Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:32 UTC
HMDB IDHMDB00414
Secondary Accession NumbersNone
Metabolite Identification
Common Name1b,3a,7a-Trihydroxy-5b-cholanoic acid
Description1b,3a,7a-Trihydroxy-5b-cholanoic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12.
Structure
Thumb
Synonyms
  1. 1 beta,3a,7a-Trihydroxy-5b-cholanoate
  2. 1 beta,3a,7a-Trihydroxy-5b-cholanoic acid
  3. 1b,3 alpha,7a-Trihydroxy-5b-cholanoate
  4. 1b,3 alpha,7a-Trihydroxy-5b-cholanoic acid
  5. 1b,3a,7 alpha-Trihydroxy-5b-cholanoate
  6. 1b,3a,7 alpha-Trihydroxy-5b-cholanoic acid
  7. 1b,3a,7a-Trihydroxy-5 beta-cholanoate
  8. 1b,3a,7a-Trihydroxy-5 beta-cholanoic acid
  9. 1b,3a,7a-Trihydroxy-5b-cholan-24-oate
  10. 1b,3a,7a-Trihydroxy-5b-cholan-24-oic acid
  11. 1b,3a,7a-Trihydroxy-5b-cholanoate
  12. 1b,3a,7a-Trihydroxy-5b-cholanoic acid
  13. 1b-Hydroxychenodeoxycholate
  14. 1b-Hydroxychenodeoxycholic acid
  15. 3-a,7-a,12-a-Trihydroxy-5-a-cholanoate
  16. 3-a,7-a,12-a-Trihydroxy-5-a-cholanoic acid
  17. 3-a,7-a,12-alpha-Trihydroxy-5-alpha-cholanoate
  18. 3-a,7-a,12-alpha-Trihydroxy-5-alpha-cholanoic acid
Chemical FormulaC24H40O5
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
IUPAC Name(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number99598-04-6
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)C[C@@H](O)[C@]12C
InChI Identifier
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(8-9-23(16,17)2)24(3)14(11-19(22)26)10-15(25)12-20(24)27/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15+,16-,17+,18+,19-,20-,22+,23-,24+/m1/s1
InChI KeyGYUVAHWOVINGNE-RWXZXXAWSA-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)
Substituents
  • 3 Hydroxy Steroid
  • 7 Hydroxy Steroid
  • Bicyclohexane
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
Direct ParentDihydroxy 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 Point238 - 240 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.08 g/LALOGPS
logP2.21ALOGPS
logP2.41ChemAxon
logS-3.7ALOGPS
pKa (strongest acidic)4.6ChemAxon
pKa (strongest basic)-0.61ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count4ChemAxon
polar surface area97.99ChemAxon
rotatable bond count4ChemAxon
refractivity110.75ChemAxon
polarizability47.11ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue Location
  • Gall Bladder
  • Intestine
  • Kidney
  • Liver
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 IDFDB022030
KNApSAcK IDNot Available
Chemspider ID4446934
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00414
Metagene LinkHMDB00414
METLIN ID5403
PubChem Compound5283846
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceTohma, Masahiko; Mahara, Reijiro; Takeshita, Hiromi; Kurosawa, Takao; Ikegawa, Shigeo; Nittono, Hiroshi. Synthesis of the 1b-hydroxylated bile acids and identification of 1b,3a,7a-trihydroxy- and 1b,3a,7a,12a-tetrahydroxy-5b-cholan-24-oic acids in human meconium. Chemical & Pharmaceutical Bulletin (1985), 33(7), 3071-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
  2. Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. Pubmed: 10203155

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