3b,5a,6b-Cholestanetriol (CHEM035612)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:55:38 UTC
Update Date2016-11-09 01:21:20 UTC
Accession NumberCHEM035612
Identification
Common Name3b,5a,6b-Cholestanetriol
ClassSmall Molecule
Description3b,5a,6b-Cholestanetriol is a product of cholesterol oxidation found in human plasma.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3beta,5alpha,6beta-CholestanetriolChEBI
3beta,5alpha,6beta-TrihydroxycholestaneChEBI
Cholestane-3-beta,5-alpha,6-beta-triolChEBI
Cholestane-3beta-5alpha,6beta-triolChEBI
3Β,5α,6β-cholestanetriolGenerator
3b,5a,6b-TrihydroxycholestaneGenerator
3Β,5α,6β-trihydroxycholestaneGenerator
Cholestane-3-b,5-a,6-b-triolGenerator
Cholestane-3-β,5-α,6-β-triolGenerator
Cholestane-3b-5a,6b-triolGenerator
Cholestane-3β-5α,6β-triolGenerator
Cholestane-3,5,6-triolMeSH
Cholestane-3,5,6-triol, (3beta, 6beta)-isomerMeSH
Cholestane-3,5,6-triol, (3beta)-isomerMeSH
Cholestane-3,5,6-triol, (3beta, 5alpha, 6alpha)-isomerMeSH
Cholestane-3,5,6-triol, (3beta, 5alpha, 6beta)-isomerMeSH
5alpha-Cholestane-3beta,5,6beta-triolMeSH
Cholestane-3 beta,5 alpha,6 beta-triolMeSH
Cholestane-3,5,6-triol, (3beta, 5beta, 6beta)-isomerMeSH
5-alpha,6-beta-DihydroxycholestanolHMDB
5alpha,6beta-DihydroxycholestanolHMDB
Cholesta-3beta,5alpha,6beta-triolHMDB
Cholestane-3beta,5alpha,6beta-triolHMDB
CTHMDB
3b,5a,6b-CholestanetriolGenerator
5a,6b-DihydroxycholestanolGenerator, HMDB
5Α,6β-dihydroxycholestanolGenerator, HMDB
Chemical FormulaC27H48O3
Average Molecular Mass420.668 g/mol
Monoisotopic Mass420.360 g/mol
CAS Registry Number1253-84-5
IUPAC Name(1S,2R,5S,7R,8R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,7,8-triol
Traditional Namecholestane-3β,5α,6β-triol
SMILES[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@@]2(O)C[C@@H](O)CC[C@]12C
InChI IdentifierInChI=1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1
InChI KeyYMMFNKXZULYSOQ-RUXQDQFYSA-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
  • 3-hydroxysteroid
  • 6-hydroxysteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-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
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 Solubility0.0018 g/LALOGPS
logP5.11ALOGPS
logP5.21ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.29ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.61 m³·mol⁻¹ChemAxon
Polarizability52.7 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-1219200000-8d218b1547f718fefb61Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3111059000-2015192f14f9faab4bbeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0003900000-853df66410948bb19a9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-4129600000-d4fc2d8df176fb497ed5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abi-8249000000-86d9b22e1f9506f0ed1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-22df76beb29491934a98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0001900000-0f11b3056c8453dc7592Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg1-2009300000-319c3b30d049804da1b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-43d1925358840679cd31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9332200000-e5493620a11f0ba7b2f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abd-9651000000-48cc8cf6870e16017674Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-722417cd9cab9945ab4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-f6043fb123be98cf6374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0004900000-d603230f2d7d3e87bf40Spectrum
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 IDHMDB0003990
FooDB IDFDB023279
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID82619
ChEBI ID28082
PubChem Compound ID5326793
Kegg Compound IDC05425
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Fieser, Louis F.; Rajagopalan, Srinivasa. Selective oxidation with N-bromosuccinimide. II. Cholestane-3b,5a,6b-triol. Journal of the American Chemical Society (1949), 71 3938-41.
2. Bjorkhem I, Breuer O, Angelin B, Wikstrom SA: Assay of unesterified cholesterol-5,6-epoxide in human serum by isotope dilution mass spectrometry. Levels in the healthy state and in hyperlipoproteinemia. J Lipid Res. 1988 Aug;29(8):1031-8.