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Literature summary extracted from

  • Colombano, G.; Albani, C.; Ottonello, G.; Ribeiro, A.; Scarpelli, R.; Tarozzo, G.; Daglian, J.; Jung, K.M.; Piomelli, D.; Bandiera, T.
    O-(triazolyl)methyl carbamates as a novel and potent class of fatty acid amide hydrolase (FAAH) inhibitors (2015), ChemMedChem, 10, 380-395.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.5.1.99 recombinant expression of FAAH-1 in HEK-293 cells Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.1.99 (1-benzhydryltriazol-4-yl)methyl N-cyclohexylcarbamate 73% inhibition at 0.1 mM Homo sapiens
3.5.1.99 (1-benzyltriazol-4-yl)methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 (1-phenethyltriazol-4-yl)methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 (1-phenyltriazol-4-yl)methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 (3-phenylphenyl)methyl N-cyclohexylcarbamate 65% inhibition at 0.1 mM Homo sapiens
3.5.1.99 (benzyl-1,2,4-triazol-3-yl)methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 1-(1-phenyl-1,2,4-triazol-3-yl)methyl N-cyclohexylcarbamate 70% inhibition at 0.1 mM Homo sapiens
3.5.1.99 2-(1-benzyltriazol-4-yl)ethyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 2-(1-phenyltriazol-4-yl)ethyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate exerts a combination of anxiolytic-like, anti-depressant-like, and analgesic effects, due to its ability to inhibit FAAH activity in the CNS and peripheral tissues. Covalent enzyme binding at Ser241 leading to irreversible inhibition, the attack at the carbonyl group by Ser 241 leads to the formation of carbamoylated, catalytically inactive FAAH and releasing the O-biphenyl moiety as the leaving group Homo sapiens
3.5.1.99 3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate covalent enzyme binding at Ser241 leading to irreversible inhibition, the attack at the carbonyl group by Ser 241 leads to the formation of carbamoylated, catalytically inactive FAAH and releasing the O-biphenyl moiety as the leaving group Rattus norvegicus
3.5.1.99 6-hydroxybiphenyl-3-yl cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 6-hydroxybiphenyl-3-yl cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 biphenyl-3-yl cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 biphenyl-3-yl cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 additional information O-(triazolyl)methyl carbamates as potent fatty acid amide hydrolase inhibitors, overview Homo sapiens
3.5.1.99 additional information O-(triazolyl)methyl carbamates as potent fatty acid amide hydrolase inhibitors, overview. These compounds show improved stability in rat plasma and kinetic solubility in buffer with respect to the lead compound O-(1,2,3-triazol-4-yl)methyl carbamate Rattus norvegicus
3.5.1.99 [1-(2-naphthylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-(m-tolylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-(o-tolylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-(p-tolylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(2,6-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(2,6-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 [1-[(2-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(2-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 [1-[(2-cyanophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(2-fluoro-3-methoxy-phenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(2-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(2-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Homo sapiens
3.5.1.99 [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Homo sapiens
3.5.1.99 [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Rattus norvegicus
3.5.1.99 [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Homo sapiens
3.5.1.99 [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Rattus norvegicus
3.5.1.99 [1-[(3,5-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(3,5-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 [1-[(3,5-dimethoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(3,5-dimethoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 [1-[(3-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(3-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 [1-[(3-cyanophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(3-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(3-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Rattus norvegicus
3.5.1.99 [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Homo sapiens
3.5.1.99 [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Rattus norvegicus
3.5.1.99 [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Homo sapiens
3.5.1.99 [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Rattus norvegicus
3.5.1.99 [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Homo sapiens
3.5.1.99 [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
Rattus norvegicus
3.5.1.99 [1-[(4-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(4-cyanophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(4-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens
3.5.1.99 [1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
Homo sapiens

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.5.1.99 membrane bound Rattus norvegicus 16020
-
3.5.1.99 membrane bound Homo sapiens 16020
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.5.1.99 anandamide + H2O Rattus norvegicus
-
ethanolamine + arachidonic acid
-
?
3.5.1.99 anandamide + H2O Homo sapiens
-
ethanolamine + arachidonic acid
-
?
3.5.1.99 anandamide + H2O Rattus norvegicus Sprague–Dawley
-
ethanolamine + arachidonic acid
-
?
3.5.1.99 N-arachidonoylethanolamine + H2O Rattus norvegicus
-
arachidonic acid + ethanolamine
-
?
3.5.1.99 N-arachidonoylethanolamine + H2O Rattus norvegicus Sprague–Dawley
-
arachidonic acid + ethanolamine
-
?

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.99 Homo sapiens O00519
-
-
3.5.1.99 Rattus norvegicus P97612
-
-
3.5.1.99 Rattus norvegicus Sprague–Dawley P97612
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.5.1.99 recombinant FAAH-1 partially from HEK-293 cells by membrane preparation Homo sapiens

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.5.1.99 brain
-
Rattus norvegicus
-
3.5.1.99 brain
-
Homo sapiens
-
3.5.1.99 liver
-
Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.99 anandamide + H2O
-
Rattus norvegicus ethanolamine + arachidonic acid
-
?
3.5.1.99 anandamide + H2O
-
Homo sapiens ethanolamine + arachidonic acid
-
?
3.5.1.99 anandamide + H2O
-
Rattus norvegicus Sprague–Dawley ethanolamine + arachidonic acid
-
?
3.5.1.99 N-arachidonoylethanolamine + H2O
-
Rattus norvegicus arachidonic acid + ethanolamine
-
?
3.5.1.99 N-arachidonoylethanolamine + H2O
-
Rattus norvegicus Sprague–Dawley arachidonic acid + ethanolamine
-
?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.99 FAAH
-
Rattus norvegicus
3.5.1.99 FAAH
-
Homo sapiens
3.5.1.99 FAAH-1
-
Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.5.1.99 37
-
assay at Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.5.1.99 7.4
-
assay at Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.5.1.99 0.0000014
-
pH 7.4, 37°C Rattus norvegicus [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000014
-
pH 7.4, 37°C Homo sapiens [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000032
-
pH 7.4, 37°C Rattus norvegicus [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000032
-
pH 7.4, 37°C Homo sapiens [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000036
-
pH 7.4, 37°C Homo sapiens [1-[(3,5-dimethoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000039
-
pH 7.4, 37°C Rattus norvegicus [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000039
-
pH 7.4, 37°C Homo sapiens [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000057
-
pH 7.4, 37°C Rattus norvegicus biphenyl-3-yl cyclohexylcarbamate
3.5.1.99 0.0000058
-
pH 7.4, 37°C Rattus norvegicus [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000058
-
pH 7.4, 37°C Homo sapiens [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000062
-
pH 7.4, 37°C Rattus norvegicus [1-[(2-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000062
-
pH 7.4, 37°C Homo sapiens [1-[(2-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000076
-
pH 7.4, 37°C Rattus norvegicus [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000076
-
pH 7.4, 37°C Homo sapiens [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000098
-
pH 7.4, 37°C Rattus norvegicus [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000098
-
pH 7.4, 37°C Homo sapiens [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.0000099
-
pH 7.4, 37°C Rattus norvegicus [1-[(2-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000099
-
pH 7.4, 37°C Homo sapiens [1-[(2-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000104
-
pH 7.4, 37°C Rattus norvegicus [1-[(3,5-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000104
-
pH 7.4, 37°C Homo sapiens [1-[(3,5-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000105
-
pH 7.4, 37°C Rattus norvegicus [1-[(3,5-dimethoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000118
-
pH 7.4, 37°C Rattus norvegicus [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000118
-
pH 7.4, 37°C Homo sapiens [1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000119
-
pH 7.4, 37°C Rattus norvegicus [1-[(2,6-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000119
-
pH 7.4, 37°C Homo sapiens [1-[(2,6-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000121
-
pH 7.4, 37°C Rattus norvegicus [1-[(3-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000121
-
pH 7.4, 37°C Homo sapiens [1-[(3-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000132
-
pH 7.4, 37°C Rattus norvegicus [1-[(3-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000132
-
pH 7.4, 37°C Homo sapiens [1-[(3-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000195
-
pH 7.4, 37°C Homo sapiens [1-[(2-cyanophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000215
-
pH 7.4, 37°C Homo sapiens [1-(o-tolylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000215
-
pH 7.4, 37°C Homo sapiens [1-[(3-cyanophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000245
-
pH 7.4, 37°C Homo sapiens [1-(m-tolylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000446
-
pH 7.4, 37°C Homo sapiens [1-[(2-fluoro-3-methoxy-phenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0000955
-
pH 7.4, 37°C Homo sapiens [1-[(4-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.000154
-
pH 7.4, 37°C Homo sapiens [1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
3.5.1.99 0.000215
-
pH 7.4, 37°C Homo sapiens [1-[(4-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.0005
-
pH 7.4, 37°C Homo sapiens [1-(p-tolylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.000627
-
pH 7.4, 37°C Homo sapiens [1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.002
-
pH 7.4, 37°C Homo sapiens [1-(2-naphthylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
3.5.1.99 0.002282
-
pH 7.4, 37°C Homo sapiens [1-[(4-cyanophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate

General Information

EC Number General Information Comment Organism
3.5.1.99 additional information the active site of FAAH is characterized by an atypical catalytic triad, consisting of Ser241-Ser217-Ly142, which is capable of hydrolyzing amide and ester bonds at similar rates Rattus norvegicus
3.5.1.99 additional information the active site of FAAH is characterized by an atypical catalytic triad, consisting of Ser241-Ser217-Ly142, which is capable of hydrolyzing amide and ester bonds at similar rates Homo sapiens