BRENDA - Enzyme Database show

Characterization of 3,3-dimethyl substituted N-aryl piperidines as potent microsomal prostaglandin E synthase-1 inhibitors

Kuklish, S.L.; Antonysamy, S.; Bhattachar, S.N.; Chandrasekhar, S.; Fisher, M.J.; Fretland, A.J.; Gooding, K.; Harvey, A.; Hughes, N.E.; Luz, J.G.; Manninen, P.R.; McGee, J.E.; Navarro, A.; Norman, B.H.; Partridge, K.M.; Quimby, S.J.; Schiffler, M.A.; Sloan, A.V.; Warshawsky, A.M.; York, J.S.; Yu, X.P.; Bioorg. Med. Chem. Lett. 26, 4824-4828 (2016)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
(4R)-1-(8-chloroquinolin-2-yl)-N-[cis-4-(hydroxymethyl)cyclohexyl]-3,3-dimethylpiperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4R)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-1-(8-chloroquinolin-2-yl)-N-[cis-4-(hydroxymethyl)cyclohexyl]-3,3-dimethylpiperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)-N-[(3S)-oxan-3-yl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)-N-[(3S)-oxolan-3-yl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-3,3-dimethyl-N-(3-methylbutan-2-yl)-1-(8-methylquinolin-2-yl)piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-N-[(3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-(8-methylquinolin-2-yl)piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
1,5-anhydro-2,3,4-trideoxy-3-[[(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)piperidine-4-carbonyl]amino]-D-glycero-hexitol
-
Homo sapiens
5.3.99.3
1-[6-(4-chlorophenyl)-5-methyl-1,3-benzoxazol-2-yl]-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]-N-[5-methyl-4-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
2-methyl-2-(cis-4-[[1-(3-methyl-5-phenylfuro[2,3-b]pyridin-6-yl)piperidine-4-carbonyl]amino]cyclohexyl)propanoic acid
-
Homo sapiens
5.3.99.3
N-cyclopentyl-1-[5,6-diamino-1-(3-amino-4-fluorophenyl)-1H-benzimidazol-2-yl]piperidine-4-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
-
-
-
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
-
747278
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
(4R)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-N-[(3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-(8-methylquinolin-2-yl)piperidine-4-carboxamide
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
1,5-anhydro-2,3,4-trideoxy-3-[[(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)piperidine-4-carbonyl]amino]-D-glycero-hexitol
5.3.99.3
0.000003
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
5.3.99.3
0.000004
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-1-(8-chloroquinolin-2-yl)-N-[cis-4-(hydroxymethyl)cyclohexyl]-3,3-dimethylpiperidine-4-carboxamide
5.3.99.3
0.000006
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)-N-[(3S)-oxolan-3-yl]piperidine-4-carboxamide
5.3.99.3
0.000007
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)-N-[(3S)-oxan-3-yl]piperidine-4-carboxamide
5.3.99.3
0.000012
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-3,3-dimethyl-N-(3-methylbutan-2-yl)-1-(8-methylquinolin-2-yl)piperidine-4-carboxamide
5.3.99.3
0.000504
-
pH and temperature not specified in the publication
Homo sapiens
(4R)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
5.3.99.3
0.00372
-
pH and temperature not specified in the publication
Homo sapiens
(4R)-1-(8-chloroquinolin-2-yl)-N-[cis-4-(hydroxymethyl)cyclohexyl]-3,3-dimethylpiperidine-4-carboxamide
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
(4R)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
5.3.99.3
0.000001
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-N-[(3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-(8-methylquinolin-2-yl)piperidine-4-carboxamide
5.3.99.3
0.000002
-
pH and temperature not specified in the publication
Homo sapiens
1,5-anhydro-2,3,4-trideoxy-3-[[(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)piperidine-4-carbonyl]amino]-D-glycero-hexitol
5.3.99.3
0.000003
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
5.3.99.3
0.000004
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-1-(8-chloroquinolin-2-yl)-N-[cis-4-(hydroxymethyl)cyclohexyl]-3,3-dimethylpiperidine-4-carboxamide
5.3.99.3
0.000006
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)-N-[(3S)-oxolan-3-yl]piperidine-4-carboxamide
5.3.99.3
0.000007
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)-N-[(3S)-oxan-3-yl]piperidine-4-carboxamide
5.3.99.3
0.000012
-
pH and temperature not specified in the publication
Homo sapiens
(4S)-3,3-dimethyl-N-(3-methylbutan-2-yl)-1-(8-methylquinolin-2-yl)piperidine-4-carboxamide
5.3.99.3
0.000504
-
pH and temperature not specified in the publication
Homo sapiens
(4R)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
5.3.99.3
0.00372
-
pH and temperature not specified in the publication
Homo sapiens
(4R)-1-(8-chloroquinolin-2-yl)-N-[cis-4-(hydroxymethyl)cyclohexyl]-3,3-dimethylpiperidine-4-carboxamide
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
(4R)-1-(8-chloroquinolin-2-yl)-N-[cis-4-(hydroxymethyl)cyclohexyl]-3,3-dimethylpiperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4R)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-1-(8-chloroquinolin-2-yl)-N-[cis-4-(hydroxymethyl)cyclohexyl]-3,3-dimethylpiperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)-N-[(3S)-oxan-3-yl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)-N-[(3S)-oxolan-3-yl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-3,3-dimethyl-N-(3-methylbutan-2-yl)-1-(8-methylquinolin-2-yl)piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-[4-(trifluoromethyl)phenyl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
(4S)-N-[(3S)-3-(hydroxymethyl)cyclohexyl]-3,3-dimethyl-1-(8-methylquinolin-2-yl)piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
1,5-anhydro-2,3,4-trideoxy-3-[[(4S)-3,3-dimethyl-1-(8-methylquinolin-2-yl)piperidine-4-carbonyl]amino]-D-glycero-hexitol
-
Homo sapiens
5.3.99.3
1-[6-(4-chlorophenyl)-5-methyl-1,3-benzoxazol-2-yl]-N-[(1S,3S)-3-(hydroxymethyl)cyclohexyl]piperidine-4-carboxamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]-N-[5-methyl-4-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
2-methyl-2-(cis-4-[[1-(3-methyl-5-phenylfuro[2,3-b]pyridin-6-yl)piperidine-4-carbonyl]amino]cyclohexyl)propanoic acid
-
Homo sapiens
5.3.99.3
N-cyclopentyl-1-[5,6-diamino-1-(3-amino-4-fluorophenyl)-1H-benzimidazol-2-yl]piperidine-4-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
-
-
?
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
-
747278
Homo sapiens
Prostaglandin E2
-
-
-
?