Information on EC 3.3.2.10 - soluble epoxide hydrolase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
3.3.2.10
-
RECOMMENDED NAME
GeneOntology No.
soluble epoxide hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an epoxide + H2O = a glycol
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2-methylpropene degradation
-
-
arachidonic acid metabolism
-
-
Arachidonic acid metabolism
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-
Chloroalkane and chloroalkene degradation
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-
Metabolic pathways
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-
Microbial metabolism in diverse environments
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-
SYSTEMATIC NAME
IUBMB Comments
epoxide hydrolase
Catalyses the hydrolysis of trans-substituted epoxides, such as trans-stilbene oxide, as well as various aliphatic epoxides derived from fatty-acid metabolism [7]. It is involved in the metabolism of arachidonic epoxides (epoxyicosatrienoic acids; EETs) and linoleic acid epoxides. The EETs, which are endogenous chemical mediators, act at the vascular, renal and cardiac levels to regulate blood pressure [4,5]. The enzyme from mammals is a bifunctional enzyme: the C-terminal domain exhibits epoxide-hydrolase activity and the N-terminal domain has the activity of EC 3.1.3.76, lipid-phosphate phosphatase [1,2]. Like EC 3.3.2.9, microsomal epoxide hydrolase, it is probable that the reaction involves the formation of an hydroxyalkyl---enzyme intermediate [4,6]. The enzyme can also use leukotriene A4, the substrate of EC 3.3.2.6, leukotriene-A4 hydrolase, but it forms 5,6-dihydroxy-7,9,11,14-icosatetraenoic acid rather than leukotriene B4 as the product [9,10]. In vertebrates, five epoxide-hydrolase enzymes have been identified to date: EC 3.3.2.6 (leukotriene-A4 hydrolase), EC 3.3.2.7 (hepoxilin-epoxide hydrolase), EC 3.3.2.9 (microsomal epoxide hydrolase), EC 3.3.2.10 (soluble epoxide hydrolase) and EC 3.3.2.11 (cholesterol 5,6-oxide hydrolase) [7].
CAS REGISTRY NUMBER
COMMENTARY hide
9048-63-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
multiple isozymes, constitutive and inducible
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-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
strain ECU1001
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-
Manually annotated by BRENDA team
strain ECU1001
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
C12
-
-
Manually annotated by BRENDA team
cress
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
SwissProt
Manually annotated by BRENDA team
Mus musculus C57BL/6J
C57BL/6J mice
SwissProt
Manually annotated by BRENDA team
Mus musculus C57BL6
C57Bl6 mice
SwissProt
Manually annotated by BRENDA team
ENU4
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and infection-induced
-
-
Manually annotated by BRENDA team
no activity in Trichoplusia ni
cell culture
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
baboon
-
-
Manually annotated by BRENDA team
strain BZS21
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-
Manually annotated by BRENDA team
strain BZS21
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-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
multiple isozymes, constitutive and inducible
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
multiple isozymes
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
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
show the reaction diagram
(11S,12S)-epoxy-5,14-cis-7,9-trans-eicosatetraenoic acid + H2O
(11R,12S)-dihydroxy-5,14-cis-7,9-trans-eicosatetraenoic acid + H2O
show the reaction diagram
-
i.e. 11,12-leukotriene A4
-
?
(12Z)-9,10-epoxyoctadec-12-enoic acid
(12Z)-9,10-dihydroxyoctadec-12-enoic acid
show the reaction diagram
-
-
-
?
(1S,2S)-beta-methylstyrene oxide + H2O
?
show the reaction diagram
-
enzyme attacks almost exclusively at the benzylic position
-
-
?
(1S,2S)-trans-methylstyrene oxide + H2O
?
show the reaction diagram
a hydrogen bond from Tyr465 to the substrate oxygen is essential for controlling the regioselectivity of the reaction
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-
r
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
6-methoxy-2-naphthaldehyde + ?
show the reaction diagram
-
substrate for high-throughput screen
product is fluorescent
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-
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
?
show the reaction diagram
-
-
-
-
?
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxynaphthalen-2-yl)-methyl ester + H2O
6-methoxy-2-naphthaldehyde + ?
show the reaction diagram
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
show the reaction diagram
(5Z,11Z,14Z)-8,9-epoxyeicosa-8,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
show the reaction diagram
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
show the reaction diagram
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
show the reaction diagram
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid + H2O
(8R,11R,12S)-trihydroxy-(5Z,9E,14Z)-eicosatrienoic acid
show the reaction diagram
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
show the reaction diagram
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
(9Z)-12,13-epoxyoctadec-9-enoic acid + H2O
(9Z)-12,13-dihydroxyoctadec-9-enoic acid
show the reaction diagram
-
-
-
?
(R)-1-chloro-2-(2,4-difluorophenyl)-2,3-epoxypropane + H2O
(R)-3-chloro-2-(2,4-difluoro-phenyl)-propane-1,2-diol
show the reaction diagram
-
in a racemic mixture only the (R)-enantiomeric epoxide is converted to the (R)-enantiomeric diol
-
-
?
(R)-4-nitrostyrene oxide + H2O
?
show the reaction diagram
(R)-glycidyl phenyl ether + H2O
?
show the reaction diagram
(R)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
show the reaction diagram
(R)-styrene oxide + H2O
(R)-styrene glycol
show the reaction diagram
-
-
-
?
(R)-styrene oxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
(S)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
show the reaction diagram
(S)-styrene oxide + H2O
(S)-styrene glycol
show the reaction diagram
the enzyme possesses (S)-styrene oxide-preferred hydrolytic activity
-
-
?
(S)-styrene oxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
-
preferred attack at the benzylic position
-
-
-
(S)-styrene oxide + H2O
?
show the reaction diagram
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
show the reaction diagram
1,3-trans-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
show the reaction diagram
1-myristoyl-glyceral-3-phosphate + H2O
?
show the reaction diagram
-
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
11,12-leukotriene A4 + H2O
?
show the reaction diagram
-
-
-
-
?
11R,12S-epoxyeicosatrienoic acid + H2O
11R,12S-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
?
11S,12R-epoxyeicosatrienoic acid + H2O
11S,12R-hydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
?
12,13-epoxy octadeca-(9Z)-eneoic acid + H2O
?
show the reaction diagram
12-phosphonooxyoctadec-9E-enoic acid + H2O
(9E)-octadecenoic acid + phosphate
show the reaction diagram
-
-
-
-
?
12-phosphonooxyoctadec-9Z-enoic acid + H2O
(9Z)-octadecenoic acid + phosphate
show the reaction diagram
-
-
-
-
?
12-phosphonooxyoctadecanoic acid + H2O
octadecanoic acid + phosphate
show the reaction diagram
-
-
-
-
?
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
14,15-leukotriene A4 + H2O
?
show the reaction diagram
-
-
-
-
?
14R,15S-epoxyeicosatrienoic acid + H2O
14R,15S-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
?
14S,15R-epoxyeicosatrienoic acid + H2O
14S,15R-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
?
14S,15S-trans-epoxy-(5Z,8Z,10E,12E)-eicosatrienoic acid + H2O
14S,15R-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
?
2,2-dimethylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
2,3-epoxy-1,3-diphenyl-propane + H2O
?
show the reaction diagram
2,3-squalene oxide + H2O
?
show the reaction diagram
2-acetylaminofluorene + H2O
?
show the reaction diagram
2-methyl styrene oxide + H2O
(2R)-2-phenylpropane-1,2-diol
show the reaction diagram
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
2-methylphenyl glycidyl ether + H2O
?
show the reaction diagram
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester 2-oxiraneacetic acid + H2O
6-methoxy-2-naphthaldehyde + ?
show the reaction diagram
-
-
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
6-methoxynaphthaldehyde + ?
show the reaction diagram
-
-
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
?
show the reaction diagram
-
-
-
-
?
3-phenyl-oxiranyl-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
?
show the reaction diagram
-
-
-
-
?
4-chlorostyrene oxide + H2O
(1R)-1-(4-chlorophenyl)ethane-1,2-diol
show the reaction diagram
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 96% enantiomeric excess
-
?
4-methylphenylglycidyl ether + H2O
?
show the reaction diagram
4-nitrophenyl (2R,3R)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
4-nitrophenyl (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O
?
show the reaction diagram
-
preferred phenylpropyl carbonate substrate
-
-
?
4-nitrophenyl (2S,3S)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrophenyl [(2R,3R)-3-phenyloxiran-2-yl]methyl carbonate + H2O
?
show the reaction diagram
-
15.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
4-nitrophenyl [(2S,3S)-3-phenyloxiran-2-yl]methyl carbonate + H2O
?
show the reaction diagram
-
38% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
4-nitrophenyl-trans-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
4-nitrostyrene 7,8-oxide + H2O
?
show the reaction diagram
4-nitrostyrene oxide + H2O
(1R)-1-(4-nitrophenyl)ethane-1,2-diol
show the reaction diagram
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 80% enantiomeric excess
-
?
4-nitrostyrene oxide + H2O
?
show the reaction diagram
4-t-butylstyrene oxide + H2O
(1R)-1-(4-t-butylphenyl)ethane-1,2-diol
show the reaction diagram
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
5,6-epoxyeicosatrienoic acid + H2O
5,6-dihydroxyeicosatrienoic acid
show the reaction diagram
5,6-epoxyeicosatrienoic acid + H2O
5,6-hydroxyeicosatrienoic acid
show the reaction diagram
5,6-leukotriene A4 + H2O
?
show the reaction diagram
-
-
-
-
?
5alpha-cholest-2-ene beta-oxide + H2O
?
show the reaction diagram
-
-
-
-
?
6,8-difluoro-4-methylumbelliferyl trans-2,3-epoxy-3-phenylpropylcarbonate + H2O
?
show the reaction diagram
-
-
-
-
?
8,9-epoxyeicosatrienoic acid + H2O
8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
8,9-epoxyeicosatrienoic acid + H2O
8,9-hydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
-
?
8R,9S-epoxyeicosatrienoic acid + H2O
8R,9S-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
?
8S,9R-epoxyeicosatrienoic acid + H2O
8S,9R-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
?
9(10),12(13)-diepoxyoctadecanoic acid + H2O
9,10,12,13-tetrahydroxyoctadecanoic acid
show the reaction diagram
-
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
9,10-epoxy-18-hydroxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
9-hydroxy-10,11-epoxy octadeca-(12Z)-eneoic acid + H2O
?
show the reaction diagram
allylbenzene + H2O
?
show the reaction diagram
alpha-cyanocarbonate epoxide + H2O
?
show the reaction diagram
arachidonic acid 11,12-oxide + H2O
11,12-dihydroxyarachidonic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid 14,15-oxide + H2O
14,15-dihydroxyarachidonic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid 5,6-oxide + H2O
5,6-dihydroxyarachidonic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid 8,9-oxide + H2O
8,9-dihydroxyarachidonic acid
show the reaction diagram
-
-
-
-
?
arochlor 1254 + H2O
?
show the reaction diagram
AttoPhos + H2O
?
show the reaction diagram
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
show the reaction diagram
chalcone oxides + H2O
?
show the reaction diagram
cholesterol 5,6-alpha-oxide + H2O
?
show the reaction diagram
-
very weak activity
-
-
?
cis-(9R,10S)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
show the reaction diagram
-
-
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
show the reaction diagram
-
-
enantioselective, low production rate of the (9R,10R)-diol by wild-type and E404D mutant
-
?
cis-1,2-dimethylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-1,3-diphenylpropene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
-
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
show the reaction diagram
cis-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
cis-11,12-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
cis-11,12-epoxyeicosatrienoic acid + H2O
cis-11,12-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
cis-14,15-epoxyeicosatrienoic acid + H2O
cis-14,15-dihydroxyeicosatrienoic acid
show the reaction diagram
preferred eicosatrienoic acid-substrate
-
-
?
cis-2-methylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
cis-8,9-epoxyeicosatrienoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
cis-8,9-epoxyeicosatrienoic acid + H2O
cis-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
-
-
-
?
cis-8-ethylstyrene 7,8-oxide + H2O
?
show the reaction diagram
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
show the reaction diagram
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
?
show the reaction diagram
-
5.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearate + H2O
threo-9,10-dihydroxystearate
show the reaction diagram
-
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
show the reaction diagram
cis-9,10-epoxystearic acid + H2O
?
show the reaction diagram
-
7.9% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
show the reaction diagram
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
cis-stilbene oxide + H2O
?
show the reaction diagram
clofibrate + H2O
?
show the reaction diagram
cyano(2-methoxy-naphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl) acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
cyano(2-methoxynaphthalen-6-yl)methyl trans-(3-phenyl-oxiran-2-yl)methyl carbonate + H2O
?
show the reaction diagram
-
a fluorogenic substrate
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(3-phenyloxiran-2-yl)methylcarbonate + H2O
?
show the reaction diagram
-
-
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(3-phenyloxyran-2-yl) methylcarbonate + H2O
?
show the reaction diagram
-
-
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl(3-phenyloxiran-2-yl)methyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
cyano(6-methoxy-2-naphthyl)methyl (3,3-dimethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
cyano(6-methoxy-2-naphthyl)methyl (3-ethyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)acetate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
cyano(6-methoxy-2-naphthyl)methyl (3-propyloxiran-2-yl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
cyano(6-methoxy-2-naphthyl)methyl [3-(4-nitrophenyl)oxiran-2-yl]methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxiran-2-yl)methyl] carbonate + H2O
?
show the reaction diagram
cyano(6-methoxynaphthalen-2-yl)methyl (3-phenyloxiran-2-yl)acetate + H2O
[1,2-dihydroxy-2-(3-phenyloxiran-2-yl)ethoxy](6-methoxynaphthalen-2-yl)acetonitrile
show the reaction diagram
cyano-(2-methoxynaphthalen-6-yl)-methyl trans-(3-phenyl-oxiran-2-yl)-methyl carbonate + H2O
?
show the reaction diagram
-
CMNPC, a fluorescent substrate with an epoxide group, which releases a strong fluorophore 6-methoxy-2-naphthaldehyde after hydrolysis of the epoxide
-
-
?
cyano-(2-methoxynaphthalen-6-yl)-methyl trans-(3-phenyl-oxyran-2-yl)-methyl carbonate + H2O
?
show the reaction diagram
-
-
-
-
?
cyclohexene oxide + H2O
?
show the reaction diagram
di(2-ethylhexyl)phthalate + H2O
?
show the reaction diagram
dihydronaphthalene oxide + H2O
(1S,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol
show the reaction diagram
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
Epoxy Fluor 7 + H2O
?
show the reaction diagram
-
i.e. cyano(6-methoxy-2-napthalenyl)methyl[(2,3)-3-phenyloxiranyl]methyl ester
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-
?
epoxy stearic acid + H2O
?
show the reaction diagram
epoxyeicosatrienoic acid + H2O
dihydroxyeicosatrienoic acid
show the reaction diagram
erythro-10-hydroxy-9-phosphonooxy-octadecanoic acid + H2O
10-hydroxy-octadecanoic acid + phosphate
show the reaction diagram
-
-
-
-
?
glycidyl phenyl ether + H2O
?
show the reaction diagram
-
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
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-
?
hepoxilin A3 + H2O
?
show the reaction diagram
hepoxilin B3 + H2O
?
show the reaction diagram
juvenile hormone III + H2O
?
show the reaction diagram
lanosterol + H2O
?
show the reaction diagram
-
-
-
-
?
leukotoxin + H2O
leukotoxin diol
show the reaction diagram
leukotoxin + H2O
leukotoxin-1,2-diol
show the reaction diagram
-
-
-
-
?
leukotriene A4 + H2O
5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid
show the reaction diagram
-
-
i.e. compound D, product identification by GC-MS
-
?
leukotriene A4 + H2O
?
show the reaction diagram
naphthalene 1,2-oxide + H2O
?
show the reaction diagram
p-nitrophenyl phosphate + H2O
?
show the reaction diagram
-
-
-
-
?
p-nitrostyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
phenanthrene-9,10-oxide + H2O
?
show the reaction diagram
phenobarbital + H2O
?
show the reaction diagram
rac trans-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
racemic 4-nitrophenyl-trans-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
show the reaction diagram
racemic ethyl 3-phenylglycidate + H2O
?
show the reaction diagram
racemic trans-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
squalene 2,3-23,24-dioxide + H2O
?
show the reaction diagram
-
-
-
-
?
squalene diepoxide + H2O
?
show the reaction diagram
-
-
-
?
squalene oxide + H2O
?
show the reaction diagram
-
weak substrate
-
-
?
squalene-2,3-epoxide + H2O
?
show the reaction diagram
-
-
-
?
stearic acid epoxide + H2O
?
show the reaction diagram
-
-
-
-
?
styrene 7,8-oxide + H2O
?
show the reaction diagram
styrene 7,8-oxide + H2O
styrene glycol
show the reaction diagram
styrene oxide + H2O
(1R)-1-phenylethane-1,2-diol
show the reaction diagram
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 90% enantiomeric excess
-
?
styrene oxide + H2O
?
show the reaction diagram
styrene oxide + H2O
styrene glycol
show the reaction diagram
threo-10-hydroxy-9-phosphonooxy-octadecanoic acid + H2O
10-hydroxy-octadecanoic acid + phosphate
show the reaction diagram
-
-
-
-
?
trans-1,2-dimethylstyrene oxide + H2O
?
show the reaction diagram
-
hydration by microsomal enzyme, no activity with cytosolic enzyme
-
-
?
trans-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
show the reaction diagram
trans-1,3-diphenylpropene oxide + H2O
?
show the reaction diagram
trans-2-methylstyrene oxide + H2O
?
show the reaction diagram
trans-8-ethylstyrene 7,8-oxide + H2O
?
show the reaction diagram
trans-9,10-epoxystearate + H2O
?
show the reaction diagram
trans-9,10-epoxystearate + H2O
threo-9,10-dihydroxystearate
show the reaction diagram
-
-
-
?
trans-beta-methyl-styrene oxide + H2O
?
show the reaction diagram
trans-beta-methylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-beta-propylstyrene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-diphenyl propene oxide + H2O
?
show the reaction diagram
-
-
-
-
?
trans-diphenylpropene oxide + H2O
?
show the reaction diagram
trans-ethyl styrene oxide + H2O
?
show the reaction diagram
trans-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
show the reaction diagram
trans-stilbene oxide + H2O
?
show the reaction diagram
[3-(4-chlorophenyl)oxiran-2-yl]methyl cyano(6-methoxy-2-naphthyl)methyl carbonate + H2O
6-methoxy-2-naphthaldehyde + CN- + ?
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid + H2O
(10R,11R,12S)-trihydroxy-(5Z,8Z,14Z)-eicosatrienoic acid
show the reaction diagram
-
i.e. hepoxilin B3
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
show the reaction diagram
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid