You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:29 UTC
Update Date2020-02-26 21:23:40 UTC
HMDB IDHMDB0001968
Secondary Accession Numbers
  • HMDB01968
Metabolite Identification
Common Name5b-Cholestane-3a,7a,12a,23-Tetrol
Description5b-Cholestane-3a,7a,12a,23-Tetrol belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Thus, 5b-cholestane-3a,7a,12a,23-tetrol is considered to be a bile acid lipid molecule. 5b-Cholestane-3a,7a,12a,23-Tetrol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752220
Synonyms
ValueSource
(3a,5b,7a,12a)-Cholestane-3,7,12,23-tetrolHMDB
Chemical FormulaC27H48O4
Average Molecular Weight436.6676
Monoisotopic Molecular Weight436.355260024
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-4-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
Traditional Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-4-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
CAS Registry Number30673-09-7
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)CC(O)CC(C)C
InChI Identifier
InChI=1S/C27H48O4/c1-15(2)10-19(29)11-16(3)20-6-7-21-25-22(14-24(31)27(20,21)5)26(4)9-8-18(28)12-17(26)13-23(25)30/h15-25,28-31H,6-14H2,1-5H3/t16-,17+,18-,19?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyVGCSSPQIZFVVCH-UVBCEDGCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • 23-hydroxysteroid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
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 Solubility0.03 g/LALOGPS
logP3.47ALOGPS
logP3.59ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.54 m³·mol⁻¹ChemAxon
Polarizability53.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ko-2449800000-93820315c41fb7c76c17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000i-2110159000-8b13bca0a8a63a5bcd32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000900000-7950bd2792cc6bad073fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-3005900000-a5d03f8ad5d28c8983aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-4009100000-817e6322f5b9047ab17dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0001900000-60349b29ea462565d721Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1003900000-dead6b17fc57cf8148a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-7009600000-f2635f5c50245cf34447Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB022769
KNApSAcK IDNot Available
Chemspider ID4447296
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6406
PubChem Compound5284208
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wolthers BG, Volmer M, van der Molen J, Koopman BJ, de Jager AE, Waterreus RJ: Diagnosis of cerebrotendinous xanthomatosis (CTX) and effect of chenodeoxycholic acid therapy by analysis of urine using capillary gas chromatography. Clin Chim Acta. 1983 Jun 30;131(1-2):53-65. [PubMed:6883710 ]