Index Ligand Name Ligand ID Canonical SMILES #Protein-Ligand Complex(es) 1 1,1,1,3,3,3-hexafluoropropan-2-yl 3-(3-phenyl-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate COVPDB597 c1ccccc1-c2nc(on2)C3CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F 1 2 1,1'-(1E)-(1,2-Ethenediyl)bis[2-chloro-4-boronic acid]benzene COVPDB961 OB(O)c1ccc(c(Cl)c1)/C=C/c2ccc(cc2Cl)B(O)O 1 3 1,1,1-TRIFLUORO-3-ACETAMIDO-4-PHENYL BUTAN-2-ONE(N-ACETYL-L-PHENYLALANYL TRIFLUOROMETHYL KETONE) COVPDB503 CC(=O)N[C@H](C(=O)C(F)(F)F)Cc1ccccc1 1 4 1,2-Benzenedisulfonyl fluoride COVPDB921 FS(=O)(=O)c1ccccc1S(F)(=O)=O 1 5 1-[2-(S)-AMINO-3-BIPHENYL-4-YL-PROPIONYL]-PYRROLIDINE-2-(S)-CARBONITRILE COVPDB992 N#C[C@@H]1CCCN1C(=O)[C@@H](N)Cc2ccc(cc2)-c3ccccc3 1 6 1-[(3S,5S)-5-[(2S)-2-cyanopyrrolidine-1-carbonyl]-1-(4-phenylbutanoyl)pyrrolidin-3-yl]triaza-1,2-dien-2-ium COVPDB228 [N-]=[N+]=N[C@H]1C[C@H](N(C1)C(=O)CCCc1ccccc1)C(=O)N1CCC[C@H]1C#N 1 7 [1-(5-chloro-4-oxo-4H-3,1-benzoxazin-2-yl)-2-methylpropyl] carbamic acid 1,1-dimethylethyl ester COVPDB940 CC(C)(C)OC(=O)N[C@@H](C(C)C)c(oc1=O)nc(c12)cccc2Cl 1 8 16-epi-Vellosimine COVPDB773 C/C=C([C@@H]12)/CN3[C@@H](C2)c4c(C[C@H]3[C@H]1C=O)c5c([nH]4)cccc5 1 9 1-acetyl-L-prolyl-L-valyl-L-tyrosyl-3-methyl-L-valyl-N~1~-[(1R)-1-phosphonoethyl]-L-glutamamide COVPDB857 CC(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)N[C@@H](C(C)(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C)P(=O)(Oc3ccccc3)Oc4ccccc4 1 10 1-dodecanesulfonyl chloride COVPDB715 CCCCCCCCCCCCS(Cl)(=O)=O 1 11 1-hydroxy-2,6-dioxa-3-oxo-4-phenylphosphorinone COVPDB647 OP1(=O)OC=C(C(=O)O1)c1ccccc1 1 12 1-{[hydroxy(phosphonooxy)boranyl]methyl}-1H-1,2,3-triazole-4-carboxylic acid COVPDB465 OB(Cn1cc(nn1)C(O)=O)OP(O)(O)=O 1 13 [(1R)-1-[(2,6-difluorophenyl)formamido]ethyl]boronic acid COVPDB730 OB(O)[C@H](C)NC(=O)c1c(F)cccc1F 1 14 (1R)-1-(2-THIENYLACETYLAMINO)-1-(3-CARBOXYPHENYL)METHYLBORONIC ACID COVPDB1317 OB(O)[C@@H](NC(=O)Cc1cccs1)c1cccc(c1)C(O)=O 5 15 (1R)-1-(2-THIENYLACETYLAMINO)-1-PHENYLMETHYLBORONIC ACID COVPDB1318 c1ccccc1[C@@H](B(O)O)NC(=O)Cc2cccs2 3 16 (1R)-1-(2-THIOPHEN-2-YL-ACETYLAMINO)-1-(3-(2-CARBOXYVINYL)-PHENYL) METHYLBORONIC ACID COVPDB1319 OB(O)[C@@H](NC(=O)Cc1cccs1)c1cccc(\C=C\C(O)=O)c1 1 17 (1R)-1-Acetamido-2-(3-carboxy-2-hydroxyphenyl)ethylboronic acid COVPDB565 CC(=O)N[C@@H](Cc1cccc(C(O)=O)c1O)B(O)O 1 18 (1R)-1-Phenylacetamido-2-(3-carboxyphenyl)ethylboronic acid COVPDB566 CC(=O)N[C@@H](Cc1cccc(c1)C(O)=O)B(O)O 1 19 (1R)-2-{[AMINO(IMINO)METHYL]AMINO}-1-{4-[(4R)-4-(HYDROXYMETHYL)-1,3,2-DIOXABOROLAN-2-YL]PHENYL}ETHYL NICOTINATE COVPDB177 NC(=N)NC[C@H](OC(=O)c1cccnc1)c1ccc(cc1)B1OC[C@@H](CO)O1 1 20 (1R)-2-PHENYLACETAMIDO-2-(3-CARBOXYPHENYL)ETHYL BORONIC ACID COVPDB569 OB(O)[C@H](Cc1cccc(c1)C(O)=O)NC(=O)Cc1ccccc1 1 21 (1R,2S,5R)‐2‐isopropyl‐5‐methylcyclohexylhexylphosphonochloridate COVPDB1102 CCCCCC[P@@](Cl)(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C 2 22 [(1S)-1-[(2,6-difluorophenyl)formamido]ethyl]boronic acid COVPDB762 OB(O)[C@@H](C)NC(=O)c1c(F)cccc1F 1 23 [(1S)-1-[(2-benzylphenyl)formamido]ethyl]boronic acid COVPDB731 OB(O)[C@@H](C)NC(=O)c1ccccc1Cc2ccccc2 1 24 [(1S)-1-{[2-(propan-2-yl)phenyl]formamido}ethyl]boronic acid COVPDB732 OB(O)[C@@H](C)NC(=O)c1ccccc1C(C)C 1 25 [(1S)-1-({3-fluoro-[1,1'-biphenyl]-2-yl}formamido)ethyl]boronic acid COVPDB1495 OB(O)[C@@H](C)NC(=O)c1c(F)cccc1-c2ccccc2 1 26 (1S)-1-(PHENOXYMETHYL)PROPYL METHYLPHOSPHONOCHLORIDOATE COVPDB1234 O=[P@](Cl)(C)O[C@@H](CC)COc1ccccc1 1 27 (1S,5R)-2-{[4-(methylamino)butyl]carbamoyl}-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid COVPDB196 CNCCCCNC(=O)N1CC[C@@H]2[C@H]1C(=O)N2S(O)(=O)=O 1 28 (1S,5R)-2-{[(4R)-azepan-4-yl]carbamoyl}-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid COVPDB1510 OS(=O)(=O)N1[C@@H]2CCN([C@@H]2C1=O)C(=O)N[C@@H]1CCCNCC1 1 29 (1S,5R)-2-{[(4S)-1-(2-aminoethyl)azepan-4-yl]carbamoyl}-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid COVPDB1294 NCCN1CCC[C@@H](CC1)NC(=O)N1CC[C@@H]2[C@H]1C(=O)N2S(O)(=O)=O 1 30 (1S,5R)-2-{[(4S)-azepan-4-yl]carbamoyl}-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid COVPDB1509 OS(=O)(=O)N1[C@@H]2CCN([C@@H]2C1=O)C(=O)N[C@H]1CCCNCC1 1 31 (1S,7S)-7-amino-7-benzyl-N-[(1S)-4-carbamimidamido-1-{(1S)-1,2-dioxo-2-[(2-phenylethyl)amino]ethyl}butyl]-8-oxohexahydro-1H-pyrazolo[1,2-a]pyridazine-1-carboxamide COVPDB2 NC(=N)NCCC[C@H](NC(=O)[C@@H]1CCN2CC[C@@](N)(Cc3ccccc3)C(=O)N12)C(=O)C(=O)NCCc1ccccc1 1 32 (1S,7S)-7-amino-N-[(2R,3S)-7-amino-1-(cyclohexylamino)-2-keto-1-oxoheptan-3-yl]-7-benzyl-8-oxohexahydro-1H-pyrazolo[1,2-a]pyridazine-1-carboxamide COVPDB1 NCCCC[C@H](NC(=O)[C@@H]1CCN2CC[C@@](N)(Cc3ccccc3)C(=O)N12)C(=O)C(=O)NC1CCCCC1 1 33 1-thioxy-3-hydroxy-acetone COVPDB1305 OCC(=O)CSO 1 34 2-((1-(4-Bromophenyl)-1H-1,2,3-triazol-4-yl)methyl)-4,4-dimethyl-1,2-thiazetidin-3-one 1,1-dioxide COVPDB963 CC1(C)C(=O)N(S1(=O)=O)Cc2cn(nn2)Cc3ccc(Br)cc3 1 35 2-(2-(3,4-DICHLOROPHENYL)-5-(ISOPROPYLAMINO)-6-OXOPYRIMIDIN-1(6H)-YL)-N-((S)-1-OXO-1-(THIAZOL-2-YL)-5-GUANIDINOPENTAN-2-YL)ACETAMIDE COVPDB290 CC(C)Nc1cnc(-c2ccc(Cl)c(Cl)c2)n(CC(=O)N[C@@H](CCCNC(N)=N)C(=O)c2nccs2)c1=O 1 36 2, 3-(4-BENZENESULFONYL-THIOPHENE-2-SULFONYLAMINO)-PHENYLBORONIC ACID COVPDB770 OB(O)c1cccc(NS(=O)(=O)c2cc(cs2)S(=O)(=O)c2ccccc2)c1 1 37 2-[4-({2-[(2S,5R)-2-cyano-5-ethynylpyrrolidin-1-yl]-2-oxoethyl}amino)-4-methylpiperidin-1-yl]pyridine-4-carboxylic acid COVPDB515 CC1(CCN(CC1)c1cc(ccn1)C(O)=O)NCC(=O)N1[C@H](CC[C@H]1C#N)C#C 1 38 2,4‐dioxo‐1,3,2lambda5‐benzodioxaphosphinin‐2‐olate COVPDB152 OP1(=O)OC(=O)c2ccccc2O1 1 39 2-(4-hydroxyphenyl)-N-(5-methylene-2-oxotetrahydrofuran-3-yl)acetamide COVPDB1178 Oc1ccc(cc1)CC(=O)N[C@H]2CC(=C)OC2=O 1 40 2-[(4R)-4-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxy]imino}acetamido]-3-oxo-1,2-oxazolidin-2-yl]-5-oxooxolane-2-carboxylic acid COVPDB154 Nc1nc(cs1)C(=N\OCc1cc(=O)c(O)cn1[O-])\C(=O)N[C@@H]1CON(C1=O)[C@@]1(CCC(=O)O1)C(O)=O 1 41 2-[5-AMINO-6-OXO-2-(2-THIENYL)-1,6-DIHYDROPYRIMIDIN-1-YL)-N-[3,3-DIFLUORO -1-ISOPROPYL-2-OXO-3-(N-(2-MORPHOLINO ETHYL)CARBAMOYL]PROPYL]ACETAMIDE COVPDB551 O=c1c(N)cnc(-c2cccs2)n1CC(=O)N[C@@H](C(C)C)C(=O)C(F)(F)C(=O)NCCN3CCOCC3 1 42 2-(5-AMINO-6-OXO-2-M-TOLYL-6H-PYRIMIDIN-1-YL)-N-[4-GUANIDINO-1-(THIAZOLE-2-CARBONYL)-BUTYL]-ACETAMIDE COVPDB291 Cc1cccc(c1)-c1ncc(N)c(=O)n1CC(=O)N[C@@H](CCCNC(N)=N)C(=O)c1nccs1 1 43 2-(5-BENZYLAMINO-2-METHYLSULFANYL-6-OXO-6H-PYRIMIDIN-1-YL)-N-[4-GUANIDINO-1-(THIAZOLE-2-CARBONYL)-BUTYL]-ACETAMIDE COVPDB292 CSc1ncc(NCc2ccccc2)c(=O)n1CC(=O)N[C@@H](CCCNC(N)=N)C(=O)c1nccs1 1 44 [2,5-bis(oxidanylidene)pyrrolidin-1-yl] (1~{S},5~{R})-6-[1-(4-fluorophenyl)pyrazol-3-yl]-3-azabicyclo[3.1.0]hexane-3-carboxylate COVPDB735 Fc1ccc(cc1)-n2ccc(n2)[C@H]3[C@@H]([C@@H]34)CN(C4)C(=O)ON5C(=O)CCC5=O 1 45 2-[5-METHANESULFONYLAMINO-2-(4-AMINOPHENYL)-6-OXO-1,6-DIHYDRO-1-PYRIMIDINYL]-N-(3,3,3-TRIFLUORO-1-ISOPROPYL-2-OXOPROPYL)ACETAMIDE COVPDB1385 CC(C)[C@H](NC(=O)Cn1c(ncc(NS(C)(=O)=O)c1=O)-c1ccc(N)cc1)C(=O)C(F)(F)F 1 46 (2,6-bis[(dimethylamino-kappaN)methyl]-4-{3-[(S)-ethoxy(4-nitrophenoxy)phosphoryl]propyl}phenyl-kappaC~1~)(chloro)platinum(2+) COVPDB1156 CCO[P@@](=O)(CCCc1cc(CN(C)C)c([Pt]Cl)c(CN(C)C)c1)Oc1ccc(cc1)[N+]([O-])=O 3 47 {[(2,6-difluorophenyl)formamido]methyl}boronic acid COVPDB1499 OB(O)CNC(=O)c1c(F)cccc1F 1 48 {[(2,6-dimethoxyphenyl)formamido]methyl}boronic acid COVPDB464 COc1cccc(OC)c1C(=O)NCB(O)O 1 49 [(2-AMINO-ALPHA-METHOXYIMINO-4-THIAZOLYLACETYL)AMINO]METHYLBORONIC ACID COVPDB663 OB(O)CNC(=O)/C(=N\OC)c1csc(n1)N 1 50 2-boronic acid-1-[(1E)-2-(3-boronic acid)ethenyl]-4-chlorobenzene COVPDB384 OB(O)c1cccc(c1)/C=C/c2ccc(cc2Cl)B(O)O 1 51 [[2-chloranyl-4-(1H-1,2,3,4-tetrazol-5-yl)phenyl]sulfonylamino]methylboronic acid COVPDB37 OB(O)CNS(=O)(=O)c1ccc(cc1Cl)-c1nnn[nH]1 1 52 2-CHLOROBENZAMIDOMETHYLBORONIC ACID COVPDB1496 OB(O)CNC(=O)c1c(Cl)cccc1 1 53 2-[(E)-[1-(2-Amino-1,3-thiazol-4-yl)-2-[[(2S,3S)-2-[[3-(1,5-dihydroxy-4-oxopyridin-2-yl)-1,2-oxazole-5-carbonyl]oxymethyl]-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid COVPDB48 CC(C)(O\N=C(\C(=O)N[C@H]1[C@@H](COC(=O)c2cc(no2)-c2cc(=O)c(O)cn2[O-])N(C1=O)S(O)(=O)=O)c1csc(N)n1)C(O)=O 1 54 (2E)-3-[2-(dihydroxyboranyl)-1-benzothiophen-3-yl]prop-2-enoic acid COVPDB136 OB(O)c1sc2ccccc2c1\C=C\C(O)=O 1 55 [(2-ETHOXY-1-NAPHTHOYL)AMINO]METHYLBORONIC ACID COVPDB1137 OB(O)CNC(=O)c(c(cc1)OCC)c(c12)cccc2 2 56 2-FLUOROBENZAMIDOMETHYLBORONIC ACID COVPDB1498 OB(O)CNC(=O)c1c(F)cccc1 1 57 2-METHOXYMALONIC ACID COVPDB737 COC(C(O)=O)C(O)=O 1 58 2-METHYLMALONIC ACID COVPDB728 CC(C(O)=O)C(O)=O 1 59 [(2R)-1-(L-ALANYL-L-ISOLEUCYL)PYRROLIDIN-2-YL]BORONIC ACID COVPDB492 CC[C@H](C)[C@H](NC(=O)[C@H](C)N)C(=O)N1CCC[C@H]1B(O)O 2 60 (2R)-2,3-bis(hexyloxy)propyl 4-nitrophenyl pentylphosphonate COVPDB612 CCCCCCOC[C@@H](OCCCCCC)CO[P@@](=O)(CCCCC)Oc1ccc([N+]([O-])=O)cc1 1 61 (2R)-2,3-dibutoxypropyl 4-nitrophenyl octylphosphonate COVPDB138 CCCCCCCC[P@](=O)(Oc1ccc([N+]([O-])=O)cc1)OC[C@H](OCCCC)COCCCC 1 62 (2R)-2,3-dibutoxypropyl 4-nitrophenyl propylphosphonate COVPDB923 CCCCOC[C@@H](OCCCC)CO[P@@](=O)(CCC)Oc1ccc([N+]([O-])=O)cc1 1 63 [[(2R)-2-[(4-ethyl-2,3-dioxo-piperazin-1-yl)carbonylamino]-4-(4-hydroxyphenyl)butanoyl]amino]methylboronic acid COVPDB668 Oc1ccc(cc1)CC[C@H](C(=O)NCB(O)O)NC(=O)N2CCN(C(=O)C2=O)CC 1 64 {[(2R)-2-hydroxy-4,5-dioxoheptyl]oxy}phosphonic acid COVPDB1066 CCC(=O)C(=O)C[C@@H](O)COP(O)(O)=O 1 65 (2S)-1-[(2R)-2-(methylamino)-3-phenyl-propanoyl]-N-[(2S)-4,4,5,5,5-pentafluoro-1-(1H-indol-3-yl)-3-oxo-pentan-2-yl]pyrrolidine-2-carboxamide COVPDB1090 CN[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)C(F)(F)C(F)(F)F 1 66 [(2S)-2,3-dihydroxypropoxy]boronic acid COVPDB129 OC[C@H](O)COB(O)O 1 67 (2S)-4-methyl-2-[(morpholine-4-carbonyl)amino]-N-[(2S)-1-oxo-1-(5-phenyl-1,2,4-oxadiazol-3-yl)butan-2-yl]pentanamide COVPDB317 c1ccccc1-c2nc(no2)C(=O)[C@H](CC)NC(=O)[C@H](CC(C)C)NC(=O)N3CCOCC3 1 68 (2S,4R)-1-ACETYL-N-[(1S)-4-[(AMINOIMINOMETHYL)AMINO]-1-(2-BENZOTHIAZOLYLCARBONYL)BUTYL]-4-HYDROXY-2-PYRROLIDINECARBOXAMIDE COVPDB478 CC(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)c1nc2ccccc2s1 1 69 (2S,5R)-1-[2-[[1-(hydroxymethyl)cyclopentyl]amino]ethanoyl]pyrrolidine-2,5-dicarbonitrile COVPDB414 OCC1(CCCC1)NCC(=O)N1[C@@H](CC[C@@H]1C#N)C#N 1 70 (2S,5R,6R)-6-[(6S)-6-(2-aminoacetamido)-6-carboxyhexanamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid COVPDB901 CC1(C)S[C@@H]2[C@H](NC(=O)CCCC[C@H](NC(=O)CN)C(O)=O)C(=O)N2[C@H]1C(O)=O 1 71 (2S,5R,6R)-6-[(6S)-6-amino-6-carboxyhexanamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid COVPDB907 CC1(C)S[C@@H]2[C@H](NC(=O)CCCC[C@H](N)C(O)=O)C(=O)N2[C@H]1C([O-])=O 1 72 (2S)-N-[(2S)-1-(1,3-benzothiazol-2-yl)-5-carbamimidamido-1-oxopentan-2-yl]-3-methyl-2-[(2S)-2-(3-phenylpropanamido)-3-(1,3-thiazol-4-yl)propanamido]butanamide COVPDB1028 CC(C)[C@H](NC(=O)[C@H](Cc1cscn1)NC(=O)CCc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)c1nc2ccccc2s1 1 73 (2S)-N-[(2S)-5-carbamimidamido-1-oxo-1-(1,3-thiazol-2-yl)pentan-2-yl]-2-(carbamoylamino)-3-methylbutanamide COVPDB299 CC(C)[C@H](NC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)c1nccs1 1 74 2-{[(Z)-[(2-amino-1,3-thiazol-4-yl)({[(2R,3S)-2-[({[(1,5-dihydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl]carbamoyl}amino)methyl]-4-oxo-1-sulfoazetidin-3-yl]carbamoyl})methylidene]amino]oxy}-2-methylpropanoic acid COVPDB1221 CC(C)(O\N=C(/C(=O)N[C@H]1[C@@H](CNC(=O)NCc2cc(=O)c(O)cn2[O-])N(C1=O)S(O)(=O)=O)c1csc(N)n1)C(O)=O 1 75 [3-(1-aminoisoquinolin-6-yl)phenyl]boronic acid COVPDB662 OB(O)c1cccc(c1)-c(c2)ccc(c23)c(N)ncc3 1 76 3-[(2R)-2-{[(2R)-2-amino-2-phenylacetyl]amino}-2-(dihydroxyboranyl)ethyl]benzoic acid COVPDB158 N[C@@H](C(=O)N[C@@H](Cc1cccc(c1)C(O)=O)B(O)O)c1ccccc1 2 77 3-[(2R)-2-[(benzylsulfonyl)amino]-2-(dihydroxyboranyl)ethyl]benzoic acid COVPDB582 OB(O)[C@H](Cc1cccc(c1)C(O)=O)NS(=O)(=O)Cc1ccccc1 1 78 3-{[(2S)-1-[(2S)-2-{[(1S)-1-(diphenoxyphosphoryl)-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}propanoic acid COVPDB1445 CC(C)[C@H](NC(=O)CCC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](Cc1ccccc1)P(=O)(Oc1ccccc1)Oc1ccccc1 1 79 3,3-dimethyl-7-oxo-6-[2-(2-oxo-imidazolidin-1-ylamino)-2-phenyl-acetylamino]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid COVPDB805 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NN3CCNC3=O)c3ccccc3)C(=O)N2[C@@H]1C(O)=O 1 80 [({3-[(3S,16R,21aS)-1,4,5,14,17-pentaoxo-16-(2-phenylethyl)-icosahydro-1H-pyrrolo[1,2-d]1,4,7,11-tetraazacyclononadecan-3-yl]propyl}amino)(amino)methylidene]azanium COVPDB102 NC(=N)NCCC[C@@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@@H](CCc2ccccc2)NC(=O)CCCCCCCNC(=O)C1=O 1 81 3-(4-AMINO-CYCLOHEXYL)-2-OXO-3-[(4-OXO-2-PHENYLMETHANESULFONYL-1,2,3,4-TETRAHYDRO-PYRROLO[1,2-A]PYRAZINE-6-CARBONYL)-AMINO]-PROPIONIC ACID BUTYL ESTER COVPDB55 CCCCOC(=O)C(=O)[C@@H](NC(=O)c1ccc2CN(CC(=O)n12)S(=O)(=O)Cc1ccccc1)[C@H]1CC[C@H](N)CC1 1 82 3,4-DICHLOROISOCOUMARIN COVPDB701 c1cccc(c12)c(=O)oc(Cl)c2Cl 1 83 3-(4-DIETHYLAMINO-2-HYDROXY-PHENYL)-2-METHYL-PROPIONIC ACID COVPDB708 CCN(CC)c1ccc(\C=C(/C)C(O)=O)c(O)c1 1 84 3-(5,7,7-trihydroxy-2,2,7-trioxo-6-oxa-2lambda~6~-thia-3-aza-7lambda~5~-phospha-5-boraheptan-1-yl)benzoic acid COVPDB467 OB(CNS(=O)(=O)Cc1cccc(c1)C(O)=O)OP(O)(O)=O 1 85 (3,5-di-tert-butylphenyl)boronic acid COVPDB117 OB(O)c1cc(C(C)(C)C)cc(c1)C(C)(C)C 1 86 3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-2-one COVPDB548 O=C(O1)O[C@@H]([C@@H]12)CC=CC2 1 87 (3aR,7aR)-tetrahydro-2H-[1,2]dithiino[4,5-d][1,3]dioxol-2-one COVPDB682 O=C(O1)O[C@H]([C@@H]12)CSSC2 6 88 [3-(benzyloxy)-4-methylphenyl]boronic acid COVPDB378 Cc1ccc(B(O)O)cc1OCc2ccccc2 1 89 (3-bromo-4-methylphenyl)boronic acid COVPDB377 OB(O)c1ccc(C)c(Br)c1 1 90 (3-bromo-5-phenoxyphenyl)boronic acid COVPDB376 OB(O)c1cc(cc(Br)c1)Oc2ccccc2 1 91 [3-bromo-5-(pyrrolidin-1-yl)phenyl]boronic acid COVPDB381 OB(O)c1cc(Br)cc(c1)N2CCCC2 2 92 [({[3-chloro-4-(1H-tetrazol-5-yl)phenyl]sulfonyl}amino)methyl]boronic acid COVPDB36 OB(O)CNS(=O)(=O)c1ccc(-c2nnn[nH]2)c(Cl)c1 1 93 {3-chloro-4-[(2-fluorophenyl)methoxy]phenyl}boronic acid COVPDB374 OB(O)c1ccc(c(Cl)c1)OCc2ccccc2F 1 94 3-(dihydroxyboranyl)-5-acetamidobenzoic acid COVPDB1494 CC(=O)Nc1cc(cc(c1)C(O)=O)B(O)O 1 95 3-({[(dihydroxyboranyl)methyl]sulfamoyl}methyl)benzoic acid COVPDB33 OB(O)CNS(=O)(=O)Cc1cccc(c1)C(O)=O 1 96 (3-{[(furan-2-yl)methyl]carbamoyl}phenyl)boronic acid COVPDB1003 OB(O)c1cccc(c1)C(=O)NCc2ccco2 1 97 3-METHOXY-4-CHLORO-7-AMINOISOCOUMARIN COVPDB941 CCOc(oc1=O)c(Cl)c(c12)ccc(c2)N 1 98 3-METHOXYPHENYL BORONIC ACID COVPDB1257 COc1cccc(c1)B(O)O 1 99 3-[[(METHYLAMINO)SULFONYL]AMINO]-2-OXO-6-PHENYL-N-[3,3,3-TRIFLUORO-1-(1-METHYLETHYL)-2-OXOPHENYL]-1(2H)-PYRIDINE ACETAMIDE COVPDB1386 FC(F)(F)C(=O)[C@H](C(C)C)NC(=O)Cn1c(-c2ccccc2)ccc(c1=O)NS(=O)(=O)NC 1 100 3-nitrophenylboronic acid COVPDB1151 OB(O)c1cc([N+]([O-])=O)ccc1 2 101 3‐oxopropanoic acid COVPDB190 OC(=O)CC=O 1 102 [(3R)-1-hydroxy-4,5-dimethyl-6-(pyrazin-2-yloxy)-1,3-dihydro-2,1-benzoxaborol-3-yl]acetic acid COVPDB205 Cc1c2[C@@H](CC(O)=O)OB(O)c2cc(Oc2cnccn2)c1C 1 103 (3R,3aR,6aS)-3-(prop-2-en-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one COVPDB83 C=CC[C@@H](C(=O)O1)[C@H]([C@@H]12)CCC2 1 104 (3R)-3-(cyclohexylcarbonylamino)-2-oxidanyl-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid COVPDB613 OB1Oc2c(C[C@@H]1NC(=O)C1CCCCC1)cccc2C(O)=O 2 105 (3R,5R)-4-bromo-9-{3-[(R)-ethoxy(4-nitrophenoxy)phosphoryl]propyl}-3,5-dimethyl-3,5-dithia-4-palladatricyclo[5.3.1.0⁴,¹¹]undeca-1(11),7,9-triene-3,5-diium COVPDB1329 CCO[P@](=O)(CCCc1cc2c3c(c1)C[S@+]([Pd]3([S@@+](C2)C)Br)C)Oc4ccc(cc4)[N+](=O)[O-] 2 106 {(3R)-6-[(3-amino-1,2,4-thiadiazol-5-yl)oxy]-1-hydroxy-4,5-dimethyl-1,3-dihydro-2,1-benzoxaborol-3-yl}acetic acid COVPDB206 Cc1c2[C@@H](CC(O)=O)OB(O)c2cc(Oc2nc(N)ns2)c1C 2 107 (3S)-3-(benzylsulfanyl)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid COVPDB1035 OB1Oc2c(C[C@H]1SCc1ccccc1)cccc2C(O)=O 1 108 (3S,4R)-1-TOSYL-3-ETHYL-AZETIDIN-2-ONE-4-CARBOXYLIC ACID COVPDB127 CC[C@H]1[C@@H](N(C1=O)S(=O)(=O)c1ccc(C)cc1)C(O)=O 1 109 (3S,4S)‐4‐ethyl‐1‐(4‐methylbenzenesulfonyl)‐5‐oxopyrrolidine‐3‐carboxylic acid COVPDB1394 [H][C@]1(CN(C(=O)[C@@]1([H])CC)S(=O)(=O)c1ccc(C)cc1)C(O)=O 3 110 (3S,4S)‐4‐ethyl‐1‐(4‐nitrobenzenesulfonyl)‐5‐oxopyrrolidine‐3‐carboxylic acid COVPDB1395 CC[C@H]1[C@@H](CN(C1=O)S(=O)(=O)c1ccc(cc1)[N+]([O-])=O)C(O)=O 3 111 {3-[(tert-butoxycarbonyl)amino]phenyl}boronic acid COVPDB1002 OB(O)c1cccc(c1)NC(=O)OC(C)(C)C 1 112 3-tert-butyl-4-{[(2R,5S)-5-[(2S)-2-cyanopyrrolidine-1-carbonyl]pyrrolidin-2-yl]methoxy}benzoic acid COVPDB482 CC(C)(C)c1cc(ccc1OC[C@H]1CC[C@H](N1)C(=O)N1CCC[C@H]1C#N)C(O)=O 1 113 4'-{1-[(2R)-2-phenylpiperidine-1-carbonyl]-1H-1,2,4-triazol-3-yl}-[1,1'-biphenyl]-4-carboxylic acid COVPDB333 OC(=O)c1ccc(cc1)-c1ccc(cc1)-c1ncn(n1)C(=O)N1CCCC[C@@H]1c1ccccc1 1 114 [[4-(1H-1,2,3,4-tetrazol-5-yl)-2-(trifluoromethyl)phenyl]sulfonylamino]methylboronic acid COVPDB38 OB(O)CNS(=O)(=O)c1ccc(cc1C(F)(F)F)-c1nnn[nH]1 1 115 [({[4-(1H-tetrazol-5-yl)phenyl]sulfonyl}amino)methyl]boronic acid COVPDB34 OB(O)CNS(=O)(=O)c1ccc(cc1)-c1nnn[nH]1 1 116 {4‐[(2S)‐2‐{[(1R)‐4‐{[amino(iminio)methyl]amino}‐1‐(dihydroxyboranyl)butyl]carbamoyl}‐2‐(phenylformamido)ethyl]phenyl}methanaminium COVPDB301 NCc1ccc(C[C@H](NC(=O)c2ccccc2)C(=O)N[C@@H](CCCNC(N)=N)B(O)O)cc1 1 117 4-[[(3~{S})-1-oxidanyl-3,4-dihydro-2,1-benzoxaborinin-3-yl]methylamino]benzenecarboximidamide COVPDB1064 NC(=N)c1ccc(NC[C@@H]2Cc3ccccc3B(O)O2)cc1 1 118 4,4'-BIPHENYLDIBORONIC ACID COVPDB550 OB(O)c1ccc(cc1)-c2ccc(cc2)B(O)O 1 119 4,4-Dimethyl-2-((1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-1,2-thiazetidin-3-one 1,1-dioxide COVPDB962 CC1(C)C(=O)N(S1(=O)=O)Cc2cn(nn2)Cc3ccc([N+]([O-])=O)cc3 1 120 4-Amino-5-fluoro-2-methyl-3-(3-trifluoroacetylbenzylthiomethyl)quinoline COVPDB786 Cc1nc2cccc(F)c2c(N)c1CSCc1cccc(c1)C(=O)C(F)(F)F 1 121 {4-[(azetidin-1-yl)sulfonyl]phenyl}boronic acid COVPDB1004 OB(O)c1ccc(cc1)S(=O)(=O)N2CCC2 1 122 {4-[(carbamimidoylsulfanyl)methyl]phenyl}boronic acid COVPDB967 NC(=N)SCc1ccc(cc1)B(O)O 1 123 4-CARBOXYPHENYLboronic acid COVPDB223 OB(O)c1ccc(cc1)C(O)=O 1 124 4-(carboxyvin-2-yl)phenylboronic acid COVPDB658 OB(O)c1ccc(\C=C\C(O)=O)cc1 1 125 4-chloro-3-{[(2R,5S)-5-[(2S)-2-cyanopyrrolidine-1-carbonyl]pyrrolidin-2-yl]methoxy}benzoic acid COVPDB480 OC(=O)c1ccc(Cl)c(OC[C@H]2CC[C@H](N2)C(=O)N2CCC[C@H]2C#N)c1 1 126 4-CHLORO-3-ETHOXY-7-GUANIDINO-ISOCOUMARIN COVPDB863 CCOc1oc(=O)c2cc(NC(N)=N)ccc2c1Cl 1 127 4-(dihydroxyboranyl)-2-[[4-(phenylsulfonyl)thiophen-2-yl]sulfonylamino]benzoic acid COVPDB621 OB(O)c1ccc(C(O)=O)c(NS(=O)(=O)c2cc(cs2)S(=O)(=O)c2ccccc2)c1 1 128 4-(dihydroxyboranylmethylsulfamoylmethyl)benzoic acid COVPDB581 OB(O)CNS(=O)(=O)Cc1ccc(cc1)C(O)=O 1 129 4‐ethyl‐4‐methylcyclohexan‐1‐one COVPDB744 CCC1(C)CCC(=O)CC1 4 130 4-(Ethyl(methyl)carbamoyl)phenyl boronic acid COVPDB1409 OB(O)c1ccc(cc1)C(=O)N(C)CC 1 131 4-(guanidinomethyl)-phenylboronic acid COVPDB899 NC(=[NH2+])NCc1ccc(cc1)B(O)O 1 132 4-IODO-ACETAMIDO PHENYLBORONIC ACID COVPDB936 OB(O)c1cccc(c1)NC(=O)CI 2 133 4-Methyl-pentanoic acid {1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-methyl-propyl}-amide COVPDB429 CC(C)CCC(=O)N[C@H](C(C)C)C(=O)N[C@H](CCCNC(N)=N)C(=O)c1nccs1 1 134 4-methylumbelliferyl hexylphosphonate COVPDB1094 CCCCCC[P@@](=O)(OC)Oc(c1)ccc(c12)c(C)cc(o2)=O 1 135 4-nitrophenyl tetradecyl (3-azidopropyl)phosphonate COVPDB87 CCCCCCCCCCCCCCO[P@@](=O)(CCCN=[N+]=[N-])Oc1ccc([N+]([O-])=O)cc1 1 136 4-Oxo-N,N,N-Trimethylpentanaminium COVPDB628 CC(=O)CCC[N+](C)(C)C 4 137 4-piperidinebutyric acid COVPDB602 OC(=O)CCCN1CCCCC1 1 138 5-[(3R,3aS,8aS)-5-(4-hydroxyphenyl)-2-oxo-2H,3H,3aH,8H,8aH-indeno[2,1-b]furan-3-yl]pentanimidamide COVPDB64 NC(=N)CCCC[C@@H]1[C@@H]2[C@H](Cc3ccc(cc23)-c2ccc(O)cc2)OC1=O 1 139 5-[(3R,3aS,8aS)-6-(3-methoxyphenyl)-2-oxo-2H,3H,3aH,8H,8aH-indeno[2,1-b]furan-3-yl]pentanimidamide COVPDB65 COc1cccc(c1)-c1ccc2[C@H]3[C@H](Cc2c1)OC(=O)[C@@H]3CCCCC(N)=N 1 140 [5-(aminomethyl)-1-benzothiophen-2-yl]boronic acid COVPDB898 OB(O)c(s1)cc(c12)cc(cc2)C[NH3+] 1 141 (5R)-(6Z)-6-(5,6-dihydro-8H-imidazo[2,1-c][1,4]oxazin-2-ylmethylene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-3-carboxylic acid COVPDB1458 OC(=O)C1=CN2[C@H](S1)\C(=C/c1cn3CCOCc3n1)C2=O 2 142 [({[6-(1H-tetrazol-5-yl)pyridin-3-yl]sulfonyl}amino)methyl]boronic acid COVPDB35 OB(O)CNS(=O)(=O)c1ccc(nc1)-c1nnn[nH]1 1 143 6-[2-(3-biphenyl-4-ylpropanoyl)-1,3-oxazol-5-yl]pyridine-2-carboxylic acid COVPDB781 OC(=O)c1cccc(n1)-c1cnc(o1)C(=O)CCc1ccc(cc1)-c1ccccc1 1 144 6-[2-(4-ethyl-2,3-dioxo-piperazin-1-ylamino)-2-phenyl-acetylamino]-3,3,-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid COVPDB646 CCN1CCN(N[C@@H](C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C(O)=O)c2ccccc2)C(=O)C1=O 1 145 6-[2-(7-phenylheptanoyl)-1,3-oxazol-5-yl]pyridine-2-carboxylic acid COVPDB782 OC(=O)c1cccc(n1)-c1cnc(o1)C(=O)CCCCCCc1ccccc1 1 146 6alpha-(hydroxymethyl)penicillanic acid COVPDB497 [O-]C(=O)[C@H]1C(C)(C)S[C@@H](N12)[C@H](C2=O)CO 1 147 6ALPHA-(HYDROXYPROPYL)PENICILLANATE COVPDB500 CC(C)(O)[C@@H]1[C@H]2SC(C)(C)[C@@H](N2C1=O)C(O)=O 1 148 6-aminopenicillian COVPDB1461 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O 1 149 6beta-(1-hydroxy-1-methylethyl) penicillanic acid COVPDB915 CC(C)(O)[C@H]1[C@H]2SC(C)(C)[C@@H](N2C1=O)C(O)=O 1 150 6-beta-Iodopenicillanate COVPDB564 CC1(C)S[C@@H]2[C@H](I)C(=O)N2[C@H]1C(O)=O 2 151 6-diazo-5-oxo-l-norleucine COVPDB410 N[C@@H](CCC(=O)C=[N+]=[N-])C(O)=O 12 152 (6-Phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)(5-(pyridin-2-yl)oxazol-2-yl)methanone COVPDB1183 c1cccnc1-c2oc(nc2)C(=O)[C@H](C3)CCc(c34)cc(cc4)Oc5ccccc5 1 153 (6R,7R)-3-[(3S)-3-[(4R)-4-carboxy-4-acetamidobutanamido]-3-{[(1R)-1-{[(1R)-1-carboxyethyl]carbamoyl}ethyl]carbamoyl}propyl]-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid COVPDB633 C[C@@H](NC(=O)[C@@H](C)NC(=O)[C@H](CCC1=C(N2[C@H](SC1)[C@H](NC(=O)Cc1ccccc1)C2=O)C(O)=O)NC(=O)CC[C@@H](NC(C)=O)C(O)=O)C(O)=O 1 154 (6R,7R)-3-[(acetyloxy)methyl]-7-[(6S)-6-amino-6-carboxyhexanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid COVPDB906 CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)CCCC[C@H](N)C(O)=O)C2=O)C(O)=O 1 155 (6R,7R)-3-[(ACETYLOXY)METHYL]-7-{[(6S)-6-(GLYCYLAMINO)-7-OXIDO-7-OXOHEPTANOYL]AMINO}-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCTANE-2-CARBOXYLATE COVPDB886 CC(=O)OC[C@H]1CS[C@@H]2[C@H](NC(=O)CCCC[C@H](NC(=O)CN)C(O)=O)C(=O)N2[C@@H]1C(O)=O 1 156 7,7-Dichloro-3alpha-methoxy-2-thiabicyclo[3.2.0]heptan-6-one-4-carboxylic Acid COVPDB1058 CO[C@H]1S[C@H]2[C@@H]([C@H]1C(O)=O)C(=O)C2(Cl)Cl 1 157 7-AMINO-3-(2-BROMOETHOXY)-4-CHLOROISOCOURMARIN COVPDB939 c1cc(N)cc(c12)c(=O)oc(c2Cl)OCCBr 1 158 7-AMINO-3-(2-PHENYLETHOXY)-4-CHLOROISOCOUMARIN COVPDB1328 c1cc(N)cc(c12)c(=O)oc(c2Cl)OCCc3ccccc3 1 159 7-hydroxycoumarin COVPDB1320 Oc(c1)ccc(c12)ccc(o2)=O 1 160 7-phenyl-1-[4-(pyridin-2-yl)-1,3-oxazol-2-yl]heptan-1-one COVPDB1297 c1cccnc1-c2coc(n2)C(=O)CCCCCCc3ccccc3 1 161 7-phenyl-1-[5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl]heptan-1-one COVPDB986 c1cccnc1-c2oc(nn2)C(=O)CCCCCCc3ccccc3 1 162 (8R,9R)-10(S)-[1(R)-Hydroxyethyl]-4(R)-butoxy-11-oxo-1-azatricyclo[7.2.0 .03,8]undec-2-enecarboxylic acid COVPDB1067 CCCCO[C@@H]1CCC[C@H]2[C@H]3[C@@H](CC)C(=O)N3C(C(O)=O)=C12 1 163 (8S,9R)-10(E)-Ethylidene-4(S)-methoxy-11-oxo-1-azatricyclo[7.2.0.03,8]undec -2-enecarboxylic acid COVPDB1068 CO[C@@H]1CCC[C@H]2[C@@H]3N(C(=O)\C3=C\C)C(C(O)=O)=C12 1 164 (9Z)-1-(5-pyridin-2-yl-1,3,4-oxadiazol-2-yl)octadec-9-en-1-one COVPDB1012 CCCCCCCC/C=C\CCCCCCCC(=O)c1nnc(o1)-c2ccccn2 1 165 A-230 nerve agent COVPDB1045 CCN(CC)C(\C)=N\[P@@](C)(F)=O 1 166 A-232 nerve agent COVPDB1043 CCN(CC)/C(C)=N/[P@](=O)(F)OC 3 167 AC-(D)PHE-PRO-BOROARG-OH COVPDB710 CC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)B(O)O 1 168 AC-(D)PHE-PRO-BOROHOMOLYS-OH COVPDB699 CC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCCCN)B(O)O 1 169 AC-(D)PHE-PRO-BOROHOMOORNITHINE-OH COVPDB700 CC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN)B(O)O 1 170 AC-(D)PHE-PRO-BOROLYS-OH COVPDB697 CC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCCN)B(O)O 1 171 AC-(D)PHE-PRO-BORO-N-BUTYL-AMIDINO-GLYCINE-OH COVPDB698 CC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCCC(N)=N)B(O)O 1 172 ACETYLCHOLINE COVPDB481 CC(=O)OCC[N+](C)(C)C 1 173 Ac-Leu-Phe-CF3 COVPDB1074 CC(C)C[C@H](NC(=O)C)C(=O)N[C@H](C(=O)C(F)(F)F)Cc1ccccc1 1 174 Ac-RVRHA-CONH-(2,4-dimethyl)benzyl COVPDB1454 CC(C)[C@H](NC(=O)[C@H](CCCNC(N)=N)NC(C)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](C)C(=O)C(=O)NCc1cc(C)ccc1C 1 175 ADENOSINE MONOPHOSPHATE COVPDB499 Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O 13 176 AEBSF COVPDB487 NCCc1ccc(cc1)S(F)(=O)=O 3 177 alpha-D-glucose COVPDB1515 OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O 4 178 Amoxicillin COVPDB516 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(O)=O 3 179 AMPICILLIN COVPDB493 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(O)=O 8 180 Antipain COVPDB1174 CC(C)[C@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)N[C@@H](Cc1ccccc1)C(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C=O 1 181 ATMO-penicillin COVPDB1219 CO\N=C(/C(=O)N[C@H]1[C@H]2SC(C)(C)[C@@H](N2C1=O)C(O)=O)c1csc(N)n1 1 182 avibactam COVPDB1157 [C@@H]12CC[C@@H](C(=O)N)N(C1)C(=O)N2OS([O-])(=O)=O 30 183 AZLOCILLIN COVPDB254 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NC(=O)N3CCNC3=O)c3ccccc3)C(=O)N2[C@H]1C(O)=O 1 184 Aztreonam COVPDB520 C[C@H]1[C@H](NC(=O)C(=N/OC(C)(C)C(O)=O)\c2csc(N)n2)C(=O)N1S(O)(=O)=O 6 185 BAL30072 COVPDB155 CC1(C)[C@H](NC(=O)C(=N/OCc2cc(=O)c(O)cn2[O-])\c2csc(N)n2)C(=O)N1OS(O)(=O)=O 1 186 BCL-1-(R) COVPDB139 [O-][N+](=O)c1ccc(cc1)O[P@@](=O)(CCCCCC)OC[C@H](C)Cc2ccccc2 1 187 BCL-1-(S) COVPDB140 [O-][N+](=O)c1ccc(cc1)O[P@@](=O)(CCCCCC)OC[C@@H](C)Cc2ccccc2 1 188 BENZO[B]THIOPHENE-2-boronic acid COVPDB596 OB(O)c(c1)sc(c12)cccc2 5 189 benzyl N-[(1S)-1-[bis(4-methanesulfonylphenoxy)phosphoryl]-2-phenylethyl]carbamate COVPDB932 CS(=O)(=O)c1ccc(cc1)OP(=O)(Oc2ccc(cc2)S(=O)(=O)C)[C@@H](Cc3ccccc3)NC(=O)OCc4ccccc4 1 190 benzyl N-[(1S)-5-amino-1-{[(1S)-1-{[(2S)-6-amino-1-(1,3-benzoxazol-2-yl)-1-oxohexan-2-yl]carbamoyl}-3-phenylpropyl]carbamoyl}pentyl]carbamate COVPDB532 NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCc1ccccc1)C(=O)N[C@@H](CCCCN)C(=O)c1nc2ccccc2o1 1 191 benzyl N-[(2R)-1-[(2S,4R)-2-{[(2S)-6-amino-1-(1,3-benzoxazol-2-yl)-1-oxohexan-2-yl]carbamoyl}-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate COVPDB530 Cc1ccc(CO[C@@H]2C[C@H](N(C2)C(=O)[C@@H](CCc2ccccc2)NC(=O)OCc2ccccc2)C(=O)N[C@@H](CCCCN)C(=O)c2nc3ccccc3o2)cc1 1 192 beta-D-glucose COVPDB560 OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O1)O 15 193 biapenem COVPDB1517 C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(SC3CN4C=NC=[N+]4C3)=C(N2C1=O)C(O)=O 1 194 BMS-262084 COVPDB66 CC(C)(C)NC(=O)N1CCN(CC1)C(=O)N1[C@@H]([C@@H](CCCNC(N)=N)C1=O)C(O)=O 1 195 Boc-ALA2-ALA1-NHO-Nb COVPDB543 CC(C)(C)OC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)NOC(=O)c1ccc([N+]([O-])=O)cc1 2 196 Boc-Ala-Ala-Pro-(OPh)Pval-Lac-Ala-OMe COVPDB1242 CC(C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OC(C)(C)C)[P@@](=O)(O[C@@H](C)C(=O)N[C@@H](C)C(O)=O)Oc1ccccc1 2 197 BOROLOG2 COVPDB1330 BrC(Br)CC[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)CCCC=O)Cc2ccccc2 1 198 bortezomib COVPDB574 c1ccccc1C[C@@H](C(=O)N[C@H](B(O)O)CC(C)C)NC(=O)c2cnccn2 6 199 BRL42715 COVPDB787 Cn1cc(\C=C2\[C@H]3SC=C(N3C2=O)C(O)=O)nn1 1 200 butylboronic acid COVPDB590 OB(O)CCCC 1 201 BUTYRIC ACID COVPDB589 CCCC(O)=O 1 202 C11P COVPDB1109 CCCCCCCCCCC[P@@](=O)(OC)Oc1ccc([N+]([O-])=O)cc1 1 203 C11Y4 COVPDB598 CCCCCCCCCCC[P@@](=O)(OCCCC)Oc1ccc([N+]([O-])=O)cc1 1 204 Camostat COVPDB81 CN(C)C(=O)COC(=O)Cc1ccc(OC(=O)c2ccc(NC(N)=N)cc2)cc1 1 205 carbenicillin COVPDB626 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](C(O)=O)c3ccccc3)C(=O)N2[C@H]1C(O)=O 3 206 CB2 COVPDB1184 NCc1ccc(cc1)C(=O)N[C@H]1Cc2cccc(C(O)=O)c2OB1O 1 207 CBAP COVPDB576 CC1(C)S[C@@H]2[C@H](NC(=O)c3ccccc3-c3ccccc3C(O)=O)C(=O)N2[C@H]1C(O)=O 1 208 Cefamandole COVPDB1462 Cn1nnnc1SCC1=C(N2[C@H](SC1)[C@H](NC(=O)[C@H](O)c1ccccc1)C2=O)C(O)=O 1 209 cefapirin COVPDB640 CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)CSc1ccncc1)C2=O)C(O)=O 1 210 cefixime COVPDB1158 Nc1nc(cs1)C(=N\OCC(O)=O)\C(=O)N[C@H]1[C@H]2SCC(C=C)=C(N2C1=O)C(O)=O 1 211 CEFOPERAZONE COVPDB253 CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SCC(CSc4nnnn4C)=C(N3C2=O)C(O)=O)c2ccc(O)cc2)C(=O)C1=O 1 212 cefotaxime COVPDB632 CO\N=C(\C(=O)N[C@H]1[C@H]2SCC(COC(C)=O)=C(N2C1=O)C(O)=O)c1csc(N)n1 21 213 cefoxitin COVPDB85 CO[C@]1(NC(=O)Cc2cccs2)[C@H]2SCC(COC(N)=O)=C(N2C1=O)C(O)=O 6 214 Ceftaroline COVPDB491 CCO\N=C(/C(=O)N[C@H]1[C@H]2SCC(Sc3nc(cs3)-c3cc[n+](C)cc3)=C(N2C1=O)C(O)=O)c1nsc(N)n1 3 215 ceftazidime COVPDB624 CC(C)(O\N=C(/C(=O)N[C@H]1[C@H]2SCC(C[n+]3ccccc3)=C(N2C1=O)C(O)=O)c1csc(N)n1)C(O)=O 9 216 ceftobiprole COVPDB1275 Nc1nc(ns1)C(=N\O)\C(=O)N[C@H]1[C@H]2SCC(\C=C3/CCN([C@@H]4CCNC4)C3=O)=C(N2C1=O)C(O)=O 3 217 Ceftriaxone COVPDB821 Nc1nc(cs1)/C(=N/OC)C(=O)N[C@H](C2=O)[C@H](N23)SCC(=C3C([O-])=O)CSc4nc(=O)c(=O)[n-]n4C 3 218 Cefuroxime COVPDB635 CO\N=C(\C(=O)N[C@H]1[C@H]2SCC(COC(N)=O)=C(N2C1=O)C(O)=O)c1ccco1 3 219 CENTA COVPDB293 O=[N+]([O-])c1ccc(cc1C(=O)[O-])SCC(CS2)=C(C(=O)[O-])N([C@H]23)C(=O)[C@H]3NC(=O)Cc4cccs4 2 220 cephaloridine COVPDB631 OC(=O)C1=C(C[n+]2ccccc2)CS[C@@H]2[C@H](NC(=O)Cc3cccs3)C(=O)N12 7 221 cephalosporin C COVPDB32 CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)CCC[C@@H](N)C(O)=O)C2=O)C(O)=O 1 222 Cephalotin COVPDB435 CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)Cc1cccs1)C2=O)C(O)=O 9 223 (chloromethylsulfonylamino)methylboronic acid COVPDB39 OB(O)CNS(=O)(=O)CCl 2 224 Clavatadine A COVPDB954 NC(=N)NCCCCNC(=O)Oc1c(Br)cc(O)c(CC(O)=O)c1Br 1 225 CLAVULANATE COVPDB634 OC\C=C1/O[C@@H]2CC(=O)N2[C@H]1C(O)=O 11 226 cloxacillin COVPDB664 Cc1onc(c1C(=O)N[C@H]1[C@H]2SC(C)(C)[C@@H](N2C1=O)C(O)=O)-c1ccccc1Cl 3 227 CR161 COVPDB1265 OB(CNS(=O)(=O)c1ccc(nc1)-c1nnn[nH]1)OP(O)(O)=O 1 228 CYCLOTHEONAMIDE A COVPDB656 NC(=N)NCCC[C@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@H](CNC(=O)\C=C/[C@@H](Cc2ccc(O)cc2)NC(=O)[C@@H](Cc2ccccc2)NC(=O)C1=O)NC=O 1 229 DCM-1-10 COVPDB84 CC(=O)OCC1=C(N2[C@@H](\C(=C/C(=O)OC(C)(C)C)C2=O)S(=O)(=O)C1)C(O)=O 1 230 D-glucuronic acid COVPDB552 O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O 1 231 dicloxacillin COVPDB727 Cc1onc(c1C(=O)N[C@H]1[C@H]2SC(C)(C)[C@@H](N2C1=O)C(O)=O)-c1c(Cl)cccc1Cl 1 232 diethyl-4-methylumbelliferyl phosphate COVPDB712 CCOP(=O)(OCC)OCc(cc1)cc(c12)oc(=O)cc2C 1 233 DIHYDROXY-[[(2-NITROPHENYL)CARBONYLAMINO]METHYL]BORON COVPDB1497 OB(O)CNC(=O)c1ccccc1[N+]([O-])=O 2 234 Diisopropyl fluorophosphate COVPDB959 CC(C)OP(F)(=O)OC(C)C 6 235 DIISOPROPYL PHOSPHATE COVPDB690 CC(C)OP(O)(=O)OC(C)C 11 236 diphenyl [(3R,4S)-4-hydroxy-3-methyl-2-oxohexyl]phosphonate COVPDB1237 c1ccccc1OP(=O)(CC(=O)[C@H](C)[C@@H](O)CC)Oc2ccccc2 1 237 Diphenyl (3R,4S,5S,7R)-4,8-dihydroxy-3,5,7-trimethyl-2-oxooctylphosphonate COVPDB1490 OC[C@H](C)C[C@H](C)[C@H](O)[C@@H](C)C(=O)CP(=O)(Oc1ccccc1)Oc2ccccc2 1 238 diphenyl {[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]methyl}phosphonate COVPDB1239 CC1(C)O[C@@H](CC)[C@@H](C)[C@H](O1)CP(=O)(Oc2ccccc2)Oc3ccccc3 1 239 D-LEUCINE COVPDB707 CC(C)C[C@@H](N)C(O)=O 1 240 dodecyl 4-nitrophenyl (3-azidopropyl)phosphonate COVPDB86 CCCCCCCCCCCCO[P@@](=O)(CCCN=[N+]=[N-])Oc1ccc([N+]([O-])=O)cc1 1 241 doripenem COVPDB230 C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(S[C@@H]3CN[C@H](CNS(N)(=O)=O)C3)=C(N2C1=O)C(O)=O 10 242 D-PHENYLALANINE COVPDB713 N[C@H](Cc1ccccc1)C(O)=O 1 243 D-PHENYLALANYL-N-[(1S)-4-{[(Z)-AMINO(IMINO)METHYL]AMINO}-1-(CHLOROACETYL)BUTYL]-L-PROLINAMIDE COVPDB689 N[C@H](Cc1ccccc1)C(=O)N([C@@H](CCCNC(N)=N)C(=O)CCl)C(=O)[C@@H]1CCCN1 1 244 D-phenylalanyl-N-[(2S,3S)-6-{[amino(iminio)methyl]amino}-1-chloro-2-oxohexan-3-yl]-L-prolinamide COVPDB17 N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)CCl 3 245 (D)PHE-PRO-BOROPHE(M-CN) COVPDB1235 N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1cccc(c1)C#N)B(O)O 1 246 DVR-II-41S COVPDB717 NC(=O)\C=C\C1=C(N2[C@@H](\C(=C/c3ccccn3)C2=O)S(=O)(=O)C1)C(O)=O 1 247 (~{E})-3-[2-(dihydroxyboranyl)phenyl]prop-2-enoic acid COVPDB337 OB(O)c1ccccc1\C=C\C(O)=O 2 248 (~{E})-3-[3-(dihydroxyboranyl)phenyl]prop-2-enoic acid COVPDB1040 OB(O)c1cccc(\C=C\C(O)=O)c1 1 249 EC04 COVPDB455 OB(O)[C@H](Cc1cccc(c1)C(O)=O)NC(=O)Cc1cccs1 1 250 Echothiophate COVPDB754 CCOP(=O)(OCC)SCC[N+](C)(C)C 2 251 Ertapenem COVPDB89 C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(S[C@@H]3CN[C@@H](C3)C(=O)NC3=CC=CC(=C3)C(O)=O)=C(N2C1=O)C(O)=O 6 252 ETX1317 COVPDB1460 CC1=C[C@H](N2C[C@H]1N(O[C@H](F)C(O)=O)C2=O)C(N)=O 1 253 ETX2514 COVPDB1005 CC1=C[C@H]2CN([C@@H]1C(N)=O)C(=O)N2OS(O)(=O)=O 2 254 Faropenem COVPDB268 C[C@@H](O)[C@@H]1[C@H]2SC([C@H]3CCCO3)=C(N2C1=O)C(O)=O 6 255 FLOMOX COVPDB820 Nc1nc(cs1)/C(=C/CC)C(=O)N[C@H](C2=O)[C@H](N23)SCC(COC(=O)N)=C3C(=O)OCOC(=O)C(C)(C)C 1 256 FPI-1465 COVPDB284 OS(=O)(=O)ON1[C@H]2CN([C@@H](CC2)C(=O)NO[C@H]2CCNC2)C1=O 1 257 FPI-1523 COVPDB283 CC(=O)NNC(=O)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(O)(=O)=O 2 258 FPI-1602 COVPDB286 OS(=O)(=O)ON1[C@@H]2CN([C@H](CC2)C(=O)NNC(=O)C2CNC2)C1=O 1 259 FPyne COVPDB1303 CCO[P@@](=O)(F)CCCCCCCCCCOC(=O)NCCCCCC#C 1 260 FR130180 COVPDB813 FC(F)(F)C(=O)[C@H](C(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)C)NC(=O)c2ccc(C(=O)[O-])cc2 1 261 FR136706 COVPDB811 CC(C)[C@H](NC(=O)c1ccc(cc1)C(=O)NCC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)C(F)(F)F 1 262 gabexate COVPDB859 CCOC(=O)c1ccc(OC(=O)CCCCCNC(N)=N)cc1 1 263 Ganstigmine COVPDB877 CCc1ccccc1NC(=O)Oc(c2)ccc(c2[C@@]34C)N(C)[C@H]3ON(C)CC4 1 264 GB0301 COVPDB667 Oc1ccc(cc1)[C@H](C(=O)NCB(O)O)NC(=O)n2ccn(c(=O)c2=O)CC 1 265 Glutamatic acid COVPDB871 N[C@@H](CCC(O)=O)C(O)=O 2 266 GR133487 COVPDB875 O[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@@H]1OC(=O)[C@](C)([C@@H](CC2)OC(=O)C)[C@@H]([C@]23C)CC=C4[C@@H]3C[C@H](O)[C@]5(C)[C@]4(CO)C[C@H]6[C@H]5[C@H](C(O6)=O)CC(=O)C=C(C)C 1 267 GR157368 COVPDB60 NC(=N)CCCC[C@@H]1[C@@H]2CCC[C@H]2OC1=O 1 268 GR179849 COVPDB874 CCN(CC)C(=O)c1cccc(c1)-c1ccc2[C@@H]3[C@H](Cc2c1)OC(=O)[C@@H]3CCCCC(N)=N 1 269 GR24 COVPDB1188 CC1=C[C@H](OC1=O)O/C=C(/C(=O)O2)[C@H]([C@H]23)Cc4c3cccc4 1 270 GSK3448330A COVPDB1065 NC(=N)c1ccc(cc1)[C@@H]1Cc2ccccc2B(O)O1 1 271 GW311616A COVPDB287 CC(C)[C@H]1[C@H]2[C@@H](CCN2C(=O)\C=C\CN2CCCCC2)N(C1=O)S(C)(=O)=O 1 272 H-Bz-DPP COVPDB630 N[C@H](c1ccc(cc1)C(N)=N)P(=O)(Oc1ccccc1)Oc1ccccc1 1 273 H-diaziflurane COVPDB688 FC(F)(F)COC(F)(F)F 1 274 hexadecane sulfonyl fluoride COVPDB900 CCCCCCCCCCCCCCCCS(F)(=O)=O 5 275 hexadecyl 4-nitrophenyl (3-azidopropyl)phosphonate COVPDB88 CCCCCCCCCCCCCCCCO[P@@](=O)(CCCN=[N+]=[N-])Oc1ccc([N+]([O-])=O)cc1 1 276 IC-1 COVPDB148 OCC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CC[C@H](C(C)(C)C)N2C(=O)CCCc3ccccc3 1 277 IC-2 COVPDB149 OCC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CCC=C2C(=O)NCc3ccccc3 1 278 IC-3 COVPDB150 c1ccccc1CCCC(=O)N2CCC[C@H]2C(=O)N3CCC[C@H]3C#N 1 279 IC-4 COVPDB151 OCC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CCCN2C(=O)NCc3ccccc3 1 280 IDFP COVPDB1392 CC(C)O[P@@](=O)(F)CCCCCCCCCCC=C 1 281 Imipenem COVPDB942 C[C@@H](O)[C@@H]1[C@H]2CC(SCCNC=N)=C(N2C1=O)C(O)=O 23 282 isatoic anhydride COVPDB1321 O=c1oc(=O)[nH]c(c12)cccc2 1 283 JM102 COVPDB225 CCC1(CC)C(=O)N(C1=O)c2ccc(C)nc2 1 284 KK052 COVPDB1025 c1ccccc1N2CCN(CC2)C(=O)n3ccnn3 1 285 KK073 COVPDB438 FC(F)(F)c1ccc(cc1)N2CCN(CC2)C(=O)n3ccnn3 1 286 KK094 COVPDB1038 c1cccc(c12)N(CC2)C(=O)n3ccnn3 1 287 L-1-NAPHTHYL-2-ACETAMIDO-ETHANE BORONIC ACID COVPDB1325 CC(=O)NC[C@H](B(O)O)c(ccc1)c(c12)cccc2 1 288 lactacystin COVPDB1056 CC(C)[C@H](O)[C@]1(NC(=O)[C@H](C)[C@@H]1O)C(=O)SC[C@H](NC(C)=O)C(O)=O 1 289 Lactivicin COVPDB1046 CC(=O)N[C@H]1CON(C1=O)[C@@]1(CCC(=O)O1)C(O)=O 1 290 L-alpha-glutamyl-N-{(1S)-4-{[amino(iminio)methyl]amino}-1-[(1S)-2-chloro-1-oxoethyl]butyl}glycinamide COVPDB18 N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)CCl 1 291 LMC188 COVPDB922 CC1(C)C(=O)N(S1(=O)=O)Cc2cn(nn2)Cc3ccc(Cl)cc3 1 292 LN-1-255 COVPDB1070 C[C@]1(COC(=O)Cc2ccc(O)c(O)c2)[C@@H](N2[C@@H](\C(=C/c3ccccn3)C2=O)S1(=O)=O)C(O)=O 1 293 LORACARBEF COVPDB1073 N[C@@H](C(=O)N[C@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)c1ccccc1 1 294 LP06 COVPDB625 CC(C)(O\N=C(\C(=O)NCB(O)O)c1csc(N)n1)C(O)=O 9 295 L-PARA-CHLORO-1-ACETAMIDO BORONIC ACID COVPDB1435 CC(=O)NC[C@H](B(O)O)c1ccc(Cl)cc1 1 296 L-Pyroglutamylglycyl-L-arginine-p-nitroanilide COVPDB388 NC(=N)NCCC[C@H](NC(=O)CNC(=O)[C@@H]1CCC(=O)N1)C(=O)Nc1ccc(cc1)[N+]([O-])=O 1 297 M-AMINOPHENYLBORONIC ACID COVPDB502 OB(O)c1cccc(c1)N 3 298 MC-1 COVPDB1412 CC(C)(O\N=C(/C(=O)N[C@H]1CN(C(=O)NS(=O)(=O)n2nc(-c3cc(=O)c(O)c[nH]3)n(C[C@@H](O)CO)c2=O)C1=O)c1csc(N)n1)C(O)=O 1 299 m-carboxyphenyl [[N-[(p-iodophenyl)acetyl]amino]methyl]phosphonate COVPDB957 OC(=O)c1ccc(cc1)P(O)(=O)CNC(=O)Cc1ccc(I)cc1 1 300 MDL 101,146 COVPDB1304 FC(F)(F)C(F)(F)C(=O)[C@H](C(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)C)NC(=O)c2ccc(cc2)C(=O)N3CCOCC3 1 301 ME_096 COVPDB1229 Cc1ccc(cc1)S(=O)(=O)NCc1cn(CB(O)OP(O)(O)=O)nn1 1 302 Mecillinam COVPDB693 CC1(C)S[C@@H]2[C@H](\N=C\N3CCCCCC3)C(=O)N2[C@H]1C(O)=O 1 303 meropenem COVPDB724 C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(S[C@@H]3CN[C@@H](C3)C(=O)N(C)C)=C(N2C1=O)C(O)=O 19 304 Methicillin COVPDB352 COc1cccc(OC)c1C(=O)N[C@H](C2=O)[C@H](N23)SC(C)(C)[C@@H]3C([O-])=O 1 305 METHOXYSUCCINYL-ALA-ALA-PRO-ALANINE BORONIC ACID COVPDB527 COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)B(O)O 5 306 METHOXYSUCCINYL-ALA-ALA-PRO-VALINE BORONIC ACID COVPDB529 COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H](B(O)O)C(C)C 4 307 methoxysuccinyl-alanyl-alanyl-prolyl-alanine chloromethyl ketone COVPDB498 COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)CCl 3 308 methyl 4-[({[(2R,5S)-5-[(2S)-2-cyanopyrrolidine-1-carbonyl]pyrrolidin-2-yl]methyl}carbamoyl)amino]benzoate COVPDB476 COC(=O)c1ccc(NC(=O)NC[C@H]2CC[C@H](N2)C(=O)N2CCC[C@H]2C#N)cc1 1 309 METHYL 4-NITROPHENYL HEXYLPHOSPHONATE COVPDB1093 CCCCCC[P@@](=O)(OC)Oc1ccc([N+]([O-])=O)cc1 1 310 METHYL ARACHIDONYL FLUOROPHOSPHONATE COVPDB1088 CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC[P@@](=O)(F)OC 1 311 methyl (R)-(6Z,9Z,12Z)-octadeca-6,9,12-trien-1-ylphosphonofluoridate COVPDB356 CCCCC/C=C/C/C=C\C/C=C\CCCCC[P@](=O)(F)OC 1 312 m-(N,N,N-trimethylammonio)trifluoroacetophe COVPDB1135 C[N+](C)(C)c1cccc(c1)C(=O)C(F)(F)F 1 313 MOL-127 COVPDB3 NC(=N)NCCC[C@H](NC(=O)[C@@H]1CCN2CC[C@@](N)(Cc3ccccc3)C(=O)N12)C(=O)c1nccs1 1 314 MOL-168 COVPDB51 NC(=N)NCCC[C@H](NC(=O)[C@@H]1CC[C@@H]2CC[C@](N)(Cc3ccccc3)C(=O)N12)C(=O)c1nc2ccccc2s1 1 315 monobactam L29 COVPDB1050 c1ccccc1OC(=O)N2[C@H](CC2=O)c3ccccc3 2 316 monobactam L61 COVPDB1047 CC(C)COC(=O)N1[C@H](CC1=O)c2ccccc2 1 317 monobactam L62 COVPDB1048 C1CCCC1OC(=O)N2[C@H](CC2=O)c3ccccc3 1 318 MOR-LEU-HPQ COVPDB19 CC(C)[C@H](NC(=O)CCC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](CCCCN)P(=O)(Oc1ccccc1)Oc1ccccc1 1 319 Moxalactam COVPDB191 CO[C@]1(NC(=O)[C@@H](C(O)=O)c2ccc(O)cc2)[C@H]2OCC(CSc3nnnn3C)=C(N2C1=O)C(O)=O 4 320 MPC-1 COVPDB1245 CC1(C)S[C@@H]2[C@@H]([C@H](O)CCc3cccs3)C(=O)N2[C@H]1C(O)=O 1 321 MS05 COVPDB593 SC[C@@H](C)C(=O)N[C@H](B(O)O)Cc1ccccc1 1 322 MXG COVPDB1115 C[C@H](NC(C)=O)C(=O)N[C@H](CCC(=O)N[C@@H](CCCCN)C(=O)N[C@H]1[C@H]2SCC(OC(C)=O)=C(N2C1=O)C(O)=O)C(O)=O 1 323 N1-[(1R)-1-(DIHYDROXYBORYL)ETHYL]-N2-[(TERT-BUTOXYCARBONYL)-D-GAMMA-GLUTAMYL]-N6-[(BENZYLOXY)CARBONYL-L-LYSINAMIDE COVPDB575 C[C@@H](NC(=O)[C@H](CCCCNC(=O)OCc1ccccc1)NC(=O)CC[C@H](NC(=O)OC(C)(C)C)C(O)=O)B(O)O 1 324 N-[(1R)-1-borono-3-methylbutyl]-N~2~-(2-chloro-4-methoxybenzene-1-carbonyl)-L-leucinamide COVPDB1000 CC(C)C[C@@H](B(O)O)NC(=O)[C@H](CC(C)C)NC(=O)c1ccc(cc1Cl)OC 1 325 N-((1R,2S)-2-allyl-4-oxocyclobutyl)-4-methylbenzenesulfonamide COVPDB41 Cc1ccc(cc1)S(=O)(=O)N[C@@H]2[C@H](CC2=O)CC=C 1 326 N-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}guanidine COVPDB213 CC1(C)OB(OC1(C)C)c1ccc(CCNC(N)=N)cc1 1 327 N-2-THIOPHEN-2-YL-ACETAMIDE BORONIC ACID COVPDB657 OB(O)CNC(=O)Cc1cccs1 1 328 N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]guanidine COVPDB216 CC1(C)OB(OC1(C)C)c1ccc(NC(N)=N)cc1 1 329 N-(4-methoxy-4-oxobutanoyl)-L-alanyl-L-alanyl-N-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-L-prolinamide COVPDB570 COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H](B(O)O)CC(C)C 5 330 N-(4-methoxy-4-oxobutanoyl)-L-alanyl-L-alanyl-N-[(1R)-1-(dihydroxyboranyl)pentyl]-L-prolinamide COVPDB573 CCCC[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)CCC(=O)OC 4 331 N4-(N,N-DIPHENYLCARBAMOYL)-AMINOGUANIDINE COVPDB237 c1ccccc1N(C(=O)NN=C(N)N)c2ccccc2 1 332 N-[5-METHYL-3-O-TOLYL-ISOXAZOLE-4-CARBOXYLIC ACID AMIDE] BORONIC ACID COVPDB54 OB(O)CNC(=O)c1c(C)onc1-c2ccccc2Cl 3 333 N-acetyl-L-alanyl-L-alanyl-N-[(2S)-1-oxopropan-2-yl]-L-prolinamide COVPDB123 O=C(C)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C=O)C 1 334 Nafcillin COVPDB1142 CCOc1ccc2ccccc2c1C(=O)N[C@H]1[C@H]2SC(C)(C)[C@@H](N2C1=O)C(O)=O 3 335 Nalpha-(N,N-dimethylcarbamoyl)-alpha-azalysinep-nitrophenyl ester COVPDB950 CN(C)C(=O)NN(CCCCN)C(=O)Oc1ccc(cc1)[N+]([O-])=O 1 336 naphthalen-2-ylboronic acid COVPDB375 OB(O)c(c1)ccc(c12)cccc2 1 337 N-benzoyl-beta-sultam COVPDB579 O=S1(=O)CCN1C(=O)c2ccccc2 1 338 N-BENZOYL-D-ALANINE COVPDB1295 C[C@@H](NC(=O)c1ccccc1)C(O)=O 1 339 N-benzoyl-L-norleucyl-6-ammonio-L-norleucyl-N~5~-[amino(iminio)methyl]-N-[(2S)-5-carbamimidamido-1-oxopentan-2-yl]-L-ornithinamide COVPDB1175 CCCC[C@H](NC(=O)c1ccccc1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C=O 2 340 N-Benzylcarbamoyl-4-phenylsulfonylazetidin-2-one COVPDB971 c1ccccc1CNC(=O)N2[C@H](CC2=O)S(=O)(=O)c3ccccc3 1 341 N-[(benzyloxy)carbonyl]glycyl-N-[(2S,3R)-4-chloro-3-oxo-1-phenylbutan-2-yl]glycinamide COVPDB1483 c1ccccc1C[C@@H](C(=O)CCl)NC(=O)CNC(=O)CNC(=O)OCc2ccccc2 1 342 N-carbobenzoxy-L-alanine p-nitrophenyl ester COVPDB544 [O-][N+](=O)c1ccc(cc1)OC(=O)[C@H](C)NC(=O)OCc2ccccc2 1 343 N-[(dihydroxyboranyl)methyl]-Nalpha-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]-D-tyrosinamide COVPDB669 Oc1ccc(cc1)C[C@H](C(=O)NCB(O)O)NC(=O)N2CCN(C(=O)C2=O)CC 1 344 N-Formyl 7-Aminocephalosporanic Acid COVPDB153 CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC=O)C2=O)C(O)=O 1 345 NITROCEFIN COVPDB1139 OC(=O)C1=C(CS[C@@H]2[C@H](NC(=O)Cc3cccs3)C(=O)N12)\C=C\c1ccc(cc1[N+]([O-])=O)[N+]([O-])=O 2 346 N-((R)-1-(4-bromophenyl)ethyl)urea-Asn-Val-Arg-alpha-ketothiazole COVPDB591 CC(C)[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)N[C@H](C)c1ccc(Br)cc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)[C@H]1NC=CS1 1 347 N-((tert-butoxycarbonyl)alanylprolylphenylalanyl)-0-benzoylhydroxylamine COVPDB14 CC(C)(C)OC(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc2ccccc2)C(=O)NOC(=O)c3ccccc3 1 348 N-(tert-butoxycarbonyl)-L-alanyl-N-[(1R)-1-(dihydroxyboranyl)-2-methylpropyl]-L-prolinamide COVPDB15 CC(C)[C@@H](B(O)O)N(C(=O)[C@H](C)NC(=O)OC(C)(C)C)C(=O)[C@@H]1CCCN1 1 349 N-(tert-butoxycarbonyl)-L-alanyl-N-[(1S)-5-amino-1-(diethoxyboranyl)pentyl]-L-valinamide COVPDB53 CCOB(OCC)[C@@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(C)C 1 350 N-(tert-butoxycarbonyl)-L-alanyl-N-{(1S)-5-ammonio-1-[hydroxy(3-hydroxypropoxy)boranyl]pentyl}-L-valinamide COVPDB52 CC(C)[C@H](NC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(=O)N[C@@H](CCCCN)B(O)OCCCO 2 351 N-(tert-butoxycarbonyl)-L-alpha-glutamyl-N-[(1R)-1-(carboxycarbonyl)-3,3-difluoropropyl]-L-leucinamide COVPDB169 CC(C)C[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)OC(C)(C)C)C(=O)N[C@@H](CC(F)F)C(=O)C(O)=O 2 352 n-undecyl O-methyl phosphorochloridate COVPDB711 CCCCCCCCCCC[P@@](Cl)(=O)OC 1 353 OL-135 COVPDB578 BrCc1ccc(nc1)-c2cnc(o2)C(=O)CCCCCCc3ccccc3 1 354 O-methylsuccinyl-alanyl-alanyl-prolyl-borophenylalanine COVPDB528 COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H](B(O)O)Cc2ccccc2 5 355 Omuralide COVPDB1316 O=C1O[C@@H]([C@@H](C)C(=O)N2)[C@]12[C@@H](O)C(C)C 1 356 ONO-6818 COVPDB298 CC(C)(C)c1oc(nn1)C(=O)[C@H](C(C)C)NC(=O)Cn2c(=O)c(N)cnc2-c3ccccc3 1 357 OP0595 COVPDB1186 NCCONC(=O)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(O)(=O)=O 2 358 O-[(R)-IPG] O-(p-nitrophenyl) hex-6-e COVPDB1280 CC1(C)OC[C@H](O1)CO[P@](=O)(CCCCC=C)Oc2ccc([N+]([O-])=O)cc2 1 359 Orlistat COVPDB694 CCCCCCCCCCC[C@H](OC(=O)[C@@H](NC=O)CC(C)C)C[C@@H]1OC(=O)[C@H]1CCCCCC 3 360 O-[(S)-IPG] O-(p-nitrophenyl)hex-6-e COVPDB1313 CC1(C)OC[C@@H](O1)CO[P@](=O)(CCCCC=C)Oc2ccc([N+]([O-])=O)cc2 1 361 Oxacillin COVPDB90 Cc1onc(c1C(=O)N[C@H]1[C@H]2SC(C)(C)[C@@H](N2C1=O)C(O)=O)-c1ccccc1 4 362 p-Amidinophenylpyruvate COVPDB501 NC(=N)c1ccc(CC(=O)C(O)=O)cc1 2 363 penem 1 COVPDB68 OC(=O)C1=CS[C@H]2N1C(=O)\C2=C\c1cc2CSCn2n1 1 364 PENICILLIN G COVPDB1232 CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(O)=O 10 365 penicillin V COVPDB176 CC1(C)S[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N2[C@H]1C(O)=O 2 366 PETFP COVPDB924 c1ccccc1CCSCC(=O)C(F)(F)F 1 367 PF-3845 COVPDB1224 FC(F)(F)c1ccc(nc1)Oc2cccc(c2)CC3CCN(CC3)C(=O)Nc4cccnc4 1 368 PFC_001 COVPDB1207 OB(Cn1cc(CNS(=O)(=O)CC(F)(F)F)nn1)OP(O)(O)=O 1 369 PHCH2OCO-D-DPA-PRO-BOROMPG COVPDB1341 COCCC[C@H](NC(=O)c1cccn1C(=O)[C@H](NC(=O)N1CCOCC1)C(c1ccccc1)c1ccccc1)B(O)O 1 370 PHENOXYACETYL LACTIVICIN COVPDB1231 OC(=O)[C@@]1(CCC(=O)O1)N1OC[C@H](NC(=O)COc2ccccc2)C1=O 1 371 PHENYLACETAMIDOMETHYL BORONIC ACID COVPDB808 OB(O)CNC(=O)Cc1ccccc1 1 372 phenylalanyl chloromethylketone COVPDB1222 ClCC(=O)[C@@H](N)Cc1ccccc1 2 373 PHENYL BORONIC ACID COVPDB1216 OB(O)c1ccccc1 5 374 phenyl glycyl-l-alpha-aminopimelyl-epsilon-(d-2-aminoethyl)phosphonate COVPDB1277 C[C@@H](NC(=O)CCCC[C@H](NC(=O)CN)C(O)=O)P(O)(=O)Oc1ccccc1 1 375 (phenylmethylsulfonylamino)methylboronic acid COVPDB580 OB(O)CNS(=O)(=O)Cc1ccccc1 2 376 phosphoethanolamine COVPDB1187 NCCOP(O)(O)=O 1 377 phosphonooxy-[[[4-(1~{H}-1,2,3,4-tetrazol-5-yl)-2-(trifluoromethyl)phenyl]sulfonylamino]methyl]borinic acid COVPDB466 OB(CNS(=O)(=O)c1ccc(cc1C(F)(F)F)-c1nnn[nH]1)OP(O)(O)=O 1 378 phosphonooxy-[[[4-(1~{H}-1,2,3,4-tetrazol-5-yl)phenyl]sulfonylamino]methyl]borinic acid COVPDB468 OB(CNS(=O)(=O)c1ccc(cc1)-c1nnn[nH]1)OP(O)(O)=O 1 379 Pinacol 5-Diformylaminomethylbenzo[b]thiophen-2-ylboronate COVPDB1441 OB(O)c(s1)cc(c12)cc(cc2)CN(C=O)C=O 1 380 piperacillin COVPDB994 CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C(O)=O)c2ccccc2)C(=O)C1=O 4 381 p-nitrophenyl guanidinobenzoate COVPDB849 NC(=N)Nc1ccc(cc1)C(=O)Oc1ccc(cc1)[N+]([O-])=O 4 382 p-nitrophenyl [N-(benzyloxycarbonyl)aminomethyl]phosphonate COVPDB807 OP(=O)(CNC(=O)OCc1ccccc1)Oc1ccc(cc1)[N+]([O-])=O 2 383 p-Nitrophenyl o-Hydroxy-alpha-methylcinnamate COVPDB1173 C\C(=C/c1ccccc1O)C(=O)Oc1ccc(cc1)[N+]([O-])=O 1 384 PRC1214 COVPDB583 CCC(CC)n1cc(cn1)C(=O)C(F)F 1 385 PROPYL ACETATE COVPDB240 CCCOC(=O)C 2 386 PSEUDOTYROSTATIN COVPDB1401 Oc1ccc(cc1)C[C@H](NC(=O)CC(C)C)C(=O)N[C@H](C=O)Cc2ccc(O)cc2 1 387 PSR3-226 COVPDB1324 C[C@@]1([C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O)C(=O)OCC(N)=O 1 388 PSR-3-283A COVPDB188 CC1(C)[C@@H](N2[C@@H]([C@H](CO)C2=O)S1(=O)=O)C(O)=O 1 389 PSR-4-157 COVPDB126 C[C@]1(COC(=O)CCCCC(O)=O)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O 1 390 p-Tolylmethanesulfonyl fluoride COVPDB1443 Cc1ccc(CS(F)(=O)=O)cc1 1 391 QPX7728 COVPDB1284 OB1Oc2c(ccc(F)c2C(O)=O)[C@H]2C[C@@H]12 2 392 (R)‐1,2‐dibutyl‐carbamoylglycero‐3‐O‐p‐nitrophenylbutyl‐phosphonate COVPDB1379 CCCCNC(=O)OC[C@@H](OC(=O)NCCCC)CO[P@@](=O)(CCCC)Oc1ccc([N+]([O-])=O)cc1 1 393 RC-(RP,SP)-1,2-dibutylcarbamoyl-glycero-3-O-p-nitrophenyl butylphosphonate COVPDB629 CCCCC(=O)OCC(COC(=O)CCCC)O[P@@](=O)(CCCC)Oc1ccc([N+]([O-])=O)cc1 1 394 relebactam COVPDB989 OS(=O)(=O)ON1[C@H]2CN([C@@H](CC2)C(=O)NC2CCNCC2)C1=O 10 395 RIVASTIGMINE COVPDB761 CCN(C)C(=O)OC1=CC=CC(=C1)[C@H](C)N(C)C 1 396 (RP,SP)-O-(2R)-(1-PHENOXYBUT-2-YL)-METHYLPHOSPHONIC ACID CHLORIDE COVPDB955 O=[P@](Cl)(C)O[C@H](CC)COc1ccccc1 1 397 Ruthenocenyl-7-Aminocephalosporanic Acid COVPDB1382 [Ru]123456789[C]%10[C]1[C]2[C]3[C]4%10.CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)CCC(=O)C51[C]6[C]7[C]8[C]91)C2=O)C(O)=O 1 398 Ruthenocenyl-7-Aminodesacetoxycephalosporanic Acid COVPDB396 [Ru]123456789C%10(C(CCC(N[C@H]%11[C@@H]%12N(C(=C(CS%12)C)C(O)=O)C%11=O)=O)=O)[C]1[C]2[C]3[C]4%10.[C]51[C]6[C]7[C]8[C]91 1 399 RWJ-30353 COVPDB4 N[C@H](Cc1ccccc1)C(=O)N([C@@H](CCCNC(N)=N)C(=O)c1nc2ccccc2s1)C(=O)[C@@H]1CCCN1 1 400 RWJ-51084 COVPDB1292 NC(=N)NCCC[C@H](NC(=O)C1CCCC1)C(=O)c1nc2ccccc2s1 1 401 RWJ-51438 COVPDB99 CN[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)c1nc2ccc(cc2s1)C(O)=O 1 402 S02030 COVPDB1511 O=C([O-])c1nnn(c1)C[C@@H](B(O)O)NC(=O)Cc2cccs2 2 403 S03043 COVPDB456 OB(O)[C@H](Cn1cc(nn1)-c1cccc(c1)C(O)=O)NC(=O)Cc1cccs1 1 404 S06015 COVPDB768 O=P([O-])([O-])OB(O)Cn1cc(nn1)-c2ccsc2 1 405 S17079 COVPDB1024 OB(Cn1cc(nn1)-c1cccc(c1)C(O)=O)OP(O)(O)=O 1 406 S17083 COVPDB1230 NC(=O)c1cccc(c1)-c1cn(CB(O)OP(O)(O)=O)nn1 1 407 (S)-2-(3-((R)-1-(4-BROMOPHENYL)ETHYL)UREIDO)-N-((S)-1-((S)-5-GUANIDINO-1-OXO-1-(THIAZOL-2-YL)PENTAN-2-YLAMINO)-3-METHYL-1-OXOBUTAN-2-YL)-5-UREIDOPENTANAMIDE COVPDB173 CC(C)[C@H](NC(=O)[C@H](CCCNC(N)=O)NC(=O)N[C@H](C)c1ccc(Br)cc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)c1nccs1 1 408 (S)-2-acetamido-6-amino-N-((S)-5-guanidino-1-oxopentan-2-yl)hexanamide COVPDB362 CC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C=O 2 409 SA1-204 COVPDB67 C[C@]1(COC(=O)Cc2ccccc2)[C@@H](N2[C@@H](\C(=C/c3ccccn3)C2=O)S1(=O)=O)C(O)=O 1 410 SA2-13 COVPDB1298 C[C@]1(COC(=O)CCCC(O)=O)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O 4 411 SA3-53 COVPDB1114 C[C@]1(COC(=O)NCCN)[C@@H](N2[C@@H](\C(=C/c3ccccn3)C2=O)S1(=O)=O)C(O)=O 2 412 SA4-17 COVPDB1113 C[C@]1(COC(N)=O)[C@@H](N2[C@@H](\C(=C/c3cc(ccn3)C(N)=O)C2=O)S1(=O)=O)C(O)=O 1 413 SA4-44 COVPDB1116 COC(=O)Nc1ccnc(\C=C2/[C@@H]3N([C@@H](C(O)=O)C(C)(C)S3(=O)=O)C2=O)c1 1 414 SAR127303 COVPDB294 FC(F)(F)C(C(F)(F)F)OC(=O)N1CCC(CC1)CNS(=O)(=O)c2ccc(Cl)cc2 1 415 Saxagliptin COVPDB568 N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2 1 416 saxagliptin M2 COVPDB617 N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)[C@]12C[C@H]3C[C@](O)(C[C@](O)(C3)C1)C2 1 417 Serine protease inhibitor BEZ-NLE-LYS-ARG-M9P COVPDB1086 CCCC[C@H](NC(=O)c1ccccc1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)C(F)(F)F 2 418 (S)-(methyl 4-nitrophenyl [(R)-methoxy(phenyl)methyl]phosphonate) COVPDB935 c1ccccc1[C@H](OC)[P@](=O)(OC)Oc2ccc([N+]([O-])=O)cc2 1 419 Soman COVPDB851 CC(C)(C)[C@H](C)O[P@@](F)(=O)C 4 420 Suc-Ala-Ala-Pro-Phe-chloromethylketone COVPDB1011 C[C@H](NC(=O)CCC(O)=O)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)CCl 3 421 Suc-Val-Pro-PheP-(OPh)2 COVPDB101 CC(C)[C@H](NC(=O)CCC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)P(=O)(Oc1ccccc1)Oc1ccccc1 1 422 SULBACTAM COVPDB1398 CC1(C)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O 4 423 TA1 COVPDB1390 CCO[P@@](=O)(C#N)N(CC)CC 2 424 TA4 COVPDB1378 CCO[P@@](F)(=O)NC 1 425 TA5 COVPDB1391 CCN[P@@](F)(=O)OCC 1 426 TA6 COVPDB1380 CCCN[P@@](F)(=O)OCC 1 427 Tabun COVPDB508 CCO[P@@](=O)(C#N)N(C)C 3 428 TAFC COVPDB806 C/C1=C/C(=O)N(O)CCC[C@@H](NC(=O)C)C(=O)OCC/C(C)=C\C(=O)N(O)CCC[C@@H](NC(=O)C)C(=O)OCC/C(C)=C\C(=O)N(O)CCC[C@@H](NC(=O)C)C(=O)OCC1 1 429 Taniborbactam COVPDB1034 NCCN[C@@H]1CC[C@H](CC(=O)N[C@H]2Cc3cccc(C(O)=O)c3OB2O)CC1 4 430 TAZOBACTAM COVPDB1377 O=C(C1)N([C@@H]12)[C@@H](C([O-])=O)[C@](S2(=O)=O)(C)Cn3ccnn3 6 431 Tebipenem COVPDB1383 CC(C)(C)C(=O)OCOC(=O)C1=C([C@H](C)[C@@H](N12)[C@H](C2=O)[C@@H](C)O)SC3CN(C3)C4=NCCS4 1 432 Telaprevir COVPDB801 C1CC1NC(=O)C(=O)[C@H](CCC)NC(=O)[C@H]([C@H]([C@H]23)CCC3)N(C2)C(=O)[C@H](C(C)(C)C)NC(=O)[C@H](C4CCCCC4)NC(=O)c5cnccn5 6 433 temocillin COVPDB1388 CO[C@]1(NC(=O)C(C(O)=O)C2=CSC=C2)[C@H]2SC(C)(C)[C@@H](N2C1=O)C(O)=O 2 434 tert-Butyl ((1-((3S,5S)-5-((S)-2-Cyanopyrrolidine-1-carbonyl)-1-(4-phenylbutanoyl)pyrrolidin-3-yl)-1H-1,2,3-triazol-4-yl)methyl)carbamate COVPDB990 CC(C)(C)OC(=O)NCc1cn(nn1)[C@H]2C[C@@H](C(=O)N3CCC[C@H]3C#N)N(C2)C(=O)CCCc4ccccc4 1 435 tert-butyl (1-hydroxy-1,3-dihydro-2,1-benzoxaborol-6-yl)carbamate COVPDB968 C1OB(O)c(c12)cc(cc2)NC(=O)OC(C)(C)C 1 436 tert-butyl (3-methyl-5-methylene-2-oxotetrahydrofuran-3-yl)carbamate COVPDB1179 CC(C)(C)OC(=O)N[C@@]1(C)CC(=C)OC1=O 1 437 tert-butyl N-[(1R)-1-{5-[(2-chloro-6-fluorophenyl)methanesulfonyl]-1,3,4-oxadiazol-2-yl}-2-methylpropyl]carbamate COVPDB1199 CC(C)(C)OC(=O)N[C@H](C(C)C)c1nnc(o1)S(=O)(=O)Cc2c(F)cccc2Cl 1 438 tert-butyl N-[(1S)-1-{5-[(2-chloro-6-fluorophenyl)methanesulfonyl]-1,3,4-oxadiazol-2-yl}-2-methylpropyl]carbamate COVPDB1200 CC(C)(C)OC(=O)N[C@@H](C(C)C)c1nnc(o1)S(=O)(=O)Cc2c(F)cccc2Cl 1 439 ticarcillin COVPDB1471 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](C(O)=O)c3ccsc3)C(=O)N2[C@H]1C(O)=O 1 440 TLCK COVPDB644 Cc1ccc(cc1)S(=O)(=O)N[C@@H](CCCCN)C(=O)CCl 3 441 tosyl fluoride COVPDB1399 Cc1ccc(S(F)(=O)=O)cc1 1 442 TRI166 COVPDB1333 CCC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCSC(N)=N)B(O)O 1 443 tridecylboronic acid COVPDB522 OB(O)CCCCCCCCCCCCC 1 444 TYROSTATIN COVPDB1402 Oc1ccc(cc1)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)CC(C)C)Cc2ccc(O)cc2 1 445 uPA-I2 COVPDB1314 CC(C)COC(=O)N[C@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C=O 1 446 uPA-I4 COVPDB1315 NC(=N)NCCC[C@H](NC(=O)CN1c2ccccc2C(=N[C@H](NS(=O)(=O)Cc2ccccc2)C1=O)c1ccccc1)C=O 1 447 uPA-I6 COVPDB1306 C[C@H](NC(=O)[C@@H](CO)NS(=O)(=O)CCc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C=O 1 448 URB597 COVPDB1180 NC(=O)c1cccc(c1)-c2cc(ccc2)OC(=O)NC3CCCCC3 2 449 Vaborbactam COVPDB224 OB1O[C@H](CC(O)=O)CC[C@@H]1NC(=O)Cc1cccs1 3 450 Val-BoroPro COVPDB869 CC(C)[C@@H](N)C(=O)N1CCC[C@H]1B(O)O 1 451 vildagliptin COVPDB1061 OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N 2 452 VX COVPDB1452 CCO[P@](C)(=O)SCCN(C(C)C)C(C)C 9 453 WAY185229 COVPDB1457 OC(=O)C1=CS[C@H]2N1C(=O)\C2=C\c1cn2c3CCCc3sc2n1 2 454 WCK 4234 COVPDB619 OS(=O)(=O)ON1[C@H]2CN([C@@H](CC2)C#N)C1=O 2 455 WCK 5107 COVPDB618 OS(=O)(=O)ON1[C@H]2CN([C@@H](CC2)C(=O)NNC(=O)[C@@H]2CCCNC2)C1=O 1 456 WCK 5153 COVPDB620 OS(=O)(=O)ON1[C@H]2CN([C@@H](CC2)C(=O)NNC(=O)[C@@H]2CCNC2)C1=O 1 457 WL-001 COVPDB562 SC[C@@H](C)C(=O)N[C@H](B(O)O)c1ccc(F)cc1 2 458 Z-(4-AmPhGly)P(OPh)2 COVPDB1501 NC(=N)c1ccc(cc1)[C@H](NC(=O)OCc1ccccc1)P(=O)(Oc1ccccc1)Oc1ccccc1 2 459 ZAIB COVPDB40 CC[C@H](C)[C@@H](B(O)O)NC(=O)[C@H](C)NC(=O)OCc1ccccc1 1 460 Z-ALA PROLINAL COVPDB1500 c1ccccc1COC(=O)N2CCC[C@H]2C(=O)N3CCC[C@H]3C=O 5 461 Z-d-Dpa-Pro-Mpgp(OPh)2 COVPDB1223 c1ccccc1OP(=O)(Oc2ccccc2)[C@@H](CCCOC)NC(=O)[C@@H]3CCCN3C(=O)[C@@H](C(c4ccccc4)c5ccccc5)NC(=O)OCc6ccccc6 1 462 Z-Leu-Leu-Leu-B(OH)2 COVPDB642 CC(C)C[C@@H](B(O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1 2