1.14.15.15: cholestanetriol 26-monooxygenase
This is an abbreviated version!
For detailed information about cholestanetriol 26-monooxygenase, go to the full flat file.
Word Map on EC 1.14.15.15
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1.14.15.15
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bile
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xanthomatosis
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cerebrotendinous
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27-hydroxycholesterol
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chenodeoxycholic
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cholestanol
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tendon
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xanthomas
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oxysterols
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cataract
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cyp7a1
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27-hydroxylation
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cholic
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12alpha-hydroxylase
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cholecalciferol
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lipid-storage
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lxralpha
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7alpha-hydroxylated
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cholestyramine
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7-ketocholesterol
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7alpha-hydroxy-4-cholesten-3-one
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alpha-hydroxyvitamin
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medicine
-
lithogenic
- 1.14.15.15
- bile
- xanthomatosis
-
cerebrotendinous
- 27-hydroxycholesterol
-
chenodeoxycholic
- cholestanol
- tendon
- xanthomas
- oxysterols
- cataract
- cyp7a1
-
27-hydroxylation
-
cholic
-
12alpha-hydroxylase
- cholecalciferol
-
lipid-storage
-
lxralpha
-
7alpha-hydroxylated
- cholestyramine
- 7-ketocholesterol
- 7alpha-hydroxy-4-cholesten-3-one
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alpha-hydroxyvitamin
- medicine
-
lithogenic
Reaction
Synonyms
5beta-cholestane-3 alpha,7alpha,12alpha,26-tetrol dehydrogenase, 5beta-cholestane-3 alpha,7alpha,12alpha-triol-26-al oxidoreductase, 5beta-cholestane-3alpha,7alpha,12alpha-triol 26-hydroxylase, 5beta-cholestane-3alpha,7alpha,12alpha-triol 27-monooxygenase, 5beta-cholestane-3alpha,7alpha,12alpha-triol hydroxylase, cholestanetriol 26-hydroxylase, cholestanetriol 27-hydroxylase, cholesterol C-26 hydroxylase, cholesterol hydroxylase, CYP125A4, CYP27, CYP27A, CYP27A1, cytochrome P-450 sterol 26-hydroxylase, cytochrome P-450A, cytochrome P450 125A4, cytochrome P450 27A, cytochrome P450c27, dehydrogenase, cholestanetetrol 26-, EC 1.1.1.161, EC 1.14.13.15, EC 1.2.1.40, hydroxylase, 5beta-cholestane-3alpha,7alpha,12alpha-triol, More, oxygenase, cholestanetriol 26-mono-, P450 27A1, sterol 27-hydroxylase, TEHC-NAD oxidoreductase, vitamin D3 25-hydroxylase
ECTree
1.14.15.15 cholestanetriol 26-monooxygenaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.14.15.15 - cholestanetriol 26-monooxygenase
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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
(24S)-3beta-hydroxy-24-methyl-5alpha-cholesta-8(14),22-dien-15-one + reduced adrenodoxin + H+ + O2
?
(25R)-5beta-cholestane-3alpha,7alpha,12alpha,27-tetraol + reduced adrenodoxin + O2
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid + oxidized adrenodoxin + H2O
-
-
-
-
?
1alpha-hydroxyvitamin D3 + reduced adrenodoxin + O2
1alpha,25-dihydroxyvitamin D3 + oxidized adrenodoxin + H2O
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-27-al + reduced adrenodoxin + O2
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid + oxidized adrenodoxin + H2O
-
-
-
-
?
5-cholestene-3beta,7alpha-diol + reduced adrenodoxin + O2
5-cholestene-3alpha,7alpha,26-triol + oxidized adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + reduced adrenodoxin + O2
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al + oxidized adrenodoxin + H2O
5beta-cholestane-3alpha,7alpha,12alpha,27-tetraol + reduced adrenodoxin + O2
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestane-27-oic acid + oxidized adrenodoxin + H2O
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oxidation to the corresponding C27-acid
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + H+ + O2
(25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + oxidized adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
(25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + oxidized adrenodoxin + H2O
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
(25R)-5beta-cholestane-3alpha,7alpha,12alpha,27-tetraol + oxidized adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid + oxidzed adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + oxidized adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O
5beta-cholestane-3alpha,7alpha-diol + reduced adrenodoxin + O2
5beta-cholestane-3alpha,7alpha,26-triol + oxidized adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha-diol + reduced adrenodoxin + O2
?
-
-
-
-
?
7-dehydrocholesterol + 4 reduced adrenodoxin + 2 H+ + 2 O2
25-hydroxy-7-dehydrocholesterol + 26/27-hydroxy-7-dehydrocholesterol + 4 oxidzed adrenodoxin + 2 H2O
-
-
metabolites detected in serum of a patient with Smith-Lemli-Opitz syndrome. 25-hydroxy-7-dehydrocholesterol activates liver X receptors LXRalpha, LXRbeta and vitamin D receptor and 26/27-hydroxy-7-dehydrocholesterol induces activation of LXRalpha and LXRbeta, although the activities of both compounds on LXRs are weak. 26/27-Hydroxy-7-dehydrocholesterol is (3S,25S)-cholesta-5,7-diene-3,26-diol or (3S,25R)-cholesta-5,7-diene-3,26-diol
-
?
7alpha-hydroxy-4-cholesten-3-one + reduced adrenodoxin + O2
7alpha,26-dihydroxy-4-cholesten-3-one + oxidized adrenodoxin + H2O
-
-
-
-
?
beta-sitosterol + reduced adrenodoxin + O2
26-hydroxy-beta-sitosterol + 29-hydroxy-beta-sitosterol + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + H+ + O2
26-hydroxycholesterol + oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + reduced adrenodoxin + O2
24-hydroxycholesterol + oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + reduced adrenodoxin + O2
25-hydroxycholesterol + oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + reduced adrenodoxin + O2
26-hydroxycholesterol + oxidized adrenodoxin + H2O
-
-
-
?
ergosterol + reduced adrenodoxin + O2
24-hydroxyergosterol + 26-hydroxyergosterol + 28-hydroxyergosterol + oxidized adrenodoxin + H2O
-
-
-
?
(24S)-3beta-hydroxy-24-methyl-5alpha-cholesta-8(14),22-dien-15-one + reduced adrenodoxin + H+ + O2
?
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the substrate is a potential drug for lowering cholesterol in the treatment and/or prevention of coronary artery disease, but it is rapidly metabolized in the liver
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-
?
(24S)-3beta-hydroxy-24-methyl-5alpha-cholesta-8(14),22-dien-15-one + reduced adrenodoxin + H+ + O2
?
-
28-hydroxylation by CYP27A1, enzyme activity assay in presence of adrenodoxin, adrenodoxin reductase and NADPH
massspectrometric product analysis, 2 products, overview
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?
1alpha-hydroxyvitamin D3 + reduced adrenodoxin + O2
1alpha,25-dihydroxyvitamin D3 + oxidized adrenodoxin + H2O
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25-hydroxylation
-
-
?
1alpha-hydroxyvitamin D3 + reduced adrenodoxin + O2
1alpha,25-dihydroxyvitamin D3 + oxidized adrenodoxin + H2O
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25-hydroxylation
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?
3beta-hydroxy-5alpha-cholest-8(14)-en-15-one + reduced adrenodoxin + H+ + O2
?
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the substrate is a potential drug for lowering cholesterol in the treatment and/or prevention of coronary artery disease, but it is rapidly metabolized in the liver
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-
?
3beta-hydroxy-5alpha-cholest-8(14)-en-15-one + reduced adrenodoxin + H+ + O2
?
-
28-hydroxylation by CYP27A1, enzyme activity assay in presence of adrenodoxin, adrenodoxin reductase and NADPH
massspectrometric product analysis, 2 products, overview
-
?
5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + reduced adrenodoxin + O2
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al + oxidized adrenodoxin + H2O
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + reduced adrenodoxin + O2
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al + oxidized adrenodoxin + H2O
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + reduced adrenodoxin + O2
3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al + oxidized adrenodoxin + H2O
-
-
-
r
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
(25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + oxidized adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
(25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + oxidized adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O
-
microsomal enzyme also catalyzes 25-hydroxylation of 5beta-cholestane-3alpha,7 alpha,12alpha-triol
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O
-
isocitrate can act as electron donor
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O
-
microsomal enzyme also catalyzes 25-hydroxylation of 5beta-cholestane-3alpha,7 alpha,12alpha-triol
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O
-
mitochondrial enzyme is specific for 26-hydroxylation whereas the reaction with the microsomal enzyme hydroxylates at position 23, 24, 25 and 26
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
?
-
-
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
?
-
conversion of cholesterol to cholic acid
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
?
-
metabolism of cholesterol
-
-
?
5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2
?
-
mitochondrial cytochrome P450 forms a complex with the substrate
-
-
?
cholesterol + reduced adrenodoxin + O2
27-hydroxycholesterol + oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + reduced adrenodoxin + O2
27-hydroxycholesterol + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
27-hydroxycholesterol + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
27-hydroxycholesterol + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
27-hydroxycholesterol + oxidized adrenodoxin + H2O
-
-
-
-
?
additional information
?
-
-
the regioselectivity of the reaction is determined by residues of the helix F loop, e.g. F207, I211, and F215, substrate regiospecificity of wild-type and mutant enzymes, overview, 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid and 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-27-al are poor substrates
-
-
?
additional information
?
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-
CYP27A1 catalyzes sterol 27-hydroxylation in many extrahepatic tissues and metabolizes bile acid intermediates in the liver, and vitamin D3 in the kidney
-
-
?
additional information
?
-
human CYP27A1 catalyzes hydroxylation of beta-sitosterol and ergosterol, CYP27A1 catalyzes the 26-hydroxylation of cholesterol to form the physiologically active product 26-hydroxycholesterol. CYP27A1 is also able to accept other steroids with structural similarity to cholesterol as substrates such as vitamin D3 and its precursor 7-dehydrocholesterol. NMR spectroscopic product analysis
-
-
?
additional information
?
-
-
enzyme CYP125A4 also oxidizes cholesterol, although it has a much higher activity for the oxidation of 7alpha-hydroxycholesterol, EC 1.14.14.23. The enzyme forms 7alpha,26-dihydroxycholesterol
-
-
?
additional information
?
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-
the enzyme catalyzes the first step in the oxidation of the side chain of sterol intermediates in the biosynthesis of bile acids
-
-
?
additional information
?
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-
a multifunctional enzyme catalyzing also the reaction of 25-hydroxyvitamin D3 1alpha-hydroxylase, EC 1.14.13.13, as well as the 24- and 25-hydroxylation of cholesterol, the truncated enzyme form is less efficient than the full-length CYP27A in the 27-hydroxylation of C27-sterols, and much less efficient in the 25-hydroxylation of 1alpha-hydroxyvitamin D3
-
-
?
additional information
?
-
-
the enzyme does not perform 7alpha-, 12alpha-, or 25-hydroxylations on C27-steroids
-
-
?
additional information
?
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-
the sterol 27-hydroxylase performs multiple monooxygenations in the conversion of 58-cholestane-3alpha,7alpha,12alpha-triol into 3alpha,7alpha,l2alpha-trihydroxy-5beta-cholestanoic acid, product identification by gas spectrometry
-
-
?
additional information
?
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-
sterol 27-hydroxylase is regulated by liver X receptor signaling, overview
-
-
?
