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 hide
3.3.2.9
-
RECOMMENDED NAME
GeneOntology No.
microsomal epoxide hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
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 hide
9048-63-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. rapaceum
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
glassy-winged sharpshooter
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Mus musculus 129S1/SvImJ
strain 129S1/SvImJ
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-
Manually annotated by BRENDA team
Mus musculus B6C3F1
strain B6C3F1
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-
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
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-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
var. samsun, infected with Tobacco mosaic virus
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-
Manually annotated by BRENDA team
var. rosa marchetti
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Manually annotated by BRENDA team
Pigeon
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain BZS21
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-
Manually annotated by BRENDA team
strain BZS21
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-
Manually annotated by BRENDA team
quail
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
toad
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Manually annotated by BRENDA team
var. kamut
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Manually annotated by BRENDA team
trout
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-
-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
var. blizzar
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
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
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
(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
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
(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
(1R)-1-phenylethane-1,2-diol
show the reaction diagram
-
R-enantiomer is preferred
-
-
?
(R)-styrene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
(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-1,4,4a,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
1,2-epoxybutane + H2O
2-hydroxy-n-butanol
show the reaction diagram
-
-
-
-
?
1-methyl-1-phenyloxirane + H2O
?
show the reaction diagram
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
-
-
?
16,17-epoxyandrost-4-en-3-one + H2O
16,17-dihydroxyandrost-4-en-3-one
show the reaction diagram
16alpha,17alpha-epoxyandrosten-3-one + H2O
?
show the reaction diagram
2,3-epoxypropyl ether + H2O
?
show the reaction diagram
-
-
-
-
?
2,3-epoxypropyl-p-methoxyphenyl ether + H2O
?
show the reaction diagram
-
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
-
?
2-bromoethylene 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
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 diepoxide + H2O
4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane
show the reaction diagram
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
7,12-dimethylbenz[a]anthracene + 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-glycidoxycoumarin + H2O
?
show the reaction diagram
-
-
-
-
?
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
benzene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzo(a)pyrene 4,5-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 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
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
cis-(9S,10R)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
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
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
(+)-(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
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
?
cis-stilbene oxide + H2O
?
show the reaction diagram
clofibrate + H2O
?
show the reaction diagram
cyano(2-methoxynaphthalen-6-yl)methyl trans-(2-(3-phenyloxiran-2-yl))acetate + H2O
?
show the reaction diagram
-
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl)acetate + H2O
?
show the reaction diagram
-
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate + H2O
?
show the reaction diagram
cyano(6-methoxy-naphthalen-2-yl)methyl oxiran-2-ylmethyl carbonate + H2O
?
show the reaction diagram
-
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxiran-2-yl)methyl]carbonate + H2O
?
show the reaction diagram
-
-
-
?
cyano-(6-methoxy-naphthalen-2-yl)-methyl 3,3-dimethyl-oxiranylmethyl carbonate + H2O
?
show the reaction diagram
-
-
-
?
cyano-(6-methoxy-naphthalen-2-yl)-methyl trans-((3-ethyl-oxiran-2-yl)methyl) carbonate + H2O
?
show the reaction diagram
-
-
-
?
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
di(2-ethylhexyl)phthalate + 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
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
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
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
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
racemic ethyl 3-phenylglycidate + H2O
(2R,3S)-ethyl 3-phenylglycidate
show the reaction diagram
styrene 7,8-oxide + H2O
1-phenyl-ethane-1,2-diol
show the reaction diagram
styrene 7,8-oxide + H2O
styrene glycol
show the reaction diagram
styrene epoxide + H2O
1-phenyl-ethane-1,2-diol
show the reaction diagram
-
-
-
-
?
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
styrene glycol
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-diphenylpropene oxide + H2O
?
show the reaction diagram
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
trans-stilbene oxide + H2O
?
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
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
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
16,17-epoxyandrost-4-en-3-one + H2O
16,17-dihydroxyandrost-4-en-3-one
show the reaction diagram
7,12-dimethylbenz[a]anthracene + H2O
7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide
show the reaction diagram
P07687
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
juvenile hormone III + H2O
?
show the reaction diagram
L7R9X8
poor substrate
-
-
?
trans-diphenylpropene oxide + H2O
?
show the reaction diagram
L7R9X8
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
L7R9X8
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
no cofactos required
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
no effect by 1 mM Al3+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
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 oxide
1,1,1-trifluoro-2-propanone
-
-
1,1-diphenyloxirane
1,3-dicyclohexylurea
-
-
1,3-diphenylurea
-
-
-
1-chloro-2,3-epoxypropane
-
non-competitive inhibitor
1-isopropyl-1-phenyloxirane
1-methyl-1-phenyloxirane
1-methylcyclohexene oxide
1-trichloropropene oxide
-
-
10-hydroxystearamide
-
-
-
12-hydroxyoctadecanamide
2-(nonylsulfanyl)propanamide
2-Bromo-4'-nitroacetophenone
2-nonylsulfanyl-propionamide
-
-
3,3,3-trichloropropene oxide
3,3,3-trifluoropropene oxide
3,3-dimethylbutene oxide
3-(decylthio)-1,1,1-trifluoropropan-2-one
-
moderate inhibition
-
3-(dodecylthio)-1,1,1-trifluoropropan-2-one
-
moderate inhibition
-
3-(octylthio)-1,1,1-trifluoropropan-2-one
-
moderate inhibition
3-methylbutene 1,2-oxide
3-methylcyclohexene oxide
3-phenylpropene 1,2-oxide
4-Chlorophenyl-2,3-epoxypropyl ether
-
competitive
4-Phenylchalcone oxide
5,5'-dithiobis(2-nitrobenzoic acid)
-
-
7-oxabicyclo[4.1.0]heptane
-
IC50 is 0.0022 mM
androstene oxide
-
inhibits hydration of estroxide and styrene 7,8-oxide
Chalcone oxide
-
-
cis-2-methyl-1-phenyloxirane
cis-stilbene oxide
cyclohexane oxide
-
-
Cyclohexene oxide
elaidamide
Emulgen 911
estroxide
-
inhibits hydration of androstene oxide and styrenen 7,8-oxide
indene 1,2-oxide
iodoacetamide
juvenile hormone I
-
competitive
Lipid
-
above the critrical micelle concentration gives kinetic pattern that mimics competitive inhibition
Lubrol
m-bromostyrene oxide
m-nitrostyrene oxide
Mersalyl
-
0.09 mM, 13% inhibition
methoxyarachidonyl fluorophosphate
-
-
-
methyl-p-epoxymethylbenzoate
Metyrapone
-
strong inhibition of hydration of benzopyrene 11,12-oxide and dibenzoanthracene 5,6-oxide
N-(phenylcarbamothioyl)acetamide
-
-
N-(phenylcarbamothioyl)benzamide
-
-
N-(pyridin-4-ylcarbamothioyl)acetamide
-
-
N-(pyridin-4-ylcarbamothioyl)benzamide
-
-
N-(tert-butylcarbamothioyl)acetamide
-
-
N-(tert-butylcarbamothioyl)benzamide
-
-
N-acetyl-N'-adamantyl thiourea
-
-
-
N-acetyl-N'-[(3-trifluoromethyl-4-bromo)phenyl] thiourea
-
-
-
N-benzoyl-N'-adamantyl thiourea
-
-
-
N-benzoyl-N'-[(3-trifluoromethyl-4-bromo)phenyl] thiourea
-
-
-
n-octene 1,2-oxide
N-[(2,6-dichlorophenyl)carbamothioyl]acetamide
-
-
N-[(2,6-dichlorophenyl)carbamothioyl]benzamide
-
-
N-[(2,6-diethoxyphenyl)carbamothioyl]acetamide
-
-
N-[(2,6-diethoxyphenyl)carbamothioyl]benzamide
-
-
N-[(2-methoxy-4-methylphenyl)carbamothioyl]acetamide
-
-
N-[(2-methoxy-4-methylphenyl)carbamothioyl]benzamide
-
-
N-[(2-methoxy-4-nitrophenyl)carbamothioyl]acetamide
-
-
N-[(2-methoxy-4-nitrophenyl)carbamothioyl]benzamide
-
-
N-[(2-methylphenyl)carbamothioyl]acetamide
-
-
N-[(2-methylphenyl)carbamothioyl]benzamide
-
-
N-[(4-bromonaphthalen-1-yl)carbamothioyl]acetamide
-
-
N-[(4-bromonaphthalen-1-yl)carbamothioyl]benzamide
-
-
N-[(4-bromophenyl)carbamothioyl]acetamide
-
-
N-[(4-bromophenyl)carbamothioyl]benzamide
-
-
N-[(4-chlorophenyl)carbamothioyl]acetamide
-
-
N-[(4-chlorophenyl)carbamothioyl]benzamide
-
-
N-[(4-phenoxyphenyl)carbamothioyl]acetamide
-
-
N-[(4-phenoxyphenyl)carbamothioyl]benzamide
-
-
N-[[4-(morpholin-4-yl)phenyl]carbamothioyl]acetamide
-
-
-
N-[[4-(morpholin-4-yl)phenyl]carbamothioyl]benzamide
-
-
-
naphthalene 1,2-oxide
omega-bromo-nitro-acetophenone
-
-
p-bromostyrene oxide
p-chlorophenyl 2,3-epoxypropyl ether
p-hydroxymercuribenzoate
p-nitrostyrene oxide
p-phenylstyrene oxide
progabide
propene oxide
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
styrene oxide
trans-stilbene oxide
-
inhibits hydration of estroxide, androstene oxide and styrene 7,8-oxide
trichloropropene oxide
Tween-80
urea derivatives
valpromide
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1(2-naphthyl)-2-phenylethanedione
-
stimulates
-
1-(2-cyanophenyl)-imidazole
1-(2-Isopropylphenyl)-imidazole
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
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
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
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
hepatitis B spliced protein
Isoquinoline
Lubrol Px
-
2fold activation
Metyrapone
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
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
-
-
0.042
2-arachidonoylglycerol
-
at pH 7.4 and 37C
0.012 - 0.022
4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate
0.17
7-glycidoxycoumarin
-
-
0.0024 - 0.141
cis-stilbene oxide
0.0023 - 0.0038
cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate
0.00061
juvenile hormone I
-
-
0.00055
juvenile hormone II
-
-
0.00028 - 0.0138
juvenile hormone III
0.0055
phenanthrene 9,10-oxide
-
-
0.98
styrene 7,8-oxide
-
-
0.53 - 0.67
styrene oxide
0.35
trans-beta-ethylstyrene oxide
-
-
0.01
trans-stilbene oxide
-
-
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
53
1,10-phenanthroline 5,6-oxide
Rattus norvegicus
-
-
0.002 - 0.08
juvenile hormone III
0.5
phenanthrene 9,10-oxide
Rattus norvegicus
-
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid