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Literature summary for 3.3.2.9 extracted from

  • Morisseau, C.; Hammock, B.D.
    Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles (2005), Annu. Rev. Pharmacol. Toxicol., 45, 311-333.
    View publication on PubMed
Search for more literature for 3.3.2.9

Application

Application Comment Organism
drug development the enzyme is a target for inhibitor design Mus musculus
drug development the enzyme is a target for inhibitor design Homo sapiens
drug development the enzyme is a target for inhibitor design Rattus norvegicus

Protein Variants

Protein Variants Comment Organism
additional information mEH knockout mice are less sensitive to the carcinogenic activity of 7,12-dimethylbenz[a]anthracene compared to wild-type mice, but show no altered phenotype Mus musculus

Inhibitors

Inhibitors Comment Organism Structure
elaidamide mixed inhibition type Homo sapiens
elaidamide mixed inhibition type Mus musculus
elaidamide mixed inhibition type Rattus norvegicus
trichloropropene oxide
-
 Homo sapiens
trichloropropene oxide
-
 Mus musculus
trichloropropene oxide
-
 Rattus norvegicus
urea derivatives
-
 Homo sapiens
urea derivatives
-
 Mus musculus
urea derivatives
-
 Rattus norvegicus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information kinetics Mus musculus
additional information
-
 additional information kinetics Homo sapiens
additional information
-
 additional information kinetics Rattus norvegicus

Localization

Localization Comment Organism GeneOntology No. Textmining
membrane orientation of the enzyme depends on the membrane type Mus musculus 16020
-
membrane orientation of the enzyme depends on the membrane type Homo sapiens 16020
-
membrane orientation of the enzyme depends on the membrane type Rattus norvegicus 16020
-
microsome
-
 Mus musculus
-
-
microsome
-
 Homo sapiens
-
-
microsome
-
 Rattus norvegicus
-
-
plasma membrane in liver Mus musculus 5886
-
plasma membrane in liver Homo sapiens 5886
-
plasma membrane in liver Rattus norvegicus 5886
-
smooth endoplasmic reticulum in liver Mus musculus 5790
-
smooth endoplasmic reticulum in liver Homo sapiens 5790
-
smooth endoplasmic reticulum in liver Rattus norvegicus 5790
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
16,17-epoxyandrost-4-en-3-one + H2O Mus musculus high activity 16,17-dihydroxyandrost-4-en-3-one
-
 ?
16,17-epoxyandrost-4-en-3-one + H2O Homo sapiens high activity 16,17-dihydroxyandrost-4-en-3-one
-
 ?
16,17-epoxyandrost-4-en-3-one + H2O Rattus norvegicus high activity 16,17-dihydroxyandrost-4-en-3-one
-
 ?
additional information Rattus norvegicus the enzyme is involved in xenobiotic metabolism and detoxification, e.g. of 1,3-butadiene oxide, styrene oxide, and benzo[a]pyrene-4,5-oxide ?
-
 ?
additional information Homo sapiens the enzyme is involved in xenobiotic metabolism and detoxification, e.g. of 1,3-butadiene oxide, styrene oxide, and benzo[a]pyrene-4,5-oxide, enzyme deficiency leads to acute and severe phenytoin toxicity in vivo, the enzyme is involved in transport of bile acids in the liver ?
-
 ?
additional information Mus musculus the enzyme is involved in xenobiotic metabolism and detoxification, e.g. of 1,3-butadiene oxide, styrene oxide, and benzo[a]pyrene-4,5-oxide, the enzyme is important in sexual development ?
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-
Mus musculus
-
-
-
Rattus norvegicus
-
-
-

Reaction

Reaction Comment Organism Reaction ID
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, catalytic triad Mus musculus
a
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, catalytic triad Rattus norvegicus
a
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, the catalytic triad is Asp226-His431-Glu404 with polarizing residues Tyr299 and Tyr374 Homo sapiens
a

Source Tissue

Source Tissue Comment Organism Textmining
liver
-
 Mus musculus
-
liver
-
 Homo sapiens
-
liver
-
 Rattus norvegicus
-
additional information wide tissue distribution Mus musculus
-
additional information wide tissue distribution Homo sapiens
-
additional information wide tissue distribution Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
16,17-epoxyandrost-4-en-3-one + H2O high activity Mus musculus 16,17-dihydroxyandrost-4-en-3-one
-
 ?
16,17-epoxyandrost-4-en-3-one + H2O high activity Homo sapiens 16,17-dihydroxyandrost-4-en-3-one
-
 ?
16,17-epoxyandrost-4-en-3-one + H2O high activity Rattus norvegicus 16,17-dihydroxyandrost-4-en-3-one
-
 ?
cis-stilbene oxide + H2O
-
 Mus musculus (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
-
 ?
cis-stilbene oxide + H2O
-
 Homo sapiens (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
-
 ?
cis-stilbene oxide + H2O
-
 Rattus norvegicus (1R,2R)-1,2-diphenylethane-1,2-diol
-
 ?
additional information the enzyme is involved in xenobiotic metabolism and detoxification, e.g. of 1,3-butadiene oxide, styrene oxide, and benzo[a]pyrene-4,5-oxide Rattus norvegicus ?
-
 ?
additional information the enzyme is involved in xenobiotic metabolism and detoxification, e.g. of 1,3-butadiene oxide, styrene oxide, and benzo[a]pyrene-4,5-oxide, enzyme deficiency leads to acute and severe phenytoin toxicity in vivo, the enzyme is involved in transport of bile acids in the liver Homo sapiens ?
-
 ?
additional information the enzyme is involved in xenobiotic metabolism and detoxification, e.g. of 1,3-butadiene oxide, styrene oxide, and benzo[a]pyrene-4,5-oxide, the enzyme is important in sexual development Mus musculus ?
-
 ?
additional information mEH prefers mono- and cis-substituted epoxides, low but highly enantioselective activity with epoxy fatty acids Homo sapiens ?
-
 ?
additional information mEH prefers mono- and cis-substituted epoxides, low but highly enantioselective activity with epoxy fatty acids, the enzyme acts as an antiestrogen binding site subunit Mus musculus ?
-
 ?
additional information mEH prefers mono- and cis-substituted epoxides, low but highly enantioselective activity with epoxy fatty acids, the enzyme acts as an antiestrogen binding site subunit Rattus norvegicus ?
-
 ?

Subunits

Subunits Comment Organism
More the enzyme possesses a long N-terminal transmembrane domain of 20 amino acids which acts as an anchor for cellular membranes Mus musculus
More the enzyme possesses a long N-terminal transmembrane domain of 20 amino acids which acts as an anchor for cellular membranes Homo sapiens
More the enzyme possesses a long N-terminal transmembrane domain of 20 amino acids which acts as an anchor for cellular membranes Rattus norvegicus

Synonyms

Synonyms Comment Organism
mEH
-
 Mus musculus
mEH
-
 Homo sapiens
mEH
-
 Rattus norvegicus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8 9
-
 Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00007
-
 elaidamide pH 7.4 Homo sapiens