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Literature summary for 3.3.2.10 extracted from

  • Dietze, E.D.; Kuwano, E.; Hammock, B.D.
    The interaction of cytosolic epoxide hydrolase with chiral epoxides (1993), Int. J. Biochem., 25, 43-52.
    View publication on PubMed
Search for more literature for 3.3.2.10

Activating Compound

Activating Compound Comment Organism Structure
additional information clofibrate induces the enzyme Mus musculus

Inhibitors

Inhibitors Comment Organism Structure
2-methylglycidyl 4-nitrobenzoate IC50 for the S-enantiomer is 0.717 mM, the R-enantiomer shows 25% inhibition at 0.2 mM Mus musculus
3,3-dimethylglycidyl 4-nitrobenzoate IC50 for the S-enantiomer is 0.012 mM, 23% inhibition at 5 mM of the R-enantiomer Mus musculus
glycidyl 4-nitrobenzoate IC50 for the S-enantiomer is 0.14 mM, and for the R-enantiomer 0.51 mM Mus musculus
additional information sterical differences play a role in inhibitory potency Mus musculus
trans-(2R,3R)-3-phenylglycidol IC50 for the R-enantiomer is about 3.9 mM Mus musculus
trans-(2S,3S)-3-phenylglycidol IC50 for the S-enantiomer is about 2.2 mM Mus musculus
trans-1-phenylpropylene oxide IC50 for the S-enantiomer is 3.47 mM, and for the R-enantiomer 2.98 mM Mus musculus
trans-2-methyl-3-phenylglycidol IC50 for the S-enantiomer is 1.52 mM, and for the R-enantiomer 2.0 mM Mus musculus
trans-3-(4-bromophenyl)glycidol IC50 for the S-enantiomer is 0.12 mM, and for the R-enantiomer 0.77 mM Mus musculus
trans-3-(4-nitrophenyl)glycidol IC50 for the S-enantiomer is 0.013 mM, and for the R-enantiomer 4.24 mM Mus musculus
trans-3-(4-nitrophenyl)glycidyl acetate IC50 for the S-enantiomer is 0.232 mM, and for the R-enantiomer 0.39 mM Mus musculus
trans-3-(4-nitrophenyl)glycidyl benzoate IC50 for the S-enantiomer is 0.229 mM, and for the R-enantiomer 0.10 mM Mus musculus
trans-3-methylglycidyl 4-nitrobenzoate the S-enantiomer shows 20% inhibition at 0.8 mM, the R-enantiomer 16.5% inhibition at 0.8 mM Mus musculus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information kinetics Mus musculus
0.008
-
 4-nitrophenyl (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate pH 7.4, 25°C Mus musculus
0.015
-
 4-nitrophenyl (2R,3R)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate pH 7.4, 25°C Mus musculus
0.033
-
 4-nitrophenyl (2S,3S)-2,3-epoxy-3-phenylpropyl carbonate pH 7.4, 25°C Mus musculus
0.068
-
 4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate pH 7.4, 25°C Mus musculus

Localization

Localization Comment Organism GeneOntology No. Textmining
cytosol
-
 Mus musculus 5829
-

Organism

Organism UniProt Comment Textmining
Mus musculus
-
 Swiss Webster mice
-

Purification (Commentary)

Purification (Comment) Organism
from liver by affinity chromatography on an epoxy activated resin derivatized with benzyl thiol Mus musculus

Source Tissue

Source Tissue Comment Organism Textmining
liver
-
 Mus musculus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-nitrophenyl (2R,3R)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O
-
 Mus musculus ?
-
 ?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate + H2O
-
 Mus musculus ?
-
 ?
4-nitrophenyl (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O preferred phenylpropyl carbonate substrate Mus musculus ?
-
 ?
4-nitrophenyl (2S,3S)-2,3-epoxy-3-phenylpropyl carbonate + H2O
-
 Mus musculus ?
-
 ?

Synonyms

Synonyms Comment Organism
Cytosolic epoxide hydrolase
-
 Mus musculus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Mus musculus
37
-
 inhibition assay at Mus musculus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
4.8
-
 4-nitrophenyl (2R,3R)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate pH 7.4, 25°C Mus musculus
7.7
-
 4-nitrophenyl (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate pH 7.4, 25°C Mus musculus
15.8
-
 4-nitrophenyl (2S,3S)-2,3-epoxy-3-phenylpropyl carbonate pH 7.4, 25°C Mus musculus
26.7
-
 4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate pH 7.4, 25°C Mus musculus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
 assay at Mus musculus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.012
-
 IC50 for the S-enantiomer is 0.012 mM, 23% inhibition at 5 mM of the R-enantiomer Mus musculus 3,3-dimethylglycidyl 4-nitrobenzoate
0.013
-
 IC50 for the S-enantiomer is 0.013 mM Mus musculus trans-3-(4-nitrophenyl)glycidol
0.1
-
 IC50 for the R-enantiomer 0.10 mM Mus musculus trans-3-(4-nitrophenyl)glycidyl benzoate
0.12
-
 IC50 for the S-enantiomer is 0.12 mM Mus musculus trans-3-(4-bromophenyl)glycidol
0.14
-
 IC50 for the S-enantiomer is 0.14 mM Mus musculus glycidyl 4-nitrobenzoate
0.229
-
 IC50 for the S-enantiomer is 0.229 mM Mus musculus trans-3-(4-nitrophenyl)glycidyl benzoate
0.232
-
 IC50 for the S-enantiomer is 0.232 mM Mus musculus trans-3-(4-nitrophenyl)glycidyl acetate
0.39
-
 IC50 for the R-enantiomer 0.39 mM Mus musculus trans-3-(4-nitrophenyl)glycidyl acetate
0.514
-
 IC50 for the R-enantiomer 0.514 mM Mus musculus glycidyl 4-nitrobenzoate
0.717
-
 IC50 for the S-enantiomer is 0.717 mM, the R-enantiomer shows 25% inhibition at 0.2 mM Mus musculus 2-methylglycidyl 4-nitrobenzoate
0.77
-
 IC50 for the R-enantiomer 0.77 mM Mus musculus trans-3-(4-bromophenyl)glycidol
1.52
-
 IC50 for the S-enantiomer is 1.52 mM Mus musculus trans-2-methyl-3-phenylglycidol
2
-
 IC50 for the R-enantiomer 2.0 mM Mus musculus trans-2-methyl-3-phenylglycidol
2.2
-
 IC50 for the S-enantiomer is about 2.2 mM Mus musculus trans-(2S,3S)-3-phenylglycidol
2.98
-
 IC50 for the R-enantiomer 2.98 mM Mus musculus trans-1-phenylpropylene oxide
3.47
-
 IC50 for the S-enantiomer is 3.47 mM Mus musculus trans-1-phenylpropylene oxide
3.9
-
 IC50 for the R-enantiomer is about 3.9 mM Mus musculus trans-(2R,3R)-3-phenylglycidol
4.24
-
 IC50 for the R-enantiomer 4.24 mM Mus musculus trans-3-(4-nitrophenyl)glycidol