Hmdb loader
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
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 08:39:17 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0003990
Secondary Accession Numbers
  • HMDB03990
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
Data?1582752294
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
5alpha-Cholestane-3beta,5,6beta-triolMeSH
Cholestane-3 beta,5 alpha,6 beta-triolMeSH
Cholestane-3,5,6-triol, (3beta, 5beta, 6beta)-isomerMeSH
Cholestane-3,5,6-triol, (3beta)-isomerMeSH
Cholestane-3,5,6-triol, (3beta, 5alpha, 6alpha)-isomerMeSH
Cholestane-3,5,6-triolMeSH
Cholestane-3,5,6-triol, (3beta, 6beta)-isomerMeSH
Cholestane-3,5,6-triol, (3beta, 5alpha, 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
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.17631661259
DarkChem[M-H]-200.73531661259
DeepCCS[M-2H]-243.84130932474
DeepCCS[M+Na]+218.79830932474
AllCCS[M+H]+209.132859911
AllCCS[M+H-H2O]+207.232859911
AllCCS[M+NH4]+210.932859911
AllCCS[M+Na]+211.432859911
AllCCS[M-H]-204.732859911
AllCCS[M+Na-2H]-206.832859911
AllCCS[M+HCOO]-209.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3b,5a,6b-Cholestanetriol[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@]12C2881.5Standard polar33892256
3b,5a,6b-Cholestanetriol[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@]12C3387.0Standard non polar33892256
3b,5a,6b-Cholestanetriol[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@]12C3588.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3b,5a,6b-Cholestanetriol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3352.5Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3308.0Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3347.1Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O[Si](C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3269.8Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3286.0Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3247.2Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,3TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3257.3Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3595.6Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3537.2Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TBDMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3608.8Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3715.0Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3774.5Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TBDMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3718.8Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,3TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3921.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3b,5a,6b-Cholestanetriol GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-1219200000-8d218b1547f718fefb612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,5a,6b-Cholestanetriol GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3111059000-2015192f14f9faab4bbe2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,5a,6b-Cholestanetriol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,5a,6b-Cholestanetriol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 10V, Positive-QTOFsplash10-0uk9-0003900000-853df66410948bb19a9e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 20V, Positive-QTOFsplash10-0fe0-4129600000-d4fc2d8df176fb497ed52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 40V, Positive-QTOFsplash10-0abi-8249000000-86d9b22e1f9506f0ed1c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 10V, Negative-QTOFsplash10-014i-0000900000-22df76beb29491934a982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 20V, Negative-QTOFsplash10-0gb9-0001900000-0f11b3056c8453dc75922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 40V, Negative-QTOFsplash10-0zg1-2009300000-319c3b30d049804da1b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 10V, Positive-QTOFsplash10-00di-0000900000-43d1925358840679cd312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 20V, Positive-QTOFsplash10-05fr-9332200000-e5493620a11f0ba7b2f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 40V, Positive-QTOFsplash10-0abd-9651000000-48cc8cf6870e160176742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 10V, Negative-QTOFsplash10-014i-0000900000-722417cd9cab9945ab4a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 20V, Negative-QTOFsplash10-014i-0000900000-f6043fb123be98cf63742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 40V, Negative-QTOFsplash10-014i-0004900000-d603230f2d7d3e87bf402021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothInflammatory bowel disease details
Associated Disorders and Diseases
Disease References
Inflammatory bowel disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 References
  1. 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. [PubMed:3183516 ]