Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
5,6-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
additional information
?
-
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the substrate is a product of lipid peroxidation in the liver
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is highly substrate-specific
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
regulation, the enzyme is highly substrate specific
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is highly substrate-specific
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is highly substrate-specific
i.e. 5,6-glycol
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is highly substrate specific
-
-
?
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
better substrate
-
-
?
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
best substrate
-
-
?
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is equally active with both stereoisomers
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider xenobiotic substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider xenobiotic substrate specificity
-
-
?
additional information
?
-
-
no activity with xenobiotic alkene oxides and arene oxides, e.g. octene 1,2-oxide or benz[a]anthracene 5,6-oxide
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
additional information
?
-
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the substrate is a product of lipid peroxidation in the liver
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is highly substrate-specific
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
regulation, the enzyme is highly substrate specific
-
-
?
5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O
cholestane-3beta,5alpha,6beta-triol
-
the enzyme is highly substrate-specific
-
-
?
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
-
-
-
?
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
better substrate
-
-
?
5,6beta-epoxy-5alpha-cholestan-3beta-ol + H2O
5alpha-cholestane-3beta,5alpha,6beta-triol
-
best substrate
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider xenobiotic substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider substrate specificity
-
-
?
additional information
?
-
-
the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.9, which shows a wider xenobiotic substrate specificity
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(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-(phenylmethyl)phenoxy]ethyl]-pyrrolidine
-
-
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-[(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-oxo-5-alpha-hydroxycholestanol
-
-
6-oxo-cholestan-3beta,5alpha-diol
-
OCDO, inhibition of the ChEH activity by OCDO, at higher concentration OCDO is reported to inhibit cholesterol biosynthesis from mevalonate but not from acetate at the D8D7I step (the catalytic subunit of ChEH), leading to the accumulation of Delta-8 sterols. Identification of OCDO as an oncometabolite in humans
7-dehydrocholesterol 5,6 beta-oxide
-
specific, mechanism-based inhibitor
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
benz[a]anthracene 5,6-oxide
-
non-competitive inhibition
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
Dimethylsulfoxide
-
reduces the activity by 42% at 6.25% v/v
Emulgen 108
-
complete inactivation
-
Emulgen 911
-
complete inactivation
-
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
-
-
octene 1,2-oxide
-
non-competitive inhibition
oxidosqualene
-
IC50 is above 0.16 mM
phenyl{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}methanone
-
-
pregnenolone 16alpha-carbonitrile
-
-
tetrahydrofuran
-
reduces the activity by 86% at 6.25% v/v
trans-1,4-bis(2-chlorobenzaminomethyl)cyclohexane
-
-
[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
-
-
5,6alpha-imino-5alpha-cholestan-3beta-ol
-
strong inhibition
5,6alpha-imino-5alpha-cholestan-3beta-ol
-
strong, specific, competitive inhibition
5,6alpha-imino-5alpha-cholestane-3beta-ol
-
specific inhibition of cholesterol-5,6-epoxide hydrolase
5,6alpha-imino-5alpha-cholestane-3beta-ol
-
specific inhibition of cholesterol-5,6-epoxide hydrolase
alpha-linolenic acid
-
-
amiodarone
-
-
arachidonic acid
-
-
cholestane-3beta,5alpha,6beta-triol
-
-
cholestane-3beta,5alpha,6beta-triol
-
IC50 is 0.03 mM
cholestane-3beta,5alpha,6beta-triol
-
product inhibition
cholestane-3beta,5alpha,6beta-triol
-
-
dendrogenin A
-
-
docosahexaenoic acid
-
-
oleic acid
-
-
rimcazole
-
-
tamoxifen
-
-
tamoxifen
-
0.01 mM, competitive
trifluoroperazine
-
-
additional information
-
no inhibition by 1,1,1-trichloropropene oxide
-
additional information
-
no effect by 5,6alpha-epoxy-5alpha-cholestan-3beta-ol in vivo, and by EDTA and 2,2-dipyridyl, preferred buffer is 300 mM potassium phosphate at pH 7.4 and 37°C, low activity in Tris and HEPES buffers
-
additional information
-
comparison of inhibition level in microsomes of normal liver tissue and liver hyperplastic nodules, remaining activities, overview
-
additional information
-
no inhibition by 1,1,1-trichloropropene oxide
-
additional information
-
no inhibition by isoquinoline, styrene oxide, cyclohexane oxide, benzil, cholesterol, and cholic acid
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
0.0097
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
0.000203
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
0.0091
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
-
0.036
alpha-linolenic acid
-
pH and temperature not specified in the publication
0.0363
alpha-linolenic acid
-
pH 7.4, 37°C
0.000733
amiodarone
-
pH 7.4, 37°C
0.000733
amiodarone
-
pH and temperature not specified in the publication
0.024
arachidonic acid
-
pH 7.4, 37°C
0.024
arachidonic acid
-
pH and temperature not specified in the publication
0.0097
cholestane-3beta,5alpha,6beta-triol
-
pH 7.4, 37°C
0.0097
cholestane-3beta,5alpha,6beta-triol
-
pH and temperature not specified in the publication
0.012
docosahexaenoic acid
-
pH 7.4, 37°C
0.012
docosahexaenoic acid
-
pH and temperature not specified in the publication
0.054
oleic acid
-
pH 7.4, 37°C
0.054
oleic acid
-
pH and temperature not specified in the publication
0.000034
tamoxifen
-
pH 7.4, 37°C
0.000034
tamoxifen
-
pH and temperature not specified in the publication
0.000135
trifluoroperazine
-
pH 7.4, 37°C
0.000135
trifluoroperazine
-
pH and temperature not specified in the publication
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.000765
1-(2-(4-benzylphenoxy)ethyl)pyrrolidin hydrochloride
Homo sapiens
-
pH and temperature not specified in the publication
0.000231 - 0.00025
1-[2-[4-(phenylmethyl)phenoxy]ethyl]-pyrrolidine
0.000065 - 0.000095
4-hydroxytamoxifen
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
0.00006 - 0.000064
clomiphene
0.000313 - 0.00035
dendrogenin A
0.16
oxidosqualene
Rattus norvegicus
-
IC50 is above 0.16 mM
0.000069 - 0.0001
raloxifene
0.0000599 - 0.00011
tamoxifen
0.000172 - 0.00021
tesmilifene
0.000231
1-[2-[4-(phenylmethyl)phenoxy]ethyl]-pyrrolidine
Homo sapiens
-
MDA-MB231 cells, pH not specified in the publication, temperature not specified in the publication
0.00025
1-[2-[4-(phenylmethyl)phenoxy]ethyl]-pyrrolidine
Homo sapiens
-
MCF-7 cells, pH not specified in the publication, temperature not specified in the publication
0.000065
4-hydroxytamoxifen
Homo sapiens
-
MDA-MB231 cells, pH not specified in the publication, temperature not specified in the publication
0.000095
4-hydroxytamoxifen
Homo sapiens
-
MCF-7 cells, pH not specified in the publication, temperature not specified in the publication
0.00006
clomiphene
Homo sapiens
-
MDA-MB231 cells, pH not specified in the publication, temperature not specified in the publication
0.000064
clomiphene
Homo sapiens
-
MCF-7 cells, pH not specified in the publication, temperature not specified in the publication
0.000313
dendrogenin A
Homo sapiens
-
MDA-MB231 cells, pH not specified in the publication, temperature not specified in the publication
0.00035
dendrogenin A
Homo sapiens
-
MCF-7 cells, pH not specified in the publication, temperature not specified in the publication
0.000069
raloxifene
Homo sapiens
-
MDA-MB231 cells, pH not specified in the publication, temperature not specified in the publication
0.0001
raloxifene
Homo sapiens
-
MCF-7 cells, pH not specified in the publication, temperature not specified in the publication
0.003
rimcazole
Homo sapiens
-
MCF-7 cells, pH not specified in the publication, temperature not specified in the publication
0.0035
rimcazole
Homo sapiens
-
MDA-MB231 cells, pH not specified in the publication, temperature not specified in the publication
0.0000599
tamoxifen
Homo sapiens
-
pH and temperature not specified in the publication
0.00007
tamoxifen
Homo sapiens
-
MDA-MB231 cells, pH not specified in the publication, temperature not specified in the publication
0.00011
tamoxifen
Homo sapiens
-
MCF-7 cells, pH not specified in the publication, temperature not specified in the publication
0.000172
tesmilifene
Homo sapiens
-
MDA-MB231 cells, pH not specified in the publication, temperature not specified in the publication
0.00021
tesmilifene
Homo sapiens
-
MCF-7 cells, pH not specified in the publication, temperature not specified in the publication
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
malfunction
-
patients suffering the lysosomal storage diseases Niemann-Pick types A, B, C1 and C2 (NPA, NPB, NPC) show elevated 5alpha-cholestane-3beta,5alpha,6beta-triol in plasma, presumably derived from free radical oxidation of cholesterol to 5,6-epoxycholesterol followed by hydrolysis to the triol by enzyme cholesterol epoxide hydrolase, ChEH
metabolism
-
cholesterol-5,6-epoxide pathway in normal breast and breast cancers, overview
metabolism
-
the enzymes ChEH, HSD11B1 and HSD11B2, and CYP27A1 sit at a fulcrum balancing the formation from 5alpha,6-epoxycholesterol of the tumour suppressor DDA and from 5,6-epoxycholesterol, through 5alpha-cholestane-3beta,5alpha,6beta-triol, the oncometabolite 3beta,5alpha-diHC-6O or the bile acid 3beta,5alpha,6beta-trihydroxycholanoic acid. 26-hydroxy-7-oxocholesterol activates the Hedgehog signalling pathway, constitutive activation of which is linked to tumorigenesis further connecting the HSD11B and CYP27A1 enzymes to oncology
physiological function
-
the existence of ChEH activity in MCF-7 cells, and thus ChEH inhibition and accumulation are likely to play a role in the mechanism of induction of breast cancer cell differentiation and apoptosis by antiestrogen binding site (AEBS) ligands that require sterol autoxidation products
physiological function
-
primary and secondary products of the enzyme's activity have tumor promoting and carcinogenic activity
physiological function
-
the enzyme plays a potential role in cancer progression and resistance
physiological function
-
5,6-epoxycholesterol is hydrolysed by the enzyme cholesterol epoxide hydrolase (ChEH) to 3beta,5alpha,6beta-triol which itself is oxidised by hydroxysteroid dehydrogenase (HSD), steps leading to the acidic pathway of bile acid biosynthesis
physiological function
-
in breast tumors from patients, OCDO production as well as the expression of the enzymes involved in the pathway producing 6-oxo-cholestan-3beta,5alpha-diol (OCDO), namely ChEH subunits and 11beta-hydroxysteroid dehydrogenase of type 2 (HSD2), are higher compared to normal tissues, and overexpression of these enzymes correlates with a higher risk of patient death, indicating that this onco-metabolism is of major importance to breast cancer pathology. The ChEH product 5alpha-cholestane-3beta,5alpha,6beta-triol is metabolized into OCDO
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Levin, W.; Michaud, D.P.; Thomas, P.E.; Jerina, D.M.
Distinct rat hepatic microsomal epoxide hydrolases catalyze the hydration of cholesterol 5,6alpha-oxide and certain xenobiotic alkene and arene oxides
Arch. Biochem. Biophys.
220
485-494
1983
Rattus norvegicus
brenda
Nashed, N.T.; Michaud, D.P.; Levin, W.; Jerina, D.M.
Properties of liver microsomal cholesterol 5,6-oxide hydrolase
Arch. Biochem. Biophys.
241
149-162
1985
Oryctolagus cuniculus, Homo sapiens, Mesocricetus auratus, Mus musculus, Rattus norvegicus
brenda
Watabe, T.; Ozawa, N.; Ishii, H.; Chiba, K.; Hiratsuka, A.
Hepatic microsomal cholesterol epoxide hydrolase: selective inhibition by detergents and separation from xenobiotic epoxide hydrolase
Biochem. Biophys. Res. Commun.
140
632-637
1986
Mus musculus
brenda
Palakodety, R.B.; Vaz, A.D.; Griffin, M.J.
Microsomal cholesterol epoxide hydrolase activity in 2-acetylaminofluorene-induced rat liver hyperplastic nodules
Biochem. Pharmacol.
36
2424-2427
1987
Rattus norvegicus
brenda
Astroem, A.; Eriksson, M.; Eriksson, L.C.; Birberg, W.; Pilotti, A.; DePierre, J.W.
Subcellular and organ distribution of cholesterol epoxide hydrolase in the rat
Biochim. Biophys. Acta
882
359-366
1986
Rattus norvegicus
brenda
Oesch, F.; Timms, C.W.; Walker, C.H.; Guenthner, T.M.; Sparrow, A.; Watabe, T.; Wolf, C.R.
Existence of multiple forms of microsomal epoxide hydrolases with radically different substrate specificities
Carcinogenesis
5
7-9
1984
Oryctolagus cuniculus, Rattus norvegicus
brenda
Nashed, N.T.; Michaud, D.P.; Levin, W.; Jerina, D.M.
7-Dehydrocholesterol 5,6 beta-oxide as a mechanism-based inhibitor of microsomal cholesterol oxide hydrolase
J. Biol. Chem.
261
2510-2513
1986
Rattus norvegicus
brenda
Sevanian, A.; McLeod, L.L.
Catalytic properties and inhibition of hepatic cholesterol-epoxide hydrolase
J. Biol. Chem.
261
54-59
1986
Rattus norvegicus
brenda
de Medina, P.; Paillasse, M.R.; Segala, G.; Poirot, M.; Silvente-Poirot, S.
Identification and pharmacological characterization of cholesterol-5,6-epoxide hydrolase as a target for tamoxifen and AEBS ligands
Proc. Natl. Acad. Sci. USA
107
13520-13525
2010
Homo sapiens, Rattus norvegicus
brenda
Segala, G.; de Medina, P.; Iuliano, L.; Zerbinati, C.; Paillasse, M.R.; Noguer, E.; Dalenc, F.; Payre, B.; Jordan, V.C.; Record, M.; Silvente-Poirot, S.; Poirot, M.
5,6-Epoxy-cholesterols contribute to the anticancer pharmacology of tamoxifen in breast cancer cells
Biochem. Pharmacol.
86
175-189
2013
Homo sapiens
brenda
Poirot, M.; Silvente-Poirot, S.
Cholesterol-5,6-epoxides: chemistry, biochemistry, metabolic fate and cancer
Biochimie
95
622-631
2013
Rattus norvegicus
brenda
Silvente-Poirot, S.; Poirot, M.
Cholesterol epoxide hydrolase and cancer
Curr. Opin. Pharmacol.
12
696-703
2012
Homo sapiens
brenda
Voisin, M.; de Medina, P.; Mallinger, A.; Dalenc, F.; Huc-Claustre, E.; et, al.
Identification of a tumor-promoter cholesterol metabolite in human breast cancers acting through the glucocorticoid receptor
Proc. Natl. Acad. Sci. USA
114
E9346-E9355
2017
Homo sapiens
brenda
Poirot, M.; Soules, R.; Mallinger, A.; Dalenc, F.; Silvente-Poirot, S.
Chemistry, biochemistry, metabolic fate and mechanism of action of 6-oxo-cholestan-3beta,5alpha-diol (OCDO), a tumor promoter and cholesterol metabolite
Biochimie
153
139-149
2018
Homo sapiens
brenda
Griffiths, W.J.; Yutuc, E.; Abdel-Khalik, J.; Crick, P.J.; Hearn, T.; Dickson, A.; Bigger, B.W.; Hoi-Yee Wu, T.; Goenka, A.; Ghosh, A.; Jones, S.A.; Covey, D.F.; Ory, D.S.; Wang, Y.
Metabolism of non-enzymatically derived oxysterols clues from sterol metabolic disorders
Free Radic. Biol. Med.
144
124-133
2019
Homo sapiens
brenda