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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:17 UTC
HMDB IDHMDB0000524
Secondary Accession Numbers
  • HMDB0000655
  • HMDB00524
  • HMDB00655
Metabolite Identification
Common Name5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol
Description5β-Cholestane-3α,7α,12α,25-tetrol is an intermediate in the bile acid synthetic pathway, and is secreted into the bile and urine following glucuronidation. It does not undergo enterohepatic circulation. In cerebrotendinous xanthomatosis (CTX), a bile acid synthesis disorder caused by sterol 27-hydroxylase (CYP27) deficiency, early intermediates and cholestanol accumulate in a variety of tissues, and glucuronides of 25-hydroxylated bile alcohols are released in bile, blood, and urine (PMID: 11181760 ). Bile acid synthesis from cholesterol is tightly regulated via a feedback mechanism mediated by the farnesoid X receptor (FXR), a nuclear receptor activated by bile acids. Synthesis via the classic pathway is initiated by a series of cholesterol ring modifications and followed by the side chain cleavage. The enhanced cholesterol 7 alpha-hydroxylase (CYP7A1) expression in CYP27 deficiency may be the result of a decreased flux of bile acids and bile alcohols into the liver, while production of FXR-activating 5β-cholestane-3α,7α,12α,25-tetrol is increased (PMID: 15145977 ).
Structure
Data?1582752137
Synonyms
ValueSource
5b-Cholestane-3a,7a,12a,25-tetrolGenerator
5Β-cholestane-3α,7α,12α,25-tetrolGenerator
5 beta Cholestane-3 alpha,7 alpha,12 alpha,25-tetrolHMDB
5 beta-Cholestane-3 beta,7 alpha,12 alpha,25-tetrolHMDB
Cholestane-3,7,12,25-tetrolHMDB
(3Α,5β,7α,12α)-cholestane-3,7,12,25-tetrolHMDB
3Α,7α,12α,25-tetrahydroxycoprostaneHMDB
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12,25-tetrolHMDB
3alpha,7alpha,12alpha,25-TetrahydroxycoprostaneHMDB
5b-Cholestan-3a,7a,12a,25-tetrolHMDB
5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrolGenerator
Chemical FormulaC27H48O4
Average Molecular Weight436.677
Monoisotopic Molecular Weight436.355260026
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[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)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol
CAS Registry Number18866-87-0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)(C)O
InChI Identifier
InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChI KeyNTIXPPFPXLYJCT-RNUSRIHUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • 25-hydroxysteroid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP3.64ALOGPS
logP3.51ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.71 m³·mol⁻¹ChemAxon
Polarizability53.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000900000-ce7599af15d682b569c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1005900000-372cbf89a7b70f683e60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-2209200000-de49d287713beec95040Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0001900000-f8627b8fe61026d323eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0002900000-e0dbc20b7cbe891c1ef9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-2017900000-ec2da6f1ebd80a8be486Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022092
KNApSAcK IDNot Available
Chemspider ID146751
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5509
PubChem Compound167758
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceDayal B; Bagan E; Speck J; Salen G A facile synthesis of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol. Steroids (1980), 35(4), 439-44.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dayal B, Ertel NH, Padia J, Rapole KR, Salen G: 7 beta-hydroxy bile alcohols: facile synthesis and 2D 1H NMR studies of 5 beta-cholestane-3 alpha, 7 beta, 12 alpha, 25-tetrol. Steroids. 1997 May;62(5):409-14. [PubMed:9178427 ]
  2. Kosaka D, Hiraoka T, Kohoda T, Kajiyama G, Yamauchi T, Kihira K, Kuramoto T, Hoshita T: Stable isotope dilution assay for 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,23,25-pentol in human serum using [26,27-D6] labeled internal standards; a highly accurate approach to the serological diagnosis of cerebrotendinous xanthomatosis. Clin Chim Acta. 1991 May 31;199(1):83-9. [PubMed:1934504 ]
  3. Dayal B, Greeley DN, Williams TH, Tint GS, Salen G: Stereospecific synthesis of 3 beta-hydroxylated bile alcohols. J Lipid Res. 1984 Jun;25(6):646-50. [PubMed:6747468 ]
  4. Cronholm T: Excretion of 5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 26-tetrol and corticosterone metabolites in rat bile. Studies on the role of alcohol dehydrogenase in steroid metabolism. J Steroid Biochem. 1984 Jun;20(6A):1321-5. [PubMed:6379302 ]
  5. Dayal B, Salen G, Padia J, Shefer S, Tint GS, Sasso G, Williams TH: Bile alcohol glucuronides: regioselective O-glucuronidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol and 24-nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol. Carbohydr Res. 1993 Feb 24;240:133-42. [PubMed:8458007 ]
  6. Nishimaki-Mogami T, Une M, Fujino T, Sato Y, Tamehiro N, Kawahara Y, Shudo K, Inoue K: Identification of intermediates in the bile acid synthetic pathway as ligands for the farnesoid X receptor. J Lipid Res. 2004 Aug;45(8):1538-45. Epub 2004 May 16. [PubMed:15145977 ]
  7. Honda A, Salen G, Matsuzaki Y, Batta AK, Xu G, Leitersdorf E, Tint GS, Erickson SK, Tanaka N, Shefer S: Differences in hepatic levels of intermediates in bile acid biosynthesis between Cyp27(-/-) mice and CTX. J Lipid Res. 2001 Feb;42(2):291-300. [PubMed:11181760 ]