Information on EC 3.3.2.11 - cholesterol-5,6-oxide hydrolase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
3.3.2.11
-
RECOMMENDED NAME
GeneOntology No.
cholesterol-5,6-oxide hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O = 5alpha-cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O = 5alpha-cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
5,6alpha-epoxy-5alpha-cholestan-3beta-ol hydrolase
The enzyme appears to work equally well with either epoxide as substrate [3]. The product is a competitive inhibitor of the reaction. 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) [3].
CAS REGISTRY NUMBER
COMMENTARY hide
55467-47-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
knockdown of D8D7I (3beta-hydroxysterol-DELTA8-DELTA7-isomerase) and DHCR7 (3beta-hydroxysterol-DELTA7-reductase) abolishes ChEH activity. D8D7I and DHCR7 cooperate in the ChEH activity
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5,6-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
additional information
?
-
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
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
show the reaction diagram
-
-
-
-
?
additional information
?
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(11beta,17beta)-11-{4-[2-(Dimethylamino)ethoxy]phenyl}estra-1,3,5(10)-triene-3,17-diol
-
-
(4-(2-morpholinoethoxy)phenyl)(phenyl)methanone
-
-
(4-(6-(allyl (methyl)amino)hexyloxy)phenyl)(4-bromophenyl)methanone
-
-
(E)-N,3,6,6-tetra methyl-N-(naphthalene-1-ylmethyl)hept-2-en-4-yn-1-amine
-
-
(E)-N-(4-(3-chloro-4-cyclohexylphenyl)but-3-enyl)-N-ethylcyclohexanamine
-
-
1-(2-(4-(2-phenylpropan-2-yl) phenoxy)ethyl)pyrrolidine
-
-
1-(2-(4-benzylphenoxy)ethyl)-pyrrolidine
-
-
1-(2-(4-benzylphenoxy)ethyl)pyrrolidin hydrochloride
-
-
1-(4-(2-morpholino ethoxy)phenyl)-2-phenylethanone
-
-
1-[2-[4-[(Z)-1-(4-methoxyphenyl)-2-nitro-2-phenylethenyl]phenoxy]ethyl]pyrrolidine
-
-
2-(4-benzylphenoxy)-N,N-diethylethanamine
-
-
2-(4-chlorophenyl)-1-(4-(2-(diethylamino)ethoxy)phenyl)-1-p-tolyl ethanol
-
-
2-(diethylamino)ethyl 2,2-diphenylpentanoate
-
-
2-[4-[(Z)-2-chloro-1,2-di (phenyl)ethenyl]phenoxy]-N,N-diethylethanamine
-
-
3-beta-(2-(diethyl amino)ethoxy)androst-5-en-17-one
-
-
3-methylcholanthracene
-
-
4-(2-(4-(2-phenylpropan-2-yl)phenoxy)ethyl)morpholine
-
-
4-(2-(4-benzylphenoxy)ethyl)morpholine
-
-
4-(4-(4-chloro phenyl)-4-hydroxypiperidin-1-yl)-1-(4-fluorophenyl)butan-1-one
-
-
4-hydroxy-tamoxifen
-
-
4-[(Z)-1-[4-(2-dimethylaminoethyloxy)phenyl]-2-phenyl but-1-enyl]phenol
-
-
5,6alpha-epoxy-5alpha-cholestan-3beta-ol
-
competitive to 5,6beta-epoxy-5alpha-cholestan-3beta-ol
5,6alpha-imino-5alpha-cholestan-3beta-ol
5,6alpha-imino-5alpha-cholestane-3beta-ol
5,6beta-epoxy-5beta-cholestan-3beta-ol
-
competitive to 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
6-ketocholestanol
-
-
6-oxo-5-alpha-hydroxycholestanol
-
-
6-oxocholestanol
-
-
7-dehydrocholesterol 5,6 beta-oxide
-
specific, mechanism-based inhibitor
7-ketocholestanol
-
-
7-ketocholesterol
-
-
7-oxocholestanol
-
-
7-oxocholesterol
-
-
7alpha-hydroxycholesterol
-
-
7beta-hydroxycholesterol
-
-
9,10-iminophenanthrene
-
-
9-fluorenone
-
slight inhibition
acetone
-
reduces the activity by 85% at 1.25% v/v, by 50% at 3.75% v/v, and by 56% at 6.25% v/v
alpha-linolenic acid
amiodarone
arachidonic acid
Aroclor 1254
-
-
benz[a]anthracene 5,6-oxide
-
non-competitive inhibition
chalcone
-
-
cholestane-3beta,5alpha,6alpha-triol
-
IC50 is 0.110 mM
cholestane-3beta,5alpha,6beta-triol
cholestane-3beta,5beta,6alpha-triol
-
IC50 is 0.085 mM
cholestane-3beta,5beta,6beta-triol
-
IC50 is 0.118 mM
cholesterol
-
IC50 is above 0.125 mM
cholestyramine
-
-
-
Clofibrate
-
-
clomiphene
-
-
Dimethylsulfoxide
-
reduces the activity by 42% at 6.25% v/v
docosahexaenoic acid
Ellipticine
-
-
Emulgen 108
-
complete inactivation
-
Emulgen 911
-
complete inactivation
-
gamma-chlordane
-
-
haloperidol
-
-
ibogaine
-
-
Iminosqualene
-
-
Isoquinoline
-
slight inhibition
isosafrole
-
slight inhibition
Lubrol Px
-
complete inactivation
methanol
-
reduces the activity by 86% at 3.75% v/v
Metyrapone
-
weak inhibition in hyperplastic nodules, not in normal tissue
N-(3,4-dichlorophenethyl)-N-methyl-2-(pyrrolidin-1-yl)ethanemine
-
-
N-pyrrolidino-2-[4-(benzyl)-phenoxy]-ethanamine
-
-
norharman
-
-
octene 1,2-oxide
-
non-competitive inhibition
oleic acid
oxidosqualene
-
IC50 is above 0.16 mM
Phenobarbital
-
-
phenyl{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}methanone
-
-
pregnenolone 16alpha-carbonitrile
-
-
raloxifene
-
-
rimcazole
-
-
sodium cholate
-
-
SR31747A
-
-
tamoxifen
terbinafine
-
-
tesmilifene
-
-
tetrahydrofuran
-
reduces the activity by 86% at 6.25% v/v
trans-1,4-bis(2-chlorobenzaminomethyl)cyclohexane
-
-
trans-stilbene oxide
-
-
trifluoroperazine
Triton WR-1339
-
-
Tween 80
-
-
U-18666A
-
-
[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetonitrile
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00091
5,6-epoxy-5alpha-cholestan-3beta-ol
-
pH 7.4, 37°C, normal liver tissue microsomes
0.0037 - 0.0074
5,6alpha-epoxy-5alpha-cholestan-3beta-ol
0.0044
5,6beta-epoxy-5beta-cholestan-3beta-ol
-
pH 7.4, 37°C, versus 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000155
(11beta,17beta)-11-{4-[2-(Dimethylamino)ethoxy]phenyl}estra-1,3,5(10)-triene-3,17-diol
-
pH 7.4, 37°C
0.000241
(4-(2-morpholinoethoxy)phenyl)(phenyl)methanone
-
pH 7.4, 37°C
0.000089
(4-(6-(allyl (methyl)amino)hexyloxy)phenyl)(4-bromophenyl)methanone
-
pH 7.4, 37°C
0.0091
(E)-N,3,6,6-tetra methyl-N-(naphthalene-1-ylmethyl)hept-2-en-4-yn-1-amine
-
pH 7.4, 37°C
0.000006
(E)-N-(4-(3-chloro-4-cyclohexylphenyl)but-3-enyl)-N-ethylcyclohexanamine
-
pH 7.4, 37°C
0.000035
1-(2-(4-(2-phenylpropan-2-yl) phenoxy)ethyl)pyrrolidine
-
pH 7.4, 37°C
0.000027
1-(2-(4-benzylphenoxy)ethyl)-pyrrolidine
-
pH 7.4, 37°C
0.000902
1-(4-(2-morpholino ethoxy)phenyl)-2-phenylethanone
-
pH 7.4, 37°C
0.000018
1-[2-[4-[(Z)-1-(4-methoxyphenyl)-2-nitro-2-phenylethenyl]phenoxy]ethyl]pyrrolidine
-
pH 7.4, 37°C
0.000062
2-(4-benzylphenoxy)-N,N-diethylethanamine
-
pH 7.4, 37°C
0.000039
2-(4-chlorophenyl)-1-(4-(2-(diethylamino)ethoxy)phenyl)-1-p-tolyl ethanol
-
pH 7.4, 37°C
0.0019
2-(diethylamino)ethyl 2,2-diphenylpentanoate
-
pH 7.4, 37°C
0.000009
2-[4-[(Z)-2-chloro-1,2-di (phenyl)ethenyl]phenoxy]-N,N-diethylethanamine
-
pH 7.4, 37°C
0.00009
3-beta-(2-(diethyl amino)ethoxy)androst-5-en-17-one
-
pH 7.4, 37°C
0.000057
4-(2-(4-(2-phenylpropan-2-yl)phenoxy)ethyl)morpholine
-
pH 7.4, 37°C
0.000027
4-(2-(4-benzylphenoxy)ethyl)morpholine
-
pH 7.4, 37°C
0.018
4-(4-(4-chloro phenyl)-4-hydroxypiperidin-1-yl)-1-(4-fluorophenyl)butan-1-one
-
pH 7.4, 37°C
0.000145
4-hydroxy-tamoxifen
-
pH and temperature not specified in the publication
0.000145
4-[(Z)-1-[4-(2-dimethylaminoethyloxy)phenyl]-2-phenyl but-1-enyl]phenol
-
pH 7.4, 37°C
0.0044
5,6alpha-epoxy-5alpha-cholestan-3beta-ol
-
pH 7.4, 37°C, versus 5,6beta-epoxy-5alpha-cholestan-3beta-ol
0.000085
5,6alpha-imino-5alpha-cholestan-3beta-ol
-
pH 7.4, 37°C, versus 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
0.0037
5,6beta-epoxy-5beta-cholestan-3beta-ol
-
pH 7.4, 37°C, versus 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
0.0085
6-oxo-5-alpha-hydroxycholestanol
-
pH 7.4, 37°C
0.0023
6-oxocholestanol
-
pH 7.4, 37°C
0.0042
7-ketocholesterol
-
pH and temperature not specified in the publication
0.000864
7-oxocholestanol
-
pH 7.4, 37°C
0.0042
7-oxocholesterol
-
pH 7.4, 37°C
0.0061
7alpha-hydroxycholesterol
-
pH 7.4, 37°C
0.0069
7beta-hydroxycholesterol
-
pH 7.4, 37°C
0.126
9,10-iminophenanthrene
-
pH 7.4, 37°C, versus 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
0.0035
AC-915
-
pH 7.4, 37°C
0.036 - 0.0363
alpha-linolenic acid
0.000733
amiodarone
0.024
arachidonic acid
0.0097
cholestane-3beta,5alpha,6beta-triol
0.012
docosahexaenoic acid
0.018
haloperidol
-
pH and temperature not specified in the publication
0.002
ibogaine
-
pH 7.4, 37°C
0.0366
Iminosqualene
-
pH 7.4, 37°C, versus 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
0.000099
N-(3,4-dichlorophenethyl)-N-methyl-2-(pyrrolidin-1-yl)ethanemine
-
pH 7.4, 37°C
0.000027
N-pyrrolidino-2-[4-(benzyl)-phenoxy]-ethanamine
-
pH and temperature not specified in the publication
0.054
oleic acid
0.000203
phenyl{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}methanone
-
pH 7.4, 37°C
0.000036
raloxifene
-
pH and temperature not specified in the publication
0.0023
rimcazole
-
pH 7.4, 37°C
0.000006
SR31747A
-
pH and temperature not specified in the publication
0.000034
tamoxifen
0.0091
terbinafine
-
pH and temperature not specified in the publication
0.000062
tesmilifene
-
pH and temperature not specified in the publication
0.000649
trans-1,4-bis(2-chlorobenzaminomethyl)cyclohexane
-
pH 7.4, 37°C
0.000135
trifluoroperazine
0.00009
U-18666A
-
pH and temperature not specified in the publication
0.000036
[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
-
pH 7.4, 37°C
additional information
additional information
-
inhibition kinetics at pH 8.0, 37°C, 6.5% v/v acetonitrile
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000765
1-(2-(4-benzylphenoxy)ethyl)pyrrolidin hydrochloride
Homo sapiens
-
pH and temperature not specified in the publication
0.11
cholestane-3beta,5alpha,6alpha-triol
Rattus norvegicus
-
IC50 is 0.110 mM
0.03
cholestane-3beta,5alpha,6beta-triol
Rattus norvegicus
-
IC50 is 0.03 mM
0.085
cholestane-3beta,5beta,6alpha-triol
Rattus norvegicus
-
IC50 is 0.085 mM
0.118
cholestane-3beta,5beta,6beta-triol
Rattus norvegicus
-
IC50 is 0.118 mM
0.125
cholesterol
Rattus norvegicus
-
IC50 is above 0.125 mM
0.16
oxidosqualene
Rattus norvegicus
-
IC50 is above 0.16 mM
0.0000599
tamoxifen
Homo sapiens
-
pH and temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00004
-
liver microsomes, substrate 5,6beta-epoxy-5alpha-cholestan-3beta-ol
0.00007
-
microsomes from hyperplastic nodules
0.00014
-
liver microsomes, substrate 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
0.00017
-
microsomes from normal liver tissue
0.00018
0.0002
-
liver microsomes, substrate 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
0.00033
-
liver microsomes
0.00038
-
liver microsomes, substrate 5,6beta-epoxy-5alpha-cholestan-3beta-ol
0.00045
-
liver microsomes, substrate 5,6beta-epoxy-5alpha-cholestan-3beta-ol
0.00048
-
liver microsomes, substrate 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
0.00051
-
liver microsomes, substrate 5,6alpha-epoxy-5alpha-cholestan-3beta-ol
0.00052
-
liver microsomes, substrate 5,6beta-epoxy-5alpha-cholestan-3beta-ol
0.00065
-
smooth microsomes
0.00068
-
rough microsomes
0.00108
0.00123
-
liver microsomes
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8 - 9
-
80-90% of maximal activity at pH 6.8 and pH 7.7, 33% at pH 9.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
epithelium, low activity
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
additional information
-
tissue distribution analysis, no or poor activity in lung and spleen
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
-
subcellular distribution analysis, no or low activity in cytosol, plasma membrane, Golgi apparatus II, and nucleus, overview
-
Manually annotated by BRENDA team
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
acetone reduces the activity by 85% at 1.25% v/v, by 50% at 3.75% v/v, and by 56% at 6.25% v/v
-
660782
acetonitrile activates the enzyme at moderate concentration, maximal enzyme activity at 6.25% v/v, 19% of maximal activity at 1.25% v/v, 50% of maximal activity at 12.5% v/v, no activity at 18.8% v/v
-
660782
dimethylsulfoxide reduces the activity by 42% at 6.25% v/v
-
660782
methanol reduces the activity by 86% at 3.75% v/v
-
660782
tetrahydrofuran reduces the activity by 86% at 6.25% v/v
-
660782
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-90°C, liver microsomes, enzyme is stable during repeated freezing and thawing
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
from microsomes, separation from EC 3.3.2.9 by immunoprecipitation
liver microsome preparation
partially by microsome preparation
-
partially by subcellular fractionation
-
partially from liver by micosome preparation and immunoprecipitation, separation from the xenobiotic epoxide hydrolase, EC 3.3.2.9
-
partially from liver by micosome preparation, two steps of gel filtration, separation from the xenobiotic epoxide hydrolase, EC 3.3.2.9
-