Record Information
Version3.6
Creation Date2006-05-22 14:17:53 UTC
Update Date2013-05-29 19:36:17 UTC
HMDB IDHMDB02431
Secondary Accession NumbersNone
Metabolite Identification
Common Name12b-Hydroxy-5b-cholanoic acid
Description12-hydroxy-(5b,12b)-Cholan-24-oic acid is a naturally occurring bile acid that has been identified in human bile. (PMID: 14167657 ).
Structure
Thumb
Synonyms
  1. 12-Hydroxy-(5b,12b)-Cholan-24-oate
  2. 12-Hydroxy-(5b,12b)-Cholan-24-oic acid
  3. 12b-Hydroxy-5b-Cholan-24-oate
  4. 12b-Hydroxy-5b-Cholan-24-oic acid
  5. 12b-Hydroxy-5b-cholanic acid
  6. 12b-Hydroxy-5b-cholanoate
  7. 12b-Hydroxy-5b-cholanoic acid
  8. 12beta-Hydroxy-5beta-cholanoate
  9. 12beta-Hydroxy-5beta-cholanoic acid
Chemical FormulaC24H40O3
Average Molecular Weight376.5726
Monoisotopic Molecular Weight376.297745146
IUPAC Name(4R)-4-[(1S,2S,7S,10R,11S,14R,15R,16R)-16-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name(4R)-4-[(1S,2S,7S,10R,11S,14R,15R,16R)-16-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number15173-23-6
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CCCC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)[C@H](C)CCC(O)=O
InChI Identifier
InChI=1S/C24H40O3/c1-15(7-12-22(26)27)18-10-11-19-17-9-8-16-6-4-5-13-23(16,2)20(17)14-21(25)24(18,19)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16+,17+,18-,19+,20+,21-,23+,24-/m1/s1
InChI KeyOBUOWZOYJNAMCZ-ORVKXXEISA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassBile Acids, Alcohols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Bile Acids, Alcohols and Derivatives
  • C24 bile acids, alcohols, and derivatives(Lipidmaps)
  • Monohydroxy Bile Acids, Alcohols and Derivatives
Substituents
  • 12 Hydroxy Steroid
  • Bicyclohexane
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
Direct ParentHydroxy Bile Acids, Alcohols and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fat solubilization and Waste products
  • 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 solubility0.0011 g/LALOGPS
logP4.5ALOGPS
logP5.18ChemAxon
logS-5.5ALOGPS
pKa (strongest acidic)4.65ChemAxon
pKa (strongest basic)-0.4ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area57.53ChemAxon
rotatable bond count4ChemAxon
refractivity107.53ChemAxon
polarizability45.28ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot 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 IDFDB023003
KNApSAcK IDNot Available
Chemspider ID4446900
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02431
Metagene LinkHMDB02431
METLIN IDNot Available
PubChem Compound5283812
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. ENEROTH P: THIN-LAYER CHROMATOGRAPHY OF BILE ACIDS. J Lipid Res. 1963 Jan;4:11-6. Pubmed: 14167657

Enzymes

Gene Name:
FABP6
Uniprot ID:
P51161

Transporters

Gene Name:
ABCB11
Uniprot ID:
O95342
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Gene Name:
SLC10A1
Uniprot ID:
Q14973