Showing metabocard for 3a,7a,12a-Trihydroxy-5b-cholestanoic acid (BMDB0003873)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:25 UTC
Update Date2020-04-22 15:12:51 UTC
BMDB IDBMDB0003873
Secondary Accession Numbers
  • BMDB03873
Metabolite Identification
Common Name3a,7a,12a-Trihydroxy-5b-cholestanoic acid
Description3a,7a,12a-Trihydroxy-5b-cholestanoic acid 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. Based on a literature review a significant number of articles have been published on 3a,7a,12a-Trihydroxy-5b-cholestanoic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3alpha,5beta,7alpha,12alpha,25R)-3,7,12-Trihydroxycholestan-26-Oic acidChEBI
(3a,5b,7a,12a,25R)-3,7,12-Trihydroxycholestan-26-OateGenerator
(3a,5b,7a,12a,25R)-3,7,12-Trihydroxycholestan-26-Oic acidGenerator
(3alpha,5beta,7alpha,12alpha,25R)-3,7,12-Trihydroxycholestan-26-OateGenerator
(3Α,5β,7α,12α,25R)-3,7,12-trihydroxycholestan-26-OateGenerator
(3Α,5β,7α,12α,25R)-3,7,12-trihydroxycholestan-26-Oic acidGenerator
3a,7a,12a-Trihydroxy-5b-cholestanoateGenerator
(25R)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestan-26-OateHMDB
(25R)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestan-26-Oic acidHMDB
3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholestanateHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoateHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acidHMDB
Chemical FormulaC27H46O5
Average Molecular Weight450.6511
Monoisotopic Molecular Weight450.334524582
IUPAC Name(2R,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoic acid
Traditional Name(2R,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoic acid
CAS Registry Number547-98-8
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC[C@@H](C)C(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChI KeyCNWPIIOQKZNXBB-WBYPBBSPSA-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
  • Steroid acid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oic acid (CHEBI:48043 )
  • C27 bile acids, alcohols, and derivatives (LMST04030151 )
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
logP3.12ALOGPS
logP3.91ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity124.57 m³·mol⁻¹ChemAxon
Polarizability53.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003873
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023241
KNApSAcK IDNot Available
Chemspider ID21865494
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23657849
PDB IDNot Available
ChEBI ID48043
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available