Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary extracted from

  • 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 (2019), MedChemComm, 10, 252-262 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.5.1.60 recombinant enzyme overexpression in HEK-293 cells Rattus norvegicus

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.1.60 (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 Rattus norvegicus
3.5.1.60 (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
-
 Rattus norvegicus
3.5.1.60 1-(pyrrolidin-1-yl)-3-(thiophen-2-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 1-(pyrrolidin-1-yl)-3-(thiophen-3-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 1-(pyrrolidin-1-yl)-7-(thiophen-2-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 1-(pyrrolidin-1-yl)-7-(thiophen-3-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(2'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(2'-chloro[1,1'-biphenyl]-4-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(2'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(2'-fluoro[1,1'-biphenyl]-4-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(2'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(2'-methyl[1,1'-biphenyl]-4-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(3'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(3'-chloro[1,1'-biphenyl]-4-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(3'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(3'-fluoro[1,1'-biphenyl]-4-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(3'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(3'-methyl[1,1'-biphenyl]-4-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(4'-chloro[1,1'-biphenyl]-4-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(4'-fluoro[1,1'-biphenyl]-4-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(4'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(4'-methyl[1,1'-biphenyl]-4-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(4-phenoxycyclohexyl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(4-phenoxyphenyl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(4-phenylcyclohexyl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(cyclohexyloxy)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(pyridin-2-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(pyridin-2-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(pyridin-3-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-(pyridin-3-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(thiophen-2-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-(thiophen-3-yl)propanoic acid
-
 Rattus norvegicus
3.5.1.60 3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-cyclohexyl-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-cyclohexylpropanoic acid
-
 Rattus norvegicus
3.5.1.60 3-[4-(2H-1,3-benzodioxol-5-yl)phenyl]-1-(pyrrolidin-1-yl)propan-1-one
-
 Rattus norvegicus
3.5.1.60 3-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
-
 Rattus norvegicus
3.5.1.60 4-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
-
 Rattus norvegicus
3.5.1.60 5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)pentan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(2-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(2-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(2-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(3-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(3-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(3-hydroxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(3-methoxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(3-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(3-propylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(4-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(4-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(4-hydroxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(4-methoxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(4-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(4-propylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(pyridin-2-yl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(pyridin-2-yl)heptanoic acid
-
 Rattus norvegicus
3.5.1.60 7-(pyridin-3-yl)-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-(pyridin-3-yl)heptanoic acid
-
 Rattus norvegicus
3.5.1.60 7-(thiophen-2-yl)heptanoic acid
-
 Rattus norvegicus
3.5.1.60 7-(thiophen-3-yl)heptanoic acid
-
 Rattus norvegicus
3.5.1.60 7-cyclohexyl-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 7-cyclohexylheptanoic acid
-
 Rattus norvegicus
3.5.1.60 7-phenyl-1-(pyrrolidin-1-yl)heptan-1-one
-
 Rattus norvegicus
3.5.1.60 methyl 3-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoate
-
 Rattus norvegicus
3.5.1.60 methyl 4-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoate
-
 Rattus norvegicus
3.5.1.60 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) Rattus norvegicus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.5.1.60 additional information
-
 additional information Michaelis-Menten kinetic analysis Rattus norvegicus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.5.1.60 lysosome
-
 Rattus norvegicus 5764
-

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.60 Rattus norvegicus Q6P7S1
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.5.1.60 lung
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.60 heptadecenoylethanolamide + H2O
-
 Rattus norvegicus heptadecenoate + ethanolamine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.60 N-acylethanolamine acid amidase
-
 Rattus norvegicus
3.5.1.60 NAAA
-
 Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.5.1.60 37
-
 assay at Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.5.1.60 4.5
-
 assay at Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.5.1.60 0.0005
-
 pH 4.5, 37°C Rattus norvegicus 3-cyclohexyl-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0007
-
 pH 4.5, 37°C Rattus norvegicus 3-(cyclohexyloxy)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0018
-
 pH 4.5, 37°C Rattus norvegicus 3-(3'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0021
-
 pH 4.5, 37°C Rattus norvegicus 3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0025
-
 pH 4.5, 37°C Rattus norvegicus 7-cyclohexyl-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0028
-
 pH 4.5, 37°C Rattus norvegicus 3-(2'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0034
-
 pH 4.5, 37°C Rattus norvegicus 3-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0037
-
 pH 4.5, 37°C Rattus norvegicus 7-(3-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0056
-
 pH 4.5, 37°C Rattus norvegicus 7-(4-hydroxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0057
-
 pH 4.5, 37°C Rattus norvegicus 3-(pyridin-2-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0073
-
 pH 4.5, 37°C Rattus norvegicus 7-(3-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.008
-
 pH 4.5, 37°C Rattus norvegicus 7-(4-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0083
-
 pH 4.5, 37°C Rattus norvegicus 7-(3-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0096
-
 pH 4.5, 37°C Rattus norvegicus 7-(4-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0129
-
 pH 4.5, 37°C Rattus norvegicus 7-phenyl-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0132
-
 pH 4.5, 37°C Rattus norvegicus 1-(pyrrolidin-1-yl)-7-(thiophen-3-yl)heptan-1-one
3.5.1.60 0.0137
-
 pH 4.5, 37°C Rattus norvegicus 7-(2-fluorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0141
-
 pH 4.5, 37°C Rattus norvegicus 1-(pyrrolidin-1-yl)-7-(thiophen-2-yl)heptan-1-one
3.5.1.60 0.0165
-
 pH 4.5, 37°C Rattus norvegicus 3-(3'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0254
-
 pH 4.5, 37°C Rattus norvegicus 3-(3'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0332
-
 pH 4.5, 37°C Rattus norvegicus 3-(4'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0345
-
 pH 4.5, 37°C Rattus norvegicus 7-(4-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0354
-
 pH 4.5, 37°C Rattus norvegicus 7-(4-methoxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.0486
-
 pH 4.5, 37°C Rattus norvegicus 3-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.0684
-
 pH 4.5, 37°C Rattus norvegicus 7-(2-methylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 1-(pyrrolidin-1-yl)-3-(thiophen-2-yl)propan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 1-(pyrrolidin-1-yl)-3-(thiophen-3-yl)propan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 3-(2'-chloro[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 3-(2'-methyl[1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 3-(4-phenoxyphenyl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 3-(pyridin-3-yl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 3-[4-(2H-1,3-benzodioxol-5-yl)phenyl]-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 3-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 4-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoic acid
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 7-(2-chlorophenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 7-(3-hydroxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 7-(3-methoxyphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 7-(3-propylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 7-(4-propylphenyl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 7-(pyridin-2-yl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus 7-(pyridin-3-yl)-1-(pyrrolidin-1-yl)heptan-1-one
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus methyl 3-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoate
3.5.1.60 0.1
-
 above, pH 4.5, 37°C Rattus norvegicus methyl 4-[7-oxo-7-(pyrrolidin-1-yl)heptyl]benzoate
3.5.1.60 0.48
-
 pH 4.5, 37°C Rattus norvegicus 3-(4-phenylcyclohexyl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 1.5
-
 pH 4.5, 37°C Rattus norvegicus (2E)-3-([1,1'-biphenyl]-4-yl)-1-(pyrrolidin-1-yl)prop-2-en-1-one
3.5.1.60 2.8
-
 pH 4.5, 37°C Rattus norvegicus 3-(4-phenoxycyclohexyl)-1-(pyrrolidin-1-yl)propan-1-one
3.5.1.60 4.1
-
 pH 4.5, 37°C Rattus norvegicus (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
3.5.1.60 5.5
-
 pH 4.5, 37°C Rattus norvegicus 5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)pentan-1-one