3.5.1.60: N-(long-chain-acyl)ethanolamine deacylase
This is an abbreviated version!
For detailed information about N-(long-chain-acyl)ethanolamine deacylase, go to the full flat file.
Reaction
Synonyms
acylethanolamine acid amidase, amidase, acylethanolamine, hNAAA, N-acylethanolamine acid amidase, N-acylethanolamine amidohydrolase, N-acylethanolamine-hydrolyzing acid amidase, N-acylethanolaminehydrolyzing acid amidase, NAAA, Nacylethanolamine acid amidase, NAE-hydrolyzing acid amidase
ECTree
3.5.1.60 N-(long-chain-acyl)ethanolamine deacylaseAdvanced search results
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results (Inhibitors
Inhibitors on EC 3.5.1.60 - N-(long-chain-acyl)ethanolamine deacylase
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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
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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
3-[4-(2H-1,3-benzodioxol-5-yl)phenyl]-1-(pyrrolidin-1-yl)propan-1-one
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4-cyclohexylbutyl [(3S)-2-oxoazetidin-3-yl]carbamate
a serine-derived beta-lactam CC-ABP, competitive
5,5'-dithiobis(2-nitrobenzoic acid)
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0.5 mM: 50% inhibition of mitochondrial, 42% inhibition of microsomal enzyme
5-((biphenyl-4-yl)methyl)-N,N-dimethyl-2H-tetrazole-2-carboxamide
inhibits the enzyme in a covalent and irreversible manner
5-(4-(4-(5,5-difluoro-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-10-yl)butyl)-1H-1,2,3-triazol-1-yl)pentyl ((2S,3S)-2-methyl-1-(4-(methylsulfonyl)phenoxy)-4-oxoazetidin-3-yl)carbamate
a N-O-substituted beta-lactam BODIPY-ABP, almost complete inhibition of enzyme NAAA
5-(norbornan-2-ylmethoxy)pentyl N-[(2S,3S)-2-methyl-1-(4-methylsulfonylphenoxy)-4-oxo-azetidin-3-yl]carbamate
a norbornene-derived beta-lactam
5-azidopentyl N-[(2S,3S)-2-methyl-1-(4-methylsulfonylphenoxy)-4-oxo-azetidin-3-yl]carbamate
an azide-beta-lactam
N-benzyloxycarbonyl-L-serine beta-lactone
inhibits the enzyme in a covalent and irreversible manner
N-ethylmaleimide
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0.25 mM: 50% inhibition of mitochondrial enzyme, 0.5 mM: 50% inhibition of microsomal enzyme
N-[(2R,3S)-2-methyl-4-oxooxetan-3-yl]-3-phenylpropanamide
very low inhibition
p-chloromercuribenzoate
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0.05 mM: total inhibition of mitochondrial or microsomal enzyme
palmitic acid retro-amides N-pentadecylbenzamide
a potent and selective inhibitor
tert-butyl ((2S,3S)-2-methyl-1-(4-(methylsulfonyl)phenoxy)-4-oxoazetidin-3-yl)carbamate
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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
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
[2-(ethylsulfonyl)phenyl][(2S)-4-(6-fluoro-1,3-benzothiazol-2-yl)-2-methylpiperazin-1-yl]methanone
ARN19702, a noncovalent benzothiazole-piperazine derivative
([1,1'-biphenyl]-4-yl)methyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
inhibition through a rapid and noncompetitive mechanism, partially reversible inhibition. The compound reacts with the catalytically active N-terminal Cys126 of human enzyme to form a thioester bond
([1,1'-biphenyl]-4-yl)methyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
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modulates nociceptive responses in mice by blocking enzyme-mediated fattyacid ethanolamide degradation and restoring fattyacid ethanolamide signaling at PPAR-alpha
([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
1-isothiocyanatopentadecane
a potent, competitive, selective, and reversible inhibitor
3,5-dichloro-4-nitropyridine
AM11095, synthetis of the specific brain permeable NAAA inhibitor, a slowly reversible NAAA inhibitor
3,5-dichloro-4-nitropyridine
AM11095, synthetis is of the specific brain permeable NAAA inhibitor, a slowly reversible NAAA inhibitor
3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
i.e. F215, the NAAA inhibitor F215 is a therapeutic agent for osteoarthritis
3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
interaction mechanism with NAAA by a Yonetani-Theorell analysis
3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
i.e. F215, a NAAA inhibitor
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
ARN726, enzyme-binding structure analysis. Nucleophilic attack on the carbonyl carbon of the strained beta-lactam moiety by the Cys126 side chain
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
it blocks enzyme NAAA by covalently binding to the enzyme's catalytic cysteine and displays pronounced antiinflammatory properties in human macrophages
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
ARN726, a beta-lactam that irreversibly reacts with Cys126
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
the compound is quickly eliminated in vivo. It blocks enzyme NAAA by covalently binding to the enzyme's catalytic cysteine and displays pronounced antiinflammatory properties in mouse models
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
ARN726, enzyme-binding structure analysis. Nucleophilic attack on the carbonyl carbon of the strained beta-lactam moiety by the Cys126 side chain
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
the compound is quickly eliminated in vivo
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
ARN726, the enzyme inhibitor exerts systemic anti-inflammatory effects in mouse models of lung inflammation
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
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
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ARN077, a beta-lactone-based NAAA inhibitor that is rapidly deactivated in blood and other tissues. Analysis of properties of the NAAA inhibitor in a mouse model of allergic contact dermatitis. ARN077 suppresses DNFB-induced inflammation when administered either before or after the DNFB challenge. The effects of subchronic ARN077 are dose-dependent and comparable in size to those produced by the steroids clobetasol and dexamethasone. Unlike the latter, ARN077 does not cause skin atrophy
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
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
ARN077
N-pentadecylcyclohexancarboxamide
a potent and selective inhibitor, reversible and non-competitive inhibition mechanism
N-[(3S)-2-oxo-3-oxetanyl]-3-phenylpropanamide
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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
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
additional information
NAAA inhibitors block the substrate-binding site
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additional information
synthesis and evaluation of a series of N-(2-oxoazetidin-3-yl)amides as a novel class of enzyme inhibitors with good potency and improved physicochemical properties, suitable for systemic administration. No inhibition by 3-phenyl-N-[(S)-2-oxoazetidin-3-yl]propanamide, N-[(3S)-2-oxoazetidin-3-yl][1,1'-biphenyl]-4-carboxamide, N-(2-oxocyclobutyl)nonanamide, N-(azetidin-3-yl)nonanamide, 3-amino-N-nonanoyl-L-alanine, N-[(3S)-2-oxopyrrolidin-3-yl]nonanamide, N-[(S)-1-methyl-2-oxo-azetidin-3-yl]nonanamide, N-methyl-N-[(S)-2-oxoazetidin-3-yl]nonanamide, and (S)-3-(nonylamino)azetidin-2-one
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additional information
selective alkylation of the enzyme's cysteine residues results in almost complete loss of activity
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additional information
mechanism of inactivation of human enzyme N-acylethanolamine-hydrolyzing acid amidase with selected inhibitors identified in a fluorescent based assay developed for characterization of both reversible and irreversible inhibitors, kinetic analysis using MALDI-TOF mass spectroscopy, molecular modeling, overview
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additional information
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mechanism of inactivation of human enzyme N-acylethanolamine-hydrolyzing acid amidase with selected inhibitors identified in a fluorescent based assay developed for characterization of both reversible and irreversible inhibitors, kinetic analysis using MALDI-TOF mass spectroscopy, molecular modeling, 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
inhibitor binding analysis using purified and activated human enzyme hNAAA coupled to an azide-PEG3-biotin conjugate to its terminal alkyne using click chemistry, and visualization of protein bands using streptavidin-horseradish peroxidase (HRP)
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additional information
identification of N-acylethanolamine-hydrolyzing acid amidase inhibitors able to reduce cell proliferation and migration and cause cell death on different bladder cancer cell lines. Inhibitor design of NAAA palmitic acid-retroamide inhibitors, synthesis, and characterization. Fluorescence high-throughput screening method set-up on human recombinant NAAA, using non-fluorescent but fluorogenic N-(4-methylcoumarin)palmitamide (PAMCA), that also allows to characterize the mechanism of inhibition. Reversibility of the inhibition. The NAAA inhibitors affect bladder cancer cells viability, they can be effective in inducing tumor cell death. But the inhibitors are differently effective of the different cell lines, overview
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additional information
development of two unprecedented NAAA-reactive activity-based probes as research tools for application in the discovery of inhibitors and for the in-depth characterization of NAAA in its cellular environment. Assay with lysosome-enriched extracts from hNAAA-overexpressing HEK-293 cells
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additional information
NAAA inhibitors block the substrate-binding site
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additional information
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no or poor inhibition by N-[(3R)-2-oxo-3-oxetanyl]-3-phenylpropanamide
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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
-
additional information
NAAA inhibitors block the substrate-binding site
-
additional information
NAAA inhibitors block the substrate-binding site
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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
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
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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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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