Showing Metabocard for 5beta-cholestane-3alpha,7alpha,12alpha-triol (BASm0000644)

Common Name5beta-cholestane-3alpha,7alpha,12alpha-triol
Description5beta-Cholestane-3alpha,7alpha,12alpha-triol is an intermediate in bile acid biosynthesis. 5beta-Cholestane-3alpha,7alpha,12alpha-triol is the second to last step in the synthesis of 5beta-cyprinolsulfate. It is converted from 7alpha,12alpha-dihydroxy-5beta-cholestan-3-one via enzymatic reaction, and then it is converted into 3alpha,7alpha,12alpha,26-tetrahydroxy-5beta-cholestane via the enzyme cytochrome P450 (EC 1.14.13.15). This compound inhibits la-hydroxylation (PMID: 7937829 ). It is the byproduct of cholestanetetraol 26-dehydrogenase (EC 1.1.1.161) and the reaction that catalyzes it is classified as a small molecule reaction (BioCyc).
Structure
Molecular FormulaC27H48O3
Average Mass420.66820
Monoisotopic Mass420.36035
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol
Traditional Name(1s,2s,5r,7s,9r,10r,11s,14r,15r,16s)-2,15-dimethyl-14-[(2r)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol
CAS Registry Number547-96-6
SMILESCC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
InChI IdentifierInChI=1S/C27H48O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyRIVQQZVHIVNQFH-XJZYBRFWSA-N
CHEBI IDCHEBI:16496
HMDB IDHMDB0001457
Pathways
NameSMPDB/PathBank
Primary bile acid biosynthesis
Congenital Bile Acid Synthesis Defect Type II
Cerebrotendinous Xanthomatosis (CTX)
Zellweger Syndrome
Familial Hypercholanemia (FHCA)
Congenital Bile Acid Synthesis Defect Type III
27-Hydroxylase Deficiency
StateSolid
Water Solubility5.34e-03 g/l
logP4.78
logS-4.90
pKa (Strongest Acidic)18.30
pKa (Strongest Basic)-0.16
Hydrogen Acceptor Count3
Hydrogen Donor Count3
Polar Surface Area60.69 Ų
Rotatable Bond Count5
Physiological Charge0
Formal Charge0
Refractivity122.87 m³·mol⁻¹
Polarizability52.37

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