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Literature summary for 3.5.1.99 extracted from

  • Caruano, J.; Feledziak, M.; Labar, G.; Michaux, C.; Perpete, E.A.; Muccioli, G.G.; Robiette, R.; Marchand-Brynaert, J.
    (S)-1-(Pent-4-enoyl)-4-(hydroxymethyl)-azetidin-2-one derivatives as inhibitors of human fatty acid amide hydrolase (hFAAH): synthesis, biological evaluation and molecular modelling (2014), J. Enzyme Inhib. Med. Chem., 29, 654-662.
    View publication on PubMed
Search for more literature for 3.5.1.99

Inhibitors

Inhibitors Comment Organism Structure
(3R,4R)-4-acetoxy-3-((10R)-(t-butyldimethylsilyloxy)-ethyl)-azetidin-2-one
-
 Homo sapiens
(S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl 2-(biphenyl-4-yl)acetate
-
 Homo sapiens
(S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl 3-(1H-indol-3-yl)propanoate
-
 Homo sapiens
(S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl biphenyl-4-carboxylate
-
 Homo sapiens
(S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl-4-phenylbutanoate
-
 Homo sapiens
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl (benzyloxy)acetate
-
 Homo sapiens
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 3-(1H-indol-3-yl)propanoate
-
 Homo sapiens
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 4-(pyridin-2-yl)butanoate
-
 Homo sapiens
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 4-(pyridin-4-yl)butanoate
-
 Homo sapiens
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl biphenyl-4-carboxylate
-
 Homo sapiens
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl biphenyl-4-ylacetate
-
 Homo sapiens
additional information synthesis of a series of lipophilic ester derivatives of (S)-1-(pent-40-enoyl)-4-(hydroxymethyl)-azetidin-2-one in three steps from (S)-4-(benzyloxycarbonyl)-azetidin-2-one, evaluation as reversible, beta-lactamic inhibitors of endocannabinoid-degrading enzymes, fatty acid amide hydrolase and and monoacylglycerol lipase, docking studies, overview. No inhibition by 1b, 1d, and 1f Homo sapiens
[(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl (benzyloxy)acetate
-
 Homo sapiens
[(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl 4-(pyridin-2-yl)butanoate
-
 Homo sapiens
[(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl 4-(pyridin-4-yl)butanoate
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
N-arachidonoylethanolamine + H2O Homo sapiens
-
 arachidonic acid + ethanolamine
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens O00519
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
N-arachidonoylethanolamine + H2O
-
 Homo sapiens arachidonic acid + ethanolamine
-
 ?

Synonyms

Synonyms Comment Organism
hFAAH
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
 assay at Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000005
-
 pH 7.4, 37°C Homo sapiens (3R,4R)-4-acetoxy-3-((10R)-(t-butyldimethylsilyloxy)-ethyl)-azetidin-2-one
0.000012
-
 pH 7.4, 37°C Homo sapiens 1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl biphenyl-4-ylacetate
0.000031
-
 pH 7.4, 37°C Homo sapiens 1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl (benzyloxy)acetate
0.00031
-
 pH 7.4, 37°C Homo sapiens 1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 4-(pyridin-4-yl)butanoate
0.00091
-
 pH 7.4, 37°C Homo sapiens (S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl biphenyl-4-carboxylate
0.00503
-
 pH 7.4, 37°C Homo sapiens (S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl-4-phenylbutanoate
0.00782
-
 pH 7.4, 37°C Homo sapiens (S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl 2-(biphenyl-4-yl)acetate
0.00805
-
 pH 7.4, 37°C Homo sapiens (S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl 3-(1H-indol-3-yl)propanoate
0.04252
-
 pH 7.4, 37°C Homo sapiens [(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl (benzyloxy)acetate
0.08706
-
 pH 7.4, 37°C Homo sapiens [(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl 4-(pyridin-2-yl)butanoate
0.173
-
 pH 7.4, 37°C Homo sapiens [(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl 4-(pyridin-4-yl)butanoate