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Literature summary for 3.5.1.60 extracted from

  • 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 (2014), ChemMedChem, 9, 1602-1614.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression in HEK-293 cells Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(7E)-N-[(3S)-2-oxoazetidin-3-yl]non-7-enamide
-
Homo sapiens
(Z)-N-[(S)-2-oxoazetidin-3-yl]non-3-enamide
-
Homo sapiens
1-heptyl-3-[(S)-2-oxoazetidin-3-yl]urea
-
Homo sapiens
2,2-dimethyl-N-[(3S)-2-oxoazetidin-3-yl]nonanamide
-
Homo sapiens
2-methyl-N-[(3S)-2-oxoazetidin-3-yl]nonanamide
-
Homo sapiens
3-amino-N-nonanoyl-L-alanine
-
Homo sapiens
4-butyl-N-[(S)-2-oxoazetidin-3-yl]benzamide
-
Homo sapiens
5-phenylpentyl N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate
-
Homo sapiens
7-cyclohexyl-N-[(3S)-2-oxoazetidin-3-yl]heptanamide
-
Homo sapiens
heptyl N-[(S)-2-oxoazetidin-3-yl]carbamate
-
Homo sapiens
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 Homo sapiens
N-(2-oxocyclobutyl)nonanamide
-
Homo sapiens
N-(azetidin-3-yl)nonanamide
-
Homo sapiens
N-[(3R)-2-oxoazetidin-3-yl]nonanamide
-
Homo sapiens
N-[(3S)-2-oxoazetidin-3-yl]-4-phenylbutanamide
-
Homo sapiens
N-[(3S)-2-oxoazetidin-3-yl]-5-phenylpentanamide
-
Homo sapiens
N-[(3S)-2-oxoazetidin-3-yl]-6-phenylhexanamide
-
Homo sapiens
N-[(3S)-2-oxoazetidin-3-yl]decanamide
-
Homo sapiens
N-[(3S)-2-oxoazetidin-3-yl]heptanamide
-
Homo sapiens
N-[(3S)-2-oxoazetidin-3-yl]nonanamide
-
Homo sapiens
N-[(3S)-2-oxoazetidin-3-yl]octanamide
-
Homo sapiens
N-[(3S)-2-oxoazetidin-3-yl]undecanamide
-
Homo sapiens
N-[(S)-2-oxoazetidin-3-yl]-6-phenylhexanamide
-
Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens Q02083
-
-

Source Tissue

Source Tissue Comment Organism Textmining
spleen
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
N-(4-methylcoumarin)palmitamide + H2O
-
Homo sapiens palmitic acid + 7-amino-4-methylcoumarin
-
?

Synonyms

Synonyms Comment Organism
N-acylethanolamine acid amidase
-
Homo sapiens
NAAA
-
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
4.5
-
assay at Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0001
-
pH 5.0, 37°C Homo sapiens N-[(3S)-2-oxoazetidin-3-yl]undecanamide
0.00022
-
pH 5.0, 37°C Homo sapiens 2-methyl-N-[(3S)-2-oxoazetidin-3-yl]nonanamide
0.00024
-
pH 5.0, 37°C Homo sapiens heptyl N-[(S)-2-oxoazetidin-3-yl]carbamate
0.00024
-
pH 5.0, 37°C Homo sapiens N-[(3S)-2-oxoazetidin-3-yl]decanamide
0.00028
-
pH 5.0, 37°C Homo sapiens 7-cyclohexyl-N-[(3S)-2-oxoazetidin-3-yl]heptanamide
0.00034
-
pH 5.0, 37°C Homo sapiens N-[(3S)-2-oxoazetidin-3-yl]nonanamide
0.0006
-
pH 5.0, 37°C Homo sapiens N-[(3S)-2-oxoazetidin-3-yl]-6-phenylhexanamide
0.00076
-
pH 5.0, 37°C Homo sapiens 2,2-dimethyl-N-[(3S)-2-oxoazetidin-3-yl]nonanamide
0.0019
-
pH 5.0, 37°C Homo sapiens N-[(3S)-2-oxoazetidin-3-yl]octanamide
0.00309
-
pH 5.0, 37°C Homo sapiens (7E)-N-[(3S)-2-oxoazetidin-3-yl]non-7-enamide
0.0039
-
pH 5.0, 37°C Homo sapiens (Z)-N-[(S)-2-oxoazetidin-3-yl]non-3-enamide
0.00576
-
pH 5.0, 37°C Homo sapiens 1-heptyl-3-[(S)-2-oxoazetidin-3-yl]urea
0.0121
-
pH 5.0, 37°C Homo sapiens N-[(S)-2-oxoazetidin-3-yl]-6-phenylhexanamide
0.0138
-
pH 5.0, 37°C Homo sapiens 4-butyl-N-[(S)-2-oxoazetidin-3-yl]benzamide
0.027
-
pH 5.0, 37°C Homo sapiens N-[(3S)-2-oxoazetidin-3-yl]heptanamide
0.0272
-
pH 5.0, 37°C Homo sapiens N-[(3S)-2-oxoazetidin-3-yl]-5-phenylpentanamide
0.05
-
pH 4.5, 37°C Homo sapiens 5-phenylpentyl N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate
0.0734
-
pH 5.0, 37°C Homo sapiens N-[(3S)-2-oxoazetidin-3-yl]-4-phenylbutanamide
0.0745
-
pH 5.0, 37°C Homo sapiens N-[(3R)-2-oxoazetidin-3-yl]nonanamide

General Information

General Information Comment Organism
evolution the enzyme is a cysteine amidase that belongs to the N-terminal nucleophile (Ntn) family of enzymes and is characterized by a conserved amino acid catalytic triad Cys, Arg, and Asp Homo sapiens