Showing metabocard for 3b,5a,6b-Cholestanetriol (BMDB0003990)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:13 UTC
Update Date2020-04-22 15:13:06 UTC
BMDB IDBMDB0003990
Secondary Accession Numbers
  • BMDB03990
Metabolite Identification
Common Name3b,5a,6b-Cholestanetriol
Description3b,5a,6b-Cholestanetriol, also known as cholestane-3-b,5-a,6-b-triol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 3b,5a,6b-cholestanetriol is considered to be a sterol. Based on a literature review very few articles have been published on 3b,5a,6b-Cholestanetriol.
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 Weight420.6682
Monoisotopic Molecular Weight420.360345402
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
CAS Registry Number1253-84-5
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 Identifier
InChI=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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-1219200000-8d218b1547f718fefb61View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3111059000-2015192f14f9faab4bbeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0003900000-853df66410948bb19a9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-4129600000-d4fc2d8df176fb497ed5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abi-8249000000-86d9b22e1f9506f0ed1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-22df76beb29491934a98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0001900000-0f11b3056c8453dc7592View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg1-2009300000-319c3b30d049804da1b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-43d1925358840679cd31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9332200000-e5493620a11f0ba7b2f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abd-9651000000-48cc8cf6870e16017674View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-722417cd9cab9945ab4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-f6043fb123be98cf6374View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0004900000-d603230f2d7d3e87bf40View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003990
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023279
KNApSAcK IDNot Available
Chemspider ID82619
KEGG Compound IDC05425
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5326793
PDB IDNot Available
ChEBI ID28082
References
Synthesis ReferenceFieser, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available