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
StatusExpected but not Quantified
Creation Date2017-03-21 06:17:33 UTC
Update Date2022-03-07 03:17:54 UTC
HMDB IDHMDB0062418
Secondary Accession Numbers
  • HMDB62418
Metabolite Identification
Common Name5beta-Cholestane-3alpha,7alpha,24-triol
Description5beta-cholestane-3alpha,7alpha,24-triol, also known as 5β-cholestan-3α,7α,24-triol, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Thus, 5beta-cholestane-3alpha,7alpha,24-triol is considered to be a bile acid lipid molecule. 5beta-cholestane-3alpha,7alpha,24-triol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866309
Synonyms
ValueSource
5beta-Cholestan-3alpha,7alpha,24-triolChEBI
5b-Cholestan-3a,7a,24-triolGenerator
5Β-cholestan-3α,7α,24-triolGenerator
5b-Cholestane-3a,7a,24-triolGenerator
5Β-cholestane-3α,7α,24-triolGenerator
Chemical FormulaC27H48O3
Average Molecular Weight420.678
Monoisotopic Molecular Weight420.360345406
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R)-14-[(2R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9-diol
Traditional Name(1S,2S,5R,7S,9R,10R,11S,14R,15R)-14-[(2R)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9-diol
CAS Registry NumberNot Available
SMILES
[H]C(O)(CC[C@@]([H])(C)[C@@]1([H])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])CC[C@]12C)C(C)C
InChI Identifier
InChI=1S/C27H48O3/c1-16(2)23(29)9-6-17(3)20-7-8-21-25-22(11-13-27(20,21)5)26(4)12-10-19(28)14-18(26)15-24(25)30/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23?,24-,25+,26+,27-/m1/s1
InChI KeyVDKSIHRRZLCAGD-RESWAWEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 24-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0034 g/lALOGPS
LogP4.59ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.59ALOGPS
logP4.9ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.95 m³·mol⁻¹ChemAxon
Polarizability51.94 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.1131661259
DarkChem[M-H]-195.56331661259
DeepCCS[M-2H]-230.07530932474
DeepCCS[M+Na]+204.09330932474
AllCCS[M+H]+209.232859911
AllCCS[M+H-H2O]+207.332859911
AllCCS[M+NH4]+210.932859911
AllCCS[M+Na]+211.432859911
AllCCS[M-H]-204.432859911
AllCCS[M+Na-2H]-206.632859911
AllCCS[M+HCOO]-209.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5beta-Cholestane-3alpha,7alpha,24-triol[H]C(O)(CC[C@@]([H])(C)[C@@]1([H])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])CC[C@]12C)C(C)C2845.4Standard polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol[H]C(O)(CC[C@@]([H])(C)[C@@]1([H])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])CC[C@]12C)C(C)C3431.3Standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol[H]C(O)(CC[C@@]([H])(C)[C@@]1([H])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])CC[C@]12C)C(C)C3671.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5beta-Cholestane-3alpha,7alpha,24-triol,1TMS,isomer #1CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)O[Si](C)(C)C3433.3Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,1TMS,isomer #2CC(C)C(O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3389.7Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,1TMS,isomer #3CC(C)C(O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3445.5Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,2TMS,isomer #1CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O)O[Si](C)(C)C3411.2Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,2TMS,isomer #2CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C)O[Si](C)(C)C3347.6Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,2TMS,isomer #3CC(C)C(O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3342.1Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,3TMS,isomer #1CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C)O[Si](C)(C)C3340.8Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,1TBDMS,isomer #1CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)O[Si](C)(C)C(C)(C)C3678.5Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,1TBDMS,isomer #2CC(C)C(O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3615.2Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,1TBDMS,isomer #3CC(C)C(O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3669.6Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,2TBDMS,isomer #1CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O)O[Si](C)(C)C(C)(C)C3893.8Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,2TBDMS,isomer #2CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3802.8Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,2TBDMS,isomer #3CC(C)C(O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3791.6Semi standard non polar33892256
5beta-Cholestane-3alpha,7alpha,24-triol,3TBDMS,isomer #1CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4020.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kdl-1339400000-7e3f092d94cbfd56fea62017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol GC-MS (3 TMS) - 70eV, Positivesplash10-00di-2110159000-1853e81f0ef26deb74e92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 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 - 5beta-Cholestane-3alpha,7alpha,24-triol 10V, Positive-QTOFsplash10-0udr-0006900000-f1bb28c5c16c4cfdbf962017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 20V, Positive-QTOFsplash10-0f79-3009400000-2d2f1c2c584a1a0507e02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 40V, Positive-QTOFsplash10-05fr-3019000000-178af907a36b51804a622017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 10V, Negative-QTOFsplash10-014i-0001900000-dfd8ebbca51cda151fd02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 20V, Negative-QTOFsplash10-0uxr-0002900000-f89f338cdc33d728d2012017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 40V, Negative-QTOFsplash10-0fe0-6009200000-09d8062e8b76784f46f22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 10V, Positive-QTOFsplash10-0uk9-0114900000-848b8d23147cdd837d292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 20V, Positive-QTOFsplash10-01p9-9507100000-9ffe15db01fda4e994272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 40V, Positive-QTOFsplash10-03fs-7960000000-384aefb56ab88ecd5d852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 10V, Negative-QTOFsplash10-014i-0000900000-4672e63755105b319f432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 20V, Negative-QTOFsplash10-014i-0000900000-aa1ce4ba00b4c1f8030a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,24-triol 40V, Negative-QTOFsplash10-014i-0000900000-82495918e6c7eb0e661e2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID48700
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.