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Literature summary for 3.5.1.99 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
Search for more literature for 3.5.1.99

Cloned(Commentary)

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

Inhibitors

Inhibitors Comment Organism Structure
(1-benzhydryltriazol-4-yl)methyl N-cyclohexylcarbamate 73% inhibition at 0.1 mM Homo sapiens
(1-benzyltriazol-4-yl)methyl N-cyclohexylcarbamate
-
 Homo sapiens
(1-phenethyltriazol-4-yl)methyl N-cyclohexylcarbamate
-
 Homo sapiens
(1-phenyltriazol-4-yl)methyl N-cyclohexylcarbamate
-
 Homo sapiens
(3-phenylphenyl)methyl N-cyclohexylcarbamate 65% inhibition at 0.1 mM Homo sapiens
(benzyl-1,2,4-triazol-3-yl)methyl N-cyclohexylcarbamate
-
 Homo sapiens
1-(1-phenyl-1,2,4-triazol-3-yl)methyl N-cyclohexylcarbamate 70% inhibition at 0.1 mM Homo sapiens
2-(1-benzyltriazol-4-yl)ethyl N-cyclohexylcarbamate
-
 Homo sapiens
2-(1-phenyltriazol-4-yl)ethyl N-cyclohexylcarbamate
-
 Homo sapiens
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'-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
6-hydroxybiphenyl-3-yl cyclohexylcarbamate
-
 Homo sapiens
6-hydroxybiphenyl-3-yl cyclohexylcarbamate
-
 Rattus norvegicus
biphenyl-3-yl cyclohexylcarbamate
-
 Homo sapiens
biphenyl-3-yl cyclohexylcarbamate
-
 Rattus norvegicus
additional information O-(triazolyl)methyl carbamates as potent fatty acid amide hydrolase inhibitors, overview Homo sapiens
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
[1-(2-naphthylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-(m-tolylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-(o-tolylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-(p-tolylmethyl)triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Rattus norvegicus
[1-[(2-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(2-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Rattus norvegicus
[1-[(2-cyanophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(2-fluoro-3-methoxy-phenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(2-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(2-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Rattus norvegicus
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Rattus norvegicus
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Homo sapiens
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Homo sapiens
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Rattus norvegicus
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Homo sapiens
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Rattus norvegicus
[1-[(3,5-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(3,5-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Rattus norvegicus
[1-[(3,5-dimethoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(3,5-dimethoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Rattus norvegicus
[1-[(3-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(3-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Rattus norvegicus
[1-[(3-cyanophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(3-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(3-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Rattus norvegicus
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Rattus norvegicus
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Homo sapiens
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Rattus norvegicus
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Homo sapiens
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Rattus norvegicus
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Homo sapiens
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
 Rattus norvegicus
[1-[(4-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(4-cyanophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(4-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens
[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
 Homo sapiens

Localization

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

Natural Substrates/ Products (Substrates)

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

Organism

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

Purification (Commentary)

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

Source Tissue

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

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
FAAH
-
 Rattus norvegicus
FAAH
-
 Homo sapiens
FAAH-1
-
 Homo sapiens

Temperature Optimum [°C]

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

pH Optimum

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

IC50 Value

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

General Information

General Information Comment Organism
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
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