BRENDA - Enzyme Database show

Structure-based discovery of inhibitors of microsomal prostaglandin E2 synthase-1, 5-lipoxygenase and 5-lipoxygenase-activating protein: promising hits for the development of new anti-inflammatory agents

De Simone, R.; Chini, M.G.; Bruno, I.; Riccio, R.; Mueller, D.; Werz, O.; Bifulco, G.; J. Med. Chem. 54, 1565-1575 (2011)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
1-[2-(2-methylphenyl)ethyl]-4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1H-1,2,3-triazole
90% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid
12% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4'-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]biphenyl-4-ol
73.6% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4'-[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]biphenyl-3-ol
60.1% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4'-[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]biphenyl-4-ol
89% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4'-[1-[2-(2-methylphenyl)ethyl]-1H-1,2,3-triazol-4-yl]biphenyl-4-amine
98.2% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-(2'-[[2-chloro-5-(trifluoromethyl)phenoxy]methyl]biphenyl-4-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
91.9% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-(2'-[[2-chloro-5-(trifluoromethyl)phenoxy]methyl]biphenyl-4-yl)-1-[2-(2-methylphenyl)ethyl]-1H-1,2,3-triazole
87.9% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-(4'-phenoxybiphenyl-4-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
88.7% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[(4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1H-1,2,3-triazol-1-yl)sulfonyl]benzoic acid
59.8% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1-(3-phenylpropyl)-1H-1,2,3-triazole
96.8% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[4-(phenanthren-9-yl)phenyl]-1-(3-phenylpropyl)-1H-1,2,3-triazole
78.2% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[4-benzyl-1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-5-yl]benzaldehyde
72.1% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[[4-(biphenyl-4-yl)-1H-1,2,3-triazol-1-yl]methyl]-3-nitrobenzoic acid
most efficient inhibitor of mPGES-1, 12% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
5-(dimethylamino)-N-[4'-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]biphenyl-4-yl]naphthalene-1-sulfonamide
85% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]methyl benzoate
76.1% residual activity at 0.03 mM
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
-
-
-
Source Tissue
EC Number
Source Tissue
Commentary
Organism
Textmining
5.3.99.3
A-549 cell
-
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
-
715856
Homo sapiens
Prostaglandin E2
-
-
-
?
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.0024
-
pH and temperature not specified in the publication
Homo sapiens
3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid
5.3.99.3
0.0032
-
pH and temperature not specified in the publication
Homo sapiens
4-[[4-(biphenyl-4-yl)-1H-1,2,3-triazol-1-yl]methyl]-3-nitrobenzoic acid
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
1-[2-(2-methylphenyl)ethyl]-4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]methyl benzoate
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4'-[1-[2-(2-methylphenyl)ethyl]-1H-1,2,3-triazol-4-yl]biphenyl-4-amine
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4'-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]biphenyl-4-ol
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4'-[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]biphenyl-3-ol
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4'-[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]biphenyl-4-ol
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-(2'-[[2-chloro-5-(trifluoromethyl)phenoxy]methyl]biphenyl-4-yl)-1-[2-(2-methylphenyl)ethyl]-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-(2'-[[2-chloro-5-(trifluoromethyl)phenoxy]methyl]biphenyl-4-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1-(3-phenylpropyl)-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-[(4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1H-1,2,3-triazol-1-yl)sulfonyl]benzoic acid
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-[4-benzyl-1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-5-yl]benzaldehyde
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-[4-(phenanthren-9-yl)phenyl]-1-(3-phenylpropyl)-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-(4'-phenoxybiphenyl-4-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
5-(dimethylamino)-N-[4'-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]biphenyl-4-yl]naphthalene-1-sulfonamide
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.0024
-
pH and temperature not specified in the publication
Homo sapiens
3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid
5.3.99.3
0.0032
-
pH and temperature not specified in the publication
Homo sapiens
4-[[4-(biphenyl-4-yl)-1H-1,2,3-triazol-1-yl]methyl]-3-nitrobenzoic acid
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
1-[2-(2-methylphenyl)ethyl]-4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]methyl benzoate
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4'-[1-[2-(2-methylphenyl)ethyl]-1H-1,2,3-triazol-4-yl]biphenyl-4-amine
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4'-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]biphenyl-4-ol
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4'-[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]biphenyl-3-ol
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4'-[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]biphenyl-4-ol
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-(2'-[[2-chloro-5-(trifluoromethyl)phenoxy]methyl]biphenyl-4-yl)-1-[2-(2-methylphenyl)ethyl]-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-(2'-[[2-chloro-5-(trifluoromethyl)phenoxy]methyl]biphenyl-4-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1-(3-phenylpropyl)-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-[(4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1H-1,2,3-triazol-1-yl)sulfonyl]benzoic acid
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-[4-benzyl-1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-5-yl]benzaldehyde
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-[4-(phenanthren-9-yl)phenyl]-1-(3-phenylpropyl)-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
4-(4'-phenoxybiphenyl-4-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
5.3.99.3
0.03
-
IC50 above 0.03 mM, pH and temperature not specified in the publication
Homo sapiens
5-(dimethylamino)-N-[4'-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]biphenyl-4-yl]naphthalene-1-sulfonamide
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
1-[2-(2-methylphenyl)ethyl]-4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1H-1,2,3-triazole
90% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid
12% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4'-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]biphenyl-4-ol
73.6% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4'-[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]biphenyl-3-ol
60.1% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4'-[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]biphenyl-4-ol
89% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4'-[1-[2-(2-methylphenyl)ethyl]-1H-1,2,3-triazol-4-yl]biphenyl-4-amine
98.2% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-(2'-[[2-chloro-5-(trifluoromethyl)phenoxy]methyl]biphenyl-4-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
91.9% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-(2'-[[2-chloro-5-(trifluoromethyl)phenoxy]methyl]biphenyl-4-yl)-1-[2-(2-methylphenyl)ethyl]-1H-1,2,3-triazole
87.9% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-(4'-phenoxybiphenyl-4-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
88.7% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[(4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1H-1,2,3-triazol-1-yl)sulfonyl]benzoic acid
59.8% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[2'-[(naphthalen-1-yloxy)methyl]biphenyl-4-yl]-1-(3-phenylpropyl)-1H-1,2,3-triazole
96.8% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[4-(phenanthren-9-yl)phenyl]-1-(3-phenylpropyl)-1H-1,2,3-triazole
78.2% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[4-benzyl-1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-5-yl]benzaldehyde
72.1% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
4-[[4-(biphenyl-4-yl)-1H-1,2,3-triazol-1-yl]methyl]-3-nitrobenzoic acid
most efficient inhibitor of mPGES-1, 12% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
5-(dimethylamino)-N-[4'-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]biphenyl-4-yl]naphthalene-1-sulfonamide
85% residual activity at 0.03 mM
Homo sapiens
5.3.99.3
[1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl]methyl benzoate
76.1% residual activity at 0.03 mM
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
5.3.99.3
A-549 cell
-
Homo sapiens
-
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
-
715856
Homo sapiens
Prostaglandin E2
-
-
-
?