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Information on EC 5.3.3.5 - cholestenol DELTA-isomerase
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5.3.3.5 cholestenol DELTA-isomeraseSpecify your search results
Word Map
- 5.3.3.5
- ebp
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x-linked
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chondrodysplasia
- punctata
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stipple
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sigma1
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epiphyseal
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x-inactivation
- 8-dehydrocholesterol
- nsdhl
The enzyme appears in viruses and cellular organisms
Synonyms
emopamil binding protein, emopamil-binding protein, delta8-delta7 sterol isomerase, c-8,7 sterol isomerase, erg2p, delta8-delta7 isomerase, d8d7i, 8,7si, d8-d7 sterol isomerase, cholestenol delta-isomerase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
8,7SI
Cholestenol delta-isomerase
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D8-D7 sterol isomerase
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DELTA8,7-sterol isomerase
DELTA8-Cholestenol-DELTA7-cholestenol isomerase
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DELTA8-DELTA7 isomerase
Delta8-delta7 sterol isomerase
EBP
Emopamil binding protein
emopamil-binding protein
Isomerase, cholestenol DELTA-
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sterol 8,7-isomerase
Delta8-delta7 sterol isomerase
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Emopamil binding protein
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
5alpha-Cholest-7-en-3beta-ol = 5alpha-cholest-8-en-3beta-ol
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
intramolecular oxidoreduction
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isomerization
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
DELTA7-Cholestenol DELTA7-DELTA8-isomerase
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CAS REGISTRY NUMBER
COMMENTARY
37318-47-1
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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
26,27-dinorcholesta-8,24-dienol
26,27-dinorcholesta-7,24-dienol
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?
26-homo-cholesta-8(9),23(24) E26(26')-trienol
26-homo-cholesta-7(8),23(24)E26(26')trienol
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?
4alpha-methyl-5alpha-ergosta-8,24-dien-3beta-ol
24-methylenelophenol
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i.e. 4alpha-methyl-5alpha-ergosta-7,24-dien-3beta-ol
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?
5alpha-cholest-7-en-3beta-ol
?
enzyme of the cholesterol biosynthetic pathway, mutations are associated with Conradi-Huenermann syndrome. The enzyme may be involved in liver function, since the mRNA is only detected in hepatocytes not in connective tissue or blood vessels. The expression of the SI gene is regulated transcriptionally in vitro and in vivo by widely known regulatory agents ranging from tamoxifen, an oestrogen receptor antagonist and SI-specific inhibitor, to cholesterol-lowering drugs
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?
5alpha-cholesta-8,24-dien-3beta-ol
5alpha-cholesta-7,24-dien-3beta-ol
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?
zymosterol
cholesta-7,24-dienol
preferred substrate for DELTA7-sterol production, the reaction equilibrium for double-bond isomerization favours the forward direction, DELTA8 to DELTA7
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r
additional information
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3-desoxyzymosterol is not an active substrate
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NATURAL SUBSTRATE
NATURAL 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
5alpha-cholest-7-en-3beta-ol
?
enzyme of the cholesterol biosynthetic pathway, mutations are associated with Conradi-Huenermann syndrome. The enzyme may be involved in liver function, since the mRNA is only detected in hepatocytes not in connective tissue or blood vessels. The expression of the SI gene is regulated transcriptionally in vitro and in vivo by widely known regulatory agents ranging from tamoxifen, an oestrogen receptor antagonist and SI-specific inhibitor, to cholesterol-lowering drugs
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?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-aminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
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(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-N-methylaminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
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(1'R,3a'R,7a'R,1''R)-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitro-5-[[2-(pyrrolidin-1yl)ethyl]aminomethyl]spiro[1,3-dioxane-2,4'-octahydroindene]
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(1'R,3a'R,7a'R,1''R)-7a'-methyl-5-[N-(N,N-dimethylaminoeth-2-yl-aminomethyl)-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]]
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(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-(pent-4-en-1-ylamino)octahydro-1H-inden-4-ol
(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-[methyl(pent-4-en-1-yl)amino]octahydro-1H-inden-4-ol
(1R,3aR,4R,5S,7aR)-5-(benzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
(1R,3aR,4R,5S,7aR)-5-(dibenzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
(1R,3aR,4R,5S,7aR)-5-[benzyl(methyl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
(1R,3aR,4R,5S,7aR)-5-[benzyl(pent-4-en-1-yl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
(1R,3aR,5S,7aR)-5-(dimethylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
(R,S)-1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazine
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1',2',3',4'-tetrahydro-5-(N-benzylpiperidin-4-yl)-aminomethyl-5-nitro-6'-(4-methylpentyloxy)-spiro[1,3-dioxane-2,1'-naphthaline]
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1',2',3',4'-tetrahydro-5-(N-benzylpiperidin-4-yl)-aminomethyl-6'-methoxy-5-nitrospiro[1,3-dioxane-2,1'-naphthaline]
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1-[(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]-4-pyridin-2-ylpiperazine
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2-[4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy]-N,N-dimethylethanamine
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noncompetitive, IC50: 0.00025 mM
trans-2-[4-(1,2-diphenylbuten-1-yl)phenoxy]-N,N-dimethylethylamine
IC50: 0.0112 mM
(+)-pentazocine
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i.e. (+)-[2S-(2R,6R,11R)]-1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocine-8-ol
(-)-emopamil
IC50: 28 nM for the liver enzyme, IC50: 34 nM for the brain enzyme
(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-(pent-4-en-1-ylamino)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-(pent-4-en-1-ylamino)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-(pent-4-en-1-ylamino)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-(pent-4-en-1-ylamino)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-[methyl(pent-4-en-1-yl)amino]octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-[methyl(pent-4-en-1-yl)amino]octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-[methyl(pent-4-en-1-yl)amino]octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)-5-[methyl(pent-4-en-1-yl)amino]octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-(benzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-(benzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-(benzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-(benzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-(dibenzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-(dibenzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-(dibenzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-(dibenzylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-amino-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-amino-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-amino-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-amino-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-[benzyl(methyl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-[benzyl(methyl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-[benzyl(methyl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-[benzyl(methyl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-[benzyl(pent-4-en-1-yl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-[benzyl(pent-4-en-1-yl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-[benzyl(pent-4-en-1-yl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,4R,5S,7aR)-5-[benzyl(pent-4-en-1-yl)amino]-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,5S,7aR)-5-(dimethylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,5S,7aR)-5-(dimethylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,5S,7aR)-5-(dimethylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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(1R,3aR,5S,7aR)-5-(dimethylamino)-3a,7a-dimethyl-1-(6-methylheptan-2-yl)octahydro-1H-inden-4-ol
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ditolylguanidine
IC50: 122 nM for the liver enzyme, IC50: 36 nM for the brain enzyme
haloperidol
IC50: 6.8 nM for the liver enzyme, 23 nM for the brain enzyme
ifenprodil
IC50: 2.4 nM for the liver enzyme, 1.7 nM for the brain enzyme
Trifluoperazine
IC50: 11 nM for the liver enzyme, IC50: 13 nM for the brain enzyme
U18666A