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
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3.3.2.9
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phenobarbital
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cholesterol
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phospholipid
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hepatocytes
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monooxygenase
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hydroxylase
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triglyceride
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xenobiotics
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steroid
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nadph-cytochrome
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thyroid
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isozymes
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lipoprotein
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s-transferase
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testosterone
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aniline
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benzoapyrene
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phosphatidylcholine
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glucuronidation
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3-methylcholanthrene
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bile
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drug-metabolizing
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arachidonic
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prostaglandin
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acyltransferase
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heme
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hepatotoxicity
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nadph-dependent
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cyp2e1
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gsh
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autoimmune
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apolipoprotein
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cyp1a2
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autoantibody
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biphenyls
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polycyclic
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udp-glucuronosyltransferase
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monoxide
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glucose-6-phosphatase
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tetrachloride
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polychlorinated
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thyroglobulin
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ketoconazole
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demethylase
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ccl4
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desaturation
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n-oxide
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androstenedione
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beta-hydroxysteroid
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21-hydroxylase
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synthesis
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medicine
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drug development
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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
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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
3.3.2.9 microsomal epoxide hydrolaseAdvanced search results
results (
results (Activating Compound
Activating Compound on EC 3.3.2.9 - microsomal epoxide hydrolase
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ACTIVATING COMPOUND 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
(R)-1-(2,3-dihydro-1H-inden-1-yl)-3-(3-phenylpropyl)urea
10% activation at 0.01 mM
(R)-1-(2-hydroxy-1-phenylethyl)-3-(3-phenylpropyl)urea
7% activation at 0.01 mM
(R)-1-(3-phenylpropyl)-3-(1,2,3,4-tetrahydronaphthalen-1-yl)urea
6% activation at 0.01 mM
(S)-1-(1-phenylpropyl)-3-(3-phenylpropyl)urea
6% activation at 0.01 mM
(S)-1-(2,3-dihydro-1H-inden-1-yl)-3-(3-phenylpropyl)urea
12% activation at 0.01 mM
(S)-1-(3-phenylpropyl)-3-(1,2,3,4-tetrahydronaphthalen-1-yl)urea
6% activation at 0.01 mM
3-methylcholanthrene
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enhances nuclear hydration of phenanthrene-9,10-oxide, benzopyrene-11,12-oxide and octene-1,2-oxide, no significant effect on microsomal hydration
CHAPS
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stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
cytochrome P450
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activation of microsomal epoxide hydrolase by interaction with cytochromes P450
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Digitonin
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stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
dodecyl maltoside
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stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
erucin
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exposure of liver slices to erucin results in elevated glucuronosyl transferase and epoxide hydrolase activities and expression
glucoerucin
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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
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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
octyl-glucoside
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stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
phenethyl isothiocyanate
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exposure of liver slices to phenethyl isothiocyanate results in elevated glucuronosyl transferase and epoxide hydrolase activities and expression
Phenobarbital
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enhances nuclear and microsomal hydration of phenanthrene-9,10-oxide, benzopyrene-11,12-oxide and octene-1,2-oxide
R-sulforaphane
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exposure of liver slices to R-sulforaphane causes a marked increase in the activity and expression of the microsomal epoxide hydrolase
sucrose monolaurate
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stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
Thesit
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stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
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Zwittergent 3-12
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stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
hepatitis B spliced protein
enhances hydrolysis activity of microsomal epoxide hydrolase
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hepatitis B spliced protein
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enhances hydrolysis activity of microsomal epoxide hydrolase
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Metyrapone
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great stimulation of hydration of styrene 7,8-oxide and octene 1,2-oxide, slight stimulation of hydration of benzopyrane 4,5-oxide
additional information
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enzyme expression is induced by exogenous beta-amyloid and trimethyl-tin, a neurotoxic agent, beta-amyloid aggregation induces enzyme expression in astrocytes
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additional information
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induction of the enzyme by clofibrate and di(2-ethylhexyl)phthalate
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additional information
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benzo[a]pyrene, dibenzo[a,h]anthracene and fluoranthene give rise to a statistically significant increase in epoxide hydrolase activity, which is accompanied by a concomitant increase in epoxide hydrolase protein levels, dibenzo[a,l]pyrene, benzo[b]fluoranthene and 1-methylphenanthrene, influence neither activity nor enzyme protein levels
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additional information
minimally altering the structural elements in the immediate vicinity of the oxetane can greatly modulate the efficiency of hydrolytic ring cleavage. In particular, higher pKa in the vicinity of the oxetane and an increased distance between the oxetane ring and the benzylic nitrogen improve reaction rate, which is further enhanced by the presence of methyl groups near or on the oxetane
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additional information
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minimally altering the structural elements in the immediate vicinity of the oxetane can greatly modulate the efficiency of hydrolytic ring cleavage. In particular, higher pKa in the vicinity of the oxetane and an increased distance between the oxetane ring and the benzylic nitrogen improve reaction rate, which is further enhanced by the presence of methyl groups near or on the oxetane
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additional information
substituted imidazole, metyrapone, and ethanol activate EPHX1 in vitro
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additional information
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substituted imidazole, metyrapone, and ethanol activate EPHX1 in vitro
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additional information
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induction of the enzyme by clofibrate and di(2-ethylhexyl)phthalate
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additional information
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induction of the enzyme by clofibrate and di(2-ethylhexyl)phthalate
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additional information
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4-vinylcyclohexene diepoxide (0.005 mM) causes an increase in mEH mRNA by 0.5fold at day 10
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additional information
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increased expression of mEH mRNA is detected after 4 days of 4-vinylcyclohexene diepoxide exposure
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additional information
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mEH expression is up-regulated after 1-methyl-4-phemyl-1,2,3,6-tetrahydropyridine intoxication
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additional information
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induction of the enzyme by clofibrate and di(2-ethylhexyl)phthalate
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additional information
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maximal activity with dimethyl formamide as co-solvent, effects of solvents on enzyme activity, overview
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additional information
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enzyme expression is induced by neurotoxic agent trimethyl-tin in hippocampus and entorhinal cortex
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additional information
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induction of the enzyme by clofibrate and di(2-ethylhexyl)phthalate
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additional information
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insulin increases enzyme activity in hepatocyte cell culture
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additional information
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no effect by cholestyramine and clofibrate, phenobarbital and isosafrole induce the enzyme expression, it is also induced by trans-stilbene oxide, gamma-chlordane, Aroclor 1254, and 2-acetylamineo-fluorene in liver microsomes
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additional information
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benzo[a]pyrene, dibenzo[a,h]anthracene and fluoranthene give rise to a statistically significant increase in epoxide hydrolase activity, which is accompanied by a concomitant increase in epoxide hydrolase protein levels, dibenzo[a,l]pyrene, benzo[b]fluoranthene and 1-methylphenanthrene, influence neither activity nor enzyme protein levels
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