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Information on EC 3.5.1.60 - N-(long-chain-acyl)ethanolamine deacylase and Organism(s) Rattus norvegicus and UniProt Accession Q6P7S1
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3.5.1.60 N-(long-chain-acyl)ethanolamine deacylaseIUBMB Comments
This lysosomal enzyme acts best on palmitoyl ethanolamide, with lower activity on other N-(long-chain-acyl)ethanolamines. It is only active at acidic pH. Unlike EC 3.5.1.99, fatty acid amide hydrolase, it does not act on primary amides such as oleamide, and has only a marginal activity with anandamide. The enzyme is translated as an inactive proenzyme, followed by autocatalytic cleavage into two subunits that reassociate to form an active heterodimeric complex.
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The taxonomic range for the selected organisms is: Rattus norvegicus
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
hnaaa, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
amidase, acylethanolamine
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-
-
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N-acylethanolamine amidohydrolase
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of linear amides
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-
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SYSTEMATIC NAME
IUBMB Comments
N-(long-chain-acyl)ethanolamine amidohydrolase
This lysosomal enzyme acts best on palmitoyl ethanolamide, with lower activity on other N-(long-chain-acyl)ethanolamines. It is only active at acidic pH. Unlike EC 3.5.1.99, fatty acid amide hydrolase, it does not act on primary amides such as oleamide, and has only a marginal activity with anandamide. The enzyme is translated as an inactive proenzyme, followed by autocatalytic cleavage into two subunits that reassociate to form an active heterodimeric complex.
CAS REGISTRY NUMBER
COMMENTARY
99283-61-1
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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
heptadecenoylethanolamide + H2O
heptadecenoate + ethanolamine
-
-
-
?
(10Z)-heptadecenoylethanolamide + H2O
(10Z)-heptadec-10-enoic acid + ethanolamine
-
-
-
?
N-arachidonoylethanolamine + H2O
arachidic acid + ethanolamine
-
-
-
?
N-dodecanoylethanolamine + H2O
dodecanoic acid + ethanolamine
-
110% of activity compared to N-oleoylethanolamine
-
?
N-hexadecanoylethanolamine + H2O
hexadecanoic acid + ethanolamine
-
71% of activity compared to N-oleoylethanolamine
-
?
N-octadecanoylethanolamine + H2O
octadecanoic acid + ethanolamine
-
42% of activity compared to N-oleoylethanolamine
-
?
N-oleoylethanolamine + H2O
oleic acid + ethanolamine
-
best substrate in mixture of N-acylethanolamines
-
r
N-tetradecanoylethanolamine + H2O
tetradecanoic acid + ethanolamine
-
95% of activity compared to N-oleoylethanolamine
-
?
palmitoylethanolamide + H2O
palmitic acid + ethanolamine
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-
-
?
additional information
?
-
-
N-acylsphingosine or N,O-diacylethanolamine are no substrates
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-
?
additional information
?
-
N-acylethanolamine acid amidase is a cysteine amidase that hydrolyzes saturated or mono-unsaturated fatty acid ethanolamides, such as palmitoylethanolamide and oleoylethanolamide
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-
?
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
N-arachidonoylethanolamine + H2O
arachidic acid + ethanolamine
-
-
-
?
palmitoylethanolamide + H2O
palmitic acid + ethanolamine
-
-
-
?
additional information
?
-
N-acylethanolamine acid amidase is a cysteine amidase that hydrolyzes saturated or mono-unsaturated fatty acid ethanolamides, such as palmitoylethanolamide and oleoylethanolamide
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-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(2E)-3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)prop-2-en-1-one
a reversible and competitive NAAA inhibitor, that shows in vivo anti-inflammatory activity, the pyrrolidine ring of 4g occupies the enzyme catalytic center of NAAA, preventing the carbonyl group from forming a covalent bond with catalytic residues
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
-
3,5-dichloro-4-nitropyridine
AM11095, synthetis is of the specific brain permeable NAAA inhibitor, a slowly reversible NAAA inhibitor
3-[4-(2H-1,3-benzodioxol-5-yl)phenyl]-1-(pyrrolidin-1-yl)propan-1-one
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(S)-2-oxo-3-oxetanyl-carbamic acid benzyl ester
a serine-derived beta-lactone, weak inhibition of rat lung enzyme, structure-activity relationship studies confirm that the ability of the compound to inhibit the enzyme depends on the beta-lactone ring, rather than the carbamate fragment, because analogues lacking the beta-lactone moiety are devoid of inhibitory activity
([1,1'-biphenyl]-4-yl)methyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
reversible inhibition, modulates nociceptive responses in rats by blocking enzyme-mediated fatty acid ethanolamide degradation and restoring fattyacid ethanolamide signaling at PPAR-alpha
5,5'-dithiobis(2-nitrobenzoic acid)
-
0.5 mM: 50% inhibition of mitochondrial, 42% inhibition of microsomal enzyme
N-ethylmaleimide
-
0.25 mM: 50% inhibition of mitochondrial enzyme, 0.5 mM: 50% inhibition of microsomal enzyme
N-pentadecylcyclohexancarboxamide
a potent and selective inhibitor, reversible and non-competitive inhibition mechanism
N-[(2R,3S)-2-methyl-4-oxooxetan-3-yl]-3-phenylpropanamide
very low inhibition
N-[(3S)-2-oxo-3-oxetanyl]-3-phenylpropanamide
noncompetitive inhibition, the compound can be used as a tool to investigate the effect of enzyme inhibition on inflammatory cells. The (S) stereochemistry at the alpha-carbon of the beta-lactone ring is important for potent enzyme NAAA inhibition
p-chloromercuribenzoate
-
0.05 mM: total inhibition of mitochondrial or microsomal enzyme
undec-10-ynyl N-[(3S)-2-oxoazetidin-3-yl]carbamate
ARN14686, design and validation of this derivative of ARN726 as activity-based protein profiling (ABPP) probe for the in vivo detection of NAAA
3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
i.e. F215, a NAAA inhibitor
3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
interaction mechanism with NAAA by a Yonetani-Theorell analysis
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
ARN726, the enzyme inhibitor exerts systemic anti-inflammatory effects in mouse models of lung inflammation
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
the compound is quickly eliminated in vivo
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
ARN077
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
ARN077, the enzyme inhibitor is active in vivo by topical administration in rodent models of hyperalgesia and allodynia
additional information
synthesis, biological evaluation, and structure activity relationship study of pyrrolidine amide derivatives as N-acylethanolamine acid amidase (NAAA) inhibitors. Docking study using the crystal structure of human NAAA (PDB ID 6DY2)
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additional information
amines with a long alkyl chain, in particular alkyl amines with a chain length of 14 or15 carbon atoms, and of glycine with linearalkyl alcohols of 12-16 carbon atoms inhibit the enzyme
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additional information
amines with an alkyl chain of suitable length and lipophilic amines exhibit potent inhibition of the enzyme. No inhibition by N-pentadecylcyclohexanecarboxamide
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additional information
design and synthesis of potent N-acylethanolamine-hydrolyzing acid amidase inhibitors, derivatives of 1-pentadecanyl-carbonyl pyrrolidine, as anti-inflammatory compounds, computational docking analysis, structure-activity relationship, overview
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additional information
inhibitor desing and synthesis of a class of beta-lactam derivatives that are potent, selective, and systemically active inhibitors of intracellular NAAA activity, reaction mechanisms via acylation or alkylation of the enzyme, overview
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additional information
structure-activity relationship of oxazolidone derivatives, inhibitory mechanism, overview
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
Michaelis-Menten kinetic analysis
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.5
(2E)-3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)prop-2-en-1-one
Rattus norvegicus
pH 4.5, 37°C
4.1
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
1-(pyrrolidin-1-yl)-3-(thiophen-2-yl)propan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.1
1-(pyrrolidin-1-yl)-3-(thiophen-3-yl)propan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.0141
1-(pyrrolidin-1-yl)-7-(thiophen-2-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0132
1-(pyrrolidin-1-yl)-7-(thiophen-3-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
3-(2'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.0028
3-(2'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
3-(2'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.0254
3-(3'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0018
3-(3'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0165
3-(3'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0486
3-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0034
3-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0332
3-(4'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
2.8
3-(4-phenoxycyclohexyl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
3-(4-phenoxyphenyl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.48
3-(4-phenylcyclohexyl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0007
3-(cyclohexyloxy)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0057
3-(pyridin-2-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
3-(pyridin-3-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.0021
3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
3-[4-(2H-1,3-benzodioxol-5-yl)phenyl]-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.1
3-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
Rattus norvegicus
above, pH 4.5, 37°C
0.1
4-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
Rattus norvegicus
above, pH 4.5, 37°C
5.5
5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)pentan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
7-(2-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.0137
7-(2-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0684
7-(2-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0037
7-(3-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0073
7-(3-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
7-(3-hydroxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.1
7-(3-methoxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.0083
7-(3-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
7-(3-propylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.0345
7-(4-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.008
7-(4-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0056
7-(4-hydroxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0354
7-(4-methoxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.0096
7-(4-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.1
7-(4-propylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.1
7-(pyridin-2-yl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.1
7-(pyridin-3-yl)-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
above, pH 4.5, 37°C
0.1
methyl 3-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoate
Rattus norvegicus
above, pH 4.5, 37°C
0.1
methyl 4-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoate
Rattus norvegicus
above, pH 4.5, 37°C
0.00296
(S)-2-oxo-3-oxetanyl-carbamic acid benzyl ester
Rattus norvegicus
pH and temperature not specified in the publication
0.000007
([1,1'-biphenyl]-4-yl)methyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
Rattus norvegicus
pH and temperature not specified in the publication
0.025
1-hexadecanoylpyrrolidine
Rattus norvegicus
pH and temperature not specified in the publication
0.00068
3-(4-phenoxybenzoyl)-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00027
3-(6-phenylhexanoyl)-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00212
3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH and temperature not specified in the publication
0.00774
3-[4-(3-chlorophenoxy)benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00521
3-[4-(3-methylphenoxy)benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.0064
3-[4-(4-methylphenoxy)benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.000092
3-[4-(cyclohexyloxy)benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00012
3-[4-(cyclopentyloxy)benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00064
3-[4-(pentyloxy)benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00021
3-[4-[(4-hydroxycyclohexyl)oxy]benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00033
3-[4-[(oxan-4-yl)oxy]benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00043
3-[6-(3-bromophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.000026
3-[6-(3-chloro-4-fluorophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.000009
3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00016
3-[6-(3-fluoro-4-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00864
3-[6-(3-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00312
3-[6-(3-iodophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.0163
3-[6-(3-methoxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00035
3-[6-(3-methylphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.0157
3-[6-(4-aminophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00851
3-[6-(4-bromophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.0046
3-[6-(4-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.000061
3-[6-(4-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.44
3-[6-(4-methylphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.0128
3-[6-[3-(methylsulfanyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.000058
3-[6-[3-(trifluoromethyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00019
3-[6-[4-(hydroxymethyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00104
3-[6-[4-(trifluoromethyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.000063
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
Rattus norvegicus
pH and temperature not specified in the publication
0.05
5-phenylpentyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
Rattus norvegicus
pH and temperature not specified in the publication
0.00005
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
Rattus norvegicus
pH and temperature not specified in the publication
0.01
benzyl [(2R,3S)-2-methyl-4-oxooxetan-3-yl]carbamate
Rattus norvegicus
above, pH and temperature not specified in the publication
0.001
benzyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
Rattus norvegicus
pH and temperature not specified in the publication
0.0083
N-pentadecylbenzamide
Rattus norvegicus
pH and temperature not specified in the publication
0.0045
N-pentadecylcyclohexancarboxamide
Rattus norvegicus
pH and temperature not specified in the publication
0.1
N-[(2R,3S)-2-methyl-4-oxooxetan-3-yl]-3-phenylpropanamide
Rattus norvegicus
above, pH and temperature not specified in the publication
0.0032
N-[(2S,3R)-2-methyl-4-oxooxetan-3-yl]-3-phenylpropanamide
Rattus norvegicus
pH and temperature not specified in the publication
0.006
N-[(3R)-2-oxo-3-oxetanyl]-3-phenylpropanamide
Rattus norvegicus
pH and temperature not specified in the publication
0.00042
N-[(3S)-2-oxo-3-oxetanyl]-3-phenylpropanamide
Rattus norvegicus
pH and temperature not specified in the publication
0.00046
N-[(3S)-2-oxooxetan-3-yl]heptanamide
Rattus norvegicus
pH and temperature not specified in the publication
0.00016
N-[(3S)-2-oxooxetan-3-yl]naphthalene-2-carboxamide
Rattus norvegicus
pH and temperature not specified in the publication
0.000115
N-[(3S)-2-oxooxetan-3-yl][1,1'-biphenyl]-4-carboxamide
Rattus norvegicus
pH and temperature not specified in the publication
0.000013
undec-10-ynyl N-[(3S)-2-oxoazetidin-3-yl]carbamate
Rattus norvegicus
pH and temperature not specified in the publication
0.00048
3-[4-[(pentan-3-yl)oxy]benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.00134
3-[4-[(pentan-3-yl)oxy]benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
0.0057
pentadecylamine
Rattus norvegicus
pH and temperature not specified in the publication
additional information
3-[4-(4-hydroxyphenoxy)benzoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-(2-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-(2-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-(2-methylphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-(3,4-dimethylphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-(3-aminophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-(3-chloro-4-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-(4-iodophenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-(4-methoxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-oxo-6-(2-oxo-1,3-oxazolidin-3-yl)hexyl]benzamide
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-oxo-6-(2-oxo-1,3-oxazolidin-3-yl)hexyl]benzoic acid
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-[3-(hydroxymethyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
3-[6-[4-(methylsulfanyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
additional information
4-[6-oxo-6-(2-oxo-1,3-oxazolidin-3-yl)hexyl]benzamide
Rattus norvegicus
above 20 mM, pH and temperature not specified in the publication
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
effects of pretreatment with the NAAA inhibitor AM11095 on nicotine-related effects in the rat mesolimbic dopamine system, phenotype, detailed overview
evolution
the enzyme is a cysteine hydrolase belonging to the N-terminalnucleophile (Ntn) family of enzymes
malfunction
physiological function
malfunction
enzyme inhibitors may attenuate heat hyperalgesia and mechanical allodynia caused by local inflammation or nerve damage in animal models of pain and inflammation
malfunction
prevention against cartilage degeneration by i.p. injection of enzyme inhibitor F215 in osteoarthritis rats
physiological function
the enzyme intracellularly breaks down the analgesic and anti-inflammatory mediator palmitoylethanolamide
physiological function
N-acylethanolamine acid amidase (NAAA) is a lysosomal cysteine hydrolase involved in the degradation of saturated and monounsaturated fatty acid ethanolamides (FAEs), a family of endogenous lipid signaling molecules that includes oleoylethanolamide (OEA) and palmitoylethanolamide (PEA)
physiological function
the enzyme is implicated in osteoarthritis progression
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). ASAH1_RAT
394
0
44443
Swiss-Prot
Mitochondrion (Reliability: 1)
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene Naaa, stable transfection and functional recombinant expression in HEK-293 cells
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pharmacology
NAAA inhibitor F215 is a therapeutic agent for osteoarthritis. The therapeutic effects of F215 are blocked by the PPAR-alpha antagonist MK886
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Schmid, P.C.; Zuzarte-Augustin, M.L.; Schmid, H.H.O.
Properties of rat liver N-acylethanolamine amidohydrolase
J. Biol. Chem.
260
14145-14149
1985
Rattus norvegicus
Hansen, H.; Lauritzen, L.; Moesgaard, B.; Strand, A.M.; Hansen, H.
Formation of N-acyl-phoshatidylethanolamines and N-acylethanolamines: proposed role in neurotoxicity
Biochem. Pharmacol.
55
719-725
1998
Homo sapiens, Mus sp., Rattus norvegicus
Yamano, Y.; Tsuboi, K.; Hozaki, Y.; Takahashi, K.; Jin, X.H.; Ueda, N.; Wada, A.
Lipophilic amines as potent inhibitors of N-acylethanolamine-hydrolyzing acid amidase
Bioorg. Med. Chem.
20
3658-3665
2012
Rattus norvegicus (Q5KTC7), Rattus norvegicus Wistar/ST (Q5KTC7)
Bandiera, T.; Ponzano, S.; Piomelli, D.
Advances in the discovery of N-acylethanolamine acid amidase inhibitors
Pharmacol. Res.
86
11-17
2014
Homo sapiens (Q02083), Mus musculus, Rattus norvegicus (Q5KTC7)
Li, Y.; Yang, L.; Chen, L.; Zhu, C.; Huang, R.; Zheng, X.; Qiu, Y.; Fu, J.
Design and synthesis of potent N-acylethanolamine-hydrolyzing acid amidase (NAAA) inhibitor as anti-inflammatory compounds
PLoS ONE
7
e43023
2012
Rattus norvegicus (Q5KTC7)
Ribeiro, A.; Pontis, S.; Mengatto, L.; Armirotti, A.; Chiurchiu, V.; Capurro, V.; Fiasella, A.; Nuzzi, A.; Romeo, E.; Moreno-Sanz, G.; Maccarrone, M.; Reggiani, A.; Tarzia, G.; Mor, M.; Bertozzi, F.; Bandiera, T.; Piomelli, D.
A potent systemically active N-acylethanolamine acid amidase inhibitor that suppresses inflammation and human macrophage activation
ACS Chem. Biol.
10
1838-1846
2015
Homo sapiens (Q02083), Mus musculus (Q9D7V9), Mus musculus C57BL/6J (Q9D7V9), Rattus norvegicus (Q5KTC7)
Romeo, E.; Ponzano, S.; Armirotti, A.; Summa, M.; Bertozzi, F.; Garau, G.; Bandiera, T.; Piomelli, D.
Activity-based probe for N-acylethanolamine acid amidase
ACS Chem. Biol.
10
2057-2064
2015
Homo sapiens (Q02083), Rattus norvegicus (Q5KTC7), Rattus norvegicus Sprague-Dawley (Q5KTC7)
Li, Y.; Chen, Q.; Yang, L.; Li, Y.; Zhang, Y.; Qiu, Y.; Ren, J.; Lu, C.
Identification of highly potent N-acylethanolamine acid amidase (NAAA) inhibitors optimization of the terminal phenyl moiety of oxazolidone derivatives
Eur. J. Med. Chem.
139
214-221
2017
Rattus norvegicus (Q5KTC7)
Zhou, P.; Xiang, L.; Zhao, D.; Ren, J.; Qiu, Y.; Li, Y.
Synthesis, biological evaluation, and structure activity relationship (SAR) study of pyrrolidine amide derivatives as N-acylethanolamine acid amidase (NAAA) inhibitors
MedChemComm
10
252-262
2019
Rattus norvegicus (Q6P7S1)
Sagheddu, C.; Scherma, M.; Congiu, M.; Fadda, P.; Carta, G.; Banni, S.; Wood, J.T.; Makriyannis, A.; Malamas, M.S.; Pistis, M.
Inhibition of N-acylethanolamine acid amidase reduces nicotine-induced dopamine activation and reward
Neuropharmacology
144
327-336
2019
Homo sapiens (Q02083), Rattus norvegicus (Q6P7S1), Rattus norvegicus Sprague-Dawley (Q6P7S1)
Zhou, P.; Xiang, L.; Yang, Y.; Wu, Y.; Hu, T.; Liu, X.; Lin, F.; Xiu, Y.; Wu, K.; Lu, C.; Ren, J.; Qiu, Y.; Li, Y.
N-Acylethanolamine acid amidase (NAAA) inhibitor F215 as a novel therapeutic agent for osteoarthritis
Pharmacol. Res.
145
104264
2019
Homo sapiens (Q02083), Rattus norvegicus (Q5KTC7)
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