3.3.2.9: microsomal epoxide hydrolase
This is an abbreviated version!
For detailed information about microsomal epoxide hydrolase, go to the full flat file.
Word Map on EC 3.3.2.9
-
3.3.2.9
-
phenobarbital
-
cholesterol
-
phospholipid
-
hepatocytes
-
monooxygenase
-
hydroxylase
-
triglyceride
-
xenobiotics
-
steroid
-
nadph-cytochrome
-
thyroid
-
isozymes
-
lipoprotein
-
s-transferase
-
testosterone
-
aniline
-
benzoapyrene
-
phosphatidylcholine
-
glucuronidation
-
3-methylcholanthrene
-
bile
-
drug-metabolizing
-
arachidonic
-
prostaglandin
-
acyltransferase
-
heme
-
hepatotoxicity
-
nadph-dependent
-
cyp2e1
-
gsh
-
autoimmune
-
apolipoprotein
-
cyp1a2
-
autoantibody
-
biphenyls
-
polycyclic
-
udp-glucuronosyltransferase
-
monoxide
-
glucose-6-phosphatase
-
tetrachloride
-
polychlorinated
-
thyroglobulin
-
ketoconazole
-
demethylase
-
ccl4
-
desaturation
-
n-oxide
-
androstenedione
-
beta-hydroxysteroid
-
21-hydroxylase
-
synthesis
-
medicine
-
drug development
-
analysis
- 3.3.2.9
- phenobarbital
- cholesterol
- phospholipid
- hepatocytes
- monooxygenase
- hydroxylase
- triglyceride
- xenobiotics
- steroid
-
nadph-cytochrome
- thyroid
- isozymes
- lipoprotein
- s-transferase
- testosterone
- aniline
-
benzoapyrene
- phosphatidylcholine
-
glucuronidation
- 3-methylcholanthrene
- bile
-
drug-metabolizing
-
arachidonic
- prostaglandin
- acyltransferase
- heme
-
hepatotoxicity
-
nadph-dependent
- cyp2e1
- gsh
- autoimmune
-
apolipoprotein
- cyp1a2
- autoantibody
- biphenyls
-
polycyclic
-
udp-glucuronosyltransferase
- monoxide
- glucose-6-phosphatase
-
tetrachloride
-
polychlorinated
- thyroglobulin
- ketoconazole
- demethylase
- ccl4
-
desaturation
- n-oxide
- androstenedione
-
beta-hydroxysteroid
- 21-hydroxylase
- synthesis
- medicine
- drug development
- analysis
Reaction
Synonyms
alpha,beta fold epoxide hydrolase, alpha,beta-fold type EH, E1-b', EC 3.3.2.3, EC 4.2.1.63, EC 4.2.1.64, EH1, EH2, Eha, EHb, EPHX, EPHX 1, EPHX1, EPOX, epoxide hydrolase, HYL1, JH epoxide hydrolase, JHEH, juvenile hormone epoxide hydrolase, mEH, mEH-like protein, mEH1, mEPHX, microsomal, microsomal EH, microsomal EPHX1, Microsomal epoxide hydrolase, microsomal epoxide hydrolase 1, microsomal epoxide hydrolase-like protein, microsomal xenobiotic epoxide hydrolase, More, PNSO hydrolase, SEH, styrene-epoxide hydrolase, Tcjheh-r1, Tcjheh-r3, XEHase, xenobiotic epoxide hydrolase
ECTree
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Substrates Products
Substrates Products on EC 3.3.2.9 - microsomal epoxide hydrolase
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REACTION DIAGRAM
(3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone + H2O
(3-[4-[([[3-(hydroxymethyl)oxetan-3-yl]methyl]amino)methyl]phenoxy]azetidin-1-yl)[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
-
-
-
?
(3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone + H2O
?
-
-
-
-
?
(3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone + H2O
[3-(4-[[3,3-bis(hydroxymethyl)azetidin-1-yl]methyl]phenoxy)azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
(R)-1,2-epoxybutane + H2O
(2R)-butane-1,2-diol
very limited preference for hydrolysis of the (R)-enantiomer
-
-
?
(R)-epichlorhydrin + H2O
(R)-3-chloro-1,2-propanediol
very limited preference for hydrolysis of the (S)-enantiomer
-
-
?
(R)-glycidyl tosylate + H2O
(2R)-4-(4-methylbenzene-1-sulfonyl)butane-1,2,4-triol
very limited preference for hydrolysis of the (R)-enantiomer
-
-
?
(R)-styrene oxide + H2O
(R)-styrene glycol
preferential hydrolysis of the (R)-enantiomer
-
-
?
(S)-1,2-epoxybutane + H2O
(2S)-butane-1,2-diol
very limited preference for hydrolysis of the (R)-enantiomer
-
-
?
(S)-epichlorhydrin + H2O
(S)-3-chloro-1,2-propanediol
very limited preference for hydrolysis of the (S)-enantiomer
-
-
?
(S)-glycidyl tosylate + H2O
(2S)-4-(4-methylbenzene-1-sulfonyl)butane-1,2,4-triol
very limited preference for hydrolysis of the (R)-enantiomer
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
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
1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine + H2O
2-([[(4-methoxyphenyl)methyl](methyl)amino]methyl)-2-methylpropane-1,3-diol
-
-
-
ir
1-[3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one + H2O
1-[3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one
-
[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one
-
ir
2,3-epoxypropyl-p-methoxyphenyl ether + H2O
3-(3-methoxyphenoxy)propane-1,2-diol
-
-
-
-
?
2-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine + H2O
2-([[2-(4-methoxyphenyl)ethyl](methyl)amino]methyl)-2-methylpropane-1,3-diol
-
-
-
ir
2-methyl styrene oxide + H2O
(2R)-2-phenylpropane-1,2-diol
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
4-nitrostyrene 7,8-oxide + H2O
1-(4-nitro)phenyl-ethane-1,2-diol
-
i.e. PNSO
-
-
?
4-t-butylstyrene oxide + H2O
(1R)-1-(4-t-butylphenyl)ethane-1,2-diol
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
7,12-dimethylbenz[a]anthracene + 3 H2O
7,12-dimethylbenz[a]anthra-3,4-diol-1,2-epoxide
-
-
-
?
7,12-dimethylbenz[a]anthracene + 3 H2O
7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide
7-glycidoxycoumarin + H2O
7-(1',2'-dihydroxy-3'-propoxy)coumarin
-
substrate is a stable epoxide
-
-
?
cis-(9R,10S)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
cis-(9R,10S)-epoxystearic acid methyl ester + H2O
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
cis-(9S,10R)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
cis-(9S,10R)-epoxystearic acid methyl ester + H2O
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
cis-4,4'-dichlorostilbene oxide + H2O
(1R,2R)-1,2-bis(4-chlorophenyl)ethane-1,2-diol
-
-
product identification
-
?
cis-4,4'-diethylstilbene oxide + H2O
(1R,2R)-1,2-bis(4-ethylphenyl)ethane-1,2-diol
-
-
product identification
-
?
cis-4,4'-diisopropylstilbene oxide + H2O
(1R,2R)-1,2-bis(4-isopropylphenyl)ethane-1,2-diol
-
-
product identification
-
?
cis-4,4'-dimethylstilbene oxide + H2O
(1R,2R)-1,2-bis(4-methylphenyl)ethane-1,2-diol
-
-
product identification
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(2-(3-phenyloxiran-2-yl))acetate + H2O
?
-
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl oxiran-2-ylmethyl carbonate + H2O
?
-
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxiran-2-yl)methyl]carbonate + H2O
?
-
-
-
?
cyano-(6-methoxy-naphthalen-2-yl)-methyl 3,3-dimethyl-oxiranylmethyl carbonate + H2O
?
-
-
-
?
cyano-(6-methoxy-naphthalen-2-yl)-methyl trans-((3-ethyl-oxiran-2-yl)methyl) carbonate + H2O
?
-
-
-
?
cyano-(6-methoxynaphthalen-2-yl)methyl trans-2-pentenylacetate + H2O
?
-
prepared from trans-styrylacetic acid and 7-methoxy-2-naphthaldehyde. Enzyme EH catalyzed hydrolysis of the epoxide substrate produces an intermediate diol which lactonizes to release a fluorescent reporter after hydrolysis of the intermediate cyanohydrin
-
-
?
dihydronaphthalene oxide + H2O
(1S,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
epoxy-stearic acid + H2O
?
-
highly enantiospecific reaction, low activity
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
trans-4,5-epoxy-hexanol
1-(tetrahydrofuran-2-yl)ethanol
-
exo-tet cyclization reaction
-
-
?
trans-4,5-epoxy-hexanol
2-methyltetrahydro-2H-pyran-3-ol
-
endo-tet cyclization reaction
-
-
?
[3-(4-[[(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone + H2O
[3-(4-[[(1,3-dihydroxypropan-2-yl)amino]methyl]phenoxy)azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone
-
-
-
ir
[3-[4-([((3-methyloxetan-3-yl)methyl)amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone + H2O
[3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl]amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone
-
-
-
ir
[3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone + H2O
[3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone
-
-
-
ir
[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone + H2O
[3-(4-[[(1,3-dihydroxypropan-2-yl)amino]methyl]phenoxy)azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
-
-
ir
[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone + H2O
[3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
-
-
ir
[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone + H2O
[3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl]amino]methyl)phenoxy]azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
-
-
ir
[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([[(oxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone + H2O
[3-[4-([[3-hydroxy-2-(hydroxymethyl)propyl]amino]methyl)phenoxy]azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
-
-
ir
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
-
i.e. 11,12-EET
i.e. 11,12-DHET
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
-
i.e. 11,12-EET
i.e. 11,12-DHET
-
?
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
-
-
-
?
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
-
-
-
?
(R)-styrene oxide + H2O
(1R)-1-phenylethane-1,2-diol
-
R-enantiomer is preferred
-
-
?
?
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
Pigeon
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
quail
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
toad
-
-
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
trout
-
-
-
-
?
1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene-6,7-diol
-
excellent and selective substrate for mEH
-
-
?
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
-
excellent and selective substrate for mEH
-
-
?
16,17-dihydroxyandrost-4-en-3-one
-
high activity
-
-
?
16,17-epoxyandrost-4-en-3-one + H2O
16,17-dihydroxyandrost-4-en-3-one
-
high activity
-
-
?
16,17-epoxyandrost-4-en-3-one + H2O
16,17-dihydroxyandrost-4-en-3-one
-
high activity
-
-
?
?
-
endogenous substrate of mEH
-
-
?
16alpha,17alpha-epoxyandrosten-3-one + H2O
?
-
endogenous substrate of mEH
-
-
?
4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate + H2O
?
-
-
-
-
?
?
-
-
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-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane
-
-
-
-
?
4-vinylcyclohexene diepoxide + H2O
4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane
-
-
-
?
4-vinylcyclohexene diepoxide + H2O
4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane
-
-
-
-
?
4-vinylcyclohexene diepoxide + H2O
4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane
-
-
-
?
4-vinylcyclohexene diepoxide + H2O
4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane
-
-
-
?
7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide
-
-
-
?
7,12-dimethylbenz[a]anthracene + 3 H2O
7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide
-
-
bioactivation reaction
-
?
7,12-dimethylbenz[a]anthracene + 3 H2O
7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
-
-
-
-
?
benzopyrene 7,8-oxide + H2O
?
-
-
-
-
?
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
-
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
-
-
enantioselective production of 84% (9R,10R)-diol and 16% (9S,10S)-diol
-
?
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
-
-
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
-
-
enantioselective production of 83% (9R,10R)-diol and 17% (9S,10S)-diol
-
?
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
-
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
-
-
enantioselective production of 52% (9R,10R)-diol and 48% (9S,10S)-diol
-
?
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
-
-
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
-
-
enantioselective production of 68% (9R,10R)-diol and 32% (9S,10S)-diol
-
?
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
-
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
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
?
(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
-
-
-
-
?
?
-
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl)acetate + H2O
?
-
-
-
-
?
?
-
synthetic fluorescent substrate
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate + H2O
?
-
synthetic fluorescent substrate
-
-
?
7,12-dimethylbenz(a)anthracene-3,4-diol
-
-
-
-
?
cytochrome P450 isoform 1B1 + H2O
7,12-dimethylbenz(a)anthracene-3,4-diol
-
-
-
-
?
juvenile hormone III + H2O
?
-
activity is less than 4 pmol/min/mg protein
-
?
phenanthrene-9,10-oxide + H2O
?
-
-
-
-
?
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
30% enantioselective (9S,10S)-cis-diol production
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
94% enantioselective (9S,10S)-cis-diol production
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
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
-
94% enantioselective (9S,10S)-cis-diol production
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
74% enantioselective (9S,10S)-cis-diol production
-
-
?
racemic cis-9,10-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
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
-
59% enantioselective (9S,10S)-cis-diol production
-
-
?
(2R,3S)-ethyl 3-phenylglycidate
-
-
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
-
?
racemic ethyl 3-phenylglycidate + H2O
(2R,3S)-ethyl 3-phenylglycidate
-
-
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
-
-
-
-
?
styrene oxide + H2O
1-phenylethane-1,2-diol
-
recombinant enzyme, low activity
-
-
?
trans-9,10-epoxystearate + H2O
9,10-dihydroxy-octadecanoic acid
-
-
-
-
?
1,2-diphenylethane-1,2-diol
-
-
-
?
trans-stilbene oxide + H2O
?
-
cis-stilbene oxide hydrolase and trans-stilbene hydrolase isoenzymes are not structurally identical
-
-
?
?
-
-
enantioselectivity with fatty acid epoxide substrates
-
-
?
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 in Drosophila melanogaster is involved in xenobiotic biotransformation, but not in juvenile hormone metabolism
-
-
?
additional information
?
-
-
the enzyme in Drosophila melanogaster is involved in xenobiotic biotransformation, but not in juvenile hormone metabolism
-
-
?
additional information
?
-
-
enantioselectivity with fatty acid epoxide substrates
-
-
?
additional information
?
-
no activity with trans-stilbene oxide
-
-
?
additional information
?
-
-
no activity with trans-stilbene oxide
-
-
?
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
?
-
-
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
?
-
-
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
?
-
-
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, 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
?
-
-
mEH prefers mono- and cis-substituted epoxides, low but highly enantioselective activity with epoxy fatty acids
-
-
?
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
?
-
-
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
?
-
-
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
?
-
-
no activity with 14,15-epoxyexicosatrienoic acid
-
-
?
additional information
?
-
enzyme mEH in collaboration with cytochrome-P-450 (CYP) converts benzo(a)pyrene to more reactive intermediate, benzo(a)pyrene-7,8-dihydrodiol 8,9-epoxide (benzo(a)pyrene diolepoxide, BPDE) which displays higher mutagenic and carcinogenic potential than its substrate
-
-
?
additional information
?
-
-
enzyme mEH in collaboration with cytochrome-P-450 (CYP) converts benzo(a)pyrene to more reactive intermediate, benzo(a)pyrene-7,8-dihydrodiol 8,9-epoxide (benzo(a)pyrene diolepoxide, BPDE) which displays higher mutagenic and carcinogenic potential than its substrate
-
-
?
additional information
?
-
oxetanes are a nonepoxide class of substrates for human mEH, which is known to catalyze the hydrolytic ring opening of electrophilic and potentially toxic epoxide-containing drugs, drug metabolites, and exogenous organochemicals
-
-
?
additional information
?
-
-
oxetanes are a nonepoxide class of substrates for human mEH, which is known to catalyze the hydrolytic ring opening of electrophilic and potentially toxic epoxide-containing drugs, drug metabolites, and exogenous organochemicals
-
-
?
additional information
?
-
the enzyme converts epoxides to diols and is able to either detoxify or bioactivate a wide range of substrates. The prototypical EPHX1 reaction involves conversion of epoxides to trans-dihydrodiols. EPHX1 more readily converts xenobiotics than endogenous substrates
-
-
?
additional information
?
-
-
the enzyme converts epoxides to diols and is able to either detoxify or bioactivate a wide range of substrates. The prototypical EPHX1 reaction involves conversion of epoxides to trans-dihydrodiols. EPHX1 more readily converts xenobiotics than endogenous substrates
-
-
?
additional information
?
-
EPHX1 has a broad substrate specificity. It also metabolizes endocannabinoid 2-arachidonoylglycerol to free arachidonic acid and glycerol
-
-
?
additional information
?
-
-
EPHX1 has a broad substrate specificity. It also metabolizes endocannabinoid 2-arachidonoylglycerol to free arachidonic acid and glycerol
-
-
?
additional information
?
-
no activity with [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[methyl(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone, [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[(3-methyloxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone, 2-(4-methoxyphenyl)-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine, and 2-(4-methoxyphenyl)-N-methyl-N-[(oxetan-3-yl)methyl]ethan-1-amine
-
-
?
additional information
?
-
-
no activity with [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[methyl(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone, [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[(3-methyloxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone, 2-(4-methoxyphenyl)-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine, and 2-(4-methoxyphenyl)-N-methyl-N-[(oxetan-3-yl)methyl]ethan-1-amine
-
-
?
additional information
?
-
the microsomal epoxide hydrolase (EPHX1) is inactive with cis- or trans-allylic epoxides, such as 9R,10R-trans-epoxy-13R-hydroxy-octadeca-11E-enoic acid, 9R,10S-cis-epoxy-13R-hydroxyoctadeca-11E-enoic acid, 12,13-trans-epoxy-octadeca-9E-enoic acid, and 12,13-cis-epoxy-octadeca-9E-enoic acid, in contrast to the soluble epoxide hydrolase, (EPHX2 and EPHX3, EC 3.3.2.10)
-
-
?
additional information
?
-
-
the enzyme has the potential to catalyze the critical endo-tet cyclization of epoxy alcohols via a endo-tet cyclization, mechanism, overview. Reaction of polyepoxide pre-momensin to momensin, a polyether, or of another polyepoxide to brevetoxin B
-
-
?
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
?
-
-
the enzyme may play a significant role in the secondary metabolism of juvenile hormone acid generated by juvenile hormone esterase
-
-
?
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 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
?
-
-
probably represents an important factor in the control of reactive epoxides
-
-
?
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 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
?
-
-
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
?
-
-
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
?
-
-
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
?
-
-
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
?
-
microsomal epoxide hydrolase (mEH) has a wide substrate specificity
-
-
?
additional information
?
-
-
microsomal epoxide hydrolase (mEH) has a wide substrate specificity
-
-
?
additional information
?
-
-
enantioselectivity with fatty acid epoxide substrates
-
-
?
additional information
?
-
-
enantioselectivity with fatty acid epoxide substrates
-
-
?
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 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
?
-
stereoselective hydrolysis of epoxyeicosatrienoic acids (EETs) by sEH
-
-
?
additional information
?
-
-
enantioselectivity with fatty acid epoxide substrates
-
-
?
additional information
?
-
the enzyme exhibits broad hydrolytic activity toward several racemic epoxides including styrene oxide, epichlorohydrin, and 1,2-epoxybutane
-
-
?
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
?
-
-
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
?
-
-
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 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 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, 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 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, 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
?
-
-
not active with trans-1,3-diphenylpropene oxide
-
-
?
additional information
?
-
microsomal epoxide hydrolase (mEH) has wide a substrate specificity
-
-
?
additional information
?
-
microsomal epoxide hydrolase (mEH) has wide a substrate specificity
-
-
?
additional information
?
-
-
enantioselectivity with fatty acid epoxide substrates
-
-
?
additional information
?
-
-
enantioselectivity with fatty acid epoxide substrates
-
-
?
additional information
?
-
-
induced about threefold by 5 mM phenobarbital
-
-
?