3.5.1.99: fatty acid amide hydrolase
This is an abbreviated version!
For detailed information about fatty acid amide hydrolase, go to the full flat file.
Word Map on EC 3.5.1.99
-
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
- 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
Reaction
Synonyms
AAH, anandamide amidohydrolase, AtFAAH, endocannabinoid-degrading enzyme, FA amide hydrolase, FAAH, FAAH-1, FAAH-2, fatty acid amide hydrolase, fatty-acid amide hydrolase, hFAAH, oleamide hydrolase
ECTree
3.5.1.99 fatty acid amide hydrolaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 3.5.1.99 - fatty acid amide hydrolase
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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
(11Z)-eicosenamide + H2O
(11Z)-eicosenoic acid + NH3
-
105% of the activity with oleamide
-
-
?
(12Z)-octadecenamide + H2O
(12Z)-octadecenoic acid + NH3
-
92% of the activity with oleamide
-
-
?
(13Z)-eicosenamide + H2O
(13Z)-eicosenoic acid + NH3
-
103% of the activity with oleamide
-
-
?
(13Z)-octadecenamide + H2O
(13Z)-octadecenoic acid + NH3
-
82% of the activity with oleamide
-
-
?
(15Z)-octadecenamide + H2O
(15Z)-octadecenoic acid + NH3
-
90% of the activity with oleamide
-
-
?
(5Z)-eicosenamide + H2O
(5Z)-eicosenoic acid + NH3
-
116% of the activity with oleamide
-
-
?
(5Z,8Z,11Z,14Z)-N-(2-fluoroethyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolysis rate is 1.3fold higher than the rate of anandamide hydrolysis
-
-
?
(5Z,8Z,11Z,14Z)-N-(2-hydroxy-1,1-dimethylethyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 4.3% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-(2-methylpropyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 2% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-(3-hydroxyphenyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolysis rate is 1.5fold higher than the rate of anandamide hydrolysis
-
-
?
(5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 16% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-tert-butylicosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 1.8% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-[(1S)-1-methylpropyl]icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 6.3% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-[(2R)-2-hydroxypropyl]icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolysis rate is 1.2fold higher than the rate of anandamide hydrolysis
-
-
?
(5Z,8Z,11Z,14Z)-N-[(2S)-2-hydroxypropyl]icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 21% the rate of anandamide
-
-
?
(6Z)-octadecenamide + H2O
(6Z)-octadecenoic acid + NH3
-
91% of the activity with oleamide
-
-
?
(7Z)-octadecenamide + H2O
(7Z)-octadecenoic acid + NH3
-
109% of the activity with oleamide
-
-
?
(8Z)-eicosenamide + H2O
(8Z)-eicosenoic acid + NH3
-
112% of the activity with oleamide
-
-
?
(9E)-octadecenamide + H2O
(9E)-octadecenoic acid + NH3
-
52% of the activity with oleamide
-
-
?
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide + H2O
?
-
hydrolyzed at 61% the rate of anandamide
-
-
?
(9Z)-tetradec-9-enamide + H2O
myristoleic acid + NH3
-
86% of the activity with oleamide
-
-
?
(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide + H2O
?
-
hydrolyzed at 75% the rate of anandamide
-
-
?
(9Z,12Z)-N-[(1R)-2-hydroxy-1-methylethyl]octadeca-9,12-dienamide + H2O
?
-
hydrolyzed at 20.5% the rate of anandamide
-
-
?
(9Z,12Z)-octadeca-9,12-dienamide + H2O
(9Z,12Z)-octadeca-9,12-dienoate + NH3
-
104% of the activity with oleamide
-
-
?
(R)-alpha-methanandamide + H2O
?
-
2.4% of the activity with anandamide
-
-
?
(R)-beta-methanandamide + H2O
?
-
121% of the activity with anandamide
-
-
?
(S)-alpha-methanandamide + H2O
?
-
23% of the activity with anandamide
-
-
?
(S)-beta-methanandamide + H2O
?
-
21% of the activity with anandamide
-
-
?
11,14,17-eicosatrienamide + H2O
11,14,17-eicosatrienoic acid + NH3
-
140% of the activity with oleamide
-
-
?
11,14-eicosadienamide + H2O
? + NH3
-
127% of the activity with oleamide
-
-
?
2,2-dimethyloleamide + H2O
2,2-dimethyloleic acid + NH3
-
3% of the activity with oleamide
-
-
?
2-methyloleamide + H2O
2-methyloleic acid + NH3
-
7% of the activity with oleamide
-
-
?
8,11,14-eicosatrienamide + H2O
8,11,14-eicosatrienoic acid + NH3
-
138% of the activity with oleamide
-
-
?
all-trans-anandamide + H2O
ethanolamine + arachidonic acid
-
all-trans-anandamide is an equally good substrate for rabbit platelet FAAH compared to anandamide
-
-
?
alpha-linolenamide + H2O
? + NH3
-
138% of the activity with oleamide
-
-
?
arachidonyl-7-amino-4-methylcoumarin amide + H2O
arachidonic acid + 7-amino-4-methylcoumarin
beta-arachidonoylglycerol + H2O
?
-
hydrolysis is 2.5fold higher than the rate of anandamide hydrolysis
-
-
?
dodecanoamide + H2O
dodecanoic acid + NH3
-
74% of the activity with oleamide
-
-
?
linoelaidamide + H2O
(9E,12E)-octadeca-9,12-dienoic acid + NH3
-
54% of the activity with oleamide
-
-
?
N-(2-hydroxyethyl)-4-pyren-1-ylbutanamide + H2O
4-(pyren-1-yl)butanamide + ethylene glycol
-
-
-
?
N-(2-hydroxyethyl)-4-pyren-1-ylbutanamide + H2O
4-pyren-1-ylbutanoic acid + ?
-
-
-
-
?
N-(2-hydroxyethyl)octadecanamide + H2O
?
-
hydrolyzed at 15.0% the rate of anandamide
-
-
?
N-(4-hydroxy-2-methylphenyl) arachidonoyl amide + H2O
4-amino-m-cresol + NH3
-
the rate of metabolism of VDM11 is about 15–20% of that for anandamide
-
-
?
N-oleoyltaurine + H2O
taurine + oleic acid
4% of the activity with anandamide
-
-
?
palmitoamide + H2O
palmitic acid + NH3
-
72% of the activity with oleamide
-
-
?
palmitoleamide + H2O
palmitoleic acid + NH3
-
79% of the activity with oleamide
-
-
?
palmitoylethanolamide + H2O
palmitic acid + ethanolamine
-
substrate of FAAH and FAAH-2, the latter shows lower activity than FAAH
-
-
?
stearamide + H2O
stearic acid + NH3
-
69% of the activity with oleamide
-
-
?
2-arachidonoylglycerol + H2O
?
-
FAAH is responsible for approximately one-half of the 2-arachidonoylglycerol hydrolysis occurring in BV-2 cell homogenate
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide, LC-MS/MS analysis
-
-
?
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
arachidonic acid + ethanolamine
-
i.e. N-arachidonoylethanolamine
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
FAAH-1 plays a primary role in regulating endocannabinoid signaling
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
5% of the activity with oleamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
anandamide hydrolysis in BV-2 cells is entirely attributable to FAAH
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
fatty acid amide hydrolase is a modulator of endogenous signaling compounds affecting sleep (oleamide) and analgesia (anandamide)
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
the enzyme cleaves anandamide and regulates in vivo the magnitude and duration of the signaling induced by this lipid messenger
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
the enzyme is responsible for the hydrolysis of a number of neuromodulatory fatty acid amides, including the endogenous cannabinoid anandamide and the sleep-inducing lipid oleamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
the serine hydrolase is responsible for the degradation of endogenous oleamide and anandamide, fatty acid amides that function as chemical messengers
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
168% of the activity with oleamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
?
arachidonamide + H2O
arachidonic acid + NH3
-
311% of the activity with oleamide
-
-
?
arachidonoyl 7-amido-4-methylcoumarin + H2O
arachidonic acid + 7-amino-4-methylcoumarin
-
-
-
-
?
arachidonoyl 7-amido-4-methylcoumarin + H2O
arachidonic acid + 7-amino-4-methylcoumarin
-
-
-
-
?
arachidonyl-7-amino-4-methylcoumarin amide + H2O
arachidonic acid + 7-amino-4-methylcoumarin
fluorogenic substrate
-
-
?
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
-
-
?
myristic amide + H2O
myristic acid + NH3
-
24.3% of the activity with oleamide
-
-
?
myristic amide + H2O
myristic acid + NH3
-
24% of the activity with anandamide
-
-
?
myristic amide + H2O
myristic acid + NH3
-
83% of the activity with oleamide
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
N-oleoylethanolamine + H2O
oleic acid + ethanolamine
23% of the activity with oleamide
-
-
?
N-oleoylethanolamine + H2O
oleic acid + ethanolamine
33% of the activity with anandamide
-
-
?
N-palmitoylethanolamine + H2O
palmitic acid + ethanolamine
12% of the activity with anandamide
-
-
?
N-palmitoylethanolamine + H2O
palmitic acid + ethanolamine
2.3% of the activity with oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
57% of the activity with anandamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
fatty acid amide hydrolase is a modulator of endogenous signaling compounds affecting sleep (oleamide) and analgesia (anandamide)
-
-
?
oleamide + H2O
oleic acid + NH3
-
-
-
-
?
oleamide + H2O
oleic acid + NH3
-
enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
role of FAAH in epithelial cells of the choroid plexus may be to control the concentration of oleamide in the cerebrospinal fluid. FAAH may exert an important regulatory role in shaping the duration and magnitude of the sleep-inducing effect of endogenously or exogenously derived oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
the enzyme is responsible for the hydrolysis of a number of neuromodulatory fatty acid amides, including the endogenous cannabinoid anandamide and the sleep-inducing lipid oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
the serine hydrolase is responsible for the degradation of endogenous oleamide and anandamide, fatty acid amides that function as chemical messengers
-
-
?
oleamide + H2O
oleic acid + NH3
-
serine residue 241 acts as the catalytic nucleophile of the enzyme. FAAH does not utilize a histidine base for the activation of its serine nucleophile
-
-
?
palmitic amide + H2O
palmitic acid + NH3
33% of the activity with anandamide
-
-
?
palmitic amide + H2O
palmitic acid + NH3
-
10% of the activity with anandamide
-
-
?
palmitic amide + H2O
palmitic acid + NH3
-
9.9% of the activity with oleamide
-
-
?
stearic amide + H2O
stearic acid + NH3
5.8% of the activity with anandamide
-
-
?
stearic amide + H2O
stearic acid + NH3
-
5.8% of the activity with anandamide
-
-
?
stearic amide + H2O
stearic acid + NH3
-
5.8% of the activity with oleamide
-
-
?
additional information
?
-
-
the substrate specificity of fatty acid ethanolamides decreased with decreasing length, number of double bonds, and lipophilicity of the fatty acid skeleton
-
-
?
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
-
-
?
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
?
-
-
catalytic efficiency (kcat/Km) of FAAH for nonanoyl p-nitroanilide is approximately 50fold higher than for hexanoyl p-nitroanilide. NAI491 participates in hydrophobic binding interactions with medium-chain FAAH substrates. Use of p-nitroanilide substrates allows for the precise monitoring of enzymatic hydrolysis rates by following the increase in UV absorbance at 382 nm due to the release of p-nitroaniline. p-Nitroanilides are slower FAAH substrates than the corresponding primary amides, however, the binding affinities of these two classes of substrates are equivalent. Due to the slower rates of p-nitroanilide hydrolysis relative to the corresponding primary amides, it can be assumed that pNA substrates are hydrolyzed by FAAH in an acylation rate-limiting manner, allowing for the direct measurement of substrate binding constants through the determination of Km values
-
-
?
additional information
?
-
-
FAAH is an enzyme of broad substrate specificity and is capable of hydrolyzing a wide array of unsaturated, and to a lesser extent saturated, fatty acid primary amides. However, when substituted adjacent to the amide carbonyl, the substrates can be made sterically or electronically resistant to hydrolysis. Long chain saturated fatty acid amides are hydrolyzed slower than the corresponding Z unsaturated fatty acid amides and the rate of hydrolysis increases incrementally with increases in the degree of unsaturation
-
-
?
additional information
?
-
-
hybrid quantum mechanics/molecular mechanics (QM/MM) calculations reveal a new mechanism of nucleophile activation involving a Lys–Ser–Ser catalytic triad. The proposed mechanism, shows that Lys142 and cis-Ser217 have a direct role in the activation of Ser241, in agreement with kinetic labelling experiments employing the highly reactive fluorophosphonatetetramethyl rhodamine. The greater reduction of Ser241 labelling rate in the K142A/S217A double mutant, compared to the K142A and S217A single mutants, suggests that Lys142 and Ser217 cooperate to deprotonate Ser241
-
-
?
additional information
?
-
-
N,N-bis(2-hydroxyethyl)arachidonamide is not hydrolyzed
-
-
?
