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Information on EC 3.3.2.9 - microsomal epoxide hydrolase and Organism(s) Homo sapiens

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EC Tree
     3 Hydrolases
         3.3 Acting on ether bonds
             3.3.2 Ether hydrolases
                3.3.2.9 microsomal epoxide hydrolase
IUBMB Comments
This is a key hepatic enzyme that catalyses the hydrolytic ring opening of oxiranes (epoxides) and oxetanes to give the corresponding diols. The enzyme is involved in the metabolism of numerous substrates including the stereoselective hydrolytic ring opening of 7-oxabicyclo[4.1.0]hepta-2,4-dienes (arene oxides) to the corresponding trans-dihydrodiols. The reaction proceeds via a triad mechanism and involves the formation of an hydroxyalkyl-enzyme intermediate. Five epoxide-hydrolase enzymes have been identified in vertebrates to date: EC 3.3.2.6 (leukotriene-A4 hydrolase), EC 3.3.2.7 (hepoxilin-epoxide hydrolase), EC 3.3.2.9 (microsomal epoxide hydrolase), EC 3.3.2.10 (soluble epoxide hydrolase) and EC 3.3.2.11 (cholesterol-5,6-oxide hydrolase).
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Homo sapiens
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Word Map
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Synonyms
microsomal, meh, microsomal epoxide hydrolase, ephx1, mephx, microsomal eh, jh epoxide hydrolase, juvenile hormone epoxide hydrolase, microsomal epoxide hydrolase 1, xenobiotic epoxide hydrolase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
E1-b'
-
transcript
EPHX1
epoxide hydrolase
-
microsomal
-
microsomal EH
-
microsomal EPHX1
-
Microsomal epoxide hydrolase
-
microsomal epoxide hydrolase 1
-
PNSO hydrolase
-
-
additional information
-
microsomal epoxide hydrolase is a member of the family of epoxide hydrolases
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 SOURCE
PATHWAYS
SYSTEMATIC NAME
IUBMB Comments
cis-stilbene-oxide hydrolase
This is a key hepatic enzyme that catalyses the hydrolytic ring opening of oxiranes (epoxides) and oxetanes to give the corresponding diols. The enzyme is involved in the metabolism of numerous substrates including the stereoselective hydrolytic ring opening of 7-oxabicyclo[4.1.0]hepta-2,4-dienes (arene oxides) to the corresponding trans-dihydrodiols. The reaction proceeds via a triad mechanism and involves the formation of an hydroxyalkyl-enzyme intermediate. Five epoxide-hydrolase enzymes have been identified in vertebrates to date: EC 3.3.2.6 (leukotriene-A4 hydrolase), EC 3.3.2.7 (hepoxilin-epoxide hydrolase), EC 3.3.2.9 (microsomal epoxide hydrolase), EC 3.3.2.10 (soluble epoxide hydrolase) and EC 3.3.2.11 (cholesterol-5,6-oxide hydrolase).
CAS REGISTRY NUMBER
COMMENTARY hide
9048-63-9
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(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
show the 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
?
show the 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-[[3,3-bis(hydroxymethyl)azetidin-1-yl]methyl]phenoxy)azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
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
-
i.e. 11,12-EET
i.e. 11,12-DHET
-
?
(R)-styrene oxide + H2O
(1R)-1-phenylethane-1,2-diol
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
-
excellent and selective substrate for mEH
-
-
?
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
show the reaction diagram
-
-
-
ir
1-methyl-1-phenyloxirane + H2O
?
show the reaction diagram
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
show the reaction diagram
-
[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one
-
ir
11,12-epoxyeicosatrienoate + H2O
11,12-hydroxyeicosatrienoate
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-(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
show the reaction diagram
-
-
-
ir
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
-
?
2-chloroethylene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
3-methylcholanthrene 11,12-oxide + 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
-
-
?
7,12-dimethylbenz[a]anthracene + H2O
?
show the reaction diagram
-
-
-
-
?
aflatoxin-B1-8,9-exo-epoxide + H2O
?
show the reaction diagram
-
-
-
-
?
androstene oxide + H2O
?
show the reaction diagram
androstene oxide + H2O
androstene diol
show the reaction diagram
-
-
-
?
benzene + 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
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
benzopyrene 7,8-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzo[a]pyrene 5-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
benzo[a]pyrene 7,8-oxide + H2O
benzo[a]pyrene 7,8-diol
show the reaction diagram
-
-
-
?
benzo[a]pyrene-7,8-epoxide + H2O
benzo[a]pyrene-7,8-dihydrodiol
show the reaction diagram
-
-
-
-
?
benz[a]pyrene 4,5-oxide + H2O
4,5-dihydro-benzo[def]chrysene-4,5-diol
show the reaction diagram
-
-
-
-
?
butadiene + H2O
butadienol
show the reaction diagram
-
-
-
?
carbamazepine-10,11-epoxide + H2O
?
show the reaction diagram
-
-
-
-
?
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
?
show the reaction diagram
-
-
-
-
?
clofibrate + H2O
?
show the reaction diagram
-
-
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate + H2O
?
show the reaction diagram
-
synthetic fluorescent substrate
-
-
?
cyclohexene + H2O
cyclohexadiol
show the reaction diagram
-
-
-
?
cyclohexene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
di(2-ethylhexyl)phthalate + H2O
?
show the reaction diagram
-
-
-
-
?
dibenzanthracene 5,6-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
epoxy-stearic acid + H2O
?
show the reaction diagram
-
highly enantiospecific reaction, low activity
-
-
?
epoxyestratrienol + H2O
?
show the reaction diagram
-
-
-
?
epoxyestratrienol + H2O
dihydroxyestratrienol
show the reaction diagram
-
-
-
?
estroxide + H2O
?
show the reaction diagram
-
-
-
-
?
ethylene oxide + H2O
ethane-1,2-diol
show the reaction diagram
-
-
-
-
?
ethylene oxide + H2O
ethylene glycol
show the reaction diagram
-
-
-
?
indene 1,2-oxide + 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
-
-
-
-
?
p-nitrostyrene 7,8-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
phenanthrene-9,10-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
styrene + H2O
?
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 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-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
-
-
-
?
trans-stilbene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
[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
show the reaction diagram
-
-
-
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
show the reaction diagram
-
-
-
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
show the reaction diagram
-
-
-
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
show the reaction diagram
-
-
-
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
show the reaction diagram
-
-
-
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
show the reaction diagram
-
-
-
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
show the reaction diagram
-
-
-
ir
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
16,17-epoxyandrost-4-en-3-one + H2O
16,17-dihydroxyandrost-4-en-3-one
show the reaction diagram
-
high activity
-
-
?
androstene oxide + H2O
?
show the reaction diagram
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
epoxyestratrienol + H2O
?
show the reaction diagram
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Al3+
-
slight inhibition at 1 mM
Ba2+
-
15% inhibition at 1 mM
Ca2+
-
20% inhibition at 1 mM
Cd2+
-
20% inhibition at 1 mM
Co2+
-
20% inhibition at 1 mM
Cu2+
-
slight inhibition at 1 mM
Fe2+
-
40% activation at 1 mM
Fe3+
-
50% activation at 1 mM
Hg2+
-
90% inhibition at 1 mM
Mg2+
-
30% inhibition at 1 mM
Mn2+
-
10% inhibition at 1 mM
Ni2+
-
30% inhibition at 1 mM
Pb2+
-
10% inhibition at 1 mM
Zn2+
-
80% inhibition at 1 mM
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(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-diphenyloxirane
-
-
1,3-dicyclohexylurea
-
-
1,3-diphenylurea
-
-
1-isopropyl-1-phenyloxirane
-
-
1-methyl-1-phenyloxirane
-
-
1-methylcyclohexene 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
-
-
Al3+
-
slight inhibition at 1 mM
Ba2+
-
15% inhibition at 1 mM
Ca2+
-
20% inhibition at 1 mM
Cd2+
-
20% inhibition at 1 mM
cis-2-methyl-1-phenyloxirane
-
-
cis-stilbene oxide
-
-
Co2+
-
20% inhibition at 1 mM
Cyclohexene oxide
elaidamide
Hg2+
-
90% inhibition at 1 mM
indene 1,2-oxide
-
-
m-bromostyrene oxide
-
-
m-nitrostyrene oxide
-
-
methoxyarachidonyl fluorophosphate
-
-
methyl-p-epoxymethylbenzoate
-
-
Metyrapone
-
strong inhibition of hydration of benzopyrene 11,12-oxide and dibenzoanthracene 5,6-oxide
Mg2+
-
30% inhibition at 1 mM
Mn2+
-
10% inhibition at 1 mM
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
-
-
Ni2+
-
30% inhibition at 1 mM
p-bromostyrene oxide
-
-
p-chlorophenyl 2,3-epoxypropyl ether
-
-
p-nitrostyrene oxide
-
-
p-phenylstyrene oxide
-
-
Pb2+
-
10% inhibition at 1 mM
progabide
propene oxide
-
-
styrene oxide
-
-
trichloropropene oxide
-
-
urea derivatives
-
-
valpromide
Zn2+
-
80% inhibition at 1 mM
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-(2-cyanophenyl)-imidazole
-
2 mM, stimulates
1-(2-Isopropylphenyl)-imidazole
-
2 mM, stimulates
benzil
-
stimulates
clotrimazole
-
stimulates
ethanol
-
2.7 M, stimulates
hepatitis B spliced protein
enhances hydrolysis activity of microsomal epoxide hydrolase
-
Metyrapone
N-acetylaminofluorene
-
-
Phenobarbitone
-
-
Phospholipids
-
the enzyme is tightly associated with phospholipids
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.542
(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
-
at pH 7.4 and 37°C
0.352
1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine
pH 7.4, 37°C, liver microsomes
0.139 - 0.684
2-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine
0.042
2-arachidonoylglycerol
-
at pH 7.4 and 37°C
0.012
4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate
-
pH 9.0, 37°C
0.004 - 0.141
cis-stilbene oxide
0.0038
cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate
-
pH 9.0, 37°C
0.98
styrene 7,8-oxide
-
-
0.027 - 0.067
[3-[4-([((3-methyloxetan-3-yl)methyl)amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone
0.028 - 0.089
[3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone
0.05 - 0.051
[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone
0.026 - 0.047
[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00007
elaidamide
0.061
Zn2+
-
pH 7.4, 37°C, competitive inhibition type
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001 - 0.14
(9E)-octadec-9-enamide
0.00016
1,3-dicyclohexylurea
Homo sapiens
-
pH and temperature not specified in the publication
0.0012
1,3-diphenylurea
Homo sapiens
-
pH and temperature not specified in the publication
0.0026 - 0.2
12-hydroxyoctadecanamide
0.0005 - 0.006
2-(nonylsulfanyl)propanamide
0.0000079
methoxyarachidonyl fluorophosphate
Homo sapiens
-
at pH 7.4 and 37°C
0.00235
N-(phenylcarbamothioyl)acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00129
N-(phenylcarbamothioyl)benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00207
N-(pyridin-4-ylcarbamothioyl)acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00228
N-(pyridin-4-ylcarbamothioyl)benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0027
N-(tert-butylcarbamothioyl)acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00158
N-(tert-butylcarbamothioyl)benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00112
N-acetyl-N'-adamantyl thiourea
Homo sapiens
-
pH and temperature not specified in the publication
0.00139
N-acetyl-N'-[(3-trifluoromethyl-4-bromo)phenyl] thiourea
Homo sapiens
-
pH and temperature not specified in the publication
0.00101
N-benzoyl-N'-adamantyl thiourea
Homo sapiens
-
pH and temperature not specified in the publication
0.00117
N-benzoyl-N'-[(3-trifluoromethyl-4-bromo)phenyl] thiourea
Homo sapiens
-
pH and temperature not specified in the publication
0.00229
N-[(2,6-dichlorophenyl)carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00215
N-[(2,6-dichlorophenyl)carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00253
N-[(2,6-diethoxyphenyl)carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00204
N-[(2,6-diethoxyphenyl)carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00169
N-[(2-methoxy-4-methylphenyl)carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00254
N-[(2-methoxy-4-methylphenyl)carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00187
N-[(2-methoxy-4-nitrophenyl)carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00165
N-[(2-methoxy-4-nitrophenyl)carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0015
N-[(2-methylphenyl)carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00354
N-[(2-methylphenyl)carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00242
N-[(4-bromonaphthalen-1-yl)carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00188
N-[(4-bromonaphthalen-1-yl)carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00164
N-[(4-bromophenyl)carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00344
N-[(4-bromophenyl)carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00221
N-[(4-chlorophenyl)carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00164
N-[(4-chlorophenyl)carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0037
N-[(4-phenoxyphenyl)carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0021
N-[(4-phenoxyphenyl)carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00259
N-[[4-(morpholin-4-yl)phenyl]carbamothioyl]acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00172
N-[[4-(morpholin-4-yl)phenyl]carbamothioyl]benzamide
Homo sapiens
-
pH and temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.021
-
substrate 4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate, pH 9.0, 37°C
0.025
-
substrate cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate, pH 9.0, 37°C
0.0272
-
-
0.051
-
substrate 4-nitrophenyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate, pH 9.0, 37°C
0.072
-
substrate 4-nitrophenyl 3-(oxiran-2-yl)propanoate, pH 9.0, 37°C
0.118
-
-
0.121
-
-
0.618
-
-
additional information
-
several analytical and activity assay methods
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8 - 9
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
synovial blood vessels and lining cells
Manually annotated by BRENDA team
-
numerous cancer cell lines and primary cells
Manually annotated by BRENDA team
-
bronchial
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
-
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
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
in neoplastic livers
Manually annotated by BRENDA team
type I enzyme form, microsomal epoxide hydrolase (mEH) is expressed on the hepatocyte endoplasmic reticulum membrane in two distinct topological orientations
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
additional information
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
microsomal epoxide hydrolase (EPHX1) is an evolutionarily highly conserved biotransformation enzyme for converting epoxides to diols. EPHX1 belongs to the family of alpha/beta hydrolases
malfunction
metabolism
physiological function
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
HYEP_HUMAN
455
0
52949
Swiss-Prot
Secretory Pathway (Reliability: 2)
Q6FGZ3_HUMAN
455
0
52961
TrEMBL
Secretory Pathway (Reliability: 2)
R4SBI6_HUMAN
455
0
52949
TrEMBL
Secretory Pathway (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
130000
-
gel filtration
49000
-
x * 49000, SDS-PAGE
50000
51000
-
x * 51000, SDS-PAGE
53000
-
x * 53000, calculated from amino acid sequence
58000
-
x * 58000, SDS-PAGE
additional information
-
-
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
-
additional information
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
-
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
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
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
Y133H
-
naturally occuring mutation, frequencies in hepatocellular carcinoma, controls, and the chronic viral hepatitis subjects, respectively, overview
additional information
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, stable for at least 3 months
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hydrophobic chromatography: a one-step method
-
multiple enzyme forms
-
partial
-
partially from liver
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
-
gene EPHX1, located on chromosome 1 (1q42.12) consists of nine exons, and spans about 35 kb, exons 2-9 of EPHX1 encode three transcription variants differing in the 5'-untranslated region, while each translated protein product has 455 amino acids. Human EPHX1 expression in the liver is selectively driven by the proximal E1 promoter, but an alternative promoter region (E1-b promoter) drives expression in other tissues from both adult and fetal sources, e.g. an EPHX1 transcript (E1-b') generated from the upstream promoter is reported to be expressed in a tissue-selective manner with the highest level in human ovary. The E1-b promoter region harbors several functionally important polymorphisms including a double Alu insertion, which may influence interindividual susceptibility to toxicity of xenobiotics
gene EPHX1, mEH genotyping
gene EPHX1, sequencing of the EPHX1 5' region (-784/-1), 9 exons, intron 1, exon intron boundaries and the 3' untranslated region, analysis of EPHX1 transcriptional activity mediated by the proximal promoter region in HepG2 cells
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
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
CEBPA (116897) interacts with DNA-bound NFY (A subunit, 189903, B subunit, 189904, C subunit, 605344) as an additional regulator of EPHX1 expression. Nuclear receptors HNF4A (600281), CAR (NR1I3, 603881), and RXR (RXRA, 180245 and RXRB, 180246) also bind to the proximal EPHX1 promoter region and regulate its expression in human hepatocytes
GATA4 (OMIM: 600576) is the major activator of EPHX1 expression. EPHX1 expression is induced by phenobarbital, beta-naphthoflavone, benzanthracene, and trans-stilbene oxide in human fetal hepatocytes in vitro
HNF3 (FOXA1, 602294 and FOXB1, 600288) acts as a co-repressor in HepG2 cells
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
-
mEH expression is regulated by progesterone, but only in the presence of the progesterone receptors as well as estrogene receptor alpha, overview
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Wixtrom, R.N.; Hammock, B.D.
Membrane-bound and soluble-fraction epoxide hydrolases
Biochem. Pharmacol. Toxicol.
1
1-93
1985
Oryctolagus cuniculus, Homo sapiens, Macaca mulatta, Mus musculus, Rattus norvegicus
-
Manually annotated by BRENDA team
Lu, A.Y.H.; Miwa, G.T.
Molecular properties and biological functions of microsomal epoxide hydrase
Annu. Rev. Pharmacol. Toxicol.
20
513-531
1980
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Oesch, F.
Epoxide hydratase
Mises Point Biochim. Pharmacol.
1
127-148
1977
Cavia porcellus, Oryctolagus cuniculus, Homo sapiens, Macaca mulatta, Mus musculus, Rattus norvegicus
-
Manually annotated by BRENDA team
Oesch, F.
Purification and specificity of a human microsomal epoxide hydratase
Biochem. J.
139
77-88
1974
Cavia porcellus, Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Lu, A.Y.H.; Thomas, P.E.; Ryan, D.; Jerina, D.M.; Levin, W.
Purification of human liver microsomal epoxide hydrase. Differences in the properties of the human and rat enzymes
J. Biol. Chem.
254
5878-5881
1979
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Guengerich, F.P.; Wang, P.; Mitchell, M.B.; Mason, P.S.
Rat and human liver microsomal epoxide hydratase. Purification and evidence for the existence of multiple forms
J. Biol. Chem.
254
12248-12254
1979
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Wang, P.; Meijer, J.; Guengerich, F.P.
Purification of human liver cytosolic epoxide hydrolase and comparison to the microsomal enzyme
Biochemistry
21
5769-5776
1982
Homo sapiens
Manually annotated by BRENDA team
Guengerich, F.P.
Epoxide hydratase: properties and metabolic roles
Rev. Biochem. Toxicol.
4
5-30
1982
Bos taurus, Cavia porcellus, Homo sapiens, Mus musculus, Rattus norvegicus
-
Manually annotated by BRENDA team
Papadopoulos, D.; Seidegard, J.; Georgellis, A.; Rydstroem, J.
Subcellular distribution, catalytic properties and partial purification of epoxide hydrolase in the human adrenal gland
Chem. Biol. Interact.
55
249-260
1985
Homo sapiens
Manually annotated by BRENDA team
Meijer, J.; Lundqvist, G.; DePierre, J.W.
Comparison of the sex and subcellular distributions, catalytic and immunochemical reactivities of hepatic epoxide hydrolases in seven mammalian species
Eur. J. Biochem.
167
269-279
1987
Cavia porcellus, Oryctolagus cuniculus, Cricetinae, Homo sapiens, Platyrrhini, Mus musculus
Manually annotated by BRENDA team
Beaune, P.H.; Cresteil, T.; Flinois, J.P.; Leroux, J.P.
Hydrophobic chromatography: a one-step method for the purification of human liver microsomal epoxide hydrolase
J. Chromatogr.
426
169-176
1988
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Morisseau, C.; Hammock, B.D.
Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles
Annu. Rev. Pharmacol. Toxicol.
45
311-333
2005
Homo sapiens, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Robien, K.; Curtin, K.; Ulrich, C.M.; Bigler, J.; Samowitz, W.; Caan, B.; Potter, J.D.; Slattery, M.L.
Microsomal epoxide hydrolase polymorphisms are not associated with colon cancer risk
Cancer Epidemiol. Biomarkers Prev.
14
1350-1352
2005
Homo sapiens
Manually annotated by BRENDA team
Lin, Y.C.; Wu D.C.; Lee, J.M.; Hsu, H.K.; Kao, E.L.; Yang, C.H.; Wu, M.T.
The association between microsomal epoxide hydrolase genotypes and esophageal sqamous-cell-carcinoma in Taiwan: interaction between areca chewing and smoking
Cancer Lett.
237
281-288
2006
Homo sapiens
Manually annotated by BRENDA team
Liu, M.; Sun, A.; Shin, E.J.; Liu, X.; Kim, S.G.; Runyons, C.R.; Markesbery, W.; KIm, H.C.; Bing, G.
Expression of microsomal epoxide hydrolase is elevated in Alzheimer's hippocampus and induced by exogenous beta-amyloid and trimethyl-tin
Eur. J. Neurosci.
23
2027-2034
2006
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Park, J.Y.; Chen, L.; Wadhwa, N.; Tockman, M.S.
Polymorphisms for microsomal epoxide hydrolase and genetic susceptibility to COPD
Int. J. Mol. Med.
15
443-448
2005
Homo sapiens
Manually annotated by BRENDA team
Liang, S.H.; Hassett, C.; Omiecinski, C.J.
Alternative promoters determine tissue-specific expression profiles of the human microsomal epoxide hydrolase gene (EPHX1)
Mol. Pharmacol.
67
220-230
2005
Homo sapiens (P07099), Homo sapiens
Manually annotated by BRENDA team
Newman, J.W.; Morisseau, C.; Hammock, B.D.
Epoxide hydrolases: their roles and interactions with lipid metabolism
Prog. Lipid Res.
44
1-51
2005
Homo sapiens, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Lewis, D.F.V.; Lake, B.G.; Bird, M.G.
Molecular modelling of human microsomal epoxide hydrolase (EH) by homology with fungal (Aspergillus niger) EH crystal structure of 1.8 A resolution: structure-activity relationships in epoxides inhibiting EH activity
Toxicol. In Vitro
19
517-522
2005
Homo sapiens
Manually annotated by BRENDA team
Draper, A.J.; Hammock, B.D.
Inhibition of soluble and microsomal epoxide hydrolase by zinc and other metals
Toxicol. Sci.
52
26-32
1999
Homo sapiens, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Cornelis, M.C.; El-Sohemy, A.; Campos, H.
Microsomal epoxide hydrolase genotype and risk of myocardial infarction
Arch. Toxicol.
81
641-645
2007
Homo sapiens
Manually annotated by BRENDA team
Mittal, R.D.; Srivastava, D.L.
Cytochrome P4501A1 and microsomal epoxide hydrolase gene polymorphisms: gene-environment interaction and risk of prostate cancer
DNA Cell Biol.
26
791-798
2007
Homo sapiens
Manually annotated by BRENDA team
Matheson, M.C.; Raven, J.; Walters, E.H.; Abramson, M.J.; Ellis, J.A.
Microsomal epoxide hydrolase is not associated with COPD in a community-based sample
Hum. Biol.
78
705-717
2006
Homo sapiens
Manually annotated by BRENDA team
Ada, A.O.; Suzen, H.S.; Iscan, M.
Polymorphisms of microsomal epoxide hydrolase and glutathione S-transferase P1 in a male Turkish population
Int. J. Toxicol.
26
41-46
2007
Homo sapiens
Manually annotated by BRENDA team
Lin, T.S.; Huang, H.H.; Fan, Y.H.; Chiou, S.H.; Chow, K.C.
Genetic polymorphism and gene expression of microsomal epoxide hydrolase in non-small cell lung cancer
Oncol. Rep.
17
565-572
2007
Homo sapiens (P07099), Homo sapiens
Manually annotated by BRENDA team
Salam, M.T.; Lin, P.C.; Avol, E.L.; Gauderman, W.J.; Gilliland, F.D.
Microsomal epoxide hydrolase, glutathione S-transferase P1, traffic and childhood asthma
Thorax
62
1050-1057
2007
Homo sapiens
Manually annotated by BRENDA team
Chappell, S.; Daly, L.; Morgan, K.; Guetta-Baranes, T.; Roca, J.; Rabinovich, R.; Lotya, J.; Millar, A.B.; Donnelly, S.C.; Keatings, V.; MacNee, W.; Stolk, J.; Hiemstra, P.S.; Miniati, M.; Monti, S.; OConnor, C.M.; Kalsheker, N.
Genetic variants of microsomal epoxide hydrolase and glutamate-cysteine ligase in COPD
Eur. Respir. J.
32
931-937
2008
Homo sapiens
Manually annotated by BRENDA team
Srivastava, D.S.; Mandhani, A.; Mittal, R.D.
Genetic polymorphisms of cytochrome P450 CYP1A1 (*2A) and microsomal epoxide hydrolase gene, interactions with tobacco-users, and susceptibility to bladder cancer: a study from North India
Arch. Toxicol.
82
633-639
2008
Homo sapiens
Manually annotated by BRENDA team
Decker, M.; Arand, M.; Cronin, A.
Mammalian epoxide hydrolases in xenobiotic metabolism and signalling
Arch. Toxicol.
83
297-318
2009
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Cheong, A.W.; Lee, Y.L.; Liu, W.M.; Yeung, W.S.; Lee, K.F.
Oviductal microsomal epoxide hydrolase (EPHX1) reduces reactive oxygen species (ROS) level and enhances preimplantation mouse embryo development
Biol. Reprod.
81
126-132
2009
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Zidzik, J.; Slaba, E.; Joppa, P.; Kluchova, Z.; Dorkova, Z.; Skyba, P.; Habalova, V.; Salagovic, J.; Tkacova, R.
Glutathione S-transferase and microsomal epoxide hydrolase gene polymorphisms and risk of chronic obstructive pulmonary disease in Slovak population
Croat. Med. J.
49
182-191
2008
Homo sapiens
Manually annotated by BRENDA team
Kiran, M.; Chawla, Y.K.; Kaur, J.
Glutathione-S-transferase and microsomal epoxide hydrolase polymorphism and viral-related hepatocellular carcinoma risk in India
DNA Cell Biol.
27
687-694
2008
Homo sapiens
Manually annotated by BRENDA team
Lacko, M.; Roelofs, H.M.; Te Morsche, R.H.; Voogd, A.C.; Oude Ophuis, M.B.; Peters, W.H.; Manni, J.J.
Microsomal epoxide hydrolase genotypes and the risk for head and neck cancer
Head Neck
30
836-844
2008
Homo sapiens
Manually annotated by BRENDA team
Yang, X.; Liang, S.H.; Weyant, D.M.; Lazarus, P.; Gallagher, C.J.; Omiecinski, C.J.
The expression of human microsomal epoxide hydrolase is predominantly driven by a genetically polymorphic far upstream promoter
J. Pharmacol. Exp. Ther.
330
23-30
2009
Homo sapiens
Manually annotated by BRENDA team
Graziano, C.; Comin, C.E.; Crisci, C.; Novelli, L.; Politi, L.; Messerini, L.; Andreani, M.; Porfirio, B.
Functional polymorphisms of the microsomal epoxide hydrolase gene: a reappraisal on a early-onset lung cancer patients series
Lung Cancer
63
187-193
2009
Homo sapiens
Manually annotated by BRENDA team
Pushparajah, D.S.; Umachandran, M.; Plant, K.E.; Plant, N.; Ioannides, C.
Differential response of human and rat epoxide hydrolase to polycyclic aromatic hydrocarbon exposure: studies using precision-cut tissue slices
Mutat. Res.
640
153-161
2008
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Ockenga, J.; Strunck, S.; Post, C.; Schulz, H.U.; Halangk, J.; Pfuetzer, R.H.; Loehr, M.; Oettle, H.; Kage, A.; Rosendahl, J.; Keim, V.; Drenth, J.P.; Jansen, J.B.; Lochs, H.; Witt, H.
The role of epoxide hydrolase Y113H gene variant in pancreatic diseases
Pancreas
38
e97-e101
2009
Homo sapiens
Manually annotated by BRENDA team
Morisseau, C.; Hammock, B.D.
Gerry Brooks and epoxide hydrolases: four decades to a pharmaceutical
Pest Manag. Sci.
64
594-609
2008
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Hu, G.; Shi, Z.; Hu, J.; Zou, G.; Peng, G.; Ran, P.
Association between polymorphisms of microsomal epoxide hydrolase and COPD: results from meta-analyses
Respirology
13
837-850
2008
Homo sapiens
Manually annotated by BRENDA team
Jain, M.; Tilak, A.R.; Upadhyay, R.; Kumar, A.; Mittal, B.
Microsomal epoxide hydrolase (EPHX1), slow (exon 3, 113His) and fast (exon 4, 139Arg) alleles confer susceptibility to squamous cell esophageal cancer
Toxicol. Appl. Pharmacol.
230
247-251
2008
Homo sapiens
Manually annotated by BRENDA team
Makmor-Bakry, M.; Sills, G.J.; Hitiris, N.; Butler, E.; Wilson, E.A.; Brodie, M.J.
Genetic variants in microsomal epoxide hydrolase influence carbamazepine dosing
Clin. Neuropharmacol.
32
205-212
2009
Homo sapiens
Manually annotated by BRENDA team
Kiran, M.; Chawla, Y.K.; Jain, M.; Kaur, J.
Haplotypes of microsomal epoxide hydrolase and x-ray cross-complementing group 1 genes in Indian hepatocellular carcinoma patients
DNA Cell Biol.
28
573-577
2009
Homo sapiens
Manually annotated by BRENDA team
Lee, J.; Nordestgaard, B.G.; Dahl, M.
EPHX1 polymorphisms, COPD and asthma in 47,000 individuals and in meta-analysis
Eur. Respir. J.
37
18-25
2011
Homo sapiens
Manually annotated by BRENDA team
Popp, S.L.; Abele, I.S.; Buck, M.B.; Stope, M.B.; Blok, L.J.; Hanifi-Moghaddam, P.; Burger, C.W.; Fritz, P.; Knabbe, C.
Microsomal epoxide hydrolase expression in the endometrial uterine corpus is regulated by progesterone during the menstrual cycle
J. Mol. Histol.
41
111-119
2010
Homo sapiens
Manually annotated by BRENDA team
Morisseau, C.; Bernay, M.; Escaich, A.; Sanborn, J.R.; Lango, J.; Hammock, B.D.
Development of fluorescent substrates for microsomal epoxide hydrolase and application to inhibition studies
Anal. Biochem.
414
154-162
2011
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Chen, J.Y.; Chen, W.N.; Jiao, B.Y.; Lin, W.S.; Wu, Y.L.; Liu, L.L.; Lin, X.
Hepatitis B spliced protein (HBSP) promotes the carcinogenic effects of benzo [alpha] pyrene by interacting with microsomal epoxide hydrolase and enhancing its hydrolysis activity
BMC Cancer
14
282
2014
Mus musculus, Homo sapiens (P07099)
Manually annotated by BRENDA team
Nithipatikom, K.; Endsley, M.P.; Pfeiffer, A.W.; Falck, J.R.; Campbell, W.B.
A novel activity of microsomal epoxide hydrolase: metabolism of the endocannabinoid 2-arachidonoylglycerol
J. Lipid Res.
55
2093-2102
2014
Homo sapiens
Manually annotated by BRENDA team
Shen, W.; Fang, Y.; Tong, A.; Zhu, Q.
Synthesis and structure-activity relationship of acylthiourea derivatives as inhibitors of microsomal epoxide hydrolase
Med. Chem. Res.
21
4214-4218
2012
Homo sapiens
-
Manually annotated by BRENDA team
Nguyen, H.L.; Yang, X.; Omiecinski, C.J.
Expression of a novel mRNA transcript for human microsomal epoxide hydrolase (EPHX1) is regulated by short open reading frames within its 5-untranslated region
RNA
19
752-766
2013
Homo sapiens
Manually annotated by BRENDA team
Duan, H.; Takagi, A.; Kayano, H.; Koyama, I.; Morisseau, C.; Hammock, B.D.; Akatsuka, T.
Monoclonal antibodies reveal multiple forms of expression of human microsomal epoxide hydrolase
Toxicol. Appl. Pharmacol.
260
27-34
2012
Homo sapiens
Manually annotated by BRENDA team
Li, X.Q.; Hayes, M.A.; Groenberg, G.; Berggren, K.; Castagnoli, N.Jr.; Weidolf, L.
Discovery of a novel microsomal epoxide hydrolase-catalyzed hydration of a spiro oxetane
Drug Metab. Dispos.
44
1341-1348
2016
Homo sapiens
Manually annotated by BRENDA team
Toselli, F.; Fredenwall, M.; Svensson, P.; Li, X.Q.; Johansson, A.; Weidolf, L.; Hayes, M.A.
Oxetane substrates of human microsomal epoxide hydrolase
Drug Metab. Dispos.
45
966-973
2017
Homo sapiens (P07099), Homo sapiens
Manually annotated by BRENDA team
Vaclavikova, R.; Hughes, D.J.; Soucek, P.
Microsomal epoxide hydrolase 1 (EPHX1) Gene, structure, function, and role in human disease
Gene
571
1-8
2015
Agrobacterium tumefaciens (O31243), Homo sapiens (P07099), Homo sapiens, Aspergillus niger (Q5EC68), Mus musculus (Q9D379)
Manually annotated by BRENDA team
Levy, D.
The role of microsomal epoxide hydrolase, Na+-taurocholate cotransporting polypeptide, and organic anion transporting polypeptide in hepatic sodium-dependent bile acid transport
Hepatology
67
1184-1185
2018
Homo sapiens (P07099)
Manually annotated by BRENDA team
Yamanashi, H.; Boeglin, W.E.; Morisseau, C.; Davis, R.W.; Sulikowski, G.A.; Hammock, B.D.; Brash, A.R.
Catalytic activities of mammalian epoxide hydrolases with cis and trans fatty acid epoxides relevant to skin barrier function
J. Lipid Res.
59
684-695
2018
Homo sapiens (P07099)
Manually annotated by BRENDA team
Nabi, S.; Bhat, G.A.; Iqbal, B.; Lone, M.M.; Lone, G.N.; Khan, M.A.; Dar, N.A.
Association of activity altering genotypes - Tyr113His and His139Arg in microsomal epoxide hydrolase enzyme with esophageal squamous cell carcinoma
Nutr. Cancer
71
806-817
2019
Homo sapiens (P07099), Homo sapiens
Manually annotated by BRENDA team
Peng, H.; Zhu, Q.S.; Zhong, S.; Levy, D.
Transcription of the human microsomal epoxide hydrolase gene (EPHX1) is regulated by PARP-1 and histone H1.2. association with sodium-dependent Bile acid transport
PLoS ONE
10
e0125318
2015
Homo sapiens (P07099), Homo sapiens
Manually annotated by BRENDA team
Saenz-Mendez, P.; Katz, A.; Perez-Kempner, M.L.; Ventura, O.N.; Vazquez, M.
Structural insights into human microsomal epoxide hydrolase by combined homology modeling, molecular dynamics simulations, and molecular docking calculations
Proteins
85
720-730
2017
Homo sapiens (P07099), Homo sapiens
Manually annotated by BRENDA team