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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-13 12:58:41 UTC
Update Date2021-09-14 15:19:57 UTC
HMDB IDHMDB0012455
Secondary Accession Numbers
  • HMDB12455
Metabolite Identification
Common Name3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane
Description3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane, also known as (25R)-5beta-cholestane-3alpha,7alpha,26-triol or (3alpha,5beta,7alpha)-cholestane-3,7,26-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. 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582753056
Synonyms
ValueSource
3 a,7 a,26-Trihydroxy-5b-cholestaneGenerator
3 Α,7 α,26-trihydroxy-5β-cholestaneGenerator
(25R)-5beta-Cholestane-3alpha,7alpha,26-triolHMDB
(3alpha,5beta,7alpha)-Cholestane-3,7,26-triolHMDB
3alpha,7alpha,26-Trihydroxy-5beta-cholestaneHMDB
5 beta-Cholestane-3 alpha,7 alpha,26-triolHMDB
5beta-Cholestan-3alpha,7alpha,26-triolHMDB
5beta-Cholestane-3alpha,7alpha,26-triolHMDB
Cholestane-3,7,26-triolHMDB
Chemical FormulaC27H48O3
Average Molecular Weight420.6682
Monoisotopic Molecular Weight420.360345402
IUPAC Name(2S,5R,9R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9-diol
Traditional Name(2S,5R,9R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9-diol
CAS Registry Number15313-69-6
SMILES
CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C27H48O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h17-25,28-30H,5-16H2,1-4H3/t17?,18-,19?,20-,21?,22?,23?,24-,25?,26+,27-/m1/s1
InChI KeyOQIJRBFRXGIHMI-KZQGXEQDSA-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
  • 26-hydroxysteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP10(4.95) g/LALOGPS
logP10(4.85) g/LChemAxon
logS10(-5.3) g/LALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-0.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.21 m³·mol⁻¹ChemAxon
Polarizability52.35 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.61131661259
DarkChem[M-H]-193.71931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,1TMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O)CO[Si](C)(C)C3554.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,1TMS,#2CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C3528.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,1TMS,#3CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O3521.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,2TMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O)CO[Si](C)(C)C3508.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,2TMS,#2CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C3469.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,2TMS,#3CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C3488.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,3TMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C3417.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,1TBDMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O)CO[Si](C)(C)C(C)(C)C3797.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,1TBDMS,#2CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3725.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,1TBDMS,#3CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O3737.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,2TBDMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O)CO[Si](C)(C)C(C)(C)C4000.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,2TBDMS,#2CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C3906.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,2TBDMS,#3CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3890.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane,3TBDMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C4127.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvi-0239300000-2d6fa65b7814b167dc142017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1310149000-9437be2a819c430e4a742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 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 - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 10V, Positive-QTOFsplash10-0udr-0006900000-db130a37a7a56760612d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 20V, Positive-QTOFsplash10-0f79-1009300000-cb8caefba28321f5829d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 40V, Positive-QTOFsplash10-05fr-2029000000-c0f180712508d632dc232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 10V, Negative-QTOFsplash10-014i-0001900000-618009004df62f6c9bf92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 20V, Negative-QTOFsplash10-0uxr-0004900000-7a224517b07b79f9aa8c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 40V, Negative-QTOFsplash10-00dr-2009100000-4d1414e27f71a6efe2852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 10V, Positive-QTOFsplash10-0uk9-0102900000-4b21863a4bcbc27f0eb32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 20V, Positive-QTOFsplash10-0079-9124200000-cdd30e3905eb978af7552021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 40V, Positive-QTOFsplash10-07kb-9420000000-0593538d66580bbdaca62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 10V, Negative-QTOFsplash10-014i-0000900000-0e0f641afc2bb1c607ec2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 20V, Negative-QTOFsplash10-014i-0000900000-e524a811b2062225068c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 40V, Negative-QTOFsplash10-014i-0002900000-2d299168fadc0554ef8f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB029071
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05444
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481409
PDB IDNot Available
ChEBI ID28540
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.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28
Reactions
3a,7a-Dihydroxy-5b-cholestane + NADPH + Oxygen → 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane + NADP + Waterdetails
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane → 3a,7a-Dihydroxy-5b-cholestan-26-aldetails