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Information on EC 3.5.1.99 - fatty acid amide hydrolase and Organism(s) Homo sapiens and UniProt Accession O00519
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3.5.1.99 fatty acid amide hydrolaseIUBMB Comments
Integral membrane protein, the enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide, occurs in mammalia.
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Word Map
- 3.5.1.99
-
endocannabinoids
- cannabinoids
- pain
- lipase
- agonist
- monoacylglycerol
- 2-arachidonoylglycerol
-
anxiety
-
analgesic
- cannabis
- n-acylethanolamines
-
vanilloid
-
2-arachidonoyl
- ethanolamide
- palmitoylethanolamide
- carbamate
-
rimonabant
- hyperalgesia
-
reward
-
tone
-
nociceptive
-
cannabimimetic
- n-arachidonoylethanolamine
- marijuana
-
anxiolytic
- nape-pld
-
antinociceptive
- oleoylethanolamide
-
emotional
-
neuropathic
- delta9-tetrahydrocannabinol
- amidase
-
amygdalar
- medicine
- catalepsy
- pharmacology
-
anti-allodynic
-
anxiolytic-like
- monoglyceride
- cannabidiol
-
psychoactive
-
sleep-inducing
-
phytocannabinoids
-
anxiety-like
-
arachidonyl
-
monoacyl
-
capsazepine
-
aversive
- tetrahydrocannabinol
- drug development
-
anti-hyperalgesic
-
neuromodulatory
- fluorophosphonate
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
+
=
+
Synonyms
fatty acid amide hydrolase, fatty-acid amide hydrolase, anandamide amidohydrolase, endocannabinoid-degrading enzyme, hfaah, oleamide hydrolase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
FAAH
-
-
FAAH-2
PATHWAY SOURCE
PATHWAYS
-
-
SYSTEMATIC NAME
IUBMB Comments
fatty acylamide amidohydrolase
Integral membrane protein, the enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide, occurs in mammalia.
CAS REGISTRY NUMBER
COMMENTARY
153301-19-0
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
arachidonyl-7-amino-4-methylcoumarin amide + H2O
arachidonic acid + 7-amino-4-methylcoumarin
fluorogenic substrate
-
-
?
myristic amide + H2O
myristic acid + NH3
65% of the activity with anandamide
-
-
?
N-oleoyltaurine + H2O
taurine + oleic acid
4% of the activity with anandamide
-
-
?
palmitic amide + H2O
palmitic acid + NH3
33% of the activity with anandamide
-
-
?
stearic amide + H2O
stearic acid + NH3
5.8% of the activity with anandamide
-
-
?
arachidonoyl 7-amido-4-methylcoumarin + H2O
arachidonic acid + 7-amino-4-methylcoumarin
-
-
-
-
?
N-oleoylethanolamine + H2O
oleic acid + ethanolamine
23% of the activity with oleamide
-
-
?
N-palmitoylethanolamine + H2O
palmitic acid + ethanolamine
2.3% of the activity with oleamide
-
-
?
palmitoylethanolamide + H2O
palmitic acid + ethanolamine
-
substrate of FAAH and FAAH-2, the latter shows lower activity than FAAH
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
FAAH-1 plays a primary role in regulating endocannabinoid signaling
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
N-oleoylethanolamine + H2O
oleic acid + ethanolamine
33% of the activity with anandamide
-
-
?
N-palmitoylethanolamine + H2O
palmitic acid + ethanolamine
12% of the activity with anandamide
-
-
?
oleamide + H2O
oleic acid + NH3
57% of the activity with anandamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
substrate of FAAH and FAAH-2, the latter shows lower activity than FAAH
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. N-arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide, LC-MS/MS analysis
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
5% of the activity with oleamide
-
-
?
additional information
?
-
FAAH is the primary N-arachidonoylethanolamine-degrading enzyme, but it is also capable of hydrolyzing other bioactive N-acylethanolamines, such as N-palmitoylethanolamine, N-oleoylethanolamine and the sleep-inducing lipid oleamide
-
-
?
additional information
?
-
-
FAAH inactivates anandamide and other bioactive N-acylethanolamines
-
-
?
additional information
?
-
-
the substrate specificity of fatty acid ethanolamides decreased with decreasing length, number of double bonds, and lipophilicity of the fatty acid skeleton
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
palmitoylethanolamide + H2O
palmitic acid + ethanolamine
-
substrate of FAAH and FAAH-2, the latter shows lower activity than FAAH
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
FAAH-1 plays a primary role in regulating endocannabinoid signaling
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
substrate of FAAH and FAAH-2, the latter shows lower activity than FAAH
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. N-arachidonoyl ethanolamide
-
-
?
additional information
?
-
FAAH is the primary N-arachidonoylethanolamine-degrading enzyme, but it is also capable of hydrolyzing other bioactive N-acylethanolamines, such as N-palmitoylethanolamine, N-oleoylethanolamine and the sleep-inducing lipid oleamide
-
-
?
additional information
?
-
-
FAAH inactivates anandamide and other bioactive N-acylethanolamines
-
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1-benzhydryltriazol-4-yl)methyl N-cyclohexylcarbamate
73% inhibition at 0.1 mM
(1H-benzo[d][1,2,3]triazol-1-yl)(4-(3-phenoxybenzyl)-piperazin-1-yl)-methanone
-
(1H-benzo[d][1,2,3]triazol-1-yl)(4-(4-phenoxybenzyl)-piperazin-1-yl)-methanone hydrochloride
-
(1H-imidazol-1-yl)(4-(4-phenoxy-benzyl)-piperazin-1-yl)-methanone hydrochloride
-
(3H-[1,2,3]triazol[4,5-b]pyridin-3-yl)(4-(3-phenoxybenzyl)-piperazin-1-yl)-methanone
-
(3R,4R)-4-acetoxy-3-((10R)-(t-butyldimethylsilyloxy)-ethyl)-azetidin-2-one
-
(4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)-piperidin-1-yl)(1H-1,2,4-triazol-1-yl)methanone
-
(4-benzhydrylpiperazin-1-yl)(4-phenyl-1H-imidazol-1-yl)methanone
62% activity remaining at 0.01 mM
(S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl 3-(1H-indol-3-yl)propanoate
-
1,1,1,3,3,3-hexafluoropropan-2-yl 4-(3-phenoxybenzyl)piperazine-1-carboxylate
-
1-(1-phenyl-1,2,4-triazol-3-yl)methyl N-cyclohexylcarbamate
70% inhibition at 0.1 mM
1-[(3S)-1-[4-(1-benzofuran-2-yl)pyrimidin-2-yl]piperidin-3-yl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one
the compound belongs to the ketobenzimidazoles, though containing a carbonyl moiety, that do not covalently modify Ser241. These inhibitors achieve potent inhibition of FAAH activity primarily from shape complementarity to the active site and through numerous hydrophobic interactions exhibiting excellent selectivity and good pharmacokinetic properties, nonmechanism-based inhibition
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 3-(1H-indol-3-yl)propanoate
-
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 4-(pyridin-2-yl)butanoate
-
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 4-(pyridin-4-yl)butanoate
-
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl biphenyl-4-carboxylate
-
1-[4-[bis(1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidin-1-yl]-3,3,3-trifluoro-2-(trifluoromethyl)propan-1-one
-
2,2,2-trichloroethyl 4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)piperidine-1-carboxylate
-
2-(methylamino)-2-oxoethyl [2-[1-(6-methylpyridin-2-yl)piperidin-4-yl]ethyl]carbamate
-
3-pyridyl 4-(phenylcarbamoyl)piperidine-1-carboxylate
i.e. ASP8477
4-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-benzhydryl-N-(4-(trifluoromethyl)phenyl)piperazine-1-carboxamide
86% activity remaining at 0.01 mM
4-benzhydryl-N-(4-butylphenyl)piperazine-1-carboxamide
84% activity remaining at 0.01 mM
4-benzhydryl-N-(4-methoxyphenyl)piperazine-1-carboxamide
89% activity remaining at 0.01 mM
4-benzhydryl-N-(4-nitrophenyl)piperazine-1-carboxamide
84% activity remaining at 0.01 mM
4-benzhydryl-N-(pyridin-2-yl)piperazine-1-carboxamide
87% activity remaining at 0.01 mM
4-benzhydryl-N-(pyridin-3-yl)piperazine-1-carboxamide
87% activity remaining at 0.01 mM
4-benzhydryl-N-phenylpiperazine-1-carboxamide
88% activity remaining at 0.01 mM
4-nitrophenyl 4-[bis(1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate
-
4-nitrophenyl-4-(bis(benzo[d][1,3]dioxol-5-yl)methyl)piperidine-1-carboxylate
-
4-[2-(2,4-difluorophenyl)pyridin-4-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[2-(2,4-difluorophenyl)pyrimidin-4-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,3-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)piperazine-1-carboxamide
-
4-[4-(2,4-difluorophenyl)pyridin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,4-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,5-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(3,4-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
analgesic effect of 21d in rat inflammatory pain model, overview
4-[4-(3,5-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[6-(2,4-difluorophenyl)pyridin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[6-(2,4-difluorophenyl)pyrimidin-4-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
5-(4-hydroxyphenyl)pentanesulfonyl fluoride
i.e. AM3506, irreversible inhibitor for both the rat and the human enzyme, that covalently modifies the enzyme
6-bromo-N-(2-fluorophenyl)-1'H,4H-spiro[1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide
an irreversible covalent inhibitor, binding structure, overview
benzyl 4-(dibenzo[d][1,3]dioxol-5-yl(hydroxy)methyl)-piperidine-1-carboxylate
-
ethyl 4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-ylcarbonyl)piperazine-1-carboxylate
-
hexadecyl sulfonylfluoride
i.e. AM374, is a potent irreversible in vitro and in vivo inhibitor of fatty acid amide hydrolase
N-(3,4-dimethyl-1,2-oxazol-5-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
-
N-(pyridazin-3-yl)-4-(3-[[5-(trifluoromethyl)pyridin-2-yl]oxy]benzylidene)piperidine-1-carboxamide
-
N-(pyridin-3-yl)-4-(3-[[5-(trifluoromethyl)pyridin-2-yl]oxy]benzyl)piperidine-1-carboxamide
-
N-phenyl-4-(3-phenyl-4,5-dihydro-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
-
[(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl 4-(pyridin-2-yl)butanoate
-
[(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl 4-(pyridin-4-yl)butanoate
-
[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
[1-[(2-fluoro-3-methoxy-phenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
[1-[(3,5-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
[1-[(3,5-dimethoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
[4-[bis(1,3-benzodioxol-5-yl)methyl]piperidin-1-yl](1H-1,2,4-triazol-1-yl)methanone
-
[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl](1H-1,2,4-triazol-1-yl)methanone
-
(1-benzothiophen-6-ylamino)([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)methanone
-
-
(1-benzylpiperidin-4-yl)[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
(4-benzylpiperazin-1-yl)[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
(5Z,8Z,11Z,14Z)-1-[1,3]oxazolo[4,5-b]pyridin-2-ylicosa-5,8,11,14-tetraen-1-one
-
-
(5Z,8Z,11Z,14Z)-1-[1,3]oxazolo[4,5-c]pyridin-2-ylicosa-5,8,11,14-tetraen-1-one
-
-
(5Z,8Z,11Z,14Z)-1-[1,3]oxazolo[5,4-c]pyridin-2-ylicosa-5,8,11,14-tetraen-1-one
-
-
(dodecylamino)[[(E)-[1-[3-(thiophen-2-yl)phenyl]ethylidene]amino]oxy]methanone
-
-
(phenylamino)[[(E)-[1-[3-(thiophen-2-yl)phenyl]ethylidene]amino]oxy]methanone
-
-
(phenylamino)[[(E)-[1-[4-(thiophen-2-yl)phenyl]ethylidene]amino]oxy]methanone
-
-
([(E)-[1-(2,2'-bithiophen-5-yl)ethylidene]amino]oxy)(naphthalen-1-ylamino)methanone
-
-
([(E)-[1-(4-cyclohexylphenyl)ethylidene]amino]oxy)(naphthalen-1-ylamino)methanone
-
-
([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)(naphthalen-1-ylamino)methanone
-
-
([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)[(4-fluorophenyl)amino]methanone
-
-
([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)[(4-methoxyphenyl)amino]methanone
-
-
([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)[(5-phenylpentyl)amino]methanone
-
-
([(E)-[1-(biphenyl-4-yl)ethylidene]