TTD_Target_ID Target_Name TTD_Drug_ID Drug_Name Drug_Highest_Status Drug_PubchemID Molecular_Formula Molecular_Weight Canonical_SMILES Activity Binder_Type T67272 Aminopeptidase N D0U2JP Sitagliptin Approved 4369359 C16H15F6N5O 407.31 C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N B03NIX (2S,4S)-Methyl 4-((E)-3-(3,4-dimethoxyphenyl)acrylamido)-1-acetylpyrrolidine-2-carboxylate Investigative 25147058 C19H24N2O6 376.4 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)/C=C/C2=CC(=C(C=C2)OC)OC IC50 = 161800 nM Poor binder T67272 Aminopeptidase N B05PIL Chembl4174570 Investigative 73672383 C21H28ClFN4O6 486.9 CC(C)C[C@@H](C(=O)OCN1C=C(C(=O)NC1=O)F)NC(=O)[C@H]([C@@H](CC2=CC=CC=C2)N)O.Cl IC50 = 65290 nM Poor binder T67272 Aminopeptidase N B07AEJ (2S,4S)-1-(3-(3,4-Dimethoxyphenyl)propanoyl)-4-(cinnamamido)-N-hydroxypyrrolidine-2-carboxamide Investigative 25147252 C25H29N3O6 467.5 COC1=C(C=C(C=C1)CCC(=O)N2C[C@H](C[C@H]2C(=O)NO)NC(=O)/C=C/C3=CC=CC=C3)OC IC50 = 96600 nM Poor binder T67272 Aminopeptidase N B0EA3Z (3S)-2-(Benzenesulfonyl)-N-hydroxy-6,11-dioxa-2-azaspiro[4.6]undecane-3-carboxamide Investigative 44576635 C15H20N2O6S 356.4 C1CCOC2(C[C@H](N(C2)S(=O)(=O)C3=CC=CC=C3)C(=O)NO)OC1 IC50 = 106700 nM Poor binder T67272 Aminopeptidase N B0LC8T 4-Benzoyloxy-1-methanesulfonyl-pyrrolidine-2-carboxylicacid methyl ester Investigative 44569059 C14H17NO6S 327.35 COC(=O)[C@@H]1C[C@H](CN1S(=O)(=O)C)OC(=O)C2=CC=CC=C2 IC50 = 53600 nM Poor binder T67272 Aminopeptidase N B15SNK (2S)-5-(Diaminomethylideneamino)-2-[[(2R)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 122195270 C29H48N12O8 692.8 C1=CC=C(C=C1)C[C@@H](C(=O)N[C@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 = 85000 nM Poor binder T67272 Aminopeptidase N B17YAU (2S,4S)-4-[[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]amino]-1-[(2S)-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]propanoyl]pyrrolidine-2-carboxylic acid Investigative 53353383 C28H33F3N4O6 578.6 C[C@@H](C(=O)N1C[C@H](C[C@H]1C(=O)O)NC(=O)C[C@@H](CC2=CC(=C(C=C2F)F)F)N)N[C@@H](CCC3=CC=CC=C3)C(=O)O IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N B1G4NY 2-(2-((3-(4-Hydroxybenzyl)-5-aminobenzamido)methyl)phenyl)acetic acid Investigative 44560557 C23H22N2O4 390.4 C1=CC=C(C(=C1)CC(=O)O)CNC(=O)C2=CC(=CC(=C2)CC3=CC=C(C=C3)O)N Ki ~ 100000 nM Poor binder T67272 Aminopeptidase N B1K0ZC (2S,5S,8Z,13S)-13-Amino-N-benzyl-2-[(4-hydroxyphenyl)methyl]-1-methyl-3,14-dioxo-1,4-diazacyclotetradec-8-ene-5-carboxamide Investigative 53259405 C28H36N4O4 492.6 CN1[C@H](C(=O)N[C@@H](CC/C=C\\CCC[C@@H](C1=O)N)C(=O)NCC2=CC=CC=C2)CC3=CC=C(C=C3)O Ki ~ 100000 nM Poor binder T67272 Aminopeptidase N B1L6NO (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(Diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]propanoic acid Investigative 70696054 C26H41N9O8 607.7 C[C@@H](C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 ~ 70000 nM Poor binder T67272 Aminopeptidase N B1P5BT (2S)-N-Hydroxy-4-methylsulfanyl-2-(2-phenylethylcarbamoylamino)butanamide Investigative 70696450 C14H21N3O3S 311.4 CSCC[C@@H](C(=O)NO)NC(=O)NCCC1=CC=CC=C1 IC50 = 110000 nM Poor binder T67272 Aminopeptidase N B1PV5K (2S,4S)-Methyl 1-acetyl-4-(benzamido)pyrrolidine-2-carboxylate Investigative 11942810 C15H18N2O4 290.31 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)C2=CC=CC=C2 IC50 = 122500 nM Poor binder T67272 Aminopeptidase N B1YV5K 1-Tosyl-4-oxo-L-proline methyl ester Investigative 44576563 C13H15NO5S 297.33 CC1=CC=C(C=C1)S(=O)(=O)N2CC(=O)C[C@H]2C(=O)OC IC50 = 54900 nM Poor binder T67272 Aminopeptidase N B20OKU (S)-2-((1R,2S)-2-Amino-1-cyano-3-phenyl-propylamino)-3-phenyl-propionic acid methyl ester Investigative 44283908 C20H23N3O2 337.4 COC(=O)[C@H](CC1=CC=CC=C1)N[C@@H](C#N)[C@H](CC2=CC=CC=C2)N IC50 = 85000 nM Poor binder T67272 Aminopeptidase N B20WPF Methyl (2S,4R)-1-(4-methylphenyl)sulfonyl-4-(4-methylphenyl)sulfonyloxypyrrolidine-2-carboxylate Investigative 391527 C20H23NO7S2 453.5 CC1=CC=C(C=C1)S(=O)(=O)N2C[C@@H](C[C@H]2C(=O)OC)OS(=O)(=O)C3=CC=C(C=C3)C IC50 = 101400 nM Poor binder T67272 Aminopeptidase N B2L8EF (2S,5S,7Z,13S)-13-Amino-N-benzyl-2-[(4-hydroxyphenyl)methyl]-1-methyl-3,14-dioxo-1,4-diazacyclotetradec-7-ene-5-carboxamide Investigative 53259403 C28H36N4O4 492.6 CN1[C@H](C(=O)N[C@@H](C/C=C\\CCCC[C@@H](C1=O)N)C(=O)NCC2=CC=CC=C2)CC3=CC=C(C=C3)O Ki ~ 100000 nM Poor binder T67272 Aminopeptidase N B2OI0M (2S)-2-[[(2S)-2-[[2-[Benzyl-[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Investigative 56953765 C29H48N12O8 692.8 C1=CC=C(C=C1)CN(CC(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N B31HXL (S)-2-((1S,2S)-2-Amino-1-cyano-3-phenyl-propylamino)-3-phenyl-propionic acid methyl ester Investigative 44283924 C20H23N3O2 337.4 COC(=O)[C@H](CC1=CC=CC=C1)N[C@H](C#N)[C@H](CC2=CC=CC=C2)N IC50 = 146000 nM Poor binder T67272 Aminopeptidase N B3V1QS 1-Methanesulfonyl-4-(3-phenyl-acryloyloxy)-pyrrolidine-2-carboxylic acid methyl ester Investigative 44569081 C16H19NO6S 353.4 COC(=O)[C@@H]1C[C@H](CN1S(=O)(=O)C)OC(=O)/C=C/C2=CC=CC=C2 IC50 = 114300 nM Poor binder T67272 Aminopeptidase N B40XSC (2S,4S)-Methyl 1-acetyl-4-(pyrazine-2-carboxamido)-pyrrolidine-2-carboxylate Investigative 25147248 C13H16N4O4 292.29 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)C2=NC=CN=C2 IC50 = 82600 nM Poor binder T67272 Aminopeptidase N B41BNM (3R)-3-Amino-1-(2-benzoyldiazepan-1-yl)-4-(2,4,5-trifluorophenyl)butan-1-one;hydrochloride Investigative 16739330 C22H25ClF3N3O2 455.9 C1CCN(N(CC1)C(=O)C2=CC=CC=C2)C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N.Cl IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N B43FLX (2S)-5-(Diaminomethylideneamino)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]pentanoic acid Investigative 70681503 C30H50N12O8 706.8 C[C@H]([C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N)O IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N B4BYV0 (S)-2-((S)-1-((S)-2-((4R,7S,10R)-10-Amino-7-(4-hydroxybenzyl)-6,9-dioxo-1,2-dithia-5,8-diazacycloundecane-4-carboxamido)-3-(1H-imidazol-5-yl)propanoyl)pyrrolidine-2-carboxamido)-3-phenylpropanoic acid Investigative 52941108 C35H42N8O8S2 766.9 C1C[C@H](N(C1)C(=O)[C@H](CC2=CN=CN2)NC(=O)[C@@H]3CSSC[C@@H](C(=O)N[C@H](C(=O)N3)CC4=CC=C(C=C4)O)N)C(=O)N[C@@H](CC5=CC=CC=C5)C(=O)O Ki = 57000 nM Poor binder T67272 Aminopeptidase N B4DQ1Y (S)-7-(Toluene-4-sulfonyl)-1,4-dioxa-7-aza-spiro[4.4]nonane-8-carboxylic acid methyl ester Investigative 44576587 C15H19NO6S 341.4 CC1=CC=C(C=C1)S(=O)(=O)N2CC3(C[C@H]2C(=O)OC)OCCO3 IC50 = 155800 nM Poor binder T67272 Aminopeptidase N B4GV3K (2S)-5-(Carbamoylamino)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 122195275 C29H47N11O9 693.8 C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=O)N)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 = 62000 nM Poor binder T67272 Aminopeptidase N B57KRT 4-Hydroxy-2-(2-methylsulfanyl-phenyl)-isoindole-1,3-dione Investigative 44368725 C15H11NO3S 285.3 CSC1=CC=CC=C1N2C(=O)C3=C(C2=O)C(=CC=C3)O IC50 = 133900 nM Poor binder T67272 Aminopeptidase N B58LGR (2S,4S)-4-[[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]amino]-1-[(2S)-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]butanoyl]pyrrolidine-2-carboxylic acid Investigative 53354470 C29H35F3N4O6 592.6 CC[C@@H](C(=O)N1C[C@H](C[C@H]1C(=O)O)NC(=O)C[C@@H](CC2=CC(=C(C=C2F)F)F)N)N[C@@H](CCC3=CC=CC=C3)C(=O)O IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N B5OUV9 (2S,4S)-Methyl 1-acetyl-4-azidopyrrolidine-2-carboxylate Investigative 44563970 C8H12N4O3 212.21 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)N=[N+]=[N-] IC50 = 73700 nM Poor binder T67272 Aminopeptidase N B5X3BL Ethyl 2-[(3S)-3-[[(2S)-2-aminopropanoyl]amino]-2,6-dioxopiperidin-1-yl]acetate;hydrochloride Investigative 44481389 C12H20ClN3O5 321.76 CCOC(=O)CN1C(=O)CC[C@@H](C1=O)NC(=O)[C@H](C)N.Cl IC50 = 64300 nM Poor binder T67272 Aminopeptidase N B6EBP3 (1-Amino-3-methylbutyl)phosphonic acid Investigative 182612 C5H14NO3P 167.14 CC(C)CC(N)P(=O)(O)O Ki = 53000 nM Poor binder T67272 Aminopeptidase N B6G9CK 4-Amino-2-(2,6-dimethylphenyl)isoindole-1,3-dione Investigative 10333136 C16H14N2O2 266.29 CC1=C(C(=CC=C1)C)N2C(=O)C3=C(C2=O)C(=CC=C3)N IC50 = 108900 nM Poor binder T67272 Aminopeptidase N B6LTQ1 (2S,4S)-Methyl 1-((E)-3-(3,4-dimethoxyphenyl)acryloyl)-4-(nicotinamido)pyrrolidine-2-carboxylate Investigative 25147249 C23H25N3O6 439.5 COC1=C(C=C(C=C1)/C=C/C(=O)N2C[C@H](C[C@H]2C(=O)OC)NC(=O)C3=CN=CC=C3)OC IC50 = 137300 nM Poor binder T67272 Aminopeptidase N B6VF3S 2-(5'-Fluoro-2'-oxospiro[1,3-dioxane-2,3'-indole]-1'-yl)-N-hydroxyacetamide Investigative 71603244 C13H13FN2O5 296.25 C1COC2(C3=C(C=CC(=C3)F)N(C2=O)CC(=O)NO)OC1 IC50 = 97490 nM Poor binder T67272 Aminopeptidase N B7J9TQ 1-Methanesulfonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid methyl ester Investigative 44569061 C14H19NO7S2 377.4 CC1=CC=C(C=C1)S(=O)(=O)O[C@@H]2C[C@H](N(C2)S(=O)(=O)C)C(=O)OC IC50 = 68900 nM Poor binder T67272 Aminopeptidase N B7NT1J 4-(4-Chloro-benzoyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester Investigative 44569011 C20H20ClNO6S 437.9 CC1=CC=C(C=C1)S(=O)(=O)N2C[C@@H](C[C@H]2C(=O)OC)OC(=O)C3=CC=C(C=C3)Cl IC50 = 51200 nM Poor binder T67272 Aminopeptidase N B7PGD9 1-Benzenesulfonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid methyl ester Investigative 44569038 C19H21NO7S2 439.5 CC1=CC=C(C=C1)S(=O)(=O)O[C@@H]2C[C@H](N(C2)S(=O)(=O)C3=CC=CC=C3)C(=O)OC IC50 = 61300 nM Poor binder T67272 Aminopeptidase N B7VJ4S trans-1-Benzenesulfonyl-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester Investigative 18445902 C12H15NO5S 285.32 COC(=O)[C@@H]1C[C@H](CN1S(=O)(=O)C2=CC=CC=C2)O IC50 = 53800 nM Poor binder T67272 Aminopeptidase N B81BUO (2S)-5-(Diaminomethylideneamino)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-4-phenylbutanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 56953762 C30H50N12O8 706.8 C1=CC=C(C=C1)CC[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 = 54000 nM Poor binder T67272 Aminopeptidase N B8SZH3 (2S,4S)-Methyl 4-amino-1-((E)-3-(3,4-dimethoxyphenyl)acryloyl)pyrrolidine-2-carboxylate Investigative 25147157 C17H22N2O5 334.4 COC1=C(C=C(C=C1)/C=C/C(=O)N2C[C@H](C[C@H]2C(=O)OC)N)OC IC50 = 70600 nM Poor binder T67272 Aminopeptidase N B9AE7Y (2S,4S)-4-[[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]amino]-1-[(2S)-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid Investigative 53354369 C31H39F3N4O6 620.7 CCCC[C@@H](C(=O)N1C[C@H](C[C@H]1C(=O)O)NC(=O)C[C@@H](CC2=CC(=C(C=C2F)F)F)N)N[C@@H](CCC3=CC=CC=C3)C(=O)O IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N B9CLD4 Methyl (8S)-7-(benzenesulfonyl)-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxylate Investigative 44576616 C14H17NO6S 327.35 COC(=O)[C@@H]1CC2(CN1S(=O)(=O)C3=CC=CC=C3)OCCO2 IC50 = 150600 nM Poor binder T67272 Aminopeptidase N B9FDB3 (S)-2-(Toluene-4-sulfonyl)-6,10-dioxa-2-aza-spiro[4.5]decane-3-carboxylic acid methyl ester Investigative 44576614 C16H21NO6S 355.4 CC1=CC=C(C=C1)S(=O)(=O)N2CC3(C[C@H]2C(=O)OC)OCCCO3 IC50 = 173700 nM Poor binder T67272 Aminopeptidase N B9I0JE Methyl (3S)-2-(4-methylphenyl)sulfonyl-6,11-dioxa-2-azaspiro[4.6]undecane-3-carboxylate Investigative 44576615 C17H23NO6S 369.4 CC1=CC=C(C=C1)S(=O)(=O)N2CC3(C[C@H]2C(=O)OC)OCCCCO3 IC50 = 124300 nM Poor binder T67272 Aminopeptidase N B9M1YW (3S)-N-Hydroxy-2-(4-methylphenyl)sulfonyl-6,10-dioxa-2-azaspiro[4.5]decane-3-carboxamide Investigative 44576631 C15H20N2O6S 356.4 CC1=CC=C(C=C1)S(=O)(=O)N2CC3(C[C@H]2C(=O)NO)OCCCO3 IC50 = 61800 nM Poor binder T67272 Aminopeptidase N B9TE2I (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-Amino-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Investigative 70683617 C38H57N13O9 839.9 C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)N IC50 = 122000 nM Poor binder T67272 Aminopeptidase N BB81XH (2S,4S)-Methyl 1-(3-(3,4-dimethoxyphenyl)propanoyl)-4-aminopyrrolidine-2-carboxylate Investigative 25146959 C17H24N2O5 336.4 COC1=C(C=C(C=C1)CCC(=O)N2C[C@H](C[C@H]2C(=O)OC)N)OC IC50 = 68400 nM Poor binder T67272 Aminopeptidase N BC47SI 1-Benzenesulfonyl-4-oxo-pyrrolidine-2-carboxylicacid methyl ester Investigative 44576564 C12H13NO5S 283.3 COC(=O)[C@@H]1CC(=O)CN1S(=O)(=O)C2=CC=CC=C2 IC50 = 75800 nM Poor binder T67272 Aminopeptidase N BCG82T (2S,4S)-Methyl 4-(4-bromobenzamido)-1-acetylpyrrolidine-2-carboxylate Investigative 25146960 C15H17BrN2O4 369.21 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)C2=CC=C(C=C2)Br IC50 = 149300 nM Poor binder T67272 Aminopeptidase N BCV1L8 (2S)-5-(Diaminomethylideneamino)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-(2,3,4,5,6-pentafluorophenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 56953636 C29H43F5N12O8 782.7 C(C[C@@H](C(=O)N[C@@H](CC1=C(C(=C(C(=C1F)F)F)F)F)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCC(=O)N)N)CN=C(N)N IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N BD0O8Q Methyl 2-((2S,4S)-4-(3,4,5-trimethoxybenzamido)-1-acetylpyrrolidine-2-carboxamido)acetate Investigative 25147155 C20H27N3O8 437.4 CC(=O)N1C[C@H](C[C@H]1C(=O)NCC(=O)OC)NC(=O)C2=CC(=C(C(=C2)OC)OC)OC IC50 = 121500 nM Poor binder T67272 Aminopeptidase N BDE8J2 2-(2-(((5R,8S,11R)-11-Amino-8-(4-hydroxybenzyl)-7,10-dioxo-1,2-dithia-6,9-diazacyclotridecane-5-carboxamido)methyl)phenyl)acetic acid Investigative 52946764 C26H32N4O6S2 560.7 C1CSSCC[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1N)CC2=CC=C(C=C2)O)C(=O)NCC3=CC=CC=C3CC(=O)O Ki = 50000 nM Poor binder T67272 Aminopeptidase N BDU26Q 1-Benzenesulfonyl-4-(3-phenyl-acryloyloxy)-pyrrolidine-2-carboxylic acid methyl ester Investigative 44569058 C21H21NO6S 415.5 COC(=O)[C@@H]1C[C@H](CN1S(=O)(=O)C2=CC=CC=C2)OC(=O)/C=C/C3=CC=CC=C3 IC50 = 134700 nM Poor binder T67272 Aminopeptidase N BE39PL 2-(2,6-Diisopropylphenyl)-4,5,6,7-tetrafluoroisoindoline-1,3-dithione Investigative 44368736 C20H17F4NS2 411.5 CC(C)C1=C(C(=CC=C1)C(C)C)N2C(=S)C3=C(C2=S)C(=C(C(=C3F)F)F)F IC50 = 98400 nM Poor binder T67272 Aminopeptidase N BE71VH (2S,4S)-Methyl 1-acetyl-4-(nicotinamido)pyrrolidine-2-carboxylate Investigative 25147352 C14H17N3O4 291.3 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)C2=CN=CC=C2 IC50 = 78400 nM Poor binder T67272 Aminopeptidase N BF89TS (2S,5S,8E,13S)-13-Amino-N-benzyl-2-[(4-hydroxyphenyl)methyl]-1-methyl-3,14-dioxo-1,4-diazacyclotetradec-8-ene-5-carboxamide Investigative 53259404 C28H36N4O4 492.6 CN1[C@H](C(=O)N[C@@H](CC/C=C/CCC[C@@H](C1=O)N)C(=O)NCC2=CC=CC=C2)CC3=CC=C(C=C3)O Ki ~ 100000 nM Poor binder T67272 Aminopeptidase N BFPQ19 (2S,3R)-2-(3-(4-Hydroxybenzyl)-5-((S)-2-amino-3-methylbutanamido)benzamido)-3-methylpentanoic acid Investigative 44560558 C25H33N3O5 455.5 CC[C@@H](C)[C@@H](C(=O)O)NC(=O)C1=CC(=CC(=C1)CC2=CC=C(C=C2)O)NC(=O)[C@H](C(C)C)N Ki = 69000 nM Poor binder T67272 Aminopeptidase N BG8AX4 (2R)-2-[4-[[[(2S)-3-[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]-1,3-thiazolidine-2-carbonyl]amino]methyl]anilino]-3-methylbutanoic acid;hydrochloride Investigative 24860299 C26H32ClF3N4O4S 589.1 CC(C)[C@H](C(=O)O)NC1=CC=C(C=C1)CNC(=O)[C@H]2N(CCS2)C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N.Cl IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N BH01MZ (2S)-6-Amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]hexanoic acid Investigative 122195273 C29H48N10O8 664.8 C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 ~ 70000 nM Poor binder T67272 Aminopeptidase N BH50KZ (3R)-3-Amino-1-(2-benzoyldiazinan-1-yl)-4-(2,4,5-trifluorophenyl)butan-1-one;hydrochloride Investigative 23628283 C21H23ClF3N3O2 441.9 C1CCN(N(C1)C(=O)C[C@@H](CC2=CC(=C(C=C2F)F)F)N)C(=O)C3=CC=CC=C3.Cl IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N BHN72Z Phe-Ser-Arg Investigative 44207184 C18H28N6O5 408.5 C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)N IC50 = 120000 nM Poor binder T67272 Aminopeptidase N BI4E5U 1-Amino-2-methylbutylphosphonic acid monophenylester Investigative 46886333 C11H18NO3P 243.24 CC(C)CC(N)P(=O)(O)OC1=CC=CC=C1 Ki = 53000 nM Poor binder T67272 Aminopeptidase N BIA8G9 (2-Diphenoxyphosphorylpyrrolidin-1-yl)-[(2R)-pyrrolidin-2-yl]methanone;hydrochloride Investigative 49795928 C21H26ClN2O4P 436.9 C1C[C@@H](NC1)C(=O)N2CCCC2P(=O)(OC3=CC=CC=C3)OC4=CC=CC=C4.Cl IC50 = 83000 nM Poor binder T67272 Aminopeptidase N BJ05MU (2R)-N-[(2S,3S)-2-Amino-3-hydroxy-3-(4-nitrophenyl)propyl]-2-[[(2S)-3-amino-2-hydroxypropanoyl]amino]-3-phenylpropanamide Investigative 56665197 C21H27N5O6 445.5 C1=CC=C(C=C1)C[C@H](C(=O)NC[C@@H]([C@H](C2=CC=C(C=C2)[N+](=O)[O-])O)N)NC(=O)[C@H](CN)O IC50 = 66340 nM Poor binder T67272 Aminopeptidase N BJ60FT (2S,4S)-4-(3,4,5-Trimethoxybenzamido)-1-acetylpyrrolidine-2-carboxylic acid Investigative 25147154 C17H22N2O7 366.4 CC(=O)N1C[C@H](C[C@H]1C(=O)O)NC(=O)C2=CC(=C(C(=C2)OC)OC)OC IC50 = 51400 nM Poor binder T67272 Aminopeptidase N BJFK14 (2S)-1-[(2S)-2-Amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide Investigative 16121107 C17H24N4O4 348.4 C[C@@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC2=CC=C(C=C2)O)N Ki = 80000 nM Poor binder T67272 Aminopeptidase N BJU7N1 Tyr-Pro-Ala Investigative 16121199 C17H23N3O5 349.4 C[C@@H](C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC2=CC=C(C=C2)O)N Ki = 100000 nM Poor binder T67272 Aminopeptidase N BL9NF6 Ethyl 2-[[4-[[4-[(2-ethoxy-2-oxoethyl)carbamoyl]phenoxy]-[1-(pyrrolidine-2-carbonyl)pyrrolidin-2-yl]phosphoryl]oxybenzoyl]amino]acetate;hydrochloride Investigative 49795932 C31H40ClN4O10P 695.1 CCOC(=O)CNC(=O)C1=CC=C(C=C1)OP(=O)(C2CCCN2C(=O)C3CCCN3)OC4=CC=C(C=C4)C(=O)NCC(=O)OCC.Cl IC50 = 104000 nM Poor binder T67272 Aminopeptidase N BLG5D0 (2S)-2-[[(2S)-3-[(2R,3R,4R,5S,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Investigative 122195277 C37H61N13O13 896 CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N)CO)O)O IC50 = 52000 nM Poor binder T67272 Aminopeptidase N BLM71O (2S)-5-(Diaminomethylideneamino)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-(3-fluorophenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 56955271 C29H47FN12O8 710.8 C1=CC(=CC(=C1)F)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N BLW9G8 (2S,4S)-4-[[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]amino]-1-[(2S)-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]pentanoyl]pyrrolidine-2-carboxylic acid Investigative 53354365 C30H37F3N4O6 606.6 CCC[C@@H](C(=O)N1C[C@H](C[C@H]1C(=O)O)NC(=O)C[C@@H](CC2=CC(=C(C=C2F)F)F)N)N[C@@H](CCC3=CC=CC=C3)C(=O)O IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N BM5X3H (2S,4S)-Methyl 1-(3-(3,4-dimethoxyphenyl)propanoyl)-4-(nicotinamido)pyrrolidine-2-carboxylate Investigative 25147059 C23H27N3O6 441.5 COC1=C(C=C(C=C1)CCC(=O)N2C[C@H](C[C@H]2C(=O)OC)NC(=O)C3=CN=CC=C3)OC IC50 = 196400 nM Poor binder T67272 Aminopeptidase N BM6KR8 Methyl (3S)-2-(benzenesulfonyl)-6,10-dioxa-2-azaspiro[4.5]decane-3-carboxylate Investigative 44576617 C15H19NO6S 341.4 COC(=O)[C@@H]1CC2(CN1S(=O)(=O)C3=CC=CC=C3)OCCCO2 IC50 = 168100 nM Poor binder T67272 Aminopeptidase N BNH3E5 (3S)-N-Hydroxy-2-(4-methylphenyl)sulfonyl-6,11-dioxa-2-azaspiro[4.6]undecane-3-carboxamide Investigative 44576632 C16H22N2O6S 370.4 CC1=CC=C(C=C1)S(=O)(=O)N2CC3(C[C@H]2C(=O)NO)OCCCCO3 IC50 = 73200 nM Poor binder T67272 Aminopeptidase N BNT2I6 (2S)-5-(Diaminomethylideneamino)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 70685541 C26H41N9O8 607.7 C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCC(=O)N)N IC50 = 65000 nM Poor binder T67272 Aminopeptidase N BO6LN7 (2S,4S)-1-Acetyl-4-(cinnamamido)-N-hydroxypyrrolidine-2-carboxamide Investigative 25147251 C16H19N3O4 317.34 CC(=O)N1C[C@H](C[C@H]1C(=O)NO)NC(=O)/C=C/C2=CC=CC=C2 IC50 = 56100 nM Poor binder T67272 Aminopeptidase N BO8PW0 2-(2-(((2S,3R)-2-(3-(4-Hydroxybenzyl)-5-aminobenzamido)-3-methylpentanamido)methyl)phenyl)acetic acid Investigative 44560412 C29H33N3O5 503.6 CC[C@@H](C)[C@@H](C(=O)NCC1=CC=CC=C1CC(=O)O)NC(=O)C2=CC(=CC(=C2)CC3=CC=C(C=C3)O)N Ki ~ 100000 nM Poor binder T67272 Aminopeptidase N BOF17Z (2S)-5-(Diaminomethylideneamino)-2-[[(2S)-2-[[(3R)-3-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 56953638 C29H48N12O8 692.8 C1=CC=C(C=C1)[C@@H](CC(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 ~ 70000 nM Poor binder T67272 Aminopeptidase N BON0V4 4-Amino-N-(2,6-dimethylphenyl)phthalimide Investigative 124031 C16H14N2O2 266.29 CC1=C(C(=CC=C1)C)N2C(=O)C3=C(C2=O)C=C(C=C3)N IC50 = 56300 nM Poor binder T67272 Aminopeptidase N BPR04C (2S,4S)-Methyl 1-acetyl-4-(cinnamamido)pyrrolidine-2-carboxylate Investigative 25147057 C17H20N2O4 316.35 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)/C=C/C2=CC=CC=C2 IC50 = 135300 nM Poor binder T67272 Aminopeptidase N BQA72O 5-Amino-2-benzyl-7-methyl-4-oxo-octanoic acid Investigative 14542149 C16H23NO3 277.36 CC(C)C[C@@H](C(=O)CC(CC1=CC=CC=C1)C(=O)O)N Ki = 79000 nM Poor binder T67272 Aminopeptidase N BQMC36 (2S,4S)-Methyl 4-(4-nitrobenzamido)-1-acetylpyrrolidine-2-carboxylate Investigative 25147159 C15H17N3O6 335.31 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)C2=CC=C(C=C2)[N+](=O)[O-] IC50 = 72300 nM Poor binder T67272 Aminopeptidase N BQS5F1 (2S)-5-(Diaminomethylideneamino)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 70692015 C29H48N12O9 708.8 C1=CC(=CC=C1C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N)O IC50 = 64000 nM Poor binder T67272 Aminopeptidase N BR1U3M (6R,7S)-7-Amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-ol;hydrochloride Investigative 53324938 C11H16ClNO 213.7 C1CC2=CC=CC=C2C[C@H]([C@H]1N)O.Cl Ki = 60000 nM Poor binder T67272 Aminopeptidase N BRS2J5 2-(((S)-1-(3-(4-Hydroxybenzyl)-5-((S)-2-amino-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)methyl)benzoic acid Investigative 44560402 C32H36N4O6 572.7 CC(C)[C@@H](C(=O)NC1=CC(=CC(=C1)C(=O)N2CCC[C@H]2C(=O)NCC3=CC=CC=C3C(=O)O)CC4=CC=C(C=C4)O)N Ki = 55000 nM Poor binder T67272 Aminopeptidase N BRTJ30 Opiorphin (1-4) Investigative 70683616 C23H36N8O7 536.6 C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CO)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 = 75000 nM Poor binder T67272 Aminopeptidase N BSNW56 (2S,4R)-Methyl 4-hydroxy-1-((E)-3-(3,4-dimethoxyphenyl)acryloyl)pyrrolidine-2-carboxylate Investigative 25146956 C17H21NO6 335.4 COC1=C(C=C(C=C1)/C=C/C(=O)N2C[C@@H](C[C@H]2C(=O)OC)O)OC IC50 = 81800 nM Poor binder T67272 Aminopeptidase N BT3Z8O 4-Benzenesulfonyloxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester Investigative 44569012 C19H21NO7S2 439.5 CC1=CC=C(C=C1)S(=O)(=O)N2C[C@@H](C[C@H]2C(=O)OC)OS(=O)(=O)C3=CC=CC=C3 IC50 = 74600 nM Poor binder T67272 Aminopeptidase N BTA9Y6 (2S)-5-(Diaminomethylideneamino)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,4-diamino-4-oxobutanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 70696244 C28H46N12O8 678.7 C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(=O)N)N IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N BTE6Q8 (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-Amino-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]hexanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Investigative 122195272 C29H48N10O8 664.8 C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)N)N IC50 ~ 70000 nM Poor binder T67272 Aminopeptidase N BTWI21 (3S)-2-(Benzenesulfonyl)-N-hydroxy-6,10-dioxa-2-azaspiro[4.5]decane-3-carboxamide Investigative 44576634 C14H18N2O6S 342.37 C1COC2(C[C@H](N(C2)S(=O)(=O)C3=CC=CC=C3)C(=O)NO)OC1 IC50 = 82700 nM Poor binder T67272 Aminopeptidase N BU6BI1 (2S,4S)-Methyl 1-acetyl-4-(isonicotinamido)pyrrolidine-2-carboxylate Investigative 25147056 C14H17N3O4 291.3 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)C2=CC=NC=C2 IC50 = 74800 nM Poor binder T67272 Aminopeptidase N BUB5S9 (2S)-5-(Diaminomethylideneamino)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]propanoyl]amino]-3-hydroxypropanoyl]amino]pentanoic acid Investigative 70681348 C23H44N12O8 616.7 C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N IC50 ~ 70000 nM Poor binder T67272 Aminopeptidase N BUH7R1 N-((3S,5S)-5-(Hydroxycarbamoyl)-1-(3-(3,4-dimethoxyphenyl)propanoyl)pyrrolidin-3-yl)nicotinamide Investigative 25147062 C22H26N4O6 442.5 COC1=C(C=C(C=C1)CCC(=O)N2C[C@H](C[C@H]2C(=O)NO)NC(=O)C3=CN=CC=C3)OC IC50 = 62200 nM Poor binder T67272 Aminopeptidase N BUP34N (2S,5S,7E,13S)-13-Amino-N-benzyl-2-[(4-hydroxyphenyl)methyl]-1-methyl-3,14-dioxo-1,4-diazacyclotetradec-7-ene-5-carboxamide Investigative 53259219 C28H36N4O4 492.6 CN1[C@H](C(=O)N[C@@H](C/C=C/CCCC[C@@H](C1=O)N)C(=O)NCC2=CC=CC=C2)CC3=CC=C(C=C3)O Ki ~ 100000 nM Poor binder T67272 Aminopeptidase N BUR2O0 (2S)-2-[[(2S)-2-[[(2S)-3-(2-Bromophenyl)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]propanoyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Investigative 56955173 C29H47BrN12O8 771.7 C1=CC=C(C(=C1)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N)Br IC50 = 65000 nM Poor binder T67272 Aminopeptidase N BV5K3Q (2S,4S)-Methyl 4-azido-1-((E)-3-(3,4-dimethoxyphenyl)acryloyl)pyrrolidine-2-carboxylate Investigative 25146957 C17H20N4O5 360.4 COC1=C(C=C(C=C1)/C=C/C(=O)N2C[C@H](C[C@H]2C(=O)OC)N=[N+]=[N-])OC IC50 = 71300 nM Poor binder T67272 Aminopeptidase N BVUR94 4-(3-Phenyl-acryloyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester Investigative 44569024 C22H23NO6S 429.5 CC1=CC=C(C=C1)S(=O)(=O)N2C[C@@H](C[C@H]2C(=O)OC)OC(=O)/C=C/C3=CC=CC=C3 IC50 = 168600 nM Poor binder T67272 Aminopeptidase N BW8AJ7 (2S,4S)-Methyl 4-(4-chlorobenzamido)-1-acetylpyrrolidine-2-carboxylate Investigative 25147158 C15H17ClN2O4 324.76 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)C2=CC=C(C=C2)Cl IC50 = 121700 nM Poor binder T67272 Aminopeptidase N BWQ3U8 (2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5S,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]butanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Investigative 122195278 C38H63N13O13 910 C[C@H]([C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCC(=O)N)N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)NC(=O)C IC50 ~ 100000 nM Poor binder T67272 Aminopeptidase N BXG5J0 Ubenimex Investigative 72172 C16H24N2O4 308.37 CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O IC50 = 54700 nM Poor binder T67272 Aminopeptidase N BXN49S CID 44593458 Investigative 44593458 C22H24N4O6 440.4 COC1=C(C=C(C=C1)/C=C/C(=O)N2C[C@H](C[C@H]2C(=O)NO)NC(=O)C3=CN=CC=C3)OC IC50 = 141900 nM Poor binder T67272 Aminopeptidase N BXWS05 1-Methanesulfonyl-4-oxo-pyrrolidine-2-carboxylicacid methyl ester Investigative 44576565 C7H11NO5S 221.23 COC(=O)[C@@H]1CC(=O)CN1S(=O)(=O)C IC50 = 92600 nM Poor binder T67272 Aminopeptidase N BY2RA7 3-Amino-N-hydroxy-4-phenyl-butyramide Investigative 44276218 C10H14N2O2 194.23 C1=CC=C(C=C1)CC(CC(=O)NO)N IC50 = 75000 nM Poor binder T67272 Aminopeptidase N BY9E4T Methyl (3S)-2-(benzenesulfonyl)-6,11-dioxa-2-azaspiro[4.6]undecane-3-carboxylate Investigative 44576618 C16H21NO6S 355.4 COC(=O)[C@@H]1CC2(CN1S(=O)(=O)C3=CC=CC=C3)OCCCCO2 IC50 = 134800 nM Poor binder T67272 Aminopeptidase N BZ85EK (2S,4S)-Methyl 4-(3,4,5-trimethoxybenzamido)-1-acetylpyrrolidine-2-carboxylate Investigative 25147153 C18H24N2O7 380.4 CC(=O)N1C[C@H](C[C@H]1C(=O)OC)NC(=O)C2=CC(=C(C(=C2)OC)OC)OC IC50 = 98400 nM Poor binder T67272 Aminopeptidase N BZH68M (8S)-7-(Benzenesulfonyl)-N-hydroxy-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxamide Investigative 44576633 C13H16N2O6S 328.34 C1COC2(O1)C[C@H](N(C2)S(=O)(=O)C3=CC=CC=C3)C(=O)NO IC50 = 57800 nM Poor binder T67272 Aminopeptidase N D0I6RL 2-(phenylsulfonamido)-1-naphthoic acid Investigative 11723962 C17H13NO4S 327.4 C1=CC=C(C=C1)S(=O)(=O)NC2=C(C3=CC=CC=C3C=C2)C(=O)O IC50 ~ 100000 nM Poor binder