=O)oc12 14594759 QOKXUEDIOODDAI-NXEZZACHSA-N 344.363 2.449 30 1 EEEF biogenic N#Cc1ccc(C(=O)N2CCC3(CC2)C(=O)Nc2ccccc23)cn1 72156577 AOGPCPSPPLBKAP-UHFFFAOYSA-N 332.363 2.079 30 1 EEEF N#Cc1cc2nc([C@@H](N)Cc3ccc([N+](=O)[O-])cc3)[nH]c2cc1C#N 587269964 GSNYACMTBBZCRJ-AWEZNQCLSA-N 332.323 2.457 30 1 EEEF CC=CC(=O)O[C@H]1[C@H](O)[C@]2(C)[C@@]3(C)CCC(C)=C[C@H]3O[C@H]1[C@]21CO1 2356845519 OFRDWLCMCXXLSX-RJHGQXRGSA-N 334.412 2.138 30 1 EEEF COC1=C(O)C(=O)c2c(O)c3c(c(OC)c2C1=O)C[C@@H](C)O[C@H]3C 40407137 UIBXAMHOHCDVSB-RQJHMYQMSA-N 334.324 2.218 30 1 EEEF biogenic,in-vitro O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1cnc(O)nc1 587887656 XGIHQUCXNQAFFZ-UHFFFAOYSA-N 336.178 2.199 30 1 EEEF COc1ccc(CCc2nc(CCC(=O)NO)cs2)cc1OC 1857550107 QCRSLSTWSPYKAJ-UHFFFAOYSA-N 336.413 2.384 30 1 EEEF C=C1C[C@@]23C[C@@H]1CC=C2[C@@]12CC[C@H](O)[C@](C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O 104377881 BSBICXIQCTXPMN-OEAMYZJLSA-N 330.380 2.056 30 1 EEEF in-man COc1ccc(S(=O)(=O)OCC[C@H]2CC(C)(C)OC2=O)cc1 64634088 XRUVELZYLVNPFK-NSHDSACASA-N 328.386 2.132 30 1 EEEF in-vitro C=C1C[C@@]23C[C@H]1CC[C@@H]2[C@@]12OC(=O)[C@@](C)(CC[C@@H]1O)[C@@H]2[C@H]3C(=O)OC 2356559837 NZAMXUVSJOQDKJ-PWQCKLAQSA-N 346.423 2.225 30 1 EEEF C[C@@]12COC(=O)N1C(=O)N(c1ccc(C#N)c(C(F)(F)F)c1)C2=O 40752888 WQKXGQFGVRREAS-ZDUSSCGKSA-N 339.229 2.255 30 1 EEEF CCCOc1ccccc1C(=O)N[C@@H](CC(C)C)C(=O)NCC#N 82064927 PHNNDUSKVAOEHT-HNNXBMFYSA-N 331.416 2.260 30 1 EEEF N#C[C@H]1CCCC[C@@H]1n1cc(C(N)=O)c(Nc2ccc(CN)cc2)n1 221195872 OPMIREBHPMXEAE-CJNGLKHVSA-N 338.415 2.439 30 1 EEEF C/C=C(\C)C(=O)O[C@H]1CCN2C[C@@H]3C[C@@H](CN4C=CC(=O)C[C@H]34)[C@@H]2C1 238753718 ANLPQANGWMODSI-CCTLBVOSSA-N 344.455 2.136 30 1 EEEF CC(C)C1=C[C@H]2[C@@H]3[C@@H](C(C(C)C)=CC(=O)[C@@]3(C)O)[C@H]1C(=O)[C@]2(C)O 263590573 YNYHPBIGKWCFOA-KDHDFKAYSA-N 332.440 2.297 30 3 EEEF CCOC(=O)C1=C(Nc2ccccc2Br)OCC1=O 1857614414 NETVPHUJELLTAS-UHFFFAOYSA-N 326.146 2.235 30 1 EEEF C=C1C(=O)[C@@]23C[C@H]1[C@H](O)C[C@@H]2[C@]1(C)CCC[C@](C)(CO)[C@@H]1C[C@@H]3O 2356404716 VFCKRZZDFUUVFU-YTBLMUGYSA-N 334.456 2.068 30 1 EEEF C=C1[C@H](O)[C@@]23C[C@H]1CC[C@H]2[C@]12CCC[C@](C)(C(=O)O1)[C@@H]2[C@H]3C(=O)O 100778344 MBNDVMTZEKAWKP-YPPSCPLWSA-N 332.396 2.136 30 1 EEEF endogenous,in-man CCN/C(=N\S(=O)(=O)c1cccc(Cl)c1)N1C[C@@H](CC)C=N1 72122808 MKGZFKFZQDUADL-NSHDSACASA-N 342.852 2.322 30 1 EEEF C=C1C(=O)O[C@H]2[C@H]1[C@H](OC(=O)/C(C)=C\C)CC(=C)[C@@H]1[C@@H](O)C=C(C)[C@H]21 238771194 JEAWGNYMYMHNGM-LSLHFRIISA-N 344.407 2.475 30 1 EEEF biogenic CCCC[C@H](O)C#C[C@@H](O)C=CCCCCC[C@H](O)CC(=O)O 2356516006 IRDUBXGVWQSMKQ-ULQDDVLXSA-N 326.433 2.244 30 1 EEEF C=CCN1C(=O)S[C@H](Cc2nc3cccc([N+](=O)[O-])c3[nH]2)C1=O 587039136 QEWKYRSZUCTWOB-SNVBAGLBSA-N 332.341 2.264 30 1 EEEF O=C1C=C[C@@]23C[C@@H](N=C4C(=O)c5[nH]cc6c5C(=NCC6)[C@H]42)SC3=C1 169723180 OVHZMAJFIKTHFC-SRBZOADZSA-N 335.388 2.099 30 1 EEEF COC1=CC(=O)[C@]2(C)c3c(O)c(C(C)=O)c(O)c(C)c3O[C@@]2(OC)C1 2356815375 CQNUVEWNKCFRQU-MSOLQXFVSA-N 348.351 2.105 30 1 EEEF N#C[C@H]1[C@H](c2ccc(-c3cccnc3)cc2)[C@@H](CO)N1C(=O)C1CC1 95896228 FYALJDMLJJPLTL-OTWHNJEPSA-N 333.391 2.337 30 1 EEEF O=C(Cc1ccc(Cl)cc1Cl)NCC#Cc1ccc(O)nn1 587890330 AQYSZIVRQTWZAN-UHFFFAOYSA-N 336.178 2.199 30 1 EEEF N#Cc1nc2nc([C@@H](CN)Cc3ccc(Cl)cc3)[nH]c2nc1C#N 587069281 HMXMPBDYVSJMIZ-SNVBAGLBSA-N 337.774 2.035 30 1 EEEF COC1=C(O)C(=O)c2c(O)c3c(c(OC)c2C1=O)C[C@H](C)O[C@@H]3C 40407146 UIBXAMHOHCDVSB-NKWVEPMBSA-N 334.324 2.218 30 1 EEEF biogenic N#CCC[C@H]1NC(=O)c2ccccc2-n2c1nc1ccccc1c2=O 2356792143 JJFMDWQPUDJAHC-OAHLLOKOSA-N 330.347 2.474 30 1 EEEF C=C1C[C@@H](O)[C@H]2O[C@]2(C)CC[C@@H]2/C(=C/C=C/C(C)(C)O)C(=O)OC[C@@H]12 40956116 DHTWVKTXQLZELP-OHFXGLPTSA-N 348.439 2.288 30 1 EEEF C=C(C#CCNC(=O)Cc1ccc(Cl)cc1Cl)C(=O)OC 587875051 NOVARGOHVFEWDD-UHFFFAOYSA-N 326.179 2.385 30 1 EEEF C=C(C)[C@@H]1CCC2=C[C@@H](OC2=O)[C@@H](C(=C)C)C(=O)C=C(C)C(=O)[C@@H]1O 2356843913 NQSGQBPUUPHFQJ-LKCYJCQHSA-N 344.407 2.462 30 1 EEEF CS/C(C)=N/OC(=O)NSNC(=O)O/N=C(\C)SC 35328278 BAKXBZPQTXCKRR-NXZHAISVSA-N 326.425 2.395 30 1 EEEF in-vitro CSCC/C(=N\Nc1ccc([N+](=O)[O-])cc1[N+](=O)[O-])C(=O)O 238785531 IRLXZFCUAWIZQW-UKTHLTGXSA-N 328.306 2.109 30 1 EEEF C=C1C[C@]23C[C@H]1C(=O)C[C@H]2[C@]1(C)CCC[C@@](C)(C(=O)O)[C@H]1[C@H](O)[C@@H]3O 238738000 VYSJMJOARWDSIN-VAEMSJHRSA-N 348.439 2.161 30 1 EEEF C=C1[C@H]2CC[C@H]3[C@](C2)([C@@H]1O)[C@H](C(=O)O)[C@H]1[C@@]2(C)CCC[C@@]31COC2=O 257483226 MJFVMFNFTCKAEV-XCNKBUIRSA-N 346.423 2.384 30 1 EEEF endogenous,in-man COc1ccc(Cl)cc1C#CC1=C(Br)[C@H](O)OC1=O 587912061 FPSASRYNGNZTSH-CYBMUJFWSA-N 343.560 2.224 30 1 EEEF C=CCNC(=S)NN1C(=O)[C@H]2[C@@H]3C[C@@H](C(C)C)[C@H](C=C3C)[C@H]2C1=O 169304345 PBDZFTMSQJXALQ-AIEDFZFUSA-N 347.484 2.021 30 1 EEEF