Showing metabocard for 2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid (BMDB0000316)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:28:28 UTC
Update Date2020-05-11 20:08:13 UTC
BMDB IDBMDB0000316
Secondary Accession Numbers
  • BMDB00316
Metabolite Identification
Common Name2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid
Description2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid, also known as 2b-hydroxycholate, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. 2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2b,3a,7a,12a-Tetrahydroxy-5b-cholanoateGenerator
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-OateHMDB
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-Oic acidHMDB
2b,3a,7a,12a-Tetrahydroxy-5b-cholanoicHMDB
2b-HydroxycholateHMDB
2b-Hydroxycholic acidHMDB
(4S)-4-[(2S,4S,5S,7R,9R,15R,16S)-4,5,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
Chemical FormulaC24H40O6
Average Molecular Weight424.5708
Monoisotopic Molecular Weight424.282489012
IUPAC Name(4S)-4-[(2S,4S,5S,7R,9R,15R,16S)-4,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name2b-hydroxycholate
CAS Registry Number60696-60-8
SMILES
[H][C@@]12C[C@H](O)[C@@H](O)C[C@]1(C)C1C[C@H](O)[C@]3(C)C(CCC3C1[C@H](O)C2)[C@@H](C)CCC(O)=O
InChI Identifier
InChI=1S/C24H40O6/c1-12(4-7-21(29)30)14-5-6-15-22-16(10-20(28)24(14,15)3)23(2)11-19(27)17(25)8-13(23)9-18(22)26/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13-,14?,15?,16?,17-,18+,19-,20-,22?,23-,24+/m0/s1
InChI KeyIMMADCCLTPCOKH-DLPNMVJGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected 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
logP1.34ALOGPS
logP1.41ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity112.15 m³·mol⁻¹ChemAxon
Polarizability48.15 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 Locations
  • Gallbladder
  • Intestine
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
GallbladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000316
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021943
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5305
PubChem Compound53477680
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceIida, Takashi; Komatsubara, Ichiro; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio. Potential bile acid metabolites. 17. Synthesis of 2b-hydroxylated bile acids. Steroids (1991), 56(3), 114-22.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]