Entry |
|
Name |
microsomal epoxide hydrolase;
microsomal oxirane/oxetane hydrolase;
epoxide hydratase (ambiguous);
microsomal epoxide hydratase (ambiguous);
epoxide hydrase;
microsomal epoxide hydrase;
arene-oxide hydratase (ambiguous);
benzo[a]pyrene-4,5-oxide hydratase;
benzo(a)pyrene-4,5-epoxide hydratase;
aryl epoxide hydrase (ambiguous);
cis-epoxide hydrolase;
mEH;
EPHX1 (gene name)
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Class |
Hydrolases;
Acting on ether bonds;
Ether hydrolases
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Sysname |
cis-stilbene-oxide hydrolase
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Reaction(IUBMB) |
(1) cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol [RN: R07627];
(2) 1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine + H2O = 2-({[(4-methoxyphenyl)methyl](methyl)amino}methyl)-2-methylpropane-1,3-diol [RN: R11930]
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Reaction(KEGG) |
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Substrate |
cis-stilbene oxide [CPD: C16014];
H2O [CPD: C00001];
1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine [CPD: C21775]
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Product |
(1R,2R)-1,2-diphenylethane-1,2-diol;
2-({[(4-methoxyphenyl)methyl](methyl)amino}methyl)-2-methylpropane-1,3-diol [CPD: C21776]
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Comment |
This is a key hepatic enzyme that catalyses the hydrolytic ring opening of oxiranes (epoxides) and oxetanes to give the corresponding diols. The enzyme is involved in the metabolism of numerous substrates including the stereoselective hydrolytic ring opening of 7-oxabicyclo[4.1.0]hepta-2,4-dienes (arene oxides) to the corresponding trans-dihydrodiols. The reaction proceeds via a triad mechanism and involves the formation of an hydroxyalkyl-enzyme intermediate. Five epoxide-hydrolase enzymes have been identified in vertebrates to date: EC 3.3.2.6 (leukotriene-A4 hydrolase), EC 3.3.2.7 (hepoxilin-epoxide hydrolase), EC 3.3.2.9 (microsomal epoxide hydrolase), EC 3.3.2.10 (soluble epoxide hydrolase) and EC 3.3.2.11 (cholesterol-5,6-oxide hydrolase).
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History |
EC 3.3.2.9 created 2006 (EC 3.3.2.3 created 1978, modified 1999, part incorporated 2006), modified 2017
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Pathway |
ec00980 | Metabolism of xenobiotics by cytochrome P450 |
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Orthology |
K01253 | microsomal epoxide hydrolase |
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Genes |
» show all
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Reference |
|
Authors |
Oesch F, Daly J. |
Title |
Solubilization, purification, and properties of a hepatic epoxide hydrase. |
Journal |
|
Reference |
2 |
Authors |
Jakoby, W.B. and Fjellstedt, T.A. |
Title |
Epoxidases. |
Journal |
In: Boyer, P.D. (Ed.), The Enzymes, 3rd ed., vol. 7, Academic Press, New York, 1972, p. 199-212. |
Reference |
|
Authors |
Oesch F. |
Title |
Mammalian epoxide hydrases: inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds. |
Journal |
|
Reference |
|
Authors |
Oesch F. |
Title |
Purification and specificity of a human microsomal epoxide hydratase. |
Journal |
|
Reference |
|
Authors |
Lu AY, Ryan D, Jerina DM, Daly JW, Levin W. |
Title |
Liver microsomal expoxide hydrase. Solubilization, purification, and characterization. |
Journal |
J Biol Chem 250:8283-8 (1975) |
Reference |
|
Authors |
Bellucci G, Chiappe C, Ingrosso G. |
Title |
Kinetics and stereochemistry of the microsomal epoxide hydrolase-catalyzed hydrolysis of cis-stilbene oxides. |
Journal |
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Reference |
|
Authors |
Fretland AJ, Omiecinski CJ. |
Title |
Epoxide hydrolases: biochemistry and molecular biology. |
Journal |
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Reference |
|
Authors |
Morisseau C, Hammock BD. |
Title |
Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles. |
Journal |
|
Reference |
|
Authors |
Newman JW, Morisseau C, Hammock BD. |
Title |
Epoxide hydrolases: their roles and interactions with lipid metabolism. |
Journal |
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Reference |
|
Authors |
Toselli F, Fredenwall M, Svensson P, Li XQ, Johansson A, Weidolf L, Hayes MA |
Title |
Oxetane Substrates of Human Microsomal Epoxide Hydrolase. |
Journal |
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Other DBs |
ExplorEnz - The Enzyme Database: | 3.3.2.9 |
ExPASy - ENZYME nomenclature database: | 3.3.2.9 |
BRENDA, the Enzyme Database: | 3.3.2.9 |
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