BRENDA - Enzyme Database show

Discovery and characterization of [(cyclopentyl)ethyl]benzoic acid inhibitors of microsomal prostaglandin E synthase-1

Partridge, K.M.; Antonysamy, S.; Bhattachar, S.N.; Chandrasekhar, S.; Fisher, M.J.; Fretland, A.; Gooding, K.; Harvey, A.; Hughes, N.E.; Kuklish, S.L.; Luz, J.G.; Manninen, P.R.; McGee, J.E.; Mudra, D.R.; Navarro, A.; Norman, B.H.; Quimby, S.J.; Schiffler, M.A.; Sloan, A.V.; Warshawsky, A.M.; Weller, J.M.; Yor, Y.o.r.k.; Bioorg. Med. Chem. Lett. 27, 1478-1483 (2017)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
1-[5-chloro-6-(4-chlorophenyl)-1,3-benzoxazol-2-yl]-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
2-chloro-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethoxy)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]pyridine-3-carboxylic acid
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-([1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-[[1-(8-methylquinolin-2-yl)piperidine-4-carbonyl]amino]cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
3-[6-([1,1'-biphenyl]-4-yl)-1-[(4-chlorophenyl)methyl]-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-([[(1S,2S)-2-(2,2-dimethylpropanamido)cyclopentyl]methyl]amino)benzoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-([[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]methyl]amino)benzoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-[([(1S,2S)-2-[(1-phenylpiperidine-4-carbonyl)amino]cyclopentyl]methyl)amino]benzoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-[[(1R,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]methoxy]benzoic acid
-
Homo sapiens
5.3.99.3
4-fluoro-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
4-methyl-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
N-(3',4'-dichloro[1,1'-biphenyl]-4-yl)-4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda~6~,2-benzothiazine-3-carboxamide
-
Homo sapiens
Localization
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
5.3.99.3
microsome
-
Homo sapiens
-
-
Natural Substrates/ Products (Substrates)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
5.3.99.3
Prostaglandin H2
Homo sapiens
-
Prostaglandin E2
-
-
?
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
5.3.99.3
Homo sapiens
O14684
-
-
Source Tissue
EC Number
Source Tissue
Commentary
Organism
Textmining
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
5.3.99.3
Prostaglandin H2
-
747279
Homo sapiens
Prostaglandin E2
-
-
-
?
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethoxy)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-[[1-(8-methylquinolin-2-yl)piperidine-4-carbonyl]amino]cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
4-fluoro-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
4-methyl-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-([1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-[[(1R,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]methoxy]benzoic acid
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-[([(1S,2S)-2-[(1-phenylpiperidine-4-carbonyl)amino]cyclopentyl]methyl)amino]benzoic acid
5.3.99.3
0.000003
-
pH and temperature not specified in the publication
Homo sapiens
1-[5-chloro-6-(4-chlorophenyl)-1,3-benzoxazol-2-yl]-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]piperidine-4-carboxamide
5.3.99.3
0.000004
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-([[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]methyl]amino)benzoic acid
5.3.99.3
0.000006
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]pyridine-3-carboxylic acid
5.3.99.3
0.000007
-
pH and temperature not specified in the publication
Homo sapiens
3-[6-([1,1'-biphenyl]-4-yl)-1-[(4-chlorophenyl)methyl]-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
5.3.99.3
0.000016
-
pH and temperature not specified in the publication
Homo sapiens
N-(3',4'-dichloro[1,1'-biphenyl]-4-yl)-4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda~6~,2-benzothiazine-3-carboxamide
5.3.99.3
0.000043
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-([[(1S,2S)-2-(2,2-dimethylpropanamido)cyclopentyl]methyl]amino)benzoic acid
5.3.99.3
0.000241
-
pH and temperature not specified in the publication
Homo sapiens
2-chloro-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethoxy)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-[[1-(8-methylquinolin-2-yl)piperidine-4-carbonyl]amino]cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
4-fluoro-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
4-methyl-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-([1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-[[(1R,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]methoxy]benzoic acid
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-[([(1S,2S)-2-[(1-phenylpiperidine-4-carbonyl)amino]cyclopentyl]methyl)amino]benzoic acid
5.3.99.3
0.000003
-
pH and temperature not specified in the publication
Homo sapiens
1-[5-chloro-6-(4-chlorophenyl)-1,3-benzoxazol-2-yl]-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]piperidine-4-carboxamide
5.3.99.3
0.000004
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-([[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]methyl]amino)benzoic acid
5.3.99.3
0.000006
-
pH and temperature not specified in the publication
Homo sapiens
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]pyridine-3-carboxylic acid
5.3.99.3
0.000007
-
pH and temperature not specified in the publication
Homo sapiens
3-[6-([1,1'-biphenyl]-4-yl)-1-[(4-chlorophenyl)methyl]-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
5.3.99.3
0.000016
-
pH and temperature not specified in the publication
Homo sapiens
N-(3',4'-dichloro[1,1'-biphenyl]-4-yl)-4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda~6~,2-benzothiazine-3-carboxamide
5.3.99.3
0.000043
-
pH and temperature not specified in the publication
Homo sapiens
4-chloro-2-([[(1S,2S)-2-(2,2-dimethylpropanamido)cyclopentyl]methyl]amino)benzoic acid
5.3.99.3
0.000241
-
pH and temperature not specified in the publication
Homo sapiens
2-chloro-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
1-[5-chloro-6-(4-chlorophenyl)-1,3-benzoxazol-2-yl]-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
2-chloro-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethoxy)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]pyridine-3-carboxylic acid
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-([1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
2-[2-[(1S,2S)-2-[[1-(8-methylquinolin-2-yl)piperidine-4-carbonyl]amino]cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
3-[6-([1,1'-biphenyl]-4-yl)-1-[(4-chlorophenyl)methyl]-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-([[(1S,2S)-2-(2,2-dimethylpropanamido)cyclopentyl]methyl]amino)benzoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-([[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]methyl]amino)benzoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-[([(1S,2S)-2-[(1-phenylpiperidine-4-carbonyl)amino]cyclopentyl]methyl)amino]benzoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
4-chloro-2-[[(1R,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]methoxy]benzoic acid
-
Homo sapiens
5.3.99.3
4-fluoro-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
4-methyl-2-[2-[(1S,2S)-2-([1-[4-(trifluoromethyl)phenyl]piperidine-4-carbonyl]amino)cyclopentyl]ethyl]benzoic acid
-
Homo sapiens
5.3.99.3
N-(3',4'-dichloro[1,1'-biphenyl]-4-yl)-4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda~6~,2-benzothiazine-3-carboxamide
-
Homo sapiens
Localization (protein specific)
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
5.3.99.3
microsome
-
Homo sapiens
-
-
Natural Substrates/ Products (Substrates) (protein specific)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
5.3.99.3
Prostaglandin H2
Homo sapiens
-
Prostaglandin E2
-
-
?
Source Tissue (protein specific)
EC Number
Source Tissue
Commentary
Organism
Textmining
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
5.3.99.3
Prostaglandin H2
-
747279
Homo sapiens
Prostaglandin E2
-
-
-
?