5beta-Cholestane-3alpha,7alpha,12alpha,23-tetrol (CHEM035290)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:38:15 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035290
Identification
Common Name5beta-Cholestane-3alpha,7alpha,12alpha,23-tetrol
ClassSmall Molecule
Description5b-Cholestane-3a,7a,12a,23-Tetrol is a bile present in the urine samples of patients with cerebrotendinous xanthomatosis (CTX). (PMID 6883710 ).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3a,5b,7a,12a)-Cholestane-3,7,12,23-tetrolHMDB
Chemical FormulaC27H48O4
Average Molecular Mass436.668 g/mol
Monoisotopic Mass436.355 g/mol
CAS Registry Number30673-09-7
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0004900000-aa0c91bf9f760064d700Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-8359700000-020c6e520227d67540cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-8930000000-bbaa5046aa9759972d67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-0c413525e4be8a74c95dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-42df38f6f19517fcfd4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0001900000-67dddf27bd385e67e912Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001968
FooDB IDFDB022769
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446160
ChEBI ID72595
PubChem Compound ID5283033
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.