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Showing metabocard for 5-b-Cholestane-3a ,7a ,12a-triol (BMDB0001457)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:15 UTC
Update Date2020-05-21 16:28:48 UTC
BMDB IDBMDB0001457
Secondary Accession Numbers
  • BMDB01457
Metabolite Identification
Common Name5-b-Cholestane-3a ,7a ,12a-triol
Description5beta-Cholestane-3alpha,7alpha,12alpha-triol, also known as 3alpha,7alpha,12alpha-trihydroxycoprostane or 3a,7a,12a-trihydroxy-5b-cholestane, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5beta-cholestane-3alpha,7alpha,12alpha-triol is considered to be a bile acid. Based on a literature review a small amount of articles have been published on 5beta-Cholestane-3alpha,7alpha,12alpha-triol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestaneChEBI
3alpha,7alpha,12alpha-TrihydroxycoprostaneChEBI
3a,7a,12a-Trihydroxy-5b-cholestaneGenerator
3Α,7α,12α-trihydroxy-5β-cholestaneGenerator
3a,7a,12a-TrihydroxycoprostaneGenerator
3Α,7α,12α-trihydroxycoprostaneGenerator
5b-Cholestane-3a,7a,12a-triolGenerator
5Β-cholestane-3α,7α,12α-triolGenerator
5-beta-Cholestane-3-alpha,7-alpha,12-alpha-triolHMDB
3,7,12-TrihydroxycholestaneMeSH, HMDB
3,7,12-TrihydroxycoprostaneMeSH, HMDB
3,7,12-Trihydroxycoprostane, (3alpha,5alpha,7alpha,12alpha)-isomerMeSH, HMDB
3,7,12-Trihydroxycoprostane, (3beta,5alpha,7alpha,12alpha)-isomerMeSH, HMDB
3,7,12-Trihydroxycoprostane, (3beta,5beta,7alpha,12alpha)-isomerMeSH, HMDB
3alpha, 7alpha,12alpha-Trihydroxy-5beta-cholestaneMeSH, HMDB
5 beta-Cholestane-3 alpha,7 alpha,12 alpha-triolMeSH, HMDB
5beta-Cholestane-3alpha,7alpha,12alpha-triolMeSH, KEGG
ChtriolMeSH, HMDB
TrihydroxycoprostaneMeSH, HMDB
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12-triolHMDB
(3α,5β,7α,12α)-Cholestane-3,7,12-triolHMDB
5beta-Cholestan-3alpha,7alpha,12alpha-triolHMDB
5β-Cholestan-3α,7α,12α-triolHMDB
Chemical FormulaC27H48O3
Average Molecular Weight420.6682
Monoisotopic Molecular Weight420.360345402
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol
Traditional Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol
CAS Registry Number547-96-6
SMILES
[H][C@@]1(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])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H48O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyRIVQQZVHIVNQFH-XJZYBRFWSA-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-skeleton
  • Cholesterol
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 12-hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.78ALOGPS
logP4.98ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.87 m³·mol⁻¹ChemAxon
Polarizability52.4 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, Positivesplash10-0kkc-0349300000-7324287f0b234066bd64View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3210079000-e1f273aa178918c83174View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-766e9dee4a7aba343c98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-0001900000-90680fd53f8266be1aceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-2209400000-a1dd0a941d753b0d75e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-722417cd9cab9945ab4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-722417cd9cab9945ab4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0010900000-aeb99a2e383b60fbc744View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0007900000-f9ed4dff04df44d2af49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-2209400000-84e3ed6130fdfe17578fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5209000000-1166d5a4d66dea526dfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0001900000-f143819ead264249729eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-9122200000-2f2c0b60a02fc711aa0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9721000000-6687d50233adfbaf7604View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001457
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022635
KNApSAcK IDNot Available
Chemspider ID141053
KEGG Compound IDC05454
BioCyc IDNot Available
BiGG ID45846
Wikipedia LinkNot Available
METLIN ID6254
PubChem Compound160520
PDB IDNot Available
ChEBI ID16496
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
5-b-Cholestane-3a ,7a ,12a-triol + 3 NADPH + 3 Oxygen → 27-Deoxy-5b-cyprinol +3 NADP +4 Waterdetails
Enzyme Details
2. Dihydrodiol dehydrogenase 3
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P52898
Molecular weight:
36784.0
Reactions
7a,12a-Dihydroxy-5b-cholestan-3-one + NADP → 5-b-Cholestane-3a ,7a ,12a-triol + NADPHdetails