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Literature summary extracted from

  • Duveau, D.Y.; Yasgar, A.; Wang, Y.; Hu, X.; Kouznetsova, J.; Brimacombe, K.R.; Jadhav, A.; Simeonov, A.; Thomas, C.J.; Maloney, D.J.
    Structure-activity relationship studies and biological characterization of human NAD(+)-dependent 15-hydroxyprostaglandin dehydrogenase inhibitors (2014), Bioorg. Med. Chem. Lett., 24, 630-635.
    View publication on PubMedView publication on EuropePMC

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.141 (1-butyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 (1-phenyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 (1-tert-butyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 (3,3-dimethylpiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
-
 Homo sapiens
1.1.1.141 (3,5-dimethylpiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
-
 Homo sapiens
1.1.1.141 (4-bromopiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
-
 Homo sapiens
1.1.1.141 (piperidin-1-yl)[1-[3-(propan-2-yl)phenyl]-1H-benzimidazol-5-yl]methanone
-
 Homo sapiens
1.1.1.141 (piperidin-1-yl)[1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-5-yl]methanone
-
 Homo sapiens
1.1.1.141 (piperidin-1-yl)[1-[4-(trifluoromethyl)phenyl]-1H-benzimidazol-5-yl]methanone
-
 Homo sapiens
1.1.1.141 2-[[(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)sulfanyl]methyl]benzonitrile
-
 Homo sapiens
1.1.1.141 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine
-
 Homo sapiens
1.1.1.141 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
-
 Homo sapiens
1.1.1.141 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9,10,11-hexahydro-5H-[1,2,4]triazolo[4,3-a]azonine
-
 Homo sapiens
1.1.1.141 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine
-
 Homo sapiens
1.1.1.141 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole
-
 Homo sapiens
1.1.1.141 3-[1-(3,4-dichlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[1-(3-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[1-(4-bromophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[1-(4-tert-butylphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[2,5-dimethyl-1-(4-methylphenyl)-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[2,5-dimethyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[2,5-dimethyl-1-[4-(naphthalen-2-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[2,5-dimethyl-1-[4-(pyridin-2-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[2,5-dimethyl-1-[4-(pyridin-3-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[2,5-dimethyl-1-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[2,5-dimethyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
-
 Homo sapiens
1.1.1.141 3-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzonitrile
-
 Homo sapiens
1.1.1.141 4-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzonitrile
-
 Homo sapiens
1.1.1.141 ethyl 4-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzoate
-
 Homo sapiens
1.1.1.141 N,N-diethyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
-
 Homo sapiens
1.1.1.141 N-butyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
-
 Homo sapiens
1.1.1.141 N-cyclopentyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
-
 Homo sapiens
1.1.1.141 [1-(2-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(3-chlorophenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methylphenyl)-1H-benzimidazol-5-yl](3-methylpiperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methylphenyl)-1H-benzimidazol-5-yl](3-phenylpiperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methylphenyl)-1H-benzimidazol-5-yl](4-methylpiperazin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methylphenyl)-1H-benzimidazol-5-yl](morpholin-4-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methylphenyl)-1H-benzimidazol-5-yl](pyrrolidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methylphenyl)-1H-benzimidazol-5-yl][3-(propan-2-yl)piperidin-1-yl]methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methylphenyl)-1H-benzimidazol-5-yl][3-(trifluoromethyl)piperidin-1-yl]methanone
-
 Homo sapiens
1.1.1.141 [1-(3-methylphenyl)-1H-benzimidazol-5-yl][4-(trifluoromethyl)piperidin-1-yl]methanone
-
 Homo sapiens
1.1.1.141 [1-(3-tert-butylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(4-chlorophenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(4-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(4-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
 Homo sapiens
1.1.1.141 [1-(4-tert-butylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
-
 Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.141 Homo sapiens P15428
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.141 A-549 cell
-
 Homo sapiens
-
1.1.1.141 LNCaP cell
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.141 prostaglandin E2 + NAD+
-
 Homo sapiens 15-oxoprostaglandin E2 + NADH + H+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.141 15-PGDH
-
 Homo sapiens
1.1.1.141 HPGD
-
 Homo sapiens
1.1.1.141 NAD+-dependent 15-hydroxyprostaglandin dehydrogenase
-
 Homo sapiens

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.141 NAD+
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.141 0.000012
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-chlorophenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
1.1.1.141 0.000019
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
1.1.1.141 0.000019
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
1.1.1.141 0.000022
-
 pH and temperature not specified in the publication Homo sapiens (1-phenyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
1.1.1.141 0.000022
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methylphenyl)-1H-benzimidazol-5-yl](3-methylpiperidin-1-yl)methanone
1.1.1.141 0.000022
-
 pH and temperature not specified in the publication Homo sapiens 3-[1-(3,4-dichlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000027
-
 pH and temperature not specified in the publication Homo sapiens [1-(2-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
1.1.1.141 0.000034
-
 pH and temperature not specified in the publication Homo sapiens (1-tert-butyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
1.1.1.141 0.000034
-
 pH and temperature not specified in the publication Homo sapiens 3-[1-(3-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000034
-
 pH and temperature not specified in the publication Homo sapiens 3-[2,5-dimethyl-1-(4-methylphenyl)-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000038
-
 pH and temperature not specified in the publication Homo sapiens 3-[1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000038
-
 pH and temperature not specified in the publication Homo sapiens ethyl 4-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzoate
1.1.1.141 0.000048
-
 pH and temperature not specified in the publication Homo sapiens (piperidin-1-yl)[1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-5-yl]methanone
1.1.1.141 0.000048
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methylphenyl)-1H-benzimidazol-5-yl][3-(propan-2-yl)piperidin-1-yl]methanone
1.1.1.141 0.000048
-
 pH and temperature not specified in the publication Homo sapiens 3-[1-(4-bromophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000048
-
 pH and temperature not specified in the publication Homo sapiens 3-[2,5-dimethyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000054
-
 pH and temperature not specified in the publication Homo sapiens [1-(4-tert-butylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
1.1.1.141 0.000054
-
 pH and temperature not specified in the publication Homo sapiens 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine
1.1.1.141 0.000068
-
 pH and temperature not specified in the publication Homo sapiens (1-butyl-1H-benzimidazol-5-yl)(piperidin-1-yl)methanone
1.1.1.141 0.000068
-
 pH and temperature not specified in the publication Homo sapiens (3,3-dimethylpiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
1.1.1.141 0.000068
-
 pH and temperature not specified in the publication Homo sapiens (piperidin-1-yl)[1-[3-(propan-2-yl)phenyl]-1H-benzimidazol-5-yl]methanone
1.1.1.141 0.000068
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methylphenyl)-1H-benzimidazol-5-yl][3-(trifluoromethyl)piperidin-1-yl]methanone
1.1.1.141 0.000068
-
 pH and temperature not specified in the publication Homo sapiens 3-[2,5-dimethyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000076
-
 pH and temperature not specified in the publication Homo sapiens (4-bromopiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
1.1.1.141 0.000076
-
 pH and temperature not specified in the publication Homo sapiens 3-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzonitrile
1.1.1.141 0.000086
-
 pH and temperature not specified in the publication Homo sapiens 3-[1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000096
-
 pH and temperature not specified in the publication Homo sapiens 4-[2,5-dimethyl-3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-1H-pyrrol-1-yl]benzonitrile
1.1.1.141 0.000108
-
 pH and temperature not specified in the publication Homo sapiens 3-[2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000108
-
 pH and temperature not specified in the publication Homo sapiens 3-[2,5-dimethyl-1-[4-(naphthalen-2-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000121
-
 pH and temperature not specified in the publication Homo sapiens 3-[1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000136
-
 pH and temperature not specified in the publication Homo sapiens 3-[1-(4-tert-butylphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000171
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-tert-butylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
1.1.1.141 0.00019
-
 pH and temperature not specified in the publication Homo sapiens [1-(4-methoxyphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
1.1.1.141 0.00019
-
 pH and temperature not specified in the publication Homo sapiens [1-(4-methylphenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
1.1.1.141 0.000192
-
 pH and temperature not specified in the publication Homo sapiens 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
1.1.1.141 0.00022
-
 pH and temperature not specified in the publication Homo sapiens [1-(4-chlorophenyl)-1H-benzimidazol-5-yl](piperidin-1-yl)methanone
1.1.1.141 0.000242
-
 pH and temperature not specified in the publication Homo sapiens 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine
1.1.1.141 0.000271
-
 pH and temperature not specified in the publication Homo sapiens (3,5-dimethylpiperidin-1-yl)[1-(3-methylphenyl)-1H-benzimidazol-5-yl]methanone
1.1.1.141 0.000271
-
 pH and temperature not specified in the publication Homo sapiens 3-[2,5-dimethyl-1-[4-(pyridin-3-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000383
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methylphenyl)-1H-benzimidazol-5-yl](pyrrolidin-1-yl)methanone
1.1.1.141 0.000383
-
 pH and temperature not specified in the publication Homo sapiens 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7,8,9,10,11-hexahydro-5H-[1,2,4]triazolo[4,3-a]azonine
1.1.1.141 0.000383
-
 pH and temperature not specified in the publication Homo sapiens 3-[2,5-dimethyl-1-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.000383
-
 pH and temperature not specified in the publication Homo sapiens N,N-diethyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
1.1.1.141 0.000429
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methylphenyl)-1H-benzimidazol-5-yl](3-phenylpiperidin-1-yl)methanone
1.1.1.141 0.00086
-
 pH and temperature not specified in the publication Homo sapiens (piperidin-1-yl)[1-[4-(trifluoromethyl)phenyl]-1H-benzimidazol-5-yl]methanone
1.1.1.141 0.000961
-
 pH and temperature not specified in the publication Homo sapiens N-cyclopentyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
1.1.1.141 0.001078
-
 pH and temperature not specified in the publication Homo sapiens 3-[2,5-dimethyl-1-[4-(pyridin-2-yl)phenyl]-1H-pyrrol-3-yl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
1.1.1.141 0.001358
-
 pH and temperature not specified in the publication Homo sapiens N-butyl-1-(3-methylphenyl)-1H-benzimidazole-5-carboxamide
1.1.1.141 0.001524
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methylphenyl)-1H-benzimidazol-5-yl][4-(trifluoromethyl)piperidin-1-yl]methanone
1.1.1.141 0.00271
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methylphenyl)-1H-benzimidazol-5-yl](4-methylpiperazin-1-yl)methanone
1.1.1.141 0.00304
-
 pH and temperature not specified in the publication Homo sapiens [1-(3-methylphenyl)-1H-benzimidazol-5-yl](morpholin-4-yl)methanone
1.1.1.141 0.00304
-
 pH and temperature not specified in the publication Homo sapiens 3-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole