3.3.2.10: soluble epoxide hydrolase
This is an abbreviated version!
For detailed information about soluble epoxide hydrolase, go to the full flat file.
Word Map on EC 3.3.2.10
-
3.3.2.10
-
epoxyeicosatrienoic
-
arachidonic
-
diol
-
s-transferase
-
hydrolases
-
hypertension
-
benzoapyrene
-
epoxygenase
-
styrene
-
dihydroxyeicosatrienoic
-
enantioselectivity
-
phenobarbital
-
dhets
-
trans-stilbene
-
leukotriene
-
eicosanoids
-
drug-metabolizing
-
cyp1a1
-
3-methylcholanthrene
-
o-deethylase
-
oxylipins
-
xenobiotic-metabolizing
-
dihydrodiols
-
enantiopure
-
ethoxyresorufin
-
lta4
-
glycidyl
-
arene
-
urea-based
-
cyclohexene
-
ethoxycoumarin
-
medicine
-
beta-naphthoflavone
-
oxirane
-
20-hydroxyeicosatetraenoic
-
udp-glucuronyltransferase
-
20-hete
-
cyp2j2
-
udp-glucuronosyl
-
1-naphthol
-
aminopyrine
-
edhfs
-
analysis
-
radiobacter
-
3-methylcholanthrene-treated
-
butadiene
-
udpgt
-
hydroxyeicosatetraenoic
-
epichlorohydrin
-
aldrin
-
synthesis
-
pentoxyresorufin
-
drug development
-
agriculture
-
adamantyl
-
pharmacology
- 3.3.2.10
-
epoxyeicosatrienoic
-
arachidonic
- diol
- s-transferase
- hydrolases
- hypertension
-
benzoapyrene
- epoxygenase
- styrene
-
dihydroxyeicosatrienoic
-
enantioselectivity
- phenobarbital
-
dhets
- trans-stilbene
-
leukotriene
-
eicosanoids
-
drug-metabolizing
- cyp1a1
- 3-methylcholanthrene
-
o-deethylase
- oxylipins
-
xenobiotic-metabolizing
-
dihydrodiols
-
enantiopure
-
ethoxyresorufin
- lta4
-
glycidyl
- arene
-
urea-based
- cyclohexene
-
ethoxycoumarin
- medicine
- beta-naphthoflavone
-
oxirane
-
20-hydroxyeicosatetraenoic
-
udp-glucuronyltransferase
- 20-hete
- cyp2j2
-
udp-glucuronosyl
- 1-naphthol
- aminopyrine
-
edhfs
- analysis
- radiobacter
-
3-methylcholanthrene-treated
- butadiene
-
udpgt
-
hydroxyeicosatetraenoic
- epichlorohydrin
- aldrin
- synthesis
-
pentoxyresorufin
- drug development
- agriculture
-
adamantyl
- pharmacology
Reaction
Synonyms
AnEH, BNSEH1, CEH, Cterm-EH, Cytosolic epoxide hydrolase, EC 3.1.3.76, EC 3.3.2.3, EC 4.2.1.63, EC 4.2.1.64, EET-metabolizing enzyme, EH, EH3, EPHX2, EPHX3, epoxide hydrolase 1, epoxide hydrolase 2, epoxide hydrolase-3, epoxyeicosatrienonic acid-metabolizing enzyme, EPXH1, EPXH2, EPXH2B, hepoxilin hydrolase, hsEH, mEH, More, PNSO hydrolase, PsEH, s-EH, SEH, soluble epoxide hydrolase, soluble-type epoxide hydrolase, SPEH1, SPEH2, TESO hydrolase, TSO hydrolase
ECTree
3.3.2.10 soluble epoxide hydrolaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 3.3.2.10 - soluble epoxide hydrolase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid + H2O
(10R,11R,12S)-trihydroxy-(5Z,8Z,14Z)-eicosatrienoic acid
(11S,12S)-epoxy-5,14-cis-7,9-trans-eicosatetraenoic acid + H2O
(11R,12S)-dihydroxy-5,14-cis-7,9-trans-eicosatetraenoic acid + H2O
-
i.e. 11,12-leukotriene A4
-
?
(12Z)-9,10-epoxyoctadec-12-enoic acid
(12Z)-9,10-dihydroxyoctadec-12-enoic acid
-
-
-
?
(1S,2S)-beta-methylstyrene oxide + H2O
?
enzyme attacks almost exclusively at the benzylic position
-
-
?
(1S,2S)-trans-methylstyrene oxide + H2O
?
a hydrogen bond from Tyr465 to the substrate oxygen is essential for controlling the regioselectivity of the reaction
-
-
r
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
6-methoxy-2-naphthaldehyde + ?
-
substrate for high-throughput screen
product is fluorescent
-
?
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
?
-
-
-
-
?
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxynaphthalen-2-yl)-methyl ester + H2O
6-methoxy-2-naphthaldehyde + ?
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
(5Z,11Z,14Z)-8,9-epoxyeicosa-8,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
(5Z,8Z)-N-((2-methoxy-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)sulfonyl)-10-(3-((Z)-oct-2-en-1-yl)oxiran-2-yl)deca-5,8-dienamide + H2O
?
-
-
-
?
(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,11Z)-N-((2-methoxy-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl) sulfonyl)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienamide + H2O
?
-
-
-
?
(5Z,8Z,11Z,14R,15S)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z,14R,15R)-14,15-dihydroxyeicosa-5,8,11-trienoic acid + (5Z,8Z,11Z,14S,15S)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
-
-
-
-
?
(5Z,8Z,11Z,14S,15R)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z,14R,15R)-14,15-dihydroxyeicosa-5,8,11-trienoic acid + (5Z,8Z,11Z,14S,15S)-14,15-dihydroxyeicosa-5,8,11-trienoic 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
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid + H2O
(8R,11R,12S)-trihydroxy-(5Z,9E,14Z)-eicosatrienoic acid
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
(9Z)-12,13-epoxyoctadec-9-enoic acid + H2O
(9Z)-12,13-dihydroxyoctadec-9-enoic acid
-
-
-
?
(R)-1-chloro-2-(2,4-difluorophenyl)-2,3-epoxypropane + H2O
(R)-3-chloro-2-(2,4-difluoro-phenyl)-propane-1,2-diol
-
in a racemic mixture only the (R)-enantiomeric epoxide is converted to the (R)-enantiomeric diol
-
-
?
(R,S)-4-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
-
-
-
-
?
(S)-styrene oxide + H2O
(S)-phenyl-1,2-ethanediol
wild-type and mutant enzymes prefer the S-enantiomer, enantioselective hydrolytic activity of sEH
-
-
?
(S)-styrene oxide + H2O
1-phenylethane-1,2-diol
preferred attack at the benzylic position
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
11,12-epoxy-eicosatrienoic acid + H2O
11,12-dihydroxy-eicosatrienoic acid
-
-
-
?
11R,12S-epoxyeicosatrienoic acid + H2O
11R,12S-dihydroxyeicosatrienoic acid
-
-
-
?
11S,12R-epoxyeicosatrienoic acid + H2O
11S,12R-hydroxyeicosatrienoic acid
-
-
-
?
12-phosphonooxyoctadec-9E-enoic acid + H2O
(9E)-octadecenoic acid + phosphate
-
-
-
-
?
12-phosphonooxyoctadec-9Z-enoic acid + H2O
(9Z)-octadecenoic acid + phosphate
-
-
-
-
?
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
-
-
-
?
14R,15S-epoxyeicosatrienoic acid + H2O
14R,15S-dihydroxyeicosatrienoic acid
-
-
-
?
14S,15R-epoxy-eicosatrienoic acid + H2O
14S,15R-dihydroxy-eicosatrienoic acid
-
-
-
?
14S,15R-epoxyeicosatrienoic acid + H2O
14S,15R-dihydroxyeicosatrienoic acid
-
-
-
?
14S,15S-trans-epoxy-(5Z,8Z,10E,12E)-eicosatetraenoic acid + H2O
14S,15R-dihydroxy-(5Z,8Z,10E,12E)-eicosatetraenoic acid
-
-
-
?
2-methyl styrene oxide + H2O
(2R)-2-phenylpropane-1,2-diol
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester 2-oxiraneacetic acid + H2O
6-methoxy-2-naphthaldehyde + ?
-
-
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
6-methoxy-2-naphtaldehyde + ?
-
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
6-methoxy-2-naphthaldehyde + ?
fluorometric activity assay substrate
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
6-methoxynaphthaldehyde + ?
-
-
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
?
-
-
-
?
3-phenyl-cyano-(6-methoxy-2-naphthalenyl)methylester-2-oxirane-acetic acid + H2O
6-methoxynaphtaldehyde + ?
the non-fluorescent substrate can be hydrolyzed by enzyme sEH to the fluorescent 6-methoxynaphtaldehyde
-
-
?
3-phenyl-oxiranyl-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
?
-
-
-
-
?
3-phenylcyano-(6-methoxy-2-naphthalenyl)methyl ester 2-oxiraneacetic acid + H2O
?
-
-
-
?
4-chlorostyrene oxide + H2O
(1R)-1-(4-chlorophenyl)ethane-1,2-diol
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 96% enantiomeric excess
-
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O
?
-
-
-
-
?
4-nitrophenyl (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O
?
-
preferred phenylpropyl carbonate substrate
-
-
?
4-nitrophenyl [(2R,3R)-3-phenyloxiran-2-yl]methyl carbonate + H2O
?
-
15.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
4-nitrophenyl [(2S,3S)-3-phenyloxiran-2-yl]methyl carbonate + H2O
?
-
38% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
4-nitrostyrene oxide + H2O
(1R)-1-(4-nitrophenyl)ethane-1,2-diol
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 80% enantiomeric excess
-
?
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
-
?
6,8-difluoro-4-methylumbelliferyl trans-2,3-epoxy-3-phenylpropylcarbonate + H2O
?
-
-
-
?
8R,9S-epoxyeicosatrienoic acid + H2O
8R,9S-dihydroxyeicosatrienoic acid
-
-
-
?
8S,9R-epoxyeicosatrienoic acid + H2O
8S,9R-dihydroxyeicosatrienoic acid
-
-
-
?
9(10),12(13)-diepoxyoctadecanoic acid + H2O
9,10,12,13-tetrahydroxyoctadecanoic acid
-
-
-
?
9R,10R-trans-epoxy-13R-hydroxy-11E-octadecenoic acid + H2O
(9R,10S,13R)-trihydroxy-11E-octadecenoic acid
9R,10S-cis-epoxy-13R-hydroxy-11E-octadecenoic acid
(9R,10R,13R)-trihydroxy-11E-octadecenoic acid
-
-
-
?
9R,10S-cis-epoxy-13R-hydroxy-11E-octadecenoic acid + H2O
(9R,10R,13R)-trihydroxy-11E-octadecenoic acid
-
-
-
?
cis-(9R,10S)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
-
enantioselective, low production rate of the (9R,10R)-diol by wild-type and E404D mutant
-
?
cis-(9S,10R)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
-
enantioselective, low production rate of the (9R,10R)-diol by wild-type and E404D mutant
-
?
cis-11,12-epoxyeicosatrienoic acid + H2O
cis-11,12-dihydroxyeicosatrienoic acid
-
-
-
?
cis-8,9-epoxyeicosatrienoic acid + H2O
cis-8,9-dihydroxyeicosatrienoic acid
-
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
?
-
5.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearic acid + H2O
?
-
7.9% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cyano(2-methoxy-naphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl) acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(3-phenyl-oxiran-2-yl)methyl carbonate + H2O
?
a fluorogenic substrate
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(3-phenyloxiran-2-yl)methylcarbonate + H2O
?
-
-
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(3-phenyloxyran-2-yl)methyl carbonate + H2O
?
-
-
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(3-phenyloxyran-2-yl)methylcarbonate + H2O
6-methoxy-2-naphthaldehyde + ?
fluorometric activity assay substrate
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl(3-phenyloxiran-2-yl)methyl carbonate + H2O
?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3,3-dimethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
cyano(6-methoxy-2-naphthyl)methyl (3-ethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
cyano(6-methoxy-2-naphthyl)methyl (3-propyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
cyano(6-methoxy-2-naphthyl)methyl [3-(4-nitrophenyl)oxiran-2-yl]methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxiran-2-yl)methyl] carbonate + H2O
?
cyano(6-methoxynaphthalen-2-yl)methyl (3-phenyloxiran-2-yl)acetate + H2O
[1,2-dihydroxy-2-(3-phenyloxiran-2-yl)ethoxy](6-methoxynaphthalen-2-yl)acetonitrile
cyano-(2-methoxynaphthalen-6-yl)-methyl trans-(3-phenyl-oxiran-2-yl)-methyl carbonate + H2O
?
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 Fluor 7 + H2O
?
i.e. cyano(6-methoxy-2-naphthalenyl)methyl[(2,3)-3-phenyloxiranyl]methyl ester
-
-
?
erythro-10-hydroxy-9-phosphonooxy-octadecanoic acid + H2O
10-hydroxy-octadecanoic acid + phosphate
-
-
-
-
?
glycidyl phenyl ether + H2O
?
-
the selectivity factor E reflecting the relative rate of the reaction of the two enantiomers is only 4.6 for the wild-type enzyme, in slight favor of the (S)-product, a value of 10.8 is observed with the natural EH variant IS002B1 with the three amino acid exchanges A217V, K332E and A390E. A value of 7.4 is observed with the natural variant IR003B1 with the amino acid exchange R219G, a value of 6.6 is observed with the natural variant IB001C2 with the amino acid exchange F340Y, a value of 6.4 is observed with the natural variant IE001H6 with the amino acid exchange A327V, a value of 6.2 is observed with the natural variant IS001H8 with the amino acid exchange A327V and a value of 5.5 is observed with the natural variant IL001D4 with the amino acid exchange P222S
-
-
?
leukotriene A4 + H2O
5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid
-
-
i.e. compound D, product identification by GC-MS
-
?
styrene oxide + H2O
(1R)-1-phenylethane-1,2-diol
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 90% enantiomeric excess
-
?
threo-10-hydroxy-9-phosphonooxy-octadecanoic acid + H2O
10-hydroxy-octadecanoic acid + phosphate
-
-
-
-
?
trans-1,2-dimethylstyrene oxide + H2O
?
-
hydration by microsomal enzyme, no activity with cytosolic enzyme
-
-
?
trans-1,3-diphenylpropene oxide + H2O
trans-1,3-diphenylpropane-1,2-diol
-
-
-
?
[3-(4-chlorophenyl)oxiran-2-yl]methyl cyano(6-methoxy-2-naphthyl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid + H2O
(10R,11R,12S)-trihydroxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
i.e. hepoxilin B3
-
-
?
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid + H2O
(10R,11R,12S)-trihydroxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
i.e. hepoxilin B3
-
-
?
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid + H2O
(10R,11R,12S)-trihydroxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
i.e. hepoxilin B3
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
-
i.e. 8,9-EET
i.e. 8,9-DHET
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
-
i.e. 8,9-EET
i.e. 8,9-DHET
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
i.e. 8,9-EET
i.e. 8,9-DHET
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
-
i.e. 8,9-EET
i.e. 8,9-DHET
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(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-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
-
i.e. 14,15-EET
i.e. 14,15-DHET
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
binding structure in the active site, docking analysis and molecular dynamics simulations
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
-
i.e. 14,15-EET
i.e. 14,15-DHET
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
i.e. 14,15-EET
i.e. 14,15-DHET
-
?
(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-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
-
i.e. 14,15-EET
i.e. 14,15-DHET
-
?
(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
-
enzyme-substrate binding, overview
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
preferred substrate
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
i.e. EETs, showing endothelium-derived hyperpolarizing factor effects dominating in microvessels independent of nitric oxide and prostacyclin. sEH reduces the beneficial effects of EETs
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
enzyme-substrate binding, overview
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
14,15-epoxyeicosatrienoic acid, i.e. 14,15-EET, is cytoprotective in vivo, which is in part mediated by STAT3, overview
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
i.e. 14,15-EET, EETs have antiinflammatory effects and are required for normal endothelial function
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
i.e. EETs, showing endothelium-derived hyperpolarizing factor effects dominating in microvessels independent of nitric oxide and prostacyclin. sEH reduces the beneficial effects of EETs
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
EETs exhibit a wide array of potentially beneficial actions in stroke, including vasodilation, neuroprotection, promotion of angiogenesis and suppression of platelet aggregation, oxidative stress and postischemic inflammation
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
i.e. EETs, showing endothelium-derived hyperpolarizing factor effects dominating in microvessels independent of nitric oxide and prostacyclin. sEH reduces the beneficial effects of EETs
-
-
?
(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-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-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-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-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
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
preferred substrate
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
-
-
-
?
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid + H2O
(8R,11R,12S)-trihydroxy-(5Z,9E,14Z)-eicosatrienoic acid
-
i.e. hepoxilin A3, hydrolysis in liver is mainly catalyzed by soluble epoxide hydrolase
-
-
?
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid + H2O
(8R,11R,12S)-trihydroxy-(5Z,9E,14Z)-eicosatrienoic acid
-
i.e. hepoxilin A3, hydrolysis in liver is mainly catalyzed by soluble epoxide hydrolase
-
-
?
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid + H2O
(8R,11R,12S)-trihydroxy-(5Z,9E,14Z)-eicosatrienoic acid
-
i.e. hepoxilin A3, hydrolysis in liver is mainly catalyzed by soluble epoxide hydrolase
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
-
i.e. 5,6-EET
i.e. 5,6-DHET
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
-
i.e. 5,6-EET
i.e. 5,6-DHET
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
i.e. 5,6-EET
i.e. 5,6-DHET
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
-
i.e. 5,6-EET
i.e. 5,6-DHET
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
-
-
?
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
-
-
-
?
(9Z)-12,13-epoxyoctadecenoic acid + H2O
(9Z)-12,13-dihydroxyoctadecenoic acid
-
-
-
?
(9Z)-12,13-epoxyoctadecenoic acid + H2O
(9Z)-12,13-dihydroxyoctadecenoic acid
-
-
-
?
(R)-glycidyl phenyl ether + H2O
?
-
the hydrolysis of (R)-epoxide in the presence of Tween-80 is 25.6 times faster than that of the (S)-epoxide
-
-
?
(R)-glycidyl phenyl ether + H2O
?
Priestia megaterium ECU1001
-
the hydrolysis of (R)-epoxide in the presence of Tween-80 is 25.6 times faster than that of the (S)-epoxide
-
-
?
(R)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
-
-
-
-
?
(R)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
-
-
-
-
?
(R)-styrene oxide + H2O
(R)-styrene glycol
low activity, the enzyme enantioselective and preferentially hydrolyzes (S)-styrene oxide
-
-
?
(R)-styrene oxide + H2O
(R)-styrene glycol
low activity, the enzyme enantioselective and preferentially hydrolyzes (S)-styrene oxide
-
-
?
(S)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
-
-
-
-
?
(S)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
-
-
-
-
?
(S)-styrene oxide + H2O
(S)-styrene glycol
the enzyme possesses (S)-styrene oxide-preferred hydrolytic activity
-
-
?
(S)-styrene oxide + H2O
(S)-styrene glycol
the enzyme enantioselective and preferentially hydrolyzes (S)-styrene oxide
-
-
?
(S)-styrene oxide + H2O
(S)-styrene glycol
the enzyme enantioselective and preferentially hydrolyzes (S)-styrene oxide
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
i.e. HEOM
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
i.e. HEOM
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
i.e. HEOM
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
i.e. HEOM
-
-
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
-
i.e. HEOM
-
-
?
1,3-trans-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
-
little to no selectivity for cis-isomer or trans-isomer
-
-
?
1,3-trans-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
-
sEH-selective substrate
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
-
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
-
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
-
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
-
-
-
-
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
-
14.6% of the activity with 2,3-epoxy-1,3-diphenyl-propane, no activity with the 2S,3S-enantiomer
-
-
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
-
5.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane, no activity with the 2S,3S-enantiomer
-
-
?
4-nitrophenyl-trans-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
-
-
-
-
?
5,6-epoxyeicosatrienoic acid + H2O
5,6-dihydroxyeicosatrienoic acid
-
-
-
?
5,6-epoxyeicosatrienoic acid + H2O
5,6-dihydroxyeicosatrienoic acid
-
-
-
-
?
8,9-epoxyeicosatrienoic acid + H2O
8,9-dihydroxyeicosatrienoic acid
-
-
-
?
8,9-epoxyeicosatrienoic acid + H2O
8,9-dihydroxyeicosatrienoic acid
-
-
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
-
the enzyme prefers the (9R,10S)-enantiomer
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
-
the enzyme strongly prefers the (9R,10S)-enantiomer, conversion of the (S)-carbon to the corresponding threo-(R,R)-diol in over 85%
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
-
no enantioselectivity of infection-induced isozymes, conversion of the (S)-carbon to the corresponding threo-(R,R)-diol in over 85%
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
-
the enzyme prefers the (9R,10S)-enantiomer, conversion of the (S)-carbon to the corresponding threo-(R,R)-diol in over 85%
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
-
no enantioselectivity
-
-
?
9,10-epoxy-18-hydroxy octadeca-(12Z)-eneoic acid + H2O
?
-
step in cutin biosynthesis
-
-
?
9R,10R-trans-epoxy-13R-hydroxy-11E-octadecenoic acid + H2O
(9R,10S,13R)-trihydroxy-11E-octadecenoic acid
-
-
-
?
9R,10R-trans-epoxy-13R-hydroxy-11E-octadecenoic acid + H2O
(9R,10S,13R)-trihydroxy-11E-octadecenoic acid
-
-
-
?
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
-
-
-
-
?
cis-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
-
little to no selectivity for cis-isomer or trans-isomer, 99% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
-
2.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
-
little to no selectivity for cis-isomer or trans-isomer, 44% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-1,3-diphenylpropene oxide + H2O
?
-
18.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-1,3-diphenylpropene oxide + H2O
?
-
3.0% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
?
simulation of substrate binding, modeling
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
cis-14,15-dihydroxyeicosatrienoic acid
preferred eicosatrienoic acid-substrate
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
cis-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
cis-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
cis-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
cis-14,15-dihydroxyeicosatrienoic acid
-
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
-
59% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
-
6.5% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
-
3.5% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
-
12% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
-
30% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
-
6.7% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
-
4.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
-
13.4% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
-
activity is 50fold lower than with trans-stilbene oxide
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
-
far greater selectivity for trans-stilbene oxide versus cis-stilbene oxide. 0.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
-
0.4% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
-
far greater selectivity for trans-stilbene oxide versus cis-stilbene oxide. 0.06% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
?
cress
-
greater selectivity for trans-stilbene oxide versus cis-stilbene oxide
-
-
?
cis-stilbene oxide + H2O
?
-
greater selectivity for trans-stilbene oxide versus cis-stilbene oxide
-
-
?
cyano(2-methoxy-naphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl) acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(2-methoxy-naphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl) acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3,3-dimethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3,3-dimethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-ethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-ethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
preferred fluorogenic substrate
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-propyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3-propyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl [3-(4-nitrophenyl)oxiran-2-yl]methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl [3-(4-nitrophenyl)oxiran-2-yl]methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxiran-2-yl)methyl] carbonate + H2O
?
-
i.e. CMNPC, a fluorescent substrate
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxiran-2-yl)methyl] carbonate + H2O
?
i.e. CMNPC, a fluorescent substrate
-
-
?
cyano(6-methoxynaphthalen-2-yl)methyl (3-phenyloxiran-2-yl)acetate + H2O
[1,2-dihydroxy-2-(3-phenyloxiran-2-yl)ethoxy](6-methoxynaphthalen-2-yl)acetonitrile
-
-
-
-
?
cyano(6-methoxynaphthalen-2-yl)methyl (3-phenyloxiran-2-yl)acetate + H2O
[1,2-dihydroxy-2-(3-phenyloxiran-2-yl)ethoxy](6-methoxynaphthalen-2-yl)acetonitrile
-
-
-
-
?
cyano-(2-methoxynaphthalen-6-yl)-methyl trans-(3-phenyl-oxiran-2-yl)-methyl carbonate + H2O
?
-
-
-
?
cyano-(2-methoxynaphthalen-6-yl)-methyl trans-(3-phenyl-oxiran-2-yl)-methyl carbonate + H2O
?
CMNPC, a fluorescent substrate with an epoxide group, which releases a strong fluorophore 6-methoxy-2-naphthaldehyde after hydrolysis of the epoxide
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
-
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
-
elimination of the biological effects of the substrate, involved in regulation of renal eicosanoid levels and blood pressure, mechanism
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
-
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
-
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
-
physiological function and regulation of the reaction, overview
-
-
?
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
-
-
-
?
juvenile hormone III + H2O
?
-
11.9% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
juvenile hormone III + H2O
?
-
6.3% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
juvenile hormone III + H2O
?
-
6.3% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
juvenile hormone III + H2O
?
-
3.5% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
juvenile hormone III + H2O
?
-
7.1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
racemic 4-nitrophenyl-trans-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
-
-
-
-
?
racemic 4-nitrophenyl-trans-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
-
-
-
-
?
racemic ethyl 3-phenylglycidate + H2O
?
-
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
?
-
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
-
-
?
trans-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
-
little to no selectivity for cis-isomer or trans-isomer
-
-
?
trans-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
tritium labeled for radiometric assay
-
-
?
trans-1,3-diphenylpropene oxide + H2O
?
the His-tag of the recombinant enzyme probably interfers with the enzyme activity
-
-
?
trans-diphenyl-propene oxide + H2O
trans-diphenyl-propene diol
-
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
-
far greater selectivity for trans-stilbene oxide versus cis-stilbene oxide. 84% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
-
2.8% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
-
highly selective for the trans-enantiomer. 1% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
-
far greater selectivity for trans-stilbene oxide versus cis-stilbene oxide. 5.6% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
trans-stilbene oxide + H2O
?
cress
-
greater selectivity for trans-stilbene oxide versus cis-stilbene oxide
-
-
?
trans-stilbene oxide + H2O
?
-
-
-
-
?
trans-stilbene oxide + H2O
?
-
highly selective for the trans-enantiomer. 1.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
trans-stilbene oxide + H2O
?
-
-
-
-
?
trans-stilbene oxide + H2O
?
-
-
-
-
?
trans-stilbene oxide + H2O
?
-
greater selectivity for trans-stilbene oxide versus cis-stilbene oxide
-
-
?
[3-(4-chlorophenyl)oxiran-2-yl]methyl cyano(6-methoxy-2-naphthyl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
[3-(4-chlorophenyl)oxiran-2-yl]methyl cyano(6-methoxy-2-naphthyl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
-
-
-
-
?
additional information
?
-
-
preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
?
additional information
?
-
-
plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
-
-
?
additional information
?
-
-
preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
?
additional information
?
-
-
plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
-
-
?
additional information
?
-
-
preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
?
additional information
?
-
-
plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
-
-
?
additional information
?
-
-
preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
?
additional information
?
-
-
plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
-
-
?
additional information
?
-
-
the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lidpi/carbohydrate metabolism, enzyme regulation, overview
-
-
?
additional information
?
-
-
the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates
-
-
?
additional information
?
-
-
the enzyme is involved in host-defense and cutin biosynthesis, preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
?
additional information
?
-
-
plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
-
-
?
additional information
?
-
degradation kinetics of styrene oxide, overview. At 10°C, the enantiopurity of (R)-styrene oxide reaches 99% with 34.8% yield and 80 min reaction time. On the contrary, a 20.5% yield is obtained at 40°C. At 50°C, the enantiopurity more than 98% cannot be obtained for 30 min-reaction. As a conclusion, the yield increased 1.7fold at 10°C, compared to 30°C
-
-
?
additional information
?
-
-
the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lidpi/carbohydrate metabolism, enzyme regulation, overview
-
-
?
additional information
?
-
-
the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates
-
-
?
additional information
?
-
-
plays an important role during germination of seeds
-
-
?
additional information
?
-
-
preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
?
additional information
?
-
-
plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
-
-
?
additional information
?
-
-
preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
-
-
?
additional information
?
-
the soluble-type epoxide hydrolase may play a crucial role in the self-defense system of the plant
-
-
?
additional information
?
-
-
the soluble-type epoxide hydrolase may play a crucial role in the self-defense system of the plant
-
-
?
additional information
?
-
-
plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
-
-
?
additional information
?
-
-
microsomal enzyme shows highest activity with trans-2-methylstyrane oxide, followed by styrene 7,8-oxide, cis-2-methylstyrene oxide, cis-1,2-dimethylstyrene oxide, trans-1,2-dimethylstyrene oxide and 2,2-dimethylstyrene oxide. With the cytosolic enzyme the same order is obtained for the first three substrates, whereas activity with 2,2-dimethylstyrene oxide is higher than with cis-1,2-dimethylstyrene oxide and no hydration occurs with trans-1,2-dimethylstyrene oxide
-
-
?
additional information
?
-
-
the N-terminal domain of the enzyme is a functional phosphatase unaffected by a number of classic phosphatase inhibitors. The phosphatase domain has high specificity for lipophilic phosphates
-
-
?
additional information
?
-
-
the enzyme is involved in regulation of blood pressure and inflammation
-
-
?
additional information
?
-
-
reaction mechanism with flurogenic substrates
-
-
?
additional information
?
-
-
substrate specificity, 2 enzymes with different specificities termed cytosolic TESO hydrolase and cytosolic PNSO hydrolase, no activity with benz[a]pyrene 4,5-oxide
-
-
?
additional information
?
-
-
substrate specificity, the microsomal enzyme rapidly hydrolyzes epoxides on cyclic systems as well as mono, 1,1-di and cis-1,2-disubstituted epoxides
-
-
?
additional information
?
-
-
the enzyme also shows phosphatase activity, EC 3.1.3.76, sEH prefers gem-di-, trans-di-, cis-di-, tri-, and tetra-substituted epoxides
-
-
?
additional information
?
-
-
the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates, overview
-
-
?
additional information
?
-
-
differential localization of the enzyme in the brain indicates an essential role in the central nervous system
-
-
?
additional information
?
-
-
kinetic analysis of the effects of human enzyme polymorphisms on the N-terminal phosphatase activity of soluble epoxide hydrolase activity
-
-
?
additional information
?
-
activity of the sEH can be regulated by the tyrosine nitration of the protein
-
-
?
additional information
?
-
-
activity of the sEH can be regulated by the tyrosine nitration of the protein
-
-
?
additional information
?
-
contribution of hydrolase and phosphatase domains in soluble epoxide hydrolase to vascular endothelial growth factor expression and cell growth, overview
-
-
?
additional information
?
-
-
contribution of hydrolase and phosphatase domains in soluble epoxide hydrolase to vascular endothelial growth factor expression and cell growth, overview
-
-
?
additional information
?
-
EETs are important regulators of cardiovascular function, of cerebral blood flow, and exhibit a wide array of potentially beneficial actions in stroke, including vasodilation, neuroprotection, promotion of angiogenesis and suppression of platelet aggregation, oxidative stress and postischemic inflammation, detailed overview
-
-
?
additional information
?
-
-
epoxyeicosatrienoic acids are substrates of sEH, enzyme regulation, overview
-
-
?
additional information
?
-
sEH rapidly hydrolyzes eicosatrienoic acids to their corresponding dihydroxyeicosatrienoic acid, DHET, metabolites, which, in general, are much less biologically active than eicosatrienoic acids. Cytochrome P450 epoxygenases, soluble epoxide hydrolase, and the regulation of cardiovascular inflammation, overview. functional impact of CYP epoxygenase-derived eicosatrienoic acids biosynthesis and sEH-mediated xyeicosatrienoic acids hydrolysis on key inflammatory process in the cardiovascular system
-
-
?
additional information
?
-
-
soluble epoxide hydrolase is an enzyme that catalyzes the hydrolysis of epoxyeicosatrienoic acids, EETs, which are lipid mediators derived from arachidonic acid through the cytochrome P450 epoxygenase pathway. EETs can activate multiple antiapoptotic targets through PI3K/Akt survival signaling and protect cardiomyocytes from hypoxia/anoxia
-
-
?
additional information
?
-
Vascular actions and antiinflammatory actions of epoxyeicosatrienoic acids, overview
-
-
?
additional information
?
-
development of a high throughput cell-based assay for soluble epoxide hydrolase using BacMam technology, determination of Cy3B-fluorescence labeled product Cy3B-DAE-14,15-DHET, i.e. 14-(2-[(2-([(5Z,8Z,11Z)-14,15-dihydroxy-5,8,11-icosatrienoyl]amino)ethyl)amino]-2-oxoethyl)-16,16,18,18-tetramethyl-6,7,7a,8a,9,10,16,18-octahydrobenzo[2'',3''] indolizino[8'',7'':5',6']pyrano[3',2':3,4]pyrido[1,2-a]indol-5-ium-2-sulfonate, overview
-
-
?
additional information
?
-
-
each monomer is comprised of two distinct structural domains, linked by a proline-rich segment, the 35 kDa C-terminal domain displays epoxide hydrolase activity, while the N-terminal domain exhibits phosphatase activity
-
-
?
additional information
?
-
sEH has phosphatase activity as well as epoxide hydrolase activity
-
-
?
additional information
?
-
-
sEH has phosphatase activity as well as epoxide hydrolase activity
-
-
?
additional information
?
-
the C-terminal domain of the soluble epoxide hydrolase metabolizes epoxyeicosatrienoic acids, EETs, to their less active diols, while the N-terminal domain demonstrates lipid phosphatase activity
-
-
?
additional information
?
-
-
the C-terminal domain of the soluble epoxide hydrolase metabolizes epoxyeicosatrienoic acids, EETs, to their less active diols, while the N-terminal domain demonstrates lipid phosphatase activity
-
-
?
additional information
?
-
the enzyme converts epoxyalcohols into linoleate triols
-
-
?
additional information
?
-
the enzyme converts epoxyalcohols into linoleate triols
-
-
?
additional information
?
-
-
the enzyme converts epoxyalcohols into linoleate triols
-
-
?
additional information
?
-
human soluble EH (sEH or EPHX2) and human or murine epoxide hydrolase-3 (EH3 or EPHX3) hydrolyze cis or trans allylic epoxides to single diastereomers, identical to the major isomers detected in epidermis. Microsomal EH (mEH or EPHX1, EC 3.3.2.9) is inactive with these substrates. 12,13-trans-Epoxy-octadeca-9E-enoic acid is completely hydrolyzed by human sEH, human EH3, and N-truncated murine EH3 and mostly hydrolyzed using the N-truncated+7aa-insert murine EH3. 12,13-cis-Epoxy-octadeca-9E-enoic acid is hardly hydrolyzed by human EH3, N-truncated murine EH3, and the N-truncated+7aa-insert murine EH3, and 30% hydrolysis is observed using human sEH. At low substrate concentrations, EPHX2 hydrolyzes 14,15-epoxyeicosatrienoic acid (EET) at twice the rate of the epidermal epoxyalcohol, 9R,10R-trans-epoxy-11E-13R-hydroxy-octadecenoic acid, whereas human or murine EPHX3 hydrolyze the allylic epoxyalcohol at 31fold and 39fold higher rates, respectively
-
-
?
additional information
?
-
human soluble EH (sEH or EPHX2) and human or murine epoxide hydrolase-3 (EH3 or EPHX3) hydrolyze cis or trans allylic epoxides to single diastereomers, identical to the major isomers detected in epidermis. Microsomal EH (mEH or EPHX1, EC 3.3.2.9) is inactive with these substrates. 12,13-trans-Epoxy-octadeca-9E-enoic acid is completely hydrolyzed by human sEH, human EH3, and N-truncated murine EH3 and mostly hydrolyzed using the N-truncated+7aa-insert murine EH3. 12,13-cis-Epoxy-octadeca-9E-enoic acid is hardly hydrolyzed by human EH3, N-truncated murine EH3, and the N-truncated+7aa-insert murine EH3, and 30% hydrolysis is observed using human sEH. At low substrate concentrations, EPHX2 hydrolyzes 14,15-epoxyeicosatrienoic acid (EET) at twice the rate of the epidermal epoxyalcohol, 9R,10R-trans-epoxy-11E-13R-hydroxy-octadecenoic acid, whereas human or murine EPHX3 hydrolyze the allylic epoxyalcohol at 31fold and 39fold higher rates, respectively
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additional information
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human soluble EH (sEH or EPHX2) and human or murine epoxide hydrolase-3 (EH3 or EPHX3) hydrolyze cis or trans allylic epoxides to single diastereomers, identical to the major isomers detected in epidermis. Microsomal EH (mEH or EPHX1, EC 3.3.2.9) is inactive with these substrates. 12,13-trans-Epoxy-octadeca-9E-enoic acid is completely hydrolyzed by human sEH, human EH3, and N-truncated murine EH3 and mostly hydrolyzed using the N-truncated+7aa-insert murine EH3. 12,13-cis-Epoxy-octadeca-9E-enoic acid is hardly hydrolyzed by human EH3, N-truncated murine EH3, and the N-truncated+7aa-insert murine EH3, and 30% hydrolysis is observed using human sEH. At low substrate concentrations, EPHX2 hydrolyzes 14,15-epoxyeicosatrienoic acid (EET) at twice the rate of the epidermal epoxyalcohol, 9R,10R-trans-epoxy-11E-13R-hydroxy-octadecenoic acid, whereas human or murine EPHX3 hydrolyze the allylic epoxyalcohol at 31fold and 39fold higher rates, respectively
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additional information
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the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lidpi/carbohydrate metabolism, enzyme regulation, overview
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additional information
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substrate specificity, the microsomal enzyme rapidly hydrolyzes epoxides on cyclic systems as well as mono, 1,1-di and cis-1,2-disubstituted epoxides
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additional information
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the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates
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additional information
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synthesis of anti-fungal substances in fruits, the enzyme is involved in host-defense and cutin biosynthesis, preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
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additional information
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plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
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additional information
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the enzyme possesses an epoxide hydrolyzing as well as a lipid phosphatase activity. Favored sEH substrates are trans-substituted over cis-substituted epoxides
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additional information
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the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lidpi/carbohydrate metabolism, enzyme regulation, overview
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additional information
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the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates
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additional information
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involvement of the Asp333-His523 pair in the catalytic mechanism
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additional information
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induced by parental exposure to N-ethyl-N-nitrosourea
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additional information
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oxygenated lipids may be endogenous substrates for the cytosolic epoxide hydrolase
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additional information
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enzyme inhibition decreases plasma levels of proinflammatory cytokines and nitric oxide metabolites while promoting the formation of lipoxins, thus supporting inflammatory resolution
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additional information
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the enzyme is involved in regulation of blood pressure and inflammation
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additional information
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the enzyme is involved in synthesis of tetrahydrofuran diol and trihydroxy furanyl lipids, enzyme regulation, overview
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additional information
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reaction mechanism with flurogenic substrates
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additional information
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sEH prefers gem-di-, trans-di-, cis-di-, tri-, and tetra-substituted epoxides
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additional information
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substrate specificity, the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates, except for the isozyme EPXH2B, overview
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additional information
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substrate specificity, the microsomal enzyme rapidly hydrolyzes epoxides on cyclic systems as well as mono, 1,1-di and cis-1,2-disubstituted epoxides
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additional information
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activity of the sEH can be regulated by the tyrosine nitration of the protein
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additional information
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activity of the sEH can be regulated by the tyrosine nitration of the protein
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additional information
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EETs are important regulators of cardiovascular function, of cerebral blood flow, and exhibit a wide array of potentially beneficial actions in stroke, including vasodilation, neuroprotection, promotion of angiogenesis and suppression of platelet aggregation, oxidative stress and postischemic inflammation, detailed overview
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additional information
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epoxyeicosatrienoic acids are substrates of sEH, enzyme regulation, overview
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additional information
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sEH catalyzes the conversion of epoxyeicosatrienoic acids, EETs, to form the corresponding dihydroxyeicosatrienoic acids, DHETs
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additional information
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sEH catalyzes the conversion of epoxyeicosatrienoic acids, EETs, to form the corresponding dihydroxyeicosatrienoic acids, DHETs
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additional information
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sEH rapidly hydrolyzes eicosatrienoic acids to their corresponding dihydroxyeicosatrienoic acid, DHET, metabolites, which, in general, are much less biologically active than eicosatrienoic acids. Cytochrome P450 epoxygenases, soluble epoxide hydrolase, and the regulation of cardiovascular inflammation, overview. functional impact of CYP epoxygenase-derived eicosatrienoic acids biosynthesis and sEH-mediated xyeicosatrienoic acids hydrolysis on key inflammatory process in the cardiovascular system
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additional information
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soluble epoxide hydrolase is an enzyme that catalyzes the hydrolysis of epoxyeicosatrienoic acids, EETs, which are lipid mediators derived from arachidonic acid through the cytochrome P450 epoxygenase pathway. EETs can activate multiple antiapoptotic targets through PI3K/Akt survival signaling and protect cardiomyocytes from hypoxia/anoxia
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additional information
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each monomer is comprised of two distinct structural domains, linked by a proline-rich segment, the 35 kDa C-terminal domain displays epoxide hydrolase activity, while the N-terminal domain exhibits phosphatase activity
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additional information
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sEH is bifunctional enzyme with C-terminal hydrolase and N-terminal phosphatase activities
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additional information
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sEH is bifunctional enzyme with C-terminal hydrolase and N-terminal phosphatase activities
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additional information
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the C-terminal domain of the soluble epoxide hydrolase metabolizes epoxyeicosatrienoic acids, EETs, to their less active diols, while the N-terminal domain demonstrates lipid phosphatase activity
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additional information
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the enzyme has a broad substrate range and shows high regio- and enantioselectivity for nucleophilic ring opening by Asp333
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additional information
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the enzyme converts epoxyalcohols into linoleate triols
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additional information
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the enzyme converts epoxyalcohols into linoleate triols
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additional information
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human soluble EH (sEH or EPHX2) and human or murine epoxide hydrolase-3 (EH3 or EPHX3) hydrolyze cis or trans allylic epoxides to single diastereomers, identical to the major isomers detected in epidermis. Microsomal EH (mEH or EPHX1, EC 3.3.2.9) is inactive with these substrates. 12,13-trans-Epoxy-octadeca-9E-enoic acid is completely hydrolyzed by human sEH, human EH3, and N-truncated murine EH3 and mostly hydrolyzed using the N-truncated+7aa-insert murine EH3. 12,13-cis-Epoxy-octadeca-9E-enoic acid is hardly hydrolyzed by human EH3, N-truncated murine EH3, and the N-truncated+7aa-insert murine EH3, and 30% hydrolysis is observed using human sEH. At low substrate concentrations, EPHX2 hydrolyzes 14,15-epoxyeicosatrienoic acid (EET) at twice the rate of the epidermal epoxyalcohol, 9R,10R-trans-epoxy-11E-13R-hydroxy-octadecenoic acid, whereas human or murine EPHX3 hydrolyze the allylic epoxyalcohol at 31fold and 39fold higher rates, respectively
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additional information
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human soluble EH (sEH or EPHX2) and human or murine epoxide hydrolase-3 (EH3 or EPHX3) hydrolyze cis or trans allylic epoxides to single diastereomers, identical to the major isomers detected in epidermis. Microsomal EH (mEH or EPHX1, EC 3.3.2.9) is inactive with these substrates. 12,13-trans-Epoxy-octadeca-9E-enoic acid is completely hydrolyzed by human sEH, human EH3, and N-truncated murine EH3 and mostly hydrolyzed using the N-truncated+7aa-insert murine EH3. 12,13-cis-Epoxy-octadeca-9E-enoic acid is hardly hydrolyzed by human EH3, N-truncated murine EH3, and the N-truncated+7aa-insert murine EH3, and 30% hydrolysis is observed using human sEH. At low substrate concentrations, EPHX2 hydrolyzes 14,15-epoxyeicosatrienoic acid (EET) at twice the rate of the epidermal epoxyalcohol, 9R,10R-trans-epoxy-11E-13R-hydroxy-octadecenoic acid, whereas human or murine EPHX3 hydrolyze the allylic epoxyalcohol at 31fold and 39fold higher rates, respectively
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additional information
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the sEH is a dual function enzyme that generates dihydroxy-fatty acids via its C-terminal hydrolase domain, while the N-terminal phosphatase domain has been proposed to have lipid phosphatase activity, bifunctional epoxide hydrolase 2 includes cytosolic epoxide hydrolase 2, sEH, EC 3.3.2.10, and lipid-phosphate phosphatase, EC 3.1.3.76
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additional information
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the sEH is a dual function enzyme that generates dihydroxy-fatty acids via its C-terminal hydrolase domain, while the N-terminal phosphatase domain has been proposed to have lipid phosphatase activity, bifunctional epoxide hydrolase 2 includes cytosolic epoxide hydrolase 2, sEH, EC 3.3.2.10, and lipid-phosphate phosphatase, EC 3.1.3.76
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additional information
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the C-terminal domain of the soluble epoxide hydrolase metabolizes epoxyeicosatrienoic acids, EETs, to their less active diols, while the N-terminal domain demonstrates lipid phosphatase activity
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additional information
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activity of the sEH can be regulated by the tyrosine nitration of the protein
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additional information
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induced by parental exposure to N-ethyl-N-nitrosourea
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additional information
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preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
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additional information
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plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
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additional information
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the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lidpi/carbohydrate metabolism, enzyme regulation, overview
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additional information
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substrate specificity, the microsomal enzyme rapidly hydrolyzes epoxides on cyclic systems as well as mono, 1,1-di and cis-1,2-disubstituted epoxides
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additional information
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the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates
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additional information
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stereoselective hydrolysis of epoxyeicosatrienoic acids (EETs) by sEH
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additional information
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stereoselective hydrolysis of epoxides by enzyme sEH, overview
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additional information
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preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
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additional information
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plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
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additional information
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the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lipid/carbohydrate metabolism, enzyme regulation, overview
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additional information
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the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates
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additional information
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Asp333, Asp495 and His523 form the catalytic triad
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additional information
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enzyme inhibition in vivo leads to increased blood pressure and heart rate due to an increase in epoxyeicosatrienoic acid-mediated generation of reactive oxygen species
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additional information
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the activity for epoxyeicosatrienoic acids is elevated 5 to 54fold in renal cortical S9 fraction from the spontaneously hypertensive rats compared to normotensive Wistar-Kyoto rats, the enzyme is involved in regulation of blood pressure
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additional information
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the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lidpi/carbohydrate metabolism, enzyme regulation, overview
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additional information
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the enzyme is involved in regulation of blood pressure and inflammation
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additional information
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the enzyme is involved in the arachidonic acid metabolic pathway
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additional information
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enantioselectivity with fatty acid epoxide substrates
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additional information
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sEH prefers gem-di-, trans-di-, cis-di-, tri-, and tetra-substituted epoxides
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additional information
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substrate specificity, no activity with benz[a]pyrene 4,5-oxide
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additional information
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substrate specificity, the microsomal enzyme rapidly hydrolyzes epoxides on cyclic systems as well as mono, 1,1-di and cis-1,2-disubstituted epoxides
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additional information
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the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates, overview
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additional information
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SEH converts cardiovascular protective epoxyeicosatrienoic acids into less active diols attenuating the protective properties, overview
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additional information
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preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
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additional information
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plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
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additional information
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the enzyme is involved in host-defense and cutin biosynthesis, synthesis of (9S,10S,11R)-trihydroxy-12(Z)-octadecenoic and (9S,12S,13S)-trihydroxy-10(E)-octadecenoic acids with potent anti-fungal properties, preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
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additional information
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plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
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additional information
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preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
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additional information
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plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
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additional information
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the enzyme is involved in metabolism of epoxide lipids in blood pressure, inflammation, reproduction and in lidpi/carbohydrate metabolism, enzyme regulation, overview
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additional information
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the enzyme prefers trans- over cis-epoxides of sterically hindered substrates like stilbene oxides, the C-terminal domain catalyzes epoxy fatty acid hydrolysis, the N-terminal catalytic domain has also phosphatase activity with specificity for fatty acid diol phosphates
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additional information
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preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
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additional information
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plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
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additional information
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preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
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additional information
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plant enzymes prefer trans- over cis-epoxides of sterically hindered substrates like stilbene oxides
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additional information
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the enzyme does not show phosphatase activity toward 4-methylumbelliferyl phosphate or several lysophosphatidic acids
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additional information
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preferred endogenous substrates are epoxides containing fatty acids, e.g. epoxides of stearic and linoleic acids, and hepoxilins
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