1.14.15.15 (24S)-3beta-hydroxy-24-methyl-5alpha-cholesta-8(14),22-dien-15-one + reduced adrenodoxin + H+ + O2 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 Homo sapiens ? - ? 406942 1.14.15.15 (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 Homo sapiens ? massspectrometric product analysis, 2 products, overview ? 406942 1.14.15.15 (25R)-5beta-cholestane-3alpha,7alpha,12alpha,27-tetraol + reduced adrenodoxin + O2 - Oryctolagus cuniculus 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid + oxidized adrenodoxin + H2O - ? 385999 1.14.15.15 1alpha-hydroxyvitamin D3 + reduced adrenodoxin + O2 25-hydroxylation Rattus norvegicus 1alpha,25-dihydroxyvitamin D3 + oxidized adrenodoxin + H2O - ? 288580 1.14.15.15 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-27-al + reduced adrenodoxin + O2 - Oryctolagus cuniculus 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid + oxidized adrenodoxin + H2O - ? 387400 1.14.15.15 3beta-hydroxy-5alpha-cholest-8(14)-en-15-one + reduced adrenodoxin + H+ + O2 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 Homo sapiens ? - ? 407055 1.14.15.15 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 Homo sapiens ? massspectrometric product analysis, 2 products, overview ? 407055 1.14.15.15 5-cholestene-3beta,7alpha-diol + reduced adrenodoxin + O2 - Oryctolagus cuniculus 5-cholestene-3alpha,7alpha,26-triol + oxidized adrenodoxin + H2O - ? 386155 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + reduced adrenodoxin + O2 - Homo sapiens 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al + oxidized adrenodoxin + H2O - ? 257109 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + reduced adrenodoxin + O2 - Rattus norvegicus 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al + oxidized adrenodoxin + H2O - ? 257109 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + reduced adrenodoxin + O2 - Rattus norvegicus 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al + oxidized adrenodoxin + H2O - r 257109 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha,27-tetraol + reduced adrenodoxin + O2 oxidation to the corresponding C27-acid Oryctolagus cuniculus 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestane-27-oic acid + oxidized adrenodoxin + H2O - ? 387627 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + H+ + O2 - Rattus norvegicus (25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + oxidized adrenodoxin + H2O - ? 407071 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 - Mus musculus 5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O - ? 288576 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 - Rattus norvegicus 5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O - ? 288576 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 isocitrate can act as electron donor Rattus norvegicus 5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O - ? 288576 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 microsomal enzyme also catalyzes 25-hydroxylation of 5beta-cholestane-3alpha,7 alpha,12alpha-triol Rattus norvegicus 5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O - ? 288576 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 microsomal enzyme also catalyzes 25-hydroxylation of 5beta-cholestane-3alpha,7 alpha,12alpha-triol Oryctolagus cuniculus 5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O - ? 288576 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 mitochondrial enzyme is specific for 26-hydroxylation whereas the reaction with the microsomal enzyme hydroxylates at position 23, 24, 25 and 26 Rattus norvegicus 5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol + oxidized adrenodoxin + H2O - ? 288576 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 - Rattus norvegicus ? - ? 370256 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 conversion of cholesterol to cholic acid Rattus norvegicus ? - ? 370256 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 metabolism of cholesterol Rattus norvegicus ? - ? 370256 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 mitochondrial cytochrome P450 forms a complex with the substrate Rattus norvegicus ? - ? 370256 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 - Homo sapiens (25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + oxidized adrenodoxin + H2O - ? 386161 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 - Oryctolagus cuniculus (25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + oxidized adrenodoxin + H2O - ? 386161 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 - Oryctolagus cuniculus 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid + oxidzed adrenodoxin + H2O - ? 386162 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 - Oryctolagus cuniculus 5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + oxidized adrenodoxin + H2O - ? 386163 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol + reduced adrenodoxin + O2 - Homo sapiens (25R)-5beta-cholestane-3alpha,7alpha,12alpha,27-tetraol + oxidized adrenodoxin + H2O - ? 387628 1.14.15.15 5beta-cholestane-3alpha,7alpha-diol + reduced adrenodoxin + O2 - Rattus norvegicus ? - ? 288577 1.14.15.15 5beta-cholestane-3alpha,7alpha-diol + reduced adrenodoxin + O2 - Oryctolagus cuniculus 5beta-cholestane-3alpha,7alpha,26-triol + oxidized adrenodoxin + H2O - ? 386164 1.14.15.15 5beta-cholestane-3alpha-ol + reduced adrenodoxin + O2 - Rattus norvegicus ? - ? 288578 1.14.15.15 7-dehydrocholesterol + 4 reduced adrenodoxin + 2 H+ + 2 O2 - Homo sapiens 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 ? 425838 1.14.15.15 7alpha-hydroxy-4-cholesten-3-one + reduced adrenodoxin + O2 - Oryctolagus cuniculus 7alpha,26-dihydroxy-4-cholesten-3-one + oxidized adrenodoxin + H2O - ? 386172 1.14.15.15 beta-sitosterol + reduced adrenodoxin + O2 - Homo sapiens 26-hydroxy-beta-sitosterol + 29-hydroxy-beta-sitosterol + oxidized adrenodoxin + H2O - ? 435360 1.14.15.15 cholesterol + reduced adrenodoxin + H+ + O2 - Oryctolagus cuniculus 26-hydroxycholesterol + oxidized adrenodoxin + H2O - ? 386397 1.14.15.15 cholesterol + reduced adrenodoxin + O2 - Rattus norvegicus ? - ? 288579 1.14.15.15 cholesterol + reduced adrenodoxin + O2 - Oryctolagus cuniculus 24-hydroxycholesterol + oxidized adrenodoxin + H2O - ? 386396 1.14.15.15 cholesterol + reduced adrenodoxin + O2 - Homo sapiens 27-hydroxycholesterol + oxidized adrenodoxin + H2O - ? 386398 1.14.15.15 cholesterol + reduced adrenodoxin + O2 - Oryctolagus cuniculus 27-hydroxycholesterol + oxidized adrenodoxin + H2O - ? 386398 1.14.15.15 cholesterol + reduced adrenodoxin + O2 - Macaca fascicularis 27-hydroxycholesterol + oxidized adrenodoxin + H2O - ? 386398 1.14.15.15 cholesterol + reduced adrenodoxin + O2 - Mus musculus 27-hydroxycholesterol + oxidized adrenodoxin + H2O - ? 386398 1.14.15.15 cholesterol + reduced adrenodoxin + O2 - Oryctolagus cuniculus 25-hydroxycholesterol + oxidized adrenodoxin + H2O - ? 388315 1.14.15.15 cholesterol + reduced adrenodoxin + O2 - Homo sapiens 26-hydroxycholesterol + oxidized adrenodoxin + H2O - ? 435398 1.14.15.15 ergosterol + reduced adrenodoxin + O2 - Homo sapiens 24-hydroxyergosterol + 26-hydroxyergosterol + 28-hydroxyergosterol + oxidized adrenodoxin + H2O - ? 435479 1.14.15.15 additional information the enzyme catalyzes the first step in the oxidation of the side chain of sterol intermediates in the biosynthesis of bile acids Oryctolagus cuniculus ? - ? 89 1.14.15.15 additional information 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 Oryctolagus cuniculus ? - ? 89 1.14.15.15 additional information the enzyme does not perform 7alpha-, 12alpha-, or 25-hydroxylations on C27-steroids Oryctolagus cuniculus ? - ? 89 1.14.15.15 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 Homo sapiens ? - ? 89 1.14.15.15 additional information 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 Oryctolagus cuniculus ? - ? 89 1.14.15.15 additional information CYP27A1 catalyzes sterol 27-hydroxylation in many extrahepatic tissues and metabolizes bile acid intermediates in the liver, and vitamin D3 in the kidney Homo sapiens ? - ? 89 1.14.15.15 additional information sterol 27-hydroxylase is regulated by liver X receptor signaling, overview Rattus norvegicus ? - ? 89 1.14.15.15 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 Mycolicibacterium smegmatis ? - ? 89 1.14.15.15 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 Homo sapiens ? - ? 89