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Showing metabocard for 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane (HMDB12455)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version3.6
Creation Date2009-07-13 12:58:41 UTC
Update Date2017-03-02 21:32:33 UTC
HMDB IDHMDB12455
Secondary Accession NumbersNone
Metabolite Identification
Common Name3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane
Description3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is found in the primary bile acid biosynthesis pathway. 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is produced from 3 alpha,7 alpha-Dihydroxy-5beta-cholestane through the action of CYP27A (E1.14.13.15). 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is then converted to 3 alpha,7 alpha-Dihydroxy-5beta-cholestan-26-al by CYP27A (E1.14.13.15).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.002 mg/mLALOGPS
logP4.95ALOGPS
logP4.85ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-0.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.21 m3·mol-1ChemAxon
Polarizability52.35 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029071
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05444
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12455
Metagene LinkHMDB12455
METLIN IDNot Available
PubChem Compound53481409
PDB IDNot Available
ChEBI ID28540
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Sterol 26-hydroxylase, mitochondrial
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