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(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
-
(2R)-2-hydroxy-N-pentadecyl-2-phenylacetamide
-
(2S)-2-hydroxy-N-pentadecyl-2-phenylacetamide
(7E)-N-[(3S)-2-oxoazetidin-3-yl]non-7-enamide
-
(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
(Z)-N-[(S)-2-oxoazetidin-3-yl]non-3-enamide
-
([1,1'-biphenyl]-4-yl)methyl cyclopentanecarboxylate
-
([1,1'-biphenyl]-4-yl)methyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
1-(2-(4-benzyloxy)phenyl)ethyl-carbonyl pyrrolidine
-
1-(2-biphenyl-4-yl)ethyl-carbonyl pyrrolidine
-
1-(2-naphthalenyl)acetyl pyrrolidine
-
1-(2-naphthalenyl)carbonyl pyrrolidine
-
1-(2-phenylethyl)-carbonyl pyrrolidine
-
1-(3-phenylpropanyl)-carbonyl pyrrolidine
-
1-(4-benzyloxy)benzyl-carbonyl pyrrolidine
-
1-(4-phenylbenzyl)-carbonyl pyrrolidine
-
1-(4-phenylbutanyl)-carbonyl pyrrolidine
-
1-(5-phenylpentanyl)-carbonyl pyrrolidine
-
1-(6-phenylhexanyl)-carbonyl pyrrolidine
-
1-(7-phenylheptanyl)-carbonyl pyrrolidine
-
1-(biphenyl-4-ylcarbonyl)pyrrolidine
-
1-(pyrrolidin-1-yl)-3-(thiophen-2-yl)propan-1-one
-
1-(pyrrolidin-1-yl)-3-(thiophen-3-yl)propan-1-one
-
1-(pyrrolidin-1-yl)-7-(thiophen-2-yl)heptan-1-one
-
1-(pyrrolidin-1-yl)-7-(thiophen-3-yl)heptan-1-one
-
1-benzyl-carbonyl pyrrolidine
-
1-heptyl-3-[(S)-2-oxoazetidin-3-yl]urea
-
1-hexadecanoylpyrrolidine
weak inhibition
1-isothiocyanatopentadecane
1-pentadecanyl-carbonyl piperidine
-
1-pentadecanyl-carbonyl pyrrole
-
1-pentadecanyl-carbonyl pyrrolidine
-
1-[3-([1,1'-biphenyl]-4-yl)propyl]pyrrolidine
-
2,2-dimethyl-N-[(3S)-2-oxoazetidin-3-yl]nonanamide
-
2,5-dihydroxy-N-pentadecylbenzamide
2-(dodecyloxy)ethan-1-amine
40% remaining activity
2-(hexadecyloxy)ethan-1-amine
91% remaining activity
2-(tetradecyloxy)ethan-1-amine
48% remaining activity
2-aminoethyl decanoate
89% remaining activity
2-aminoethyl dodecanoate
74% remaining activity
2-aminoethyl hexadecanoate
50% remaining activity
2-aminoethyl tetradecanoate
46% remaining activity
2-hydroxy-N-pentadecylbenzamide
-
2-methyl-N-[(3S)-2-oxoazetidin-3-yl]nonanamide
-
3,5-dichloro-4-nitropyridine
3-(2'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(2'-chloro[1,1'-biphenyl]-4-yl)propanoic acid
-
3-(2'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(2'-fluoro[1,1'-biphenyl]-4-yl)propanoic acid
-
3-(2'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(2'-methyl[1,1'-biphenyl]-4-yl)propanoic acid
-
3-(3'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(3'-chloro[1,1'-biphenyl]-4-yl)propanoic acid
-
3-(3'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(3'-fluoro[1,1'-biphenyl]-4-yl)propanoic acid
-
3-(3'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(3'-methyl[1,1'-biphenyl]-4-yl)propanoic acid
-
3-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(4'-chloro[1,1'-biphenyl]-4-yl)propanoic acid
-
3-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(4'-fluoro[1,1'-biphenyl]-4-yl)propanoic acid
-
3-(4'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(4'-methyl[1,1'-biphenyl]-4-yl)propanoic acid
-
3-(4-phenoxybenzoyl)-1,3-oxazolidin-2-one
-
3-(4-phenoxycyclohexyl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(4-phenoxyphenyl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(4-phenylcyclohexyl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(6-phenylhexanoyl)-1,3-oxazolidin-2-one
-
3-(benzyloxy)propyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
3-(cyclohexyloxy)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(dodecyloxy)propan-1-amine
73% remaining activity
3-(hexadecyloxy)propan-1-amine
84% remaining activity
3-(pyridin-2-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(pyridin-2-yl)propanoic acid
-
3-(pyridin-3-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-(pyridin-3-yl)propanoic acid
-
3-(tetradecyloxy)propan-1-amine
71% remaining activity
3-(thiophen-2-yl)propanoic acid
-
3-(thiophen-3-yl)propanoic acid
-
3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3-amino-N-nonanoyl-L-alanine
-
3-aminopropyl decanoate
55% remaining activity
3-aminopropyl dodecanoate
63% remaining activity
3-aminopropyl hexadecanoate
48% remaining activity
3-aminopropyl tetradecanoate
46% remaining activity
3-cyclohexyl-1-(pyrrolidin-1-yl)propan-1-one
-
3-cyclohexylpropanoic acid
-
3-[4-(2H-1,3-benzodioxol-5-yl)phenyl]-1-(pyrrolidin-1-yl)propan-1-one
-
3-[4-(3-chlorophenoxy)benzoyl]-1,3-oxazolidin-2-one
-
3-[4-(3-methylphenoxy)benzoyl]-1,3-oxazolidin-2-one
-
3-[4-(4-hydroxyphenoxy)benzoyl]-1,3-oxazolidin-2-one
-
3-[4-(4-methylphenoxy)benzoyl]-1,3-oxazolidin-2-one
-
3-[4-(cyclohexyloxy)benzoyl]-1,3-oxazolidin-2-one
-
3-[4-(cyclopentyloxy)benzoyl]-1,3-oxazolidin-2-one
-
3-[4-(pentyloxy)benzoyl]-1,3-oxazolidin-2-one
-
3-[4-[(4-hydroxycyclohexyl)oxy]benzoyl]-1,3-oxazolidin-2-one
-
3-[4-[(oxan-4-yl)oxy]benzoyl]-1,3-oxazolidin-2-one
-
3-[4-[(pentan-3-yl)oxy]benzoyl]-1,3-oxazolidin-2-one
-
3-[6-(2-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(2-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(2-methylphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3,4-dimethylphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3-aminophenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3-bromophenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3-chloro-4-fluorophenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3-chloro-4-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
3-[6-(3-fluoro-4-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3-iodophenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3-methoxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(3-methylphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(4-aminophenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(4-bromophenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(4-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(4-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(4-iodophenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(4-methoxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-(4-methylphenyl)hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-oxo-6-(2-oxo-1,3-oxazolidin-3-yl)hexyl]benzamide
-
3-[6-oxo-6-(2-oxo-1,3-oxazolidin-3-yl)hexyl]benzoic acid
-
3-[6-[3-(hydroxymethyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-[3-(methylsulfanyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-[3-(trifluoromethyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-[4-(hydroxymethyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-[4-(methylsulfanyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
-
3-[6-[4-(trifluoromethyl)phenyl]hexanoyl]-1,3-oxazolidin-2-one
-
3-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
-
4-butyl-N-[(S)-2-oxoazetidin-3-yl]benzamide
-
4-cyclohexylbutyl [(3S)-2-oxoazetidin-3-yl]carbamate
a serine-derived beta-lactam CC-ABP, competitive
4-cyclohexylbutyl-N-[(R)-2-oxoazetidin-3-yl]carbamate
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
4-[6-oxo-6-(2-oxo-1,3-oxazolidin-3-yl)hexyl]benzamide
-
4-[6-oxo-6-(2-oxo-1,3-oxazolidin-3-yl)hexyl]benzoic acid
-
4-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
-
5,5'-dithiobis(2-nitrobenzoic acid)
-
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-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)pentan-1-one
-
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
5-cyclohexylpentyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
5-phenylpentyl N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate
-
5-phenylpentyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
7-(2-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(2-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(2-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(3-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(3-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(3-hydroxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(3-methoxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(3-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(3-propylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(4-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(4-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(4-hydroxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(4-methoxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(4-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(4-propylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(pyridin-2-yl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(pyridin-2-yl)heptanoic acid
-
7-(pyridin-3-yl)-1-(pyrrolidin-1-yl)heptan-1-one
-
7-(pyridin-3-yl)heptanoic acid
-
7-(thiophen-2-yl)heptanoic acid
-
7-(thiophen-3-yl)heptanoic acid
-
7-cyclohexyl-1-(pyrrolidin-1-yl)heptan-1-one
-
7-cyclohexyl-N-[(3S)-2-oxoazetidin-3-yl]heptanamide
-
7-cyclohexylheptanoic acid
-
7-phenyl-1-(pyrrolidin-1-yl)heptan-1-one
-
benzyl [(2R,3S)-2-methyl-4-oxooxetan-3-yl]carbamate
-
benzyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
-
biphenyl-4-ylmethyl pyrrolidinyl-1-carboxylate
-
cyclobutanol
41% inhibition at 0.05 mM
Cyclopentanol
85% inhibition at 0.05 mM
cyclopentyl hexadecanoate
competitive inhibition
dodecyl 2-aminoacetate
34% remaining activity
dodecyl 3-aminopropanoate
51% remaining activity
heptyl N-[(S)-2-oxoazetidin-3-yl]carbamate
-
hexadecyl 2-aminoacetate
71% remaining activity
methyl 3-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoate
-
methyl 4-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoate
-
N-(2-oxocyclobutyl)nonanamide
-
N-(azetidin-3-yl)nonanamide
-
N-(biphenyl-4-ylmethyl)pyrrolidinyl-1-carboxamide
-
N-benzyloxycarbonyl-L-serine beta-lactone
inhibits the enzyme in a covalent and irreversible manner
N-cyclopentylpalmitamide
-
N-ethylmaleimide
-
0.25 mM: 50% inhibition of mitochondrial enzyme, 0.5 mM: 50% inhibition of microsomal enzyme
N-pentadecylcyclohexancarboxamide
N-pentadecylnaphthalene-2-carboxamide
-
N-pentadecylpyridine-4-carboxamide
N-[(2R,3S)-2-methyl-4-oxooxetan-3-yl]-3-phenylpropanamide
very low inhibition
N-[(2S,3R)-2-methyl-4-oxooxetan-3-yl]-3-phenylpropanamide
-
N-[(3R)-2-oxo-3-oxetanyl]-3-phenylpropanamide
weak inhibition
N-[(3R)-2-oxoazetidin-3-yl]nonanamide
-
N-[(3S)-2-oxo-3-oxetanyl]-3-phenylpropanamide
N-[(3S)-2-oxoazetidin-3-yl]-4-phenylbutanamide
-
N-[(3S)-2-oxoazetidin-3-yl]-5-phenylpentanamide
-
N-[(3S)-2-oxoazetidin-3-yl]-6-phenylhexanamide
-
N-[(3S)-2-oxoazetidin-3-yl]decanamide
-
N-[(3S)-2-oxoazetidin-3-yl]heptanamide
-
N-[(3S)-2-oxoazetidin-3-yl]nonanamide
N-[(3S)-2-oxoazetidin-3-yl]octanamide
-
N-[(3S)-2-oxoazetidin-3-yl]undecanamide
-
N-[(3S)-2-oxooxetan-3-yl]-3-phenylpropanamide
N-[(3S)-2-oxooxetan-3-yl]heptanamide
-
N-[(3S)-2-oxooxetan-3-yl]naphthalene-2-carboxamide
-
N-[(3S)-2-oxooxetan-3-yl][1,1'-biphenyl]-4-carboxamide
-
N-[(S)-2-oxoazetidin-3-yl]-6-phenylhexanamide
-
N-[([1,1'-biphenyl]-4-yl)methyl]cyclopentanecarboxamide
-
oleic acid
-
10 nM: 50% inhibition, 100 nM: 95% inhibition
p-chloromercuribenzoate
-
0.05 mM: total inhibition of mitochondrial or microsomal enzyme
palmitic acid retro-amides N-pentadecylbenzamide
a potent and selective inhibitor
pentadecyl 2-aminoacetate
42% remaining activity
sodium cholate
-
7.5 mg/ml: 90% inhibition
sodium dodecylsulfate
-
2.5 mg/ml: 98% inhibition
sodium taurodeoxycholate
-
15 mg/ml: 20% inhibition
tert-butyl ((2S,3S)-2-methyl-1-(4-(methylsulfonyl)phenoxy)-4-oxoazetidin-3-yl)carbamate
-
tetradecyl 2-aminoacetate
16% remaining activity
tetradecyl 3-aminopropanoate
30% remaining activity
tetrahydrofuran-3-yl palmitate
-
tridecyl 2-aminoacetate
11% remaining activity
tridecyl 3-aminopropanoate
29% remaining activity
tridecyl glycine
competitive inhibition
Triton X-100
-
5 mg/ml: 42% inhibition
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
(2S)-2-hydroxy-N-pentadecyl-2-phenylacetamide
-
(2S)-2-hydroxy-N-pentadecyl-2-phenylacetamide
a covalent beta-lactam
([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
-
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
1-isothiocyanatopentadecane
a potent, selective and reversible inhibitor
2,5-dihydroxy-N-pentadecylbenzamide
-
2,5-dihydroxy-N-pentadecylbenzamide
a non-covalent 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-(benzyloxy)propyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
-
3-(benzyloxy)propyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
-
3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
-
3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
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-[(R)-2-oxoazetidin-3-yl]carbamate
-
4-cyclohexylbutyl-N-[(R)-2-oxoazetidin-3-yl]carbamate
-
4-cyclohexylbutyl-N-[(R)-2-oxoazetidin-3-yl]carbamate
-
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
-
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
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-cyclohexylpentyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
-
5-cyclohexylpentyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
-
5-phenylpentyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
-
5-phenylpentyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
-
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
-
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
-
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
-
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
-
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-pentadecylbenzamide
-
N-pentadecylbenzamide
a potent and selective inhibitor
N-pentadecylcyclohexancarboxamide
a potent and selective inhibitor
N-pentadecylcyclohexancarboxamide
a potent and selective inhibitor, reversible and non-competitive inhibition mechanism
N-pentadecylpyridine-4-carboxamide
-
N-pentadecylpyridine-4-carboxamide
a covalent beta-lactam
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
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
N-[(3S)-2-oxoazetidin-3-yl]nonanamide
-
N-[(3S)-2-oxoazetidin-3-yl]nonanamide
-
N-[(3S)-2-oxoazetidin-3-yl]nonanamide
-
N-[(3S)-2-oxooxetan-3-yl]-3-phenylpropanamide
-
N-[(3S)-2-oxooxetan-3-yl]-3-phenylpropanamide
-
N-[(3S)-2-oxooxetan-3-yl]-3-phenylpropanamide
-
pentadecylamine
-
pentadecylamine
competitive inhibition
additional information
NAAA inhibitors block the substrate-binding site
-
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
-
additional information
selective alkylation of the enzyme's cysteine residues results in almost complete loss of activity
-
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
-
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
-
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
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)
-
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
-
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
-
additional information
NAAA inhibitors block the substrate-binding site
-
additional information
-
no or poor inhibition by N-[(3R)-2-oxo-3-oxetanyl]-3-phenylpropanamide
-
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
-
additional information
amines with an alkyl chain of suitable length and lipophilic amines exhibit potent inhibition of the enzyme. No inhibition by N-pentadecylcyclohexanecarboxamide
-
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
-
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
-
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
structure-activity relationship of oxazolidone derivatives, inhibitory mechanism, overview
-
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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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
0.02
(2R)-2-hydroxy-N-pentadecyl-2-phenylacetamide
Homo sapiens
pH and temperature not specified in the publication
0.000006 - 0.078
(2S)-2-hydroxy-N-pentadecyl-2-phenylacetamide
0.00309
(7E)-N-[(3S)-2-oxoazetidin-3-yl]non-7-enamide
Homo sapiens
pH 5.0, 37°C
0.00296
(S)-2-oxo-3-oxetanyl-carbamic acid benzyl ester
Rattus norvegicus
pH and temperature not specified in the publication
0.0039
(Z)-N-[(S)-2-oxoazetidin-3-yl]non-3-enamide
Homo sapiens
pH 5.0, 37°C
0.000007
([1,1'-biphenyl]-4-yl)methyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
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
0.00576
1-heptyl-3-[(S)-2-oxoazetidin-3-yl]urea
Homo sapiens
pH 5.0, 37°C
0.025
1-hexadecanoylpyrrolidine
Rattus norvegicus
pH and temperature not specified in the publication
0.00035 - 0.0006
1-isothiocyanatopentadecane
0.00076
2,2-dimethyl-N-[(3S)-2-oxoazetidin-3-yl]nonanamide
Homo sapiens
pH 5.0, 37°C
0.00023 - 0.038
2,5-dihydroxy-N-pentadecylbenzamide
0.011
2-hydroxy-N-pentadecylbenzamide
Homo sapiens
pH and temperature not specified in the publication
0.00022
2-methyl-N-[(3S)-2-oxoazetidin-3-yl]nonanamide
Homo sapiens
pH 5.0, 37°C
0.00002
3,5-dichloro-4-nitropyridine
Homo sapiens
pH and temperature not specified in the publication
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
0.00068
3-(4-phenoxybenzoyl)-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
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
0.00027
3-(6-phenylhexanoyl)-1,3-oxazolidin-2-one
Rattus norvegicus
above, pH and temperature not specified in the publication
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 - 0.00212
3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
0.0005
3-cyclohexyl-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
0.00774
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
0.00048 - 0.00134
3-[4-[(pentan-3-yl)oxy]benzoyl]-1,3-oxazolidin-2-one
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
0.1
3-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
Rattus norvegicus
above, pH 4.5, 37°C
0.0138
4-butyl-N-[(S)-2-oxoazetidin-3-yl]benzamide
Homo sapiens
pH 5.0, 37°C
0.000027 - 0.000073
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
0.1
4-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
Rattus norvegicus
above, pH 4.5, 37°C
0.0000072 - 0.0000077
5-((biphenyl-4-yl)methyl)-N,N-dimethyl-2H-tetrazole-2-carboxamide
5.5
5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)pentan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.00035
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
Homo sapiens
pH 7.4, 37°C
0.00006
5-(norbornan-2-ylmethoxy)pentyl N-[(2S,3S)-2-methyl-1-(4-methylsulfonylphenoxy)-4-oxo-azetidin-3-yl]carbamate
Homo sapiens
pH 7.4, 37°C
0.05
5-phenylpentyl N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate
Homo sapiens
pH 4.5, 37°C
0.000007 - 0.05
5-phenylpentyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
0.000007 - 0.00005
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
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
0.0025
7-cyclohexyl-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
0.00028
7-cyclohexyl-N-[(3S)-2-oxoazetidin-3-yl]heptanamide
Homo sapiens
pH 5.0, 37°C
0.0129
7-phenyl-1-(pyrrolidin-1-yl)heptan-1-one
Rattus norvegicus
pH 4.5, 37°C
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
0.01
cyclopentyl hexadecanoate
Homo sapiens
pH and temperature not specified in the publication
0.00024
heptyl N-[(S)-2-oxoazetidin-3-yl]carbamate
Homo sapiens
pH 5.0, 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
0.0017 - 0.0019
N-benzyloxycarbonyl-L-serine beta-lactone
0.0083 - 0.045
N-pentadecylbenzamide
0.034
N-pentadecylbutanamide
Homo sapiens
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-pentadecylnaphthalene-2-carboxamide
Homo sapiens
above, pH and temperature not specified in the publication
0.0004 - 0.098
N-pentadecylpyridine-4-carboxamide
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
0.0745
N-[(3R)-2-oxoazetidin-3-yl]nonanamide
Homo sapiens
pH 5.0, 37°C
0.00042
N-[(3S)-2-oxo-3-oxetanyl]-3-phenylpropanamide
Rattus norvegicus
pH and temperature not specified in the publication
0.0734
N-[(3S)-2-oxoazetidin-3-yl]-4-phenylbutanamide
Homo sapiens
pH 5.0, 37°C
0.0272
N-[(3S)-2-oxoazetidin-3-yl]-5-phenylpentanamide
Homo sapiens
pH 5.0, 37°C
0.0006
N-[(3S)-2-oxoazetidin-3-yl]-6-phenylhexanamide
Homo sapiens
pH 5.0, 37°C
0.00024
N-[(3S)-2-oxoazetidin-3-yl]decanamide
Homo sapiens
pH 5.0, 37°C
0.027
N-[(3S)-2-oxoazetidin-3-yl]heptanamide
Homo sapiens
pH 5.0, 37°C
0.00034
N-[(3S)-2-oxoazetidin-3-yl]nonanamide
Homo sapiens
pH 5.0, 37°C
0.0019
N-[(3S)-2-oxoazetidin-3-yl]octanamide
Homo sapiens
pH 5.0, 37°C
0.0001
N-[(3S)-2-oxoazetidin-3-yl]undecanamide
Homo sapiens
pH 5.0, 37°C
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
0.0121
N-[(S)-2-oxoazetidin-3-yl]-6-phenylhexanamide
Homo sapiens
pH 5.0, 37°C
0.000013
undec-10-ynyl N-[(3S)-2-oxoazetidin-3-yl]carbamate
Rattus norvegicus
pH and temperature not specified in the publication
0.000006
undec-10-ynyl-N-[(3S)-2-oxoazetidin-3-yl]carbamate
Homo sapiens
pH and temperature not specified in the publication
0.00023
[2-(ethylsulfonyl)phenyl][(2S)-4-(6-fluoro-1,3-benzothiazol-2-yl)-2-methylpiperazin-1-yl]methanone
Homo sapiens
pH 4.5, 37°C, recombinant enzyme
additional information
3-[4-(4-hydroxyphenoxy)benzoyl]-1,3-oxazolidin-2-one
0.000006
(2S)-2-hydroxy-N-pentadecyl-2-phenylacetamide
Homo sapiens
pH 7.4, 37°C
0.078
(2S)-2-hydroxy-N-pentadecyl-2-phenylacetamide
Homo sapiens
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
Homo sapiens
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
0.00035
1-isothiocyanatopentadecane
Homo sapiens
recombinant enzyme with substrate N-(4-methyl coumarin)palmitamide, pH not specified in the publication, 37°C
0.00035 - 0.0006
1-isothiocyanatopentadecane
Homo sapiens
pH and temperature not specified in the publication
0.0006
1-isothiocyanatopentadecane
Homo sapiens
recombinant enzyme with substrate N-palmitoylethanolamine, pH not specified in the publication, 37°C
0.00023
2,5-dihydroxy-N-pentadecylbenzamide
Homo sapiens
pH 7.4, 37°C
0.038
2,5-dihydroxy-N-pentadecylbenzamide
Homo sapiens
pH and temperature not specified in the publication
0.0021
3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
Rattus norvegicus
pH 4.5, 37°C
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
0.00048
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
0.000027
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
Homo sapiens
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
0.000073
4-cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate
Homo sapiens
pH 7.4, 37°C
0.0000072
5-((biphenyl-4-yl)methyl)-N,N-dimethyl-2H-tetrazole-2-carboxamide
Homo sapiens
recombinant enzyme with substrate N-palmitoylethanolamine, pH not specified in the publication, 37°C
0.0000077
5-((biphenyl-4-yl)methyl)-N,N-dimethyl-2H-tetrazole-2-carboxamide
Homo sapiens
recombinant enzyme with substrate N-(4-methyl coumarin)palmitamide, pH not specified in the publication, 37°C
0.000007
5-phenylpentyl [(2S,3R)-2-methyl-4-oxooxetan-3-yl]carbamate
Homo sapiens
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
0.000007
5-phenylpentyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate
Homo sapiens
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
0.0017
N-benzyloxycarbonyl-L-serine beta-lactone
Homo sapiens
recombinant enzyme with substrate N-(4-methyl coumarin)palmitamide, pH not specified in the publication, 37°C
0.0019
N-benzyloxycarbonyl-L-serine beta-lactone
Homo sapiens
recombinant enzyme with substrate N-palmitoylethanolamine, pH not specified in the publication, 37°C
0.0083
N-pentadecylbenzamide
Rattus norvegicus
pH and temperature not specified in the publication
0.045
N-pentadecylbenzamide
Homo sapiens
pH and temperature not specified in the publication
0.0004
N-pentadecylpyridine-4-carboxamide
Homo sapiens
pH 7.4, 37°C
0.098
N-pentadecylpyridine-4-carboxamide
Homo sapiens
pH and temperature not specified in the publication
0.0057
pentadecylamine
Rattus norvegicus
pH and temperature not specified in the publication
0.0057
pentadecylamine
Rattus norvegicus
pH 5.0 37°C
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
additional information
4-[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
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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
brenda
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
brenda
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)
brenda
Fiasella, A.; Nuzzi, A.; Summa, M.; Armirotti, A.; Tarozzo, G.; Tarzia, G.; Mor, M.; Bertozzi, F.; Bandiera, T.; Piomelli, D.
3-Aminoazetidin-2-one derivatives as N-acylethanolamine acid amidase (NAAA) inhibitors suitable for systemic administration
ChemMedChem
9
1602-1614
2014
Homo sapiens (Q02083)
brenda
West, J.; Zvonok, N.; Whitten, K.; Wood, J.; Makriyannis, A.
Mass spectrometric characterization of human N-acylethanolamine-hydrolyzing acid midase
J. Proteome Res.
11
972-981
2012
Homo sapiens (Q02083)
brenda
Bandiera, T.; Ponzano, S.; Piomelli, D.
Advances in the discovery of N-acylethanolamine acid amidase inhibitors
Pharmacol. Res.
86
11-17
2014
Mus musculus, Homo sapiens (Q02083), Rattus norvegicus (Q5KTC7)
brenda
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
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2012
Rattus norvegicus (Q5KTC7)
brenda
West, J.M.; Zvonok, N.; Whitten, K.M.; Vadivel, S.K.; Bowman, A.L.; Makriyannis, A.
Biochemical and mass spectrometric characterization of human N-acylethanolamine-hydrolyzing acid amidase inhibition
PLoS ONE
7
e43877
2012
Homo sapiens (Q02083), Homo sapiens
brenda
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), Rattus norvegicus (Q5KTC7), Mus musculus (Q9D7V9), Mus musculus C57BL/6J (Q9D7V9)
brenda
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)
brenda
Sakura, Y.; Tsuboi, K.; Uyama, T.; Zhang, X.; Taoka, R.; Sugimoto, M.; Kakehi, Y.; Ueda, N.
A quantitative study on splice variants of N-acylethanolamine acid amidase in human prostate cancer cells and other cells
Biochim. Biophys. Acta
1861
1951-1958
2016
Homo sapiens (Q02083)
brenda
Vago, R.; Bettiga, A.; Salonia, A.; Ciuffreda, P.; Ottria, R.
Development of new inhibitors for N-acylethanolamine-hydrolyzing acid amidase as promising tool against bladder cancer
Bioorg. Med. Chem.
25
1242-1249
2017
Homo sapiens (Q02083)
brenda
Petracca, R.; Romeo, E.; Baggelaar, M.P.; Artola, M.; Pontis, S.; Ponzano, S.; Overkleeft, H.S.; van der Stelt, M.; Piomelli, D.
Novel activity-based probes for N-acylethanolamine acid amidase
Chem. Commun. (Camb.)
53
11810-11813
2017
Homo sapiens (Q02083)
brenda
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)
brenda
Sasso, O.; Summa, M.; Armirotti, A.; Pontis, S.; De Mei, C.; Piomelli, D.
The N-Acylethanolamine acid amidase inhibitor ARN077 suppresses inflammation and pruritus in a mouse model of allergic dermatitis
J. Invest. Dermatol.
138
562-569
2018
Mus musculus, Mus musculus CD-1
brenda
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)
brenda
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)
brenda
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)
brenda
Gorelik, A.; Gebai, A.; Illes, K.; Piomelli, D.; Nagar, B.
Molecular mechanism of activation of the immunoregulatory amidase NAAA
Proc. Natl. Acad. Sci. USA
115
E10032-E10040
2018
Oryctolagus cuniculus (G1T7U7), Cavia porcellus (H0VCJ6), Homo sapiens (Q02083), Mus musculus (Q9D7V9)
brenda