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Literature summary for 3.5.1.4 extracted from

  • Duranti, A.; Tontini, A.; Antonietti, F.; Vacondio, F.; Fioni, A.; Silva, C.; Lodola, A.; Rivara, S.; Solorzano, C.; Piomelli, D.; Tarzia, G.; Mor, M.
    N-(2-Oxo-3-oxetanyl)carbamic acid esters as N-acylethanolamine acid amidase inhibitors: synthesis and structure-activity and structure-property relationships (2012), J. Med. Chem., 55, 4824-4836.
    View publication on PubMed
Search for more literature for 3.5.1.4

Inhibitors

Inhibitors Comment Organism Structure
(2R,3R)-allo-2-methyl-4-oxo-3-oxetanylcarbamic acid tert-butyl ester
-
 Rattus norvegicus
(2R,3S)-2-methyl-4-oxo-3-oxetanylcarbamic acid benzyl ester
-
 Rattus norvegicus
(2R,3S)-2-methyl-4-oxo-3-oxetanylcarbamic acid tert-butyl ester
-
 Rattus norvegicus
(2S,3R)-2-methyl-4-oxo-3-oxetanylcarbamic acid 5-phenylpentyl ester potent inhibitor, rapidly cleaved in plasma Rattus norvegicus
(2S,3R)-2-methyl-4-oxo-3-oxetanylcarbamic acid benzyl ester
-
 Rattus norvegicus
(2S,3R)-2-methyl-4-oxo-3-oxetanylcarbamic acid tert-butyl ester
-
 Rattus norvegicus
(2S,3S)-allo-2-methyl-4-oxo-3-oxetanylcarbamic acid tert-butyl ester
-
 Rattus norvegicus
(R)-(2-oxo-3-oxetanyl)carbamic acid tert-butyl ester
-
 Rattus norvegicus
(R)-1-methyl-3-(2-oxo-3-oxetanyl)urea
-
 Rattus norvegicus
(R)-2-oxo-3-oxetanylcarbamic acid benzyl ester
-
 Rattus norvegicus
(R,S)-2-oxocyclobutylcarbamic acid benzyl ester weak inhibition Rattus norvegicus
(S)-(2-oxo-3-oxetanyl)carbamic acid tert-butyl ester
-
 Rattus norvegicus
(S)-1-methyl-3-(2-oxo-3-oxetanyl)urea
-
 Rattus norvegicus
(S)-2-oxo-3-oxetanylcarbamic acid benzyl ester
-
 Rattus norvegicus
3-(4-phenylbutyl)oxetan-2-one
-
 Rattus norvegicus
6-(benzyloxy)-N-[(3S)-2-oxooxetan-3-yl]naphthalene-2-carboxamide
-
 Rattus norvegicus
6-methoxy-N-[(3S)-2-oxooxetan-3-yl]naphthalene-2-carboxamide
-
 Rattus norvegicus
cyclobutylcarbamic acid benzyl ester weak inhibition Rattus norvegicus
ethyl 6-[[(3S)-2-oxooxetan-3-yl]carbamoyl]naphthalene-2-carboxylate
-
 Rattus norvegicus
heptadecanoic acid
-
 Rattus norvegicus
additional information N-(2-oxo-3-oxetanyl)carbamic acid esters as N-acylethanolamine acid amidase inhibitors, synthesis and structure-activity and structure-property relationships, overview. The beta-lactone ring is responsible for inhibition and and low compound stability. The compounds inhibit NAAA with a rapid, noncompetitive, and reversible mechanism, consistent with the acylation of the catalytic Cys131 Rattus norvegicus
N-[(3S)-2-oxooxetan-3-yl]biphenyl-4-carboxamide
-
 Rattus norvegicus
N-[(3S)-2-oxooxetan-3-yl]naphthalene-2-carboxamide
-
 Rattus norvegicus
N-[(benzyloxy)carbonyl]-D-serine weak inhibition Rattus norvegicus
N-[(benzyloxy)carbonyl]-L-serine weak inhibition Rattus norvegicus
phenyl 6-[[(3S)-2-oxooxetan-3-yl]carbamoyl]naphthalene-2-carboxylate
-
 Rattus norvegicus

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
-
-
-

Synonyms

Synonyms Comment Organism
N-acylethanolamine acid amidase
-
 Rattus norvegicus
NAAA
-
 Rattus norvegicus

Temperature Optimum [°C]

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

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
5
-
 assay at Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000115
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus N-[(3S)-2-oxooxetan-3-yl]biphenyl-4-carboxamide
0.000127
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (2S,3R)-2-methyl-4-oxo-3-oxetanylcarbamic acid 5-phenylpentyl ester
0.00019
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (2S,3S)-allo-2-methyl-4-oxo-3-oxetanylcarbamic acid tert-butyl ester
0.00022
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (2S,3R)-2-methyl-4-oxo-3-oxetanylcarbamic acid tert-butyl ester
0.0005
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (R)-(2-oxo-3-oxetanyl)carbamic acid tert-butyl ester
0.00058
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (S)-(2-oxo-3-oxetanyl)carbamic acid tert-butyl ester
0.0007
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (R)-2-oxo-3-oxetanylcarbamic acid benzyl ester
0.001
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (2S,3R)-2-methyl-4-oxo-3-oxetanylcarbamic acid benzyl ester
0.00296
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (S)-2-oxo-3-oxetanylcarbamic acid benzyl ester
0.0049
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (2R,3R)-allo-2-methyl-4-oxo-3-oxetanylcarbamic acid tert-butyl ester
0.015
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (S)-1-methyl-3-(2-oxo-3-oxetanyl)urea
0.0492
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (R)-1-methyl-3-(2-oxo-3-oxetanyl)urea
0.08
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (2R,3S)-2-methyl-4-oxo-3-oxetanylcarbamic acid tert-butyl ester
0.1
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus N-[(benzyloxy)carbonyl]-L-serine
0.1
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus N-[(benzyloxy)carbonyl]-D-serine
0.1
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus cyclobutylcarbamic acid benzyl ester
0.1
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (R,S)-2-oxocyclobutylcarbamic acid benzyl ester
0.1
-
 pH 5.0, 37°C, recombinant enzyme Rattus norvegicus (2R,3S)-2-methyl-4-oxo-3-oxetanylcarbamic acid benzyl ester