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Literature summary for 3.5.1.99 extracted from

  • Zahov, S.; Drews, A.; Hess, M.; Schulze Elfringhoff, A.; Lehr, M.
    1-(3-biaryloxy-2-oxopropyl)indole-5-carboxylic acids and related compounds as dual inhibitors of human cytosolic phospholipase A2alpha and fatty acid amide hydrolase (2011), ChemMedChem, 6, 544-549.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(5E)-5-(4-methoxybenzylidene)-3-[1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indol-5-yl]-1,3-thiazolidine-2,4-dione
-
Rattus norvegicus
1-(2-oxo-3-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propyl)-1H-indole-5-carboxylic acid 21% inhibition at 0.01 mM Rattus norvegicus
1-(2-oxo-3-[[4'-(propan-2-yl)biphenyl-4-yl]oxy]propyl)-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-(4-octylphenoxy)-3-[5-(1H-tetrazol-5-yl)-1H-indol-1-yl]propan-2-one
-
Rattus norvegicus
1-([1,3]oxazolo[4,5-b]pyridin-2-yl)-6-phenylhexan-1-one
-
Rattus norvegicus
1-[1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indol-5-yl]-1H-benzimidazole-7-carboxylic acid
-
Rattus norvegicus
1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[2-oxo-3-[4-(2-phenoxyethoxy)phenoxy]propyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[2-oxo-3-[4-(2-phenylpropan-2-yl)phenoxy]propyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-(4-benzylphenoxy)-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indazole-5-carboxylic acid
-
Rattus norvegicus
1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-carboxamide
-
Rattus norvegicus
1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-sulfonamide
-
Rattus norvegicus
1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylic acid
-
Homo sapiens
1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylic acid structure-activity relationship, overview Rattus norvegicus
1-[3-(biphenyl-2-yloxy)-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-(biphenyl-3-yloxy)-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-(biphenyl-4-yloxy)-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[(3'-chlorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[(3'-fluorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[(3-chlorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[(3-fluorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[(3-methoxybiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[(3-methylbiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid 39% inhibition at 0.01 mM Rattus norvegicus
1-[3-[(4'-chlorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[(4'-fluorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[(4'-methoxybiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[(4'-methylbiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[4-(4-fluorophenyl)phenoxy]-2-oxopropyl]indazole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[4-(decyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[4-(heptyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[4-(hexyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[4-(nonyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[3-[4-(octyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
Rattus norvegicus
1-[5-(3-benzyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl]-3-(4-octylphenoxy)propan-2-one
-
Rattus norvegicus
1-[5-(3-ethyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl]-3-(4-octylphenoxy)propan-2-one
-
Rattus norvegicus
1-[5-(morpholin-4-ylcarbonyl)-1H-indol-1-yl]-3-(4-octylphenoxy)propan-2-one
-
Rattus norvegicus
3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate
-
Rattus norvegicus
4-[3-[4-(decyloxy)phenoxy]-2-oxopropoxy]benzoic acid
-
Rattus norvegicus
methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-ylphosphonofluoridate
-
Rattus norvegicus
additional information 1-(3-biaryloxy-2-oxopropyl)indole-5-carboxylic acids and related compounds can act as dual inhibitors of human cytosolic phospholipase A2alpha, EC 3.1.1.4, and fatty acid amide hydrolase, overview. Substituents at the indole 3- and 5-positions and replacement of the indole scaffold of this compound by other heterocycles strongly influences the inhibitory potency against FAAH Homo sapiens
additional information 1-(3-biaryloxy-2-oxopropyl)indole-5-carboxylic acids and related compounds can act as dual inhibitors of cytosolic phospholipase A2alpha, EC 3.1.1.4, and fatty acid amide hydrolase, overview. Substituents at the indole 3- and 5-positions and replacement of the indole scaffold of this compound by other heterocycles strongly influences the inhibitory potency against FAAH. No inhibition by 1-[3-(biphenyl-2-yloxy)-2-oxopropyl]-1H-indole-5-carboxylic acid, N-methyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-carboxamide, N,N-dimethyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-carboxamide, 1-[5-(morpholin-4-ylcarbonyl)-1H-indol-1-yl]-3-(4-octylphenoxy)propan-2-one, (5E)-5-(4-methoxybenzylidene)-3-[1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indol-5-yl]-1,3-thiazolidine-2,4-dione, 1-[5-(3-benzyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl]-3-(4-octylphenoxy)propan-2-one, 1-[5-(3-ethyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl]-3-(4-octylphenoxy)propan-2-one, 1-[1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indol-5-yl]-1H-benzimidazole-7-carboxylic acid, and 1-(4-octylphenoxy)-3-[5-(1H-tetrazol-5-yl)-1H-indol-1-yl]propan-2-one at 0.01 mM Rattus norvegicus
N,N-dimethyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-carboxamide
-
Rattus norvegicus
N,N-dimethyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-sulfonamide
-
Rattus norvegicus
N-methyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-carboxamide
-
Rattus norvegicus
N-methyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-sulfonamide
-
Rattus norvegicus

Localization

Localization Comment Organism GeneOntology No. Textmining
microsome
-
Homo sapiens
-
-
microsome
-
Rattus norvegicus
-
-

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-
Rattus norvegicus
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
brain
-
Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
N-(2-hydroxyethyl)-4-pyren-1-ylbutanamide + H2O
-
Rattus norvegicus 4-pyren-1-ylbutanoic acid + ?
-
?

Synonyms

Synonyms Comment Organism
FAAH
-
Homo sapiens
FAAH
-
Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000006
-
pH and temperature not specified in the publication Rattus norvegicus 1-([1,3]oxazolo[4,5-b]pyridin-2-yl)-6-phenylhexan-1-one
0.000025
-
pH and temperature not specified in the publication Rattus norvegicus methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-ylphosphonofluoridate
0.000053
-
pH and temperature not specified in the publication Rattus norvegicus 4-[3-[4-(decyloxy)phenoxy]-2-oxopropoxy]benzoic acid
0.00009
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[4-(4-fluorophenyl)phenoxy]-2-oxopropyl]indazole-5-carboxylic acid
0.00016
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indazole-5-carboxylic acid
0.00022
-
pH and temperature not specified in the publication Rattus norvegicus 3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate
0.00023
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[(3'-chlorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.00024
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[(4'-fluorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.00025
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[(3'-fluorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.00046
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-(biphenyl-4-yloxy)-2-oxopropyl]-1H-indole-5-carboxylic acid
0.00053
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[(4'-chlorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.00053
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[(4'-methoxybiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.00053
-
pH and temperature not specified in the publication Rattus norvegicus N,N-dimethyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-sulfonamide
0.00058
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[(4'-methylbiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.00059
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[(3-fluorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.00075
-
pH and temperature not specified in the publication Rattus norvegicus N-methyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-sulfonamide
0.0012
-
pH and temperature not specified in the publication Rattus norvegicus 1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indole-5-carboxylic acid
0.0016
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-sulfonamide
0.0017
-
pH and temperature not specified in the publication Rattus norvegicus 1-[2-oxo-3-[4-(2-phenoxyethoxy)phenoxy]propyl]-1H-indole-5-carboxylic acid
0.0018
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[4-(nonyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.0019
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-(4-benzylphenoxy)-2-oxopropyl]-1H-indole-5-carboxylic acid
0.0022
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[4-(octyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.0023
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-carboxylic acid
0.0026
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[4-(decyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.0029
-
pH and temperature not specified in the publication Rattus norvegicus 1-[2-oxo-3-[4-(2-phenylpropan-2-yl)phenoxy]propyl]-1H-indole-5-carboxylic acid
0.0034
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-(biphenyl-3-yloxy)-2-oxopropyl]-1H-indole-5-carboxylic acid
0.0034
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[4-(heptyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.0035
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[4-(hexyloxy)phenoxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.005
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[(3-chlorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
0.0051
-
pH and temperature not specified in the publication Rattus norvegicus 1-(2-oxo-3-[[4'-(propan-2-yl)biphenyl-4-yl]oxy]propyl)-1H-indole-5-carboxylic acid
0.0064
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-carboxamide
0.0074
-
pH and temperature not specified in the publication Rattus norvegicus 1-[3-[(3-methoxybiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid