Showing metabocard for 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane (BMDB0012455)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:38:53 UTC
Update Date2020-05-21 16:28:47 UTC
BMDB IDBMDB0012455
Secondary Accession Numbers
  • BMDB12455
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
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.21 m³·mol⁻¹ChemAxon
Polarizability52.35 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, Positivesplash10-0bvi-0239300000-2d6fa65b7814b167dc14View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1310149000-9437be2a819c430e4a74View 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, Positivesplash10-0udr-0006900000-db130a37a7a56760612dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-1009300000-cb8caefba28321f5829dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-2029000000-c0f180712508d632dc23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-618009004df62f6c9bf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-0004900000-7a224517b07b79f9aa8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-2009100000-4d1414e27f71a6efe285View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0102900000-4b21863a4bcbc27f0eb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9124200000-cdd30e3905eb978af755View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07kb-9420000000-0593538d66580bbdaca6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-0e0f641afc2bb1c607ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-e524a811b2062225068cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0002900000-2d299168fadc0554ef8fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012455
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cholesterol side-chain cleavage enzyme, mitochondrial
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the side-chain hydroxylation and cleavage of cholesterol to pregnenolone, the precursor of most steroid hormones (PubMed:11412116). Catalyzes three sequential oxidation reactions of cholesterol, namely the hydroxylation at C22 followed with the hydroxylation at C20 to yield 20R,22R-hydroxycholesterol that is further cleaved between C20 and C22 to yield the C21-steroid pregnenolone and 4-methylpentanal (PubMed:11412116). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11412116).
Gene Name:
CYP11A1
Uniprot ID:
P00189
Molecular weight:
60333.0
Reactions
3a,7a-Dihydroxy-5b-cholestane + 3 NADPH + 3 Oxygen → 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane +3 NADP +3 Waterdetails
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane → 3a,7a-Dihydroxy-5b-cholestan-26-aldetails