Information on EC 3.3.2.9 - microsomal epoxide hydrolase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
3.3.2.9
-
RECOMMENDED NAME
GeneOntology No.
microsomal epoxide hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
active site structure, quantitative structure-activity relationships, molecular modelling
-
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
formation of threo-1,2-diphenyl-1,2-ethanediols from all epoxides involving anti-stereospecific opening of the oxirane ring with about 90% preference for the (S)-carbon to give nearly optically pure (R,R)-diols
-
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
the catalytic triad is Asp223-Glu402-His429, the active site includes an oxyanion hole
-
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
the catalytic triad is Asp226-His431-Asp352, catalytic mechanism involving an ester intermediate formed by alkylation of an active site carboxyl group
-
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, catalytic triad
-
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
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
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Metabolism of xenobiotics by cytochrome P450
-
-
SYSTEMATIC NAME
IUBMB Comments
cis-stilbene-oxide hydrolase
This is a key hepatic enzyme that is involved in the metabolism of numerous xenobiotics, such as 1,3-butadiene oxide, styrene oxide and the polycyclic aromatic hydrocarbon benzo[a]pyrene 4,5-oxide [5--7]. In a series of oxiranes with a lipophilic substituent of sufficient size (styrene oxides), monosubstituted as well as 1,1- and cis-1,2-disubstituted oxiranes serve as substrates or inhibitors of the enzyme. However, trans-1,2-disubstituted, tri-and tetra-substituted oxiranes are not substrates [9]. The reaction involves the formation of an hydroxyalkyl---enzyme intermediate [10]. In vertebrates, five epoxide-hydrolase enzymes have been identified 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) [7].
CAS REGISTRY NUMBER
COMMENTARY
9048-63-9
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. rapaceum
-
-
Manually annotated by BRENDA team
Danish population
-
-
Manually annotated by BRENDA team
female and male at different ages
-
-
Manually annotated by BRENDA team
gene EPHX1
-
-
Manually annotated by BRENDA team
healthy humans and patients with Alzheimer's disease
-
-
Manually annotated by BRENDA team
Indian hepatocellular carcinoma patients
-
-
Manually annotated by BRENDA team
isoform EPHX1, children with asthma
-
-
Manually annotated by BRENDA team
isoform EPHX1, patients with a first acute non-fatal myocardial infarction
-
-
Manually annotated by BRENDA team
male Turkish population
-
-
Manually annotated by BRENDA team
mEH is single gene-encoded
Uniprot
Manually annotated by BRENDA team
non-small cell lung cancer patients
Uniprot
Manually annotated by BRENDA team
patients with epilepsy
-
-
Manually annotated by BRENDA team
patients with prostate cancer
-
-
Manually annotated by BRENDA team
C57BL/6 mice
-
-
Manually annotated by BRENDA team
male Swiss Webster mice
-
-
Manually annotated by BRENDA team
strain 129S1/SvImJ
-
-
Manually annotated by BRENDA team
strain B6C3F1
-
-
Manually annotated by BRENDA team
Swiss Webster mice
-
-
Manually annotated by BRENDA team
Mus musculus 129S1/SvImJ
strain 129S1/SvImJ
-
-
Manually annotated by BRENDA team
Mus musculus B6C3F1
strain B6C3F1
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
-
-
Manually annotated by BRENDA team
var. samsun, infected with Tobacco mosaic virus
-
-
Manually annotated by BRENDA team
New Zealand white rabbits
-
-
Manually annotated by BRENDA team
var. rosa marchetti
-
-
Manually annotated by BRENDA team
Pigeon
-
-
-
Manually annotated by BRENDA team
strain BZS21
-
-
Manually annotated by BRENDA team
Pseudomonas sp. BZS21
strain BZS21
-
-
Manually annotated by BRENDA team
quail
-
-
-
Manually annotated by BRENDA team
enzyme activity is about 2.5 to 3 times higher in male than in female
-
-
Manually annotated by BRENDA team
male F344 rats
-
-
Manually annotated by BRENDA team
male Long Evans rats
-
-
Manually annotated by BRENDA team
male Sprague-Dawley
-
-
Manually annotated by BRENDA team
male sprague-dawley rats
-
-
Manually annotated by BRENDA team
toad
-
-
-
Manually annotated by BRENDA team
gene Tcjheh-r1
UniProt
Manually annotated by BRENDA team
gene Tcjheh-r3
UniProt
Manually annotated by BRENDA team
gene Tcjheh-r4
UniProt
Manually annotated by BRENDA team
var. kamut
-
-
Manually annotated by BRENDA team
trout
-
-
-
Manually annotated by BRENDA team
var. blizzar
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
association of GSTT1 and GSTM1 null genotypes and mEPHX polymorphisms with hepatitis virus-related HCC risk in an Indian population
malfunction
-
genetically reduced EPHX1 activity is not a major risk factor for COPD and asthma, overview
metabolism
-
epoxide hydrolases comprise a family of enzymes important in detoxification and conversion of lipid signaling molecules, namely epoxyeicosatrienoic acids. Microsomal epoxide hydrolase is involved in the cerebral epoxyeicosatrienoic acid metabolism
metabolism
Mus musculus C57BL/6
-
epoxide hydrolases comprise a family of enzymes important in detoxification and conversion of lipid signaling molecules, namely epoxyeicosatrienoic acids. Microsomal epoxide hydrolase is involved in the cerebral epoxyeicosatrienoic acid metabolism
-
physiological function
-
microsomal epoxide hydrolase and cytochrome P-450 ensure the rapid detoxification of epoxides generated during the oxidative metabolism of xenobiotics
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus, Mus musculus C57BL/6
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus, Mus musculus C57BL/6
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
show the reaction diagram
-
i.e. 11,12-EET
i.e. 11,12-DHET
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus, Mus musculus C57BL/6
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus, Mus musculus C57BL/6
-
-
-
-
?
(exo)-2,3-epoxynorbornane + H2O
?
show the reaction diagram
-
-
-
-
?
(R)-1,2-epoxyhexane + H2O
n-2-hydroxyhexanol
show the reaction diagram
-
-
-
-
?
(R)-styrene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
(R)-styrene oxide + H2O
(1R)-1-phenylethane-1,2-diol
show the reaction diagram
-
R-enantiomer is preferred
-
-
?
(S)-1,2-epoxyhexane + H2O
n-2-hydroxyhexanol
show the reaction diagram
-
-
-
-
?
(S)-styrene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
1,10-phenanthroline 5,6-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
show the reaction diagram
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
show the reaction diagram
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
show the reaction diagram
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
show the reaction diagram
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
show the reaction diagram
Pigeon, Felis catus, toad, trout, quail
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene-6,7-diol
show the reaction diagram
-
excellent and selective substrate for mEH
-
-
?
1,2-epoxybutane + H2O
2-hydroxy-n-butanol
show the reaction diagram
-
-
-
-
?
1-methyl-1-phenyloxirane + H2O
?
show the reaction diagram
-
-
-
-
?
16,17-epoxyandrost-4-en-3-one + H2O
16,17-dihydroxyandrost-4-en-3-one
show the reaction diagram
-
high activity
-
-
?
16alpha,17alpha-epoxyandrosten-3-one + H2O
?
show the reaction diagram
-
endogenous substrate of mEH
-
-
?
2,3-epoxypropyl ether + H2O
?
show the reaction diagram
-
-
-
-
?
2,3-epoxypropyl-p-methoxyphenyl ether + H2O
?
show the reaction diagram
-
-
-
-
?
2-bromoethylene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
2-chloroethylene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
2-chloroethylene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
2-methyl styrene oxide + H2O
(2R)-2-phenylpropane-1,2-diol
show the reaction diagram
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
3,3,3-trichloropropylene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
3-methylcholanthrene 11,12-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
3-methylcholanthrene 11,12-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
4-chlorophenyl 2,3-epoxypropyl ether + H2O
?
show the reaction diagram
-
-
-
-
?
4-chlorophenyl 2,3-epoxypropyl ether + H2O
?
show the reaction diagram
-
-
-
-
?
4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrophenyl 3-(oxiran-2-yl)propanoate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrophenyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrostyrene 7,8-oxide + H2O
1-(4-nitro)phenyl-ethane-1,2-diol
show the reaction diagram
-
i.e. PNSO
-
-
?
4-t-butylstyrene oxide + H2O
(1R)-1-(4-t-butylphenyl)ethane-1,2-diol
show the reaction diagram
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
4-vinylcyclohexene + H2O
?
show the reaction diagram
-
-
-
-
?
4-vinylcyclohexene + H2O
?
show the reaction diagram
-
-
after exposure of ovary to 4-vinylcyclohexene, an inactive tetrol metabolite 4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane can be formed, potentially through detoxification action of mEH
-
?
4-vinylcyclohexene diepoxide + H2O
4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane
show the reaction diagram
Mus musculus, Mus musculus 129S1/SvImJ
-
-
-
-
?
4-vinylcyclohexene dioxide + H2O
?
show the reaction diagram
-
low activity
-
-
?
7,12-dimethylbenz[a]anthracene + H2O
7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide
show the reaction diagram
-
-
bioactivation reaction
-
?
7-glycidoxycoumarin + H2O
?
show the reaction diagram
-
-
-
-
?
7-glycidoxycoumarin + H2O
7-(1',2'-dihydroxy-3'-propoxy)coumarin
show the reaction diagram
-
substrate is a stable epoxide
-
-
?
7-methylbenzanthracene-5,6-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
7-methylbenzoanthracene + H2O
?
show the reaction diagram
-
-
-
-
?
aflatoxin-B1-8,9-exo-epoxide + H2O
?
show the reaction diagram
-
-
-
-
?
allylbenzene + H2O
3-phenylpropane-1,2-diol
show the reaction diagram
-
-
-
-
?
androstene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
androstene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzoanthracene 5,6-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzoanthracene 5,6-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzoanthracene-9,10-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzopyrene 11,12-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
Pigeon, Felis catus, toad, trout, quail
-
-
-
-
?
benzopyrene 7,8-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzopyrene 7,8-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzopyrene 9,10-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzo[a]pyrene 5-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzo[a]pyrene-7,8-epoxide + H2O
benzo[a]pyrene-7,8-dihydrodiol
show the reaction diagram
-
-
-
-
?
benz[a]anthracene 5,6-oxide + H2O
5,6-dihydro-chrysene-5,6-diol
show the reaction diagram
-
-
-
-
?
benz[a]pyrene 4,5-oxide + H2O
4,5-dihydro-benzo[def]chrysene-4,5-diol
show the reaction diagram
-
-
-
-
?
bisnorsqualene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
butadiene monoxide + H2O
?
show the reaction diagram
-
low activity
-
-
?
carbamazepine-10,11-epoxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-(9R,10S)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
-
enantioselective production of 80% (9R,10R)-diol and 20% (9S,10S)-diol
-
?
cis-(9R,10S)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
-
enantioselective production of 84% (9R,10R)-diol and 16% (9S,10S)-diol
-
?
cis-(9R,10S)-epoxystearic acid methyl ester + H2O
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
show the reaction diagram
-
-
enantioselective production of 79% (9R,10R)-diol and 21% (9S,10S)-diol
-
?
cis-(9R,10S)-epoxystearic acid methyl ester + H2O
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
show the reaction diagram
-
-
enantioselective production of 83% (9R,10R)-diol and 17% (9S,10S)-diol
-
?
cis-(9S,10R)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
-
enantioselective production of 39% (9R,10R)-diol and 61% (9S,10S)-diol
-
?
cis-(9S,10R)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
-
enantioselective production of 52% (9R,10R)-diol and 48% (9S,10S)-diol
-
?
cis-(9S,10R)-epoxystearic acid methyl ester + H2O
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
show the reaction diagram
-
-
enantioselective production of 48% (9R,10R)-diol and 52% (9S,10S)-diol
-
?
cis-(9S,10R)-epoxystearic acid methyl ester + H2O
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
show the reaction diagram
-
-
enantioselective production of 68% (9R,10R)-diol and 32% (9S,10S)-diol
-
?
cis-4,4'-dichlorostilbene oxide + H2O
(1R,2R)-1,2-bis(4-chlorophenyl)ethane-1,2-diol
show the reaction diagram
-
-
product identification
-
?
cis-4,4'-diethylstilbene oxide + H2O
(1R,2R)-1,2-bis(4-ethylphenyl)ethane-1,2-diol
show the reaction diagram
-
-
product identification
-
?
cis-4,4'-diisopropylstilbene oxide + H2O
(1R,2R)-1,2-bis(4-isopropylphenyl)ethane-1,2-diol
show the reaction diagram
-
-
product identification
-
?
cis-4,4'-dimethylstilbene oxide + H2O
(1R,2R)-1,2-bis(4-methylphenyl)ethane-1,2-diol
show the reaction diagram
-
-
product identification
-
?
cis-8-ethylstyrene 7,8-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
Q7KB18
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
P07099
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
the recombinant enzyme expressed in Escherichia coli acts stereospecifically on the the (R)-styrene
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
Mus musculus B6C3F1
-
-
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
Mus musculus 129S1/SvImJ
-
-
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate + H2O
?
show the reaction diagram
-
synthetic fluorescent substrate
-
-
?
cyclododecene-1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cyclohexene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cyclohexene-1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cytochrome P450 isoform 1B1 + H2O
7,12-dimethylbenz(a)anthracene-3,4-diol
show the reaction diagram
Mus musculus, Mus musculus 129S1/SvImJ
-
-
-
-
?
dibenzanthracene 5,6-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
dibenzanthracene 5,6-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
dibenzoanthracene + H2O
?
show the reaction diagram
-
-
-
-
?
dihydronaphthalene oxide + H2O
(1S,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol
show the reaction diagram
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
dl-1,3-butadiene diepoxide + H2O
?
show the reaction diagram
-
low activity
-
-
?
epibromhydrin + H2O
?
show the reaction diagram
-
-
-
-
?
epichlorhydrin + H2O
3-chloro-1,2-propanediol
show the reaction diagram
-
-
-
-
?
epifluorohydrin + H2O
?
show the reaction diagram
-
-
-
-
?
epoxy-stearic acid + H2O
?
show the reaction diagram
-
highly enantiospecific reaction, low activity
-
-
?
estroxide + H2O
?
show the reaction diagram
-
-
-
-
-
estroxide + H2O
?
show the reaction diagram
-
-
-
-
?
estroxide + H2O
?
show the reaction diagram
-
16alpha,17alpha-epoxyestratrienol
-
-
?
ethylene oxide + H2O
ethane-1,2-diol
show the reaction diagram
-
-
-
-
?
glycidyl methacrylate + H2O
?
show the reaction diagram
-
low activity
-
-
?
indene 1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
indene-1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
juvenile hormone I + H2O
?
show the reaction diagram
-
-
-
-
?
juvenile hormone II + H2O
?
show the reaction diagram
-
-
-
-
?
juvenile hormone III + H2O
?
show the reaction diagram
-
-
-
-
?
juvenile hormone III + H2O
?
show the reaction diagram
D0W011, D0W013, D0W014
-
-
-
?
N-2,3-epoxypropyl-p-methoxyphenyl ether + H2O
?
show the reaction diagram
-
-
-
-
?
naphthalene 1,2-oxide + H2O
naphthalene 1,2-diol
show the reaction diagram
-
-
-
-
?
naphthalene-1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
naphthalene-1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
-
naphthalene-1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
octene 1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
octene 1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
octene 1,2-oxide + H2O
octan-1,2-diol
show the reaction diagram
-
-
-
-
?
octene-1,2-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
p-chlorophenyl-2,3-epoxypropylether + H2O
?
show the reaction diagram
-
-
-
-
?
p-nitrostyrene 7,8-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
phenanthrene 9,10-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
phenanthrene 9,10-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
phenanthrene 9,10-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
phenanthrene-9,10-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
phenanthrene-9,10-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
propylene oxide + H2O
?
show the reaction diagram
-
low activity
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
30% enantioselective (9S,10S)-cis-diol production
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
59% enantioselective (9S,10S)-cis-diol production
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
63.5% enantioselective (9S,10S)-cis-diol production
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
74% enantioselective (9S,10S)-cis-diol production
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
90% enantioselective (9S,10S)-cis-diol production by the constitutive enzyme, 86% by the pathogen-induced enzyme
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
94% enantioselective (9S,10S)-cis-diol production
-
-
?
racemic ethyl 3-phenylglycidate + H2O
(2R,3S)-ethyl 3-phenylglycidate
show the reaction diagram
Pseudomonas sp., Pseudomonas sp. BZS21
-
-
production of (2R,3S)-ethyl 3-phenylglycidate with 95% enantiomeric excess and 26% yield in 12 h from 0.2% (w/v) of the racemat
-
?
styrene 7,8-oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene 7,8-oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene 7,8-oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
?
styrene 7,8-oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene 7,8-oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
?
styrene 7,8-oxide + H2O
1-phenyl-ethane-1,2-diol
show the reaction diagram
-
-
-
-
?
styrene 7,8-oxide + H2O
1-phenyl-ethane-1,2-diol
show the reaction diagram
-
-
-
-
?
styrene epoxide + H2O
1-phenyl-ethane-1,2-diol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
-
-
-
?
styrene oxide + H2O
styrene glycol
show the reaction diagram
Felis catus, toad, trout, quail
-
-
-
-
?
styrene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
recombinant enzyme, low activity
-
-
?
styrene oxide + H2O
1-phenyl-ethane-1,2-diol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
styrene oxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
styrene-7,8-oxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
trans-8-ethylstyrene 7,8-oxide + H2O
?
show the reaction diagram
-
i.e. TESO
-
-
?
trans-9,10-epoxystearate + H2O
9,10-dihydroxy-octadecanoic acid
show the reaction diagram
-
-
-
-
?
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
-
-
-
-
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
-
trans-beta-ethyl styrene oxide
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
cis-stilbene oxide hydrolase and trans-stilbene hydrolase isoenzymes are not structurally identical
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
Q7KB18
-
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
juvenile hormone III + H2O
?
show the reaction diagram
D0W011, D0W013, D0W014
-
activity is less than 4 pmol/min/mg protein
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
-
-
-
-
additional information
?
-
-
-
-
-
-
additional information
?
-
-
-
-
-
-
additional information
?
-
-
substrate specificity
-
-
-
additional information
?
-
-
enzyme is induced by a number of xenobiotics, the enzyme is thought to play a detoxifying role by preventing epoxides from reacting irreversibly with critical cellular macromolecules. Some evidence exists to support the hypothesis that microsomal epoxide hydrolase is closely associated with at least certain forms of cytochrome P-450, such association may influence the functional role of the microsomal epoxide hydrolase in the various pathways of bioactivation
-
-
-
additional information
?
-
-
the enzyme may play a significant role in the secondary metabolism of juvenile hormone acid generated by juvenile hormone esterase
-
-
-
additional information
?
-
-
the enzyme plays an important role in the metabolism of various xenobiotic compounds including the polycyclic aromatic hydrocarbon carcinogens. It is specifically involved in the formation of the ultimate carcinogen of benzopyrene
-
-
-
additional information
?
-
-
induced about threefold by 5 mM phenobarbital
-
-
-
additional information
?
-
-
involved in the biotransformation of epoxides produced from either xeno- or endobiotics. The diols produced are generally detoxification products but in several instances, such as 9,10-epoxybenzopyrene-7,8-diol, they are very potent mutagens and possible carcinogens. The enzyme is induced by phenobarbital
-
-
-
additional information
?
-
-
the enzyme is expected to play a purely protective role with respect to epoxides metabolically produced from pharmaceutical drugs
-
-
-
additional information
?
-
-
role in benzopyrene-induced mutagenesis and carcinogenesis
-
-
-
additional information
?
-
-
enzyme is involved in the metabolism of steroids, the microsomal enzyme plays a central role in both the inactivation of primary mutagenic and carcinogenic metabolites of polycyclic aromatic hydrocarbons, and in activating these metabolites to even more toxic or mutagenic secondary products, enzyme production is induced by 3-methylcholanthrene, phenobarbital, trans-stilbene oxide, 2(3)-tert-butyl-4-hydroxyanisol or 2-acetylaminofluorene
-
-
-
additional information
?
-
-
potent and selective induction by trans-stilbene oxide
-
-
-
additional information
?
-
-
probably represents an important factor in the control of reactive epoxides
-
-
-
additional information
?
-
Q7KB18
the enzyme in Drosophila melanogaster is involved in xenobiotic biotransformation, but not in juvenile hormone metabolism
-
-
-
additional information
?
-
-
genetic polymorphisms of the enzyme are responsible for varying susceptibility of cigarette smoking humans to chronic obstructive pulmonary disease, COPD
-
-
-
additional information
?
-
-
key enzyme in the metabolism of environmental contaminants being responsible for xenobiotic transformations, regulation of the enzyme occurs at transcriptional, translational, and post-translational level, the enzyme is also involved in cytoprotection and steroid metabolism, as well as in cellular responses to glucose metabolism and in Na+-dependent bile acid transport, the enzyme is part of a multi-transport system at the cell surface
-
-
-
additional information
?
-
-
key enzyme in the metabolism of environmental contaminants being responsible for xenobiotic transformations, regulation of the enzyme occurs at transcriptional, translational, and post-translational level. The enzyme is also involved in cytoprotection and steroid metabolism, as well as in cellular responses to glucose metabolism and in Na+-dependent bile acid transport. The enzyme is part of a multi-transport system at the cell surface
-
-
-
additional information
?
-
-
the enzyme activity in diabetic and in fasted rats is reduced by 60-71%, key enzyme in the metabolism of environmental contaminants being responsible for xenobiotic transformations, regulation of the enzyme occurs at transcriptional, translational, and post-translational level, the enzyme is also involved in cytoprotection and steroid metabolism, as well as in cellular responses to glucose metabolism and in Na+-dependent bile acid transport, the enzyme is part of a multi-transport system at the cell surface
-
-
-
additional information
?
-
-
the enzyme is a phase II biotransformation enzyme which detoxifies epoxides, including carcinogens such as polycyclic aromatic hydrocarbons found in cigarette smoke and cooked meats, enzyme polymorphisms are not associated with colon cancer risk
-
-
-
additional information
?
-
-
the enzyme is critical for biotransformations in xenobiotic metabolism and detoxification
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
additional information
?
-
-
the enzyme metabolizes xenobiotic epoxides
-
-
-
additional information
?
-
-
enantioselectivity with fatty acid epoxide substrates
-
-
-
additional information
?
-
-
mEH prefers mono- and cis-substituted epoxides, low but highly enantioselective activity with epoxy fatty acids
-
-
-
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
-
-
-
additional information
?
-
-
no activity with 5,6alpha-epoxy-5alpha-cholestan-3beta-ol and 5,6beta-epoxy-5alpha-cholestan-3beta-ol
-
-
-
additional information
?
-
-
substrate specificity, no activity with 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene,i.e. HEOM, 2-acetylaminofluorene, arochlor 1254, and benzopyrene 4,5-oxide, the cytosolic enzyme hydrates epoxides on cyclic systems very slowly, but hydrates a wide variety of aliphatic epoxides rapidly, trisubstituted terpenoid epoxides show low Km-valus, fatty acid and ester epoxides are hydrated very quickly
-
-
-
additional information
?
-
-
substrate specificity, no activity with 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene,i.e. HEOM, 2-acetylaminofluorene, arochlor 1254, and benzopyrene 4,5-oxide, the cytosolic enzyme hydrates epoxides on cyclic sytems very slowly, but hydrates a wide variety of aliphatic epoxides rapidly, trisubstituted terpenoid epoxides show low Km-values, fatty acid and ester epoxides are hydrated very quickly
-
-
-
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.11, which specifically utilizes 5,6alpha-epoxy-5alpha-cholestan-3beta-ol, that is no substrate for EC 3.3.2.9
-
-
-
additional information
?
-
-
the enzyme shows a broad substrate specificity, all epoxides with a trisubstituted oxirane ring are no or poor substrates, no activity with 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
-
-
-
additional information
?
-
-
wide substrate specificity, epoxide-containing glycerol-phospholipids are poor substrates, the enzyme prefers mono- and cis-1,2-disubstituted epoxides as substrates, while gem-di-, trans-di-, tri- and tetra-substituted epoxides are either low turnover substrates or inhibitors, the enzyme has a tamaoxifen binding site
-
-
-
additional information
?
-
-
wide substrate specificity, the enzyme prefers mono- and cis-1,2-disubstituted epoxides as substrates, while gem-di-, trans-di-, tri- and tetra-substituted epoxides are either low turnover substrates or inhibitors
-
-
-
additional information
?
-
-
EPHX1 detoxifies genotoxic compounds and participates in the removal of reactive oxygen species
-
-
-
additional information
?
-
-
mEH is capable of inactivating a large number of structurally different, highly reactive epoxides and hence is an important part of the enzymatic defence of our organism against adverse effects of foreign compounds
-
-
-
additional information
?
-
-
mEH mediates the transport of bile acid in the liver
-
-
-
additional information
?
-
-
mEH prefers mono- and cis-1,2-disubstituted epoxides, while gem-di-, trans-di-, tri- and tetrasubstituted epoxides are low-turnover substrates or inhibitors
-
-
-
additional information
?
-
-
not active with trans-1,3-diphenylpropene oxide
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus, Mus musculus C57BL/6
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus, Mus musculus C57BL/6
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus, Mus musculus C57BL/6
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
Mus musculus, Mus musculus C57BL/6
-
-
-
-
?
16,17-epoxyandrost-4-en-3-one + H2O
16,17-dihydroxyandrost-4-en-3-one
show the reaction diagram
-
high activity
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
P07099
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
-
-
-
-
additional information
?
-
-
-
-
-
-
additional information
?
-
-
-
-
-
-
additional information
?
-
-
enzyme is induced by a number of xenobiotics, the enzyme is thought to play a detoxifying role by preventing epoxides from reacting irreversibly with critical cellular macromolecules. Some evidence exists to support the hypothesis that microsomal epoxide hydrolase is closely associated with at least certain forms of cytochrome P-450, such association may influence the functional role of the microsomal epoxide hydrolase in the various pathways of bioactivation
-
-
-
additional information
?
-
-
the enzyme may play a significant role in the secondary metabolism of juvenile hormone acid generated by juvenile hormone esterase
-
-
-
additional information
?
-
-
the enzyme plays an important role in the metabolism of various xenobiotic compounds including the polycyclic aromatic hydrocarbon carcinogens. It is specifically involved in the formation of the ultimate carcinogen of benzopyrene
-
-
-
additional information
?
-
-
induced about threefold by 5 mM phenobarbital
-
-
-
additional information
?
-
-
involved in the biotransformation of epoxides produced from either xeno- or endobiotics. The diols produced are generally detoxification products but in several instances, such as 9,10-epoxybenzopyrene-7,8-diol, they are very potent mutagens and possible carcinogens. The enzyme is induced by phenobarbital
-
-
-
additional information
?
-
-
the enzyme is expected to play a purely protective role with respect to epoxides metabolically produced from pharmaceutical drugs
-
-
-
additional information
?
-
-
role in benzopyrene-induced mutagenesis and carcinogenesis
-
-
-
additional information
?
-
-
enzyme is involved in the metabolism of steroids, the microsomal enzyme plays a central role in both the inactivation of primary mutagenic and carcinogenic metabolites of polycyclic aromatic hydrocarbons, and in activating these metabolites to even more toxic or mutagenic secondary products, enzyme production is induced by 3-methylcholanthrene, phenobarbital, trans-stilbene oxide, 2(3)-tert-butyl-4-hydroxyanisol or 2-acetylaminofluorene
-
-
-
additional information
?
-
-
potent and selective induction by trans-stilbene oxide
-
-
-
additional information
?
-
-
probably represents an important factor in the control of reactive epoxides
-
-
-
additional information
?
-
Q7KB18
the enzyme in Drosophila melanogaster is involved in xenobiotic biotransformation, but not in juvenile hormone metabolism
-
-
-
additional information
?
-
-
genetic polymorphisms of the enzyme are responsible for varying susceptibility of cigarette smoking humans to chronic obstructive pulmonary disease, COPD
-
-
-
additional information
?
-
-
key enzyme in the metabolism of environmental contaminants being responsible for xenobiotic transformations, regulation of the enzyme occurs at transcriptional, translational, and post-translational level, the enzyme is also involved in cytoprotection and steroid metabolism, as well as in cellular responses to glucose metabolism and in Na+-dependent bile acid transport, the enzyme is part of a multi-transport system at the cell surface
-
-
-
additional information
?
-
-
key enzyme in the metabolism of environmental contaminants being responsible for xenobiotic transformations, regulation of the enzyme occurs at transcriptional, translational, and post-translational level. The enzyme is also involved in cytoprotection and steroid metabolism, as well as in cellular responses to glucose metabolism and in Na+-dependent bile acid transport. The enzyme is part of a multi-transport system at the cell surface
-
-
-
additional information
?
-
-
the enzyme activity in diabetic and in fasted rats is reduced by 60-71%, key enzyme in the metabolism of environmental contaminants being responsible for xenobiotic transformations, regulation of the enzyme occurs at transcriptional, translational, and post-translational level, the enzyme is also involved in cytoprotection and steroid metabolism, as well as in cellular responses to glucose metabolism and in Na+-dependent bile acid transport, the enzyme is part of a multi-transport system at the cell surface
-
-
-
additional information
?
-
-
the enzyme is a phase II biotransformation enzyme which detoxifies epoxides, including carcinogens such as polycyclic aromatic hydrocarbons found in cigarette smoke and cooked meats, enzyme polymorphisms are not associated with colon cancer risk
-
-
-
additional information
?
-
-
the enzyme is critical for biotransformations in xenobiotic metabolism and detoxification
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
additional information
?
-
-
the enzyme metabolizes xenobiotic epoxides
-
-
-
additional information
?
-
-
EPHX1 detoxifies genotoxic compounds and participates in the removal of reactive oxygen species
-
-
-
additional information
?
-
-
mEH is capable of inactivating a large number of structurally different, highly reactive epoxides and hence is an important part of the enzymatic defence of our organism against adverse effects of foreign compounds
-
-
-
additional information
?
-
-
mEH mediates the transport of bile acid in the liver
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
no cofactos required
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Al3+
-
slight inhibition at 1 mM
Ba2+
-
15% inhibition at 1 mM
Ba2+
-
slight inhibition at 1 mM
Ca2+
-
20% inhibition at 1 mM
Ca2+
-
25% inhibition at 1 mM
Ca2+
-
slight inhibition at 1 mM
Cd2+
-
20% inhibition at 1 mM
Cd2+
-
70% inhibition at 1 mM
Cd2+
-
20% inhibition at 1 mM
Co2+
-
20% inhibition at 1 mM
Co2+
-
25% inhibition at 1 mM
Cu2+
-
slight inhibition at 1 mM
Cu2+
-
25% inhibition at 1 mM
Cu2+
-
slight inhibition at 1 mM
Fe2+
-
40% activation at 1 mM
Fe2+
-
15%% activation at 1 mM
Fe2+
-
10% activation at 1 mM
Fe3+
-
50% activation at 1 mM
Fe3+
-
30%% activation at 1 mM
Fe3+
-
20% activation at 1 mM
Hg2+
-
90% inhibition at 1 mM
Hg2+
-
over 90% inhibition at 1 mM
Hg2+
-
70% inhibition at 1 mM
Mg2+
-
30% inhibition at 1 mM
Mg2+
-
10% inhibition at 1 mM
Mn2+
-
10% inhibition at 1 mM
Mn2+
-
20% inhibition at 1 mM
Ni2+
-
30% inhibition at 1 mM
Pb2+
-
10% inhibition at 1 mM
Pb2+
-
30% inhibition at 1 mM
Pb2+
-
10% inhibition at 1 mM
Zn2+
-
80% inhibition at 1 mM
Zn2+
-
over 90% inhibition at 1 mM
Zn2+
-
80% inhibition at 1 mM
Mn2+
-
10% inhibition at 1 mM
additional information
-
no effect by 1 mM Al3+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1R,2R)-1,2-epoxy-1-phenyl-1-propane
-
88% inhibition at 0.8 mM
-
(1S,2S)-1,2-epoxy-1-phenyl-1-propane
-
89% inhibition at 0.8 mM
-
(2R,3R)-1-benzyloxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
9.0% inhibition at 0.1 mM
-
(2R,3R)-3-(4-nitrophenyl)glycidol
-
8.2% inhibition at 0.2 mM
-
(2S,3S)-1-benzyloxy-2,3-epoxy-3-(4-nitrophenyl)propane
-
11% inhibition at 0.1 mM
-
(2S,3S)-3-(4-nitrophenyl)glycidol
-
17% inhibition at 0.2 mM
-
(2S,3S)-p-nitrophenyl-glycidol
-
-
-
(9E)-octadec-9-enamide
-
-
1,1,1-trichloro-2,3-epoxypropane
-
-
1,1,1-Trichloropropene 2,3-oxide
-
-
1,1,1-Trichloropropene 2,3-oxide
-
-
1,1,1-Trichloropropene 2,3-oxide
-
-
1,1,1-Trichloropropene 2,3-oxide
-
-
1,1,1-trichloropropene oxide
-
-
1,1,1-trifluoro-2-propanone
-
-
1-chloro-2,3-epoxypropane
-
non-competitive inhibitor
1-isopropyl-1-phenyloxirane
-
-
1-methyl-1-phenyloxirane
-
-
1-methylcyclohexene oxide
-
-
1-trichloropropene oxide
-
-
12-hydroxyoctadecanamide
-
-
2-(nonylsulfanyl)propanamide
-
-
2-Bromo-4'-nitroacetophenone
-
-
2-Bromo-4'-nitroacetophenone
-
-
2-Bromo-4'-nitroacetophenone
-
-
2-nonylsulfanyl-propionamide
-
-
3,3,3-trichloropropene oxide
-
-
3,3,3-trifluoropropene oxide
-
-
3,3-dimethylbutene oxide
-
-
3-methylbutene 1,2-oxide
-
-
3-methylcyclohexene oxide
-
-
3-phenylpropene 1,2-oxide
-
-
4-Chlorophenyl-2,3-epoxypropyl ether
-
competitive
4-Phenylchalcone oxide
-
-
4-Phenylchalcone oxide
-
-
5,5'-dithiobis(2-nitrobenzoic acid)
-
-
7-oxabicyclo[4.1.0]heptane
-
IC50 is 0.0022 mM
Al3+
-
slight inhibition at 1 mM
androstene oxide
-
inhibits hydration of estroxide and styrene 7,8-oxide
Ba2+
-
15% inhibition at 1 mM
Ba2+
-
slight inhibition at 1 mM
Ca2+
-
20% inhibition at 1 mM
Ca2+
-
25% inhibition at 1 mM
Ca2+
-
slight inhibition at 1 mM
Cd2+
-
20% inhibition at 1 mM
Cd2+
-
70% inhibition at 1 mM
Cd2+
-
20% inhibition at 1 mM
Chalcone oxide
-
-
cis-2-methyl-1-phenyloxirane
-
-
Co2+
-
20% inhibition at 1 mM
Co2+
-
25% inhibition at 1 mM
Cu2+
-
slight inhibition at 1 mM
Cu2+
-
25% inhibition at 1 mM
Cu2+
-
slight inhibition at 1 mM
cyclohexane oxide
-
-
Cyclohexene oxide
-
-
Cyclohexene oxide
-
-
Cyclohexene oxide
-
inhibits hydration of estroxide, androstene oxide and styrene 7,8-oxide
Cyclohexene oxide
-
-
Cyclohexene oxide
-
-
Cyclohexene oxide
-
using a post-natal day 4 Fischer 344 rat whole ovary culture system, inhibition of mEH using cyclohexene oxide during 4-vinylcyclohexene exposure results in a greater loss of primordial and small primary follicles relative to 4-vinylcyclohexene-treated ovaries. Also, relative to controls, mEH mRNA is increased on day 4 of 4-vinylcyclohexene exposure, followed by increased mEH protein after 6 days. Inhibition of PI3K signaling increases mEH mRNA and protein expression
elaidamide
-
mixed inhibition type
elaidamide
-
-
elaidamide
-
most potent inhibitor, has a mix of competitive and non-competitive inhibition kinetics
Emulgen 911
-
0.1%, 53% inhibition
-
Emulgen 911
-
slight inhibition
-
estroxide
-
inhibits hydration of androstene oxide and styrenen 7,8-oxide
Hg2+
-
90% inhibition at 1 mM
Hg2+
-
over 90% inhibition at 1 mM
Hg2+
-
70% inhibition at 1 mM
iodoacetamide
-
0.1 mM, 15% inhibition
iodoacetamide
-
-
juvenile hormone I
-
competitive
Lipid
-
above the critrical micelle concentration gives kinetic pattern that mimics competitive inhibition
Lubrol
-
0.025%
-
Lubrol
-
Lubrol PX; phospholipid reverses the inhibition
-
Lubrol
-
Lubrol PX
-
Mersalyl
-
0.09 mM, 13% inhibition
methyl-p-epoxymethylbenzoate
-
-
Metyrapone
-
strong inhibition of hydration of benzopyrene 11,12-oxide and dibenzoanthracene 5,6-oxide
Mg2+
-
30% inhibition at 1 mM
Mg2+
-
10% inhibition at 1 mM
Mn2+
-
10% inhibition at 1 mM
Mn2+
-
20% inhibition at 1 mM
Ni2+
-
30% inhibition at 1 mM
omega-bromo-nitro-acetophenone
-
-
p-chlorophenyl 2,3-epoxypropyl ether
-
-
p-hydroxymercuribenzoate
-
0.1 mM, 15% inhibition
p-hydroxymercuribenzoate
-
-
Pb2+
-
10% inhibition at 1 mM
Pb2+
-
30% inhibition at 1 mM
Pb2+
-
10% inhibition at 1 mM
progabide
-
low micromolar inhibitor
Sodium cholate
-
inhibits hydration of estroxide and androstene oxide
Sodium deoxycholate
-
inhibits hydration of estroxide and androstene oxide
Styrene 7,8-oxide
-
inhibits hydration of estroxide and androstene oxide
trans-stilbene oxide
-
inhibits hydration of estroxide, androstene oxide and styrene 7,8-oxide
trichloropropene oxide
-
inhibits hydration of estroxide, androstene oxide and styrene 7,8-oxide
trichloropropene oxide
-
-
trichloropropene oxide
-
-
trichloropropene oxide
-
-
Tween-80
-
0.025%
Tween-80
-
inhibits hydration of estroxide and androstene oxide
valpromide
-
low micromolar inhibitor
Zn2+
-
80% inhibition at 1 mM
Zn2+
-
over 90% inhibition at 1 mM
Zn2+
-
80% inhibition at 1 mM
Mn2+
-
10% inhibition at 1 mM
additional information
-
5,6alpha-epoxy-5alpha-cholestan-3beta-ol causes down-regulation of the enzyme, no effect by cholestyramine and clofibrate
-
additional information
-
no inhibition by 3-phenylglycidol enantiomers, inhibitor synthesis, overview, inhibition mechanisms, overview
-
additional information
-
no inhibition by 5,6alpha-imino-5alpha-cholestane-3beta-ol
-
additional information
-
no inhibition by isoquinoline, 7-oxocholesterol, 7-oxocholestanol, and 6-oxocholestanol
-
additional information
P07099
HNF3 negatively regulates the transactivation of E1 promoter by GATA-4 in hepatoma cells
-
additional information
-
suppression of enzyme expression by glucocorticoid, interacting with the 5'-flanking sequence, and by dexamethasone, gadolinium chloride, acriflavine, lipopolysaccharide, gem-di-, trans-di-, tri- and tetra-substituted epoxides are either low turnover substrates or inhibitors
-
additional information
-
suppression of enzyme expression by dexamethasone, gadolinium chloride, acriflavine, lipopolysaccharide
-
additional information
-
quantitative structure-activity relationships in epoxides inhibiting EH activity, molecular modelling, kinetics, overview
-
additional information
-
metal chelators like 1,10-phenanthroline, 1,7-phenanthroline, EDTA, EGTA, and dipicolinic acid preserve enzyme activity in presence of metal ions
-
additional information
-
no inhibition by Co2+ at 1 mM, metal chelators like 1,10-phenanthroline, 1,7-phenanthroline, EDTA, EGTA, and dipicolinic acid preserve enzyme activity in presence of metal ions
-
additional information
-
metal chelators like 1,10-phenanthroline, 1,7-phenanthroline, EDTA, EGTA, and dipicolinic acid preserve enzyme activity in presence of metal ions
-
additional information
D0W011, D0W013, D0W014
not inhibitory: 3-octylthio-1,1,1-trifluoro-2-propanone; not inhibitory: 3-octylthio-1,1,1-trifluoro-2-propanone; not inhibitory: 3-octylthio-1,1,1-trifluoro-2-propanone
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1(2-naphthyl)-2-phenylethanedione
-
stimulates
-
1-(2-cyanophenyl)-imidazole
-
2 mM, stimulates
1-(2-Isopropylphenyl)-imidazole
-
2 mM, stimulates
1-(2-Isopropylphenyl)-imidazole
-
stimulates
3-methylcholanthrene
-
enhances nuclear hydration of phenanthrene-9,10-oxide, benzopyrene-11,12-oxide and octene-1,2-oxide, no significant effect on microsomal hydration
benzil
-
stimulates
benzil
-
stimulates
chalcone epoxide
-
stimulates
CHAPS
-
stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
clotrimazole
-
stimulates
clotrimazole
-
stimulates
cytochrome P450
-
activation of microsomal epoxide hydrolase by interaction with cytochromes P450
-
Digitonin
-
stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
Dodecyl maltoside
-
stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
Ellipticine
-
stimulates
Emulgen 108
-
2fold activation
-
erucin
-
exposure of liver slices to erucin results in elevated glucuronosyl transferase and epoxide hydrolase activities and expression
ethanol
-
2.7 M, stimulates
flavone
-
stimulates
Glucoerucin
-
exposure of liver slices to glucoerucin causes a marked increase in the activity and expression of the microsomal epoxide hydrolase but has no effect on glucuronosyl transferase activity
-
glucoraphanin
-
exposure of liver slices to glucoraphanin causes a marked increase in the activity and expression of the microsomal epoxide hydrolase but has no effect on glucuronosyl transferase activity
Harmane
-
stimulates
Isoquinoline
-
stimulates
Isoquinoline
-
stimulates
Lubrol Px
-
2fold activation
Metyrapone
-
-
Metyrapone
-
2 mM, stimulates
Metyrapone
-
great stimulation of hydration of styrene 7,8-oxide and octene 1,2-oxide, slight stimulation of hydration of benzopyrane 4,5-oxide
Metyrapone
-
-
Metyrapone
-
stimulates
N-acetylaminofluorene
-
-
-
nitroanisil
-
stimulates
Non-idet P40
-
stimulates
norharmane
-
stimulates
octyl-glucoside
-
stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
p-anisil
-
stimulates
phenethyl isothiocyanate
-
exposure of liver slices to phenethyl isothiocyanate results in elevated glucuronosyl transferase and epoxide hydrolase activities and expression
Phenobarbital
-
enhances nuclear and microsomal hydration of phenanthrene-9,10-oxide, benzopyrene-11,12-oxide and octene-1,2-oxide
Phenobarbitone
-
-
Phospholipids
-
the enzyme is tightly associated with phospholipids
R-sulforaphane
-
exposure of liver slices to R-sulforaphane causes a marked increase in the activity and expression of the microsomal epoxide hydrolase
Sodium cholate
-
slight activation
sucrose monolaurate
-
stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
Thesit
-
stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
-
Triton WR-1339
-
nearly 2fold activation
Triton X-100
-
stimulates
Tween 80
-
slight activation
Zwittergent 3-12
-
stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
Metyrapone
-
stimulates
additional information
-
induction of the enzyme by clofibrate and di(2-ethylhexyl)phthalate
-
additional information
-
pathogens induce enzyme expression
-
additional information
-
maximal activity with dimethyl formamide as co-solvent, effects of solvents on enzyme activity, overview
-
additional information
-
no effect by cholestyramine and clofibrate, phenobarbital and isosafrole induce the enzyme expression, it is also induced by trans-stilbene oxide, gamma-chlordane, Aroclor 1254, and 2-acetylamineo-fluorene in liver microsomes
-
additional information
-
clofibrate induces the enzyme
-
additional information
-
enzyme expression is induced by exogenous beta-amyloid and trimethyl-tin, a neurotoxic agent, beta-amyloid aggregation induces enzyme expression in astrocytes
-
additional information
-
enzyme expression is induced by neurotoxic agent trimethyl-tin in hippocampus and entorhinal cortex
-
additional information
-
insulin increases enzyme activity in hepatocyte cell culture
-
additional information
-
mEH expression is up-regulated after 1-methyl-4-phemyl-1,2,3,6-tetrahydropyridine intoxication
-
additional information
-
benzo[a]pyrene, dibenzo[a,h]anthracene and fluoranthene give rise to a statistically significant increase in epoxide hydrolase activity, which is accompanied by a concomitant increase in epoxide hydrolase protein levels, dibenzo[a,l]pyrene, benzo[b]fluoranthene and 1-methylphenanthrene, influence neither activity nor enzyme protein levels
-
additional information
-
increased expression of mEH mRNA is detected after 4 days of 4-vinylcyclohexene diepoxide exposure
-
additional information
-
4-vinylcyclohexene diepoxide (0.005 mM) causes an increase in mEH mRNA by 0.5fold at day 10
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.001
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid
-
-
0.00025
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid
-
-
0.0005
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid
-
-
0.001
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid
-
-
0.59
1,10-phenanthroline 5,6-oxide
-
-
0.012
4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate
-
pH 9.0, 37C
0.022
4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate
-
pH 9.0, 37C
0.17
7-glycidoxycoumarin
-
-
0.0024
cis-stilbene oxide
-
pH 7.4, 37C
0.004
cis-stilbene oxide
-
pH 7.4, 37C
0.015
cis-stilbene oxide
-
pH 7.4, 37C
0.035
cis-stilbene oxide
-
pH 9.0, 37C
0.141
cis-stilbene oxide
-
pH 9.0, 37C
0.0023
cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate
-
pH 9.0, 37C
0.0038
cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate
-
pH 9.0, 37C
0.00061
juvenile hormone I
-
-
0.00055
juvenile hormone II
-
-
0.0055
phenanthrene 9,10-oxide
-
-
0.98
Styrene 7,8-oxide
-
-
0.53
Styrene oxide
-
-
0.53
Styrene oxide
-
-
0.67
Styrene oxide
-
-
0.35
trans-beta-ethylstyrene oxide
-
-
0.01
trans-stilbene oxide
-
-
0.00028
juvenile hormone III
-
-
additional information
additional information
-
-
-
additional information
additional information
-
kinetics
-
additional information
additional information
-
kinetics
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
53
1,10-phenanthroline 5,6-oxide
-
-
0.08
juvenile hormone III
-
-
0.5
phenanthrene 9,10-oxide
-
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.01
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid
-
-
40506
0.01
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid
-
-
40507
0.02
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid
-
-
25172
5
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid
-
-
40505
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000072
2-nonylsulfanyl-propionamide
-
in Tris/HCl buffer (0.1 M, pH 9.0), at 30C
0.0154
cyclohexane oxide
-
pH 7.4, 37C
0.00007
elaidamide
-
pH 7.4
0.00007
elaidamide
-
-
0.0076
Zn2+
-
pH 7.4, 37C, mixed inhibition type
0.012
Zn2+
-
pH 7.4, 37C, competitive inhibition type
0.061
Zn2+
-
pH 7.4, 37C, competitive inhibition type
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0005
(9E)-octadec-9-enamide
-
substrate cis-stilbene oxide, pH 9.0, 37C
0.001
(9E)-octadec-9-enamide
-
substrate cis-stilbene oxide, pH 9.0, 37C
0.063
(9E)-octadec-9-enamide
-
substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate, pH 9.0, 37C
0.14
(9E)-octadec-9-enamide
-
substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate, pH 9.0, 37C
0.0011
12-hydroxyoctadecanamide
-
substrate cis-stilbene oxide, pH 9.0, 37C
0.0026
12-hydroxyoctadecanamide
-
substrate cis-stilbene oxide, pH 9.0, 37C
0.123
12-hydroxyoctadecanamide
-
substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate, pH 9.0, 37C
0.2
12-hydroxyoctadecanamide
-
or above, substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate, pH 9.0, 37C
0.0004
2-(nonylsulfanyl)propanamide
-
substrate cis-stilbene oxide, pH 9.0, 37C
0.0005
2-(nonylsulfanyl)propanamide
-
substrate cis-stilbene oxide, pH 9.0, 37C
0.0042
2-(nonylsulfanyl)propanamide
-
substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate, pH 9.0, 37C
0.006
2-(nonylsulfanyl)propanamide
-
substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate, pH 9.0, 37C
0.0022
7-oxabicyclo[4.1.0]heptane
-
IC50 is 0.0022 mM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.000085
-
liver microsomes, substrate styrene oxide
0.000124
-
liver microsomes, substrate styrene oxide
0.00019
-
epididymis microsomes
0.00019
-
liver microsomes, substrate allylbenzene oxide
0.00035
-
liver microsomes, substrate allylbenzene oxide
0.00043
-
liver microsomes, substrate styrene oxide
0.00051
-
testis microsomes
0.0027
D0W011, D0W013, D0W014
30C, pH not specified in the publication
0.0036
-
liver microsomes, substrate allylbenzene oxide
0.0045
-
enzyme form cytosol
0.0057
-
liver microsomes
0.0064
-
liver microsomes
0.0083
-
-
0.021
-
substrate 4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate, pH 9.0, 37C
0.023
-
substrate 4-nitrophenyl 3-(oxiran-2-yl)propanoate, pH 9.0, 37C
0.025
-
substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate, pH 9.0, 37C
0.0272
-
-
0.029
-
substrate 4-nitrophenyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate, pH 9.0, 37C
0.048
-
substrate 4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate, pH 9.0, 37C
0.051
-
substrate 4-nitrophenyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate, pH 9.0, 37C
0.068
-
substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate, pH 9.0, 37C
0.072
-
substrate 4-nitrophenyl 3-(oxiran-2-yl)propanoate, pH 9.0, 37C
0.093
D0W011, D0W013, D0W014
30C, pH not specified in the publication
0.118
-
-
0.121
-
-
0.618
-
-
0.659
-
enzyme from microsomes
11.4
-
-
additional information
-
several analytical and activity assay methods
additional information
-
highly sensitive and rapid radiometric assay
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.5 - 8
-
broad maximum, recombinant enzyme
6.7
-
cytosolic and microsomal enzyme, hydration of trans-beta-ethylstyrene oxide
7
-
assay at
7.2
-
cytosolic enzyme, hydration of trans-stilbene oxide
7.4
-
hydration of benzopyrene 4,5-oxide
7.4
-
assay at
7.4
-
assay at
7.4
-
assay at
7.5 - 8.5
-
-
8 - 9
-
-
8
-
assay at
8.5 - 9
-
-
8.5
-
hydration of styrene oxide
8.9 - 9.4
-
hydration of styrene 7,8-oxide
8.9
-
hydration of benzopyrene 7,8-oxide and benzopyrene 9,10-oxide; hydration of styrene oxide, Tris buffer
8.9
-
hydration of styrene oxide, Tris buffer
9
-
hydration of styrene oxide in sodium phosphate buffer
9
-
hydration of styrene oxide in sodium phosphate buffer
9
-
benzopyrene 4,5-oxide, microsomal enzyme
9
-
assay at
9.4
-
somewhat higher than, hydration of styrene oxide in glycine buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 9.8
-
pH 6.5: about 50% of maximal activity, pH 9.8: about 55% of maximal activity
7 - 10
-
pH 7.0: about 60% of maximal activity, pH 10.0: about 25% of maximal activity
7 - 9.5
-
pH 7.0: about 35% of maximal activity, pH 9.5: about 70% of maximal activity
additional information
-
-
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
adrenalectomy elevates enzyme levels
Manually annotated by BRENDA team
-
mEH is particularly concentrated in the adrenal gland
Manually annotated by BRENDA team
-
specific nuclei
Manually annotated by BRENDA team
-
patchy distribution
Manually annotated by BRENDA team
-
very low activity
Manually annotated by BRENDA team
-
mEH distribution, immunohistochemical analysis, overview. mEH immunoreactivity is present in specific neuronal populations of the hippocampus, striatum, amygdala, and cerebellum, as well as in a fraction of astrocytes
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
mEH distribution, immunohistochemical analysis, overview. mEH immunoreactivity is present in specific neuronal populations of the hippocampus, striatum, amygdala, and cerebellum, as well as in a fraction of astrocytes
-
Manually annotated by BRENDA team
-
numerous cancer cell lines and primary cells
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
-
-
Manually annotated by BRENDA team
Pseudomonas sp. BZS21
-
-
-
Manually annotated by BRENDA team
Pseudomonas sp. BZS21
-
-
-
Manually annotated by BRENDA team
-
caput, corpus, cauda
Manually annotated by BRENDA team
-
mEH is particularly concentrated in the heart
Manually annotated by BRENDA team
-
specific nuclei
Manually annotated by BRENDA team
-
glial cell culture, enzyme expression is elevated in hippocampus and associated cortex of patients with Alzheimer's disease
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
-
-
Manually annotated by BRENDA team
P07099
hepatoma cell line
Manually annotated by BRENDA team
-
epithelium, very low activity
Manually annotated by BRENDA team
-
the E1 EPHX1 transcript is detected at high level in the kidney
Manually annotated by BRENDA team
-
harvested 7 days after inoculation with Erypsiphe graminis
Manually annotated by BRENDA team
-
highest enzyme activity, specific for
Manually annotated by BRENDA team
-
the liver enzyme is controlled by the pituitary gland
Manually annotated by BRENDA team
P07099
tissue-specific expression of the enzyme in liver
Manually annotated by BRENDA team
-
both the E1 and the E1-b EPHX1 transcripts are detected at high levels in the liver although E1-b is the major hepatic transcript, accounting for about 70% of the total EPHX1 RNA expressed in this tissue
Manually annotated by BRENDA team
-
high expression level of mEH in the liver
Manually annotated by BRENDA team
-
mEH is particularly concentrated in the liver
Manually annotated by BRENDA team
-
precision-cut liver slices
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
in the rat basal lung epoxide hydrolase activity is much lower than liver
Manually annotated by BRENDA team
-
mEH is particularly concentrated in the lung
Manually annotated by BRENDA team
-
intra-epithelial, cells show down-regulated enzyme expression
Manually annotated by BRENDA team
-
specific nuclei
Manually annotated by BRENDA team
-
pyramidal
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
-
-
Manually annotated by BRENDA team
Mus musculus B6C3F1
-
-
-
Manually annotated by BRENDA team
Mus musculus 129S1/SvImJ
-
-
-
Manually annotated by BRENDA team
-
neonatal mouse ovarian culture system. Incubation of ovaries in presence of 7,12-dimethylbenz[a]anthracene. At 1 mM 7,12-dimethylbenz[a]anthracene, follicle loss and increased microsomal epoxide hydrolase protein are measured by 6 h. mRNA encoding epoxide hydrolase markedly increases after 2 days of incubation, and this increase precedes accelerated follicle loss at 4 days
Manually annotated by BRENDA team
-
the E1 EPHX1 transcript is detected at high level in the ovary
Manually annotated by BRENDA team
-
exposure to 4-vinylcyclohexene results in increased mRNA and protein expression of microsomal epoxide hydrolase, and an inactive tetrol metabolite 4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane can be formed in mouse ovarian follicles, potentially through detoxification action of mEH
Manually annotated by BRENDA team
-
using a post-natal day 4 Fischer 344 rat whole ovary culture system, inhibition of mEH using cyclohexene oxide during 4-vinylcyclohexene exposure results in a greater loss of primordial and small primary follicles relative to 4-vinylcyclohexene-treated ovaries. Also, relative to controls, mEH mRNA is increased on day 4 of 4-vinylcyclohexene exposure, followed by increased mEH protein after 6 days. Inhibition of PI3K signaling increases mEH mRNA and protein expression
Manually annotated by BRENDA team
Mus musculus B6C3F1, Mus musculus 129S1/SvImJ
-
-
-
Manually annotated by BRENDA team
-
the transcript of Ephx1 increases in the oviductal epithelium at the estrus stage and in day 3 of pregnancy
Manually annotated by BRENDA team
-
hypophysectomy induces the liver enzyme in females and males
Manually annotated by BRENDA team
-
very low activity
Manually annotated by BRENDA team
-
membranous and glandular
Manually annotated by BRENDA team
-
mEH is particularly concentrated in the testis
Manually annotated by BRENDA team
-
regulation of mEH during the menstrual cycle: during the first half mEH expression is low, increases during the second half and reaches highest levels during pregnancy, immunohistochemical analysis, overview
Manually annotated by BRENDA team
-
endothelial and smooth muscle cells
Manually annotated by BRENDA team
additional information
-
wide tissue distribution
Manually annotated by BRENDA team
additional information
-
tissue distribution analysis
Manually annotated by BRENDA team
additional information
-
wide tissue distribution in mammalian tissue, enzyme levels vary with environmental exposure, sex, and age
Manually annotated by BRENDA team
additional information
-
wide tissue distribution in mammalian tissue, enzyme levels vary with environmental exposure, sex, and age, growth hormones are involved in sexually dimorphic liver enzyme expression
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
no activity detected
Manually annotated by BRENDA team
-
in neoplastic livers
Manually annotated by BRENDA team
-
orientation of the enzyme depends on the membrane type
Manually annotated by BRENDA team
-
mEH is also associated with the nuclear and plasma membranes
Manually annotated by BRENDA team
-
integral microsomal protein
-
Manually annotated by BRENDA team
-
slightly higher enzyme activity in smooth compared to rough microsomes
-
Manually annotated by BRENDA team
-
mEH is distributed mainly in the microsome
-
Manually annotated by BRENDA team
Mus musculus C57BL/6, Mus musculus B6C3F1, Mus musculus 129S1/SvImJ
-
-
-
-
Manually annotated by BRENDA team
-
in liver, the catalytic site facing the extracellular medium
Manually annotated by BRENDA team
-
in liver, the catalytic site facing the cytosol
Manually annotated by BRENDA team
-
mEH is mostly found attached to the smooth endoplasmic reticulum
Manually annotated by BRENDA team
additional information
-
subcellular distribution analysis
-
Manually annotated by BRENDA team
additional information
-
the enzyme shows strong hydrophobic interaction with the membrane, deletion of the N-terminal membrane anchor does not render the enzyme soluble
-
Manually annotated by BRENDA team
additional information
-
not localized in cytosol
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
31000
-
gel filtration, 2 peaks
654503
50000
-
SDS-PAGE
699685
50000
-
-
700587
50000
-
SDS-PAGE
701319
62000
-
gel filtration, 2 peaks
654503
64000
-
gel filtration
654503
130000
-
gel filtration
208901
600000
-
enzyme aggregate formed in absence of amphiphathic detergents, gel filtration
208901
800000
-
enzyme aggregate formed in absence of amphiphathic detergents, equilibrium sedimentation
208901
additional information
-
-
208901
additional information
-
enzyme aggregates in absence of amphipathic detergents
208901
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 50000, SDS-PAGE
?
-
x * 50000, SDS-PAGE
?
-
x * 50000, SDS-PAGE
?
-
x * 58000, SDS-PAGE
?
-
x * 51000, SDS-PAGE
?
-
x * 49000, SDS-PAGE
?
-
x * 53000-54000, SDS-PAGE
?
-
x * 49500 SDS-PAGE
?
-
x * 49500 SDS-PAGE
?
-
x * 50000
?
-
x * 50000, about
?
-
x * 49800, SDS-PAGE
dimer
-
mainly, in solution, recombinant enzyme, mass spectrometry
additional information
-
monomer or dimer
additional information
-
peptide mapping
additional information
-
structure analysis, amino acid sequence analysis and comparisons, the enzyme forms an alpha/beta hydrolase fold
additional information
-
the enzyme possesses a long N-terminal transmembrane domain of 20 amino acids which acts as an anchor for cellular membranes
additional information
-
the enzyme possesses an N-terminal strong hydrophobic transmembrane anchor
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
molecular modelling of human enzyme by homology with the crystal structure of the Aspergillus niger enzyme at 1.8 A resolution, structure-activity relationships in epoxides inhibiting EH activity
-
homology modeling. Structure exhibits a alpha/beta-hydrolase fold main domain with a lid domain over the active site
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
-
pH 7.0, 5 h, stable
208881, 208886
37
-
-
208881
37
-
pH 7.0, 24 h, less than 10% inactivation
208881, 208886
90
-
1 min, complete loss of activity
208935
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, stable for at least 3 months
-
-70C, stable for months
-
0C, 50 mM sodium phosphate buffer, pH 7.0, 2 months, stable
-
4C, stable for at least 3 months
-
4C, stable for up to 8 weeks
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
to homogeneity from root cytosol
-
recombinant His-tagged enzyme from Saccharomyces cerevisiae strain WA6 by nickel affinity chromatography
-
hydrophobic chromatography: a one-step method
-
multiple enzyme forms
-
partial
-
partially from liver
-
from liver microsomes
-
partially 2.4fold from liver using PEG precipitation, and to homogeneity by ion exchange, hydrophobic interaction chromatography, and hydroxylapatite chromatography
-
partially from liver by micosome preparation, two steps of gel filtration, separation from the cholesterol epoxide hydrolase, EC 3.3.2.11
-
preparation of cytosolic fraction by ultracentrifugation
-
partially by microsome preparation
-
partially from liver
-
preparation of liver microsomes, separation from the cholesterol 5,6-oxide hydrolase, EC 3.3.2.11, by immunoprecipitation
-
preparation of cytosolic fraction by ultracentrifugation
-
multiple enzyme forms
-
phenobarbital-treated animals
-
preparation of liver microsomes, separation from the cholesterol 5,6-oxide hydrolase, EC 3.3.2.11, by immunoprecipitation
-
Q-Sepharose column chromatography
-
to homogeneity from liver of phenobarbital- and isosafrole-treated rats, separation from the cholesterol 5,6-oxide hydrolase, EC 3.3.2.11, by immunoprecipitation
-
preparation of cytosolic fraction by ultracentrifugation
-
to homogeneity from seedling cytosol
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
functional expression in Escherichia coli
-
expression using a baculovirus expression system
Q7KB18
expression of His-tagged enzyme in Saccharomyces cerevisiae strain WA6, the N-terminal His-tag reduces enzyme activity by 75%, therefore a C-terminal His-tag is used
-
expressed in Escherichia coli
-
expressed in HEK-293A cells, HEK-293T cells, and MCF-7 cells
-
gene EPHX1 is located on chromosome 1, DNA and amino acid sequence determination and analysis, expression of liver enzyme in Schizosaccharomyces pombe, expression in Cos-1 cells, expression using the baculovirus system
-
gene EPHX1, located on chromosome 1
-
genotyping
-
genotyping analysis of several humans of different origin
-
genotyping of 3553 humans
-
genotyping of 497 humans
-
genotyping of patients from the Copenhagen City Heart Study for EPHX1 polymorphisms
-
the E1-b promoter functions as the primary driver of EPHX1 expression in human tissues, E1 promoter directs expression only in the liver, analysis of promoters and regulation enzyme expression in tissues, expression in Hep-G2 cells and 293A cells, co-expression of GATA-4, overview
P07099
baculovirus expression system
-
expression in Escherichia coli
-
expressed in Escherichia coli
-
expression analysis
-
expression pattern of mEH
-
baculovirus expression system
-
expressed in a baculovirus expression system in High Five insect cell cultures (derived from Trichoplusia ni)
-
expression in baculoviral system; expression in baculoviral system; expression in baculoviral system
D0W011, D0W013, D0W014
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
mEH expression is regulated by progesterone, but only in the presence of the progesterone receptors as well as estrogene receptor alpha, overview
-
increase of mEH expression after treatment with medroxy-progesterone 17-acetate in the estrogene receptor alpha-containing ECC1-PRAB72 cells, but not in estrogene receptor alpha-negative IKPRAB-36 cells
-
repeated administration of methamphetamine, METH, results in an increase in mEH-positive glia-like cells, mobilization of astroglial cells to synthesize mEH in response to METH
-
exposure to 4-vinylcyclohexene results in increased mRNA and protein expression of microsomal epoxide hydrolase
-
inhibition of PI3K signaling increases mEH mRNA and protein expression. In a post-natal day 4 Fischer 344 rat whole ovary culture system, mEH mRNA is increased on day 4 of 4-vinylcyclohexene exposure, followed by increased mEH protein after 6 days
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A139G
-
a naturally occuring polymorphism, leads to reduced EPHX1 activity, but is not involved in pathogeneiss of asthma and COPD
E404D
-
mutation of the catalytic triad residue leads to increased activity compared to the wild-type enzyme
H139R
-
mutant shows increased activity compared to the wild-type enzyme, molecular modelling
H139R
-
natural genotype, frequency of the polymorphism, the mutant enzyme shows 25% increased activity compared to the wild-type enzyme
H139R
-
natural genotype, frequency of the polymorphism, the mutant enzyme shows increased activity compared to the wild-type enzyme
H139R
-
the mutant exhibits low risk for squamous cell esophageal cancer
H139R
-
the mutation enhances enzyme activity by approximately 25%
H139R
-
the mutation is a genetic contributor to chronic obstructive pulmonary disease susceptibility
H139R
-
there is a significant association between early-onset lung cancer and the presence of EPHX1 exon 4 variant H139R
R43T
-
mutant shows reduced activity compared to the wild-type enzyme, molecular modelling
T113C
-
a naturally occuring polymorphism, leads to reduced EPHX1 activity, but is not involved in pathogeneiss of asthma and COPD
T275A
-
mutant shows similar activity compared to the wild-type enzyme, molecular modelling
Y113H
-
mutant shows similar activity compared to the wild-type enzyme, molecular modelling
Y113H
-
natural genotype, frequency of the polymorphism, the mutant enzyme shows 40% reduced activity compared to the wild-type enzyme
Y113H
-
natural genotype, frequency of the polymorphism, the mutant enzyme shows reduced activity compared to the wild-type enzyme
Y113H
-
the mutant is associated with 40-50% decrease in microsomal epoxide hydrolase activity
Y113H
-
the mutation is a genetic contributor to chronic obstructive pulmonary disease susceptibility
Y113H
-
the mutation is associated with higher risk of squamous cell esophageal cancer
Y113H
-
the mutation leads to altered enzyme activity, but is not associated with pancreatic diseases
H139R
-
the naturally occuring mutation is a risk factor for hepatocellular carcinoma with both control and chronic hepatitis-infected individuals, association of GSTT1 and GSTM1 null genotypes and mEPHX polymorphisms with hepatitis virus-related HCC risk in an Indian population. Frequencies in hepatocellular carcinoma, controls, and the chronic viral hepatitis subjects, respectively, overview
additional information
-
genotyping of 3553 humans, enzyme polymorphisms are not associated with colon cancer
additional information
-
genotyping of 497 humans, enzyme polymorphisms are associated with esophageal squamous-cell-carcinoma, ESCC, and smoking or areca chewing, higher enzyme activity can contribute to lower the risk of cancer development, overview
additional information
-
naturally occurring genetic polymorphisms of the enzyme are responsible for varying susceptibility of cigarette smoking humans to chronic obstructive pulmonary disease, COPD
additional information
-
polymorphisms associated with the onset of diseases
additional information
-
genotyping and identifcation of single nucleotide polymorphisms c416A/G, rs2234922, and c337T/C, role of the mutations in carbamazepine treatement of epilepsy, overview
Y133H
-
naturally occuring mutation, frequencies in hepatocellular carcinoma, controls, and the chronic viral hepatitis subjects, respectively, overview
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
additional information
-
significant difference in extracellular dopamine uptake is observed between mEH-/- and wild-type mice
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
-
the purified recombinant enzyme can be used as biocatalyst for kinetic resolution of racemic styrene oxide with the result of over 99% enantiopure (S)-styrene oxide in 23,5% yield
analysis
-
development of a fluorescence-based assay using substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate and application as a useful tool for the discovery of structure-activity relationships among mEH inhibitors and for the screening chemical library with high accuracy and with a Z' value of approximately 0.7
drug development
-
the enzyme is a target for inhibitor design
medicine
-
high EPHX1 activity is associated with an increased risk for lifetime asthma, which varies by glutathione S-transferase P1 Ile105Val genotype and by residential proximity to major roads. Among children with glutathione S-transferase P1 105Val/Val genotype, those who have high EPHX1 phenotype have a fourfold increased risk of lifetime asthma. Among children living within 75 metres of a major road, those with high EPHX1 activity had a 3.2-fold higher lifetime asthma risk. The results are similar for current, early persistent and late onset asthma
medicine
P07099
investigation on the expression and genetic polymorphism of microsomal epoxide hydrolase in non-small cell lung cancer patients. Enzyme is expressed in 83% of biopsies analyzed, and the major allelic expression pattern is fast type (Tyr113) in exon 3 (90.3%) and slow type (His139) in exon 4 (100%). A significant difference in patient survival is found when enzyme expression and adriamycin-containing chemotherapy are used to group patients. With respect to cancer risk and disease progression, the expression level of enzyme seems as important as genetic polymorphism
medicine
-
investigation on the influence of single nucleotide polymorphisms in EPHX1 on well characterized chronic obstructive pulmonary disease and intermediate phenotypes. The EPHX1 exon 3 polymorphism is not associated with an increased risk of chronic obstructive pulmonary disease, nor is the EPHX1 exon 4 polymorphism. In addition, none of the EPHX1 haplotypes are associated with an increased risk of any chronic obstructive pulmonary disease phenotype
medicine
-
significant association of prostate cancer risk with exon 3 variant genotypes of microsomal epoxide hydrolase alone or in combination with tobacco users, whereas in exon 4 genotypes, no association is observed. T/C polymorphism of CYPA1 gene is an additional predisposing factor
medicine
-
study on polymorphisms of microsomal epoxide hydrolase. Genotype frequencies of exon 3 are Tyr113Tyr 50.4%, Tyr113His 42.1%, His113His 7.5%, and on exon 4 His139His 69.2%, His139Arg 28.6%, Arg133Arg 2.2%
medicine
-
study on the effect of enzyme genotype on risk of myocardial infarction of smokers and non-smokers among patients with a first acute non-fatal myocardial infarction. EPHX1 genotype is not associated with risk of myocardial infarction, regardless of smoking status, and does not play a significant role in the development of coronary heart disease
medicine
-
EPHX1 does not play a role in the initiation of pancreatic inflammation or cancer
medicine
-
genetic mEPHX variants are positively associated with viral-related hepatocellular carcinoma risk
medicine
-
patients with exon 3 genotypes (Tyr113His, His113His) and 113His allele are at risk of squamous cell esophageal cancer, none of haplotype combinations of exon 3 (Y113H) and exon 4 (H139R) polymorphisms show modulation of risk for squamous cell esophageal cancer
medicine
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polymorphisms in the microsomal epoxide hydrolase gene (EPHX1 His113-His113 genotype) are associated with chronic obstructive pulmonary disease
medicine
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the exon 3 His genotype of the mEH gene polymorphism alone or in combination with tobacco-users are significantly associated with the risk of sporadic bladder cancer
medicine
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there is no association of EPHX1 gene variation with susceptibility to chronic obstructive pulmonary disease or disease severity
medicine
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there is no risk-modifying effect of genetic polymorphisms in microsomal epoxide hydrolase on head and neck carcinogenesis, except for the predicted high activity variant H139R in patients with hypopharyngeal carcinoma
synthesis
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enzyme prefers (R)-styrene oxide. Production of enantiopure (S)-styrene oxide by use of enzyme in batch kinetic resolution of racemic styrene oxide
drug development
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the enzyme is a target for inhibitor design
medicine
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incubation of ovaries in a neonatal mouse ovarian culture system in presence of 7,12-dimethylbenz[a]anthracene. At 1 mM 7,12-dimethylbenz[a]anthracene, follicle loss and increased microsomal epoxide hydrolase protein are measured by 6 h. mRNA encoding epoxide hydrolase markedly increases after 2 days of incubation, and this increase precedes accelerated follicle loss at 4 days
synthesis
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the enantioselective enzyme is useful in production of chiral substances, e.g. production of (2R,3S)-ethyl 3-phenylglycidate with 95% enantiomeric excess and 26% yield in 12 h from 0.2% (w/v) of the racemat by whole cells of Pseudomonas sp. strain BZS21, maximal activity with dimethyl formamide as co-solvent
synthesis
Pseudomonas sp. BZS21
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the enantioselective enzyme is useful in production of chiral substances, e.g. production of (2R,3S)-ethyl 3-phenylglycidate with 95% enantiomeric excess and 26% yield in 12 h from 0.2% (w/v) of the racemat by whole cells of Pseudomonas sp. strain BZS21, maximal activity with dimethyl formamide as co-solvent
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analysis
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development of a fluorescence-based assay using substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate and application as a useful tool for the discovery of structure-activity relationships among mEH inhibitors and for the screening chemical library with high accuracy and with a Z' value of approximately 0.7
drug development
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the enzyme is a target for inhibitor design
synthesis
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highly enantioselective synthesis of chiral 1,2 diols from epoxides in ionic liquid [bmim][PF6] or [bmim][Tf2N] in presence of 10% water