Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:31 UTC
HMDB IDHMDB00312
Secondary Accession NumbersNone
Metabolite Identification
Common Name3a,7a,12b-Trihydroxy-5b-cholanoic acid
Description3a,7a,12b-Trihydroxy-5b-cholanoic acid is a bile acid; bile acids with b-hydroxyl and carbonyl groups at the C-3,7 and/or 12 positions are bile acids usually found in the urine of healthy humans (PMID 8743575 ). 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. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).
Structure
Thumb
Synonyms
  1. 12b-Hydroxyisocholate
  2. 12b-Hydroxyisocholic acid
  3. 3a,7a,12b-Trihydroxy-5b-cholanate
  4. 3a,7a,12b-Trihydroxy-5b-cholanic acid
  5. 3a,7a,12b-Trihydroxy-5b-cholanoate
  6. 3a,7a,12b-Trihydroxy-5b-cholanoic acid
  7. Lagocholate
  8. Lagocholic acid
Chemical FormulaC24H40O5
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-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,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number71883-64-2
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(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/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/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 KeyBHQCQFFYRZLCQQ-KRHHAYMPSA-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
Substituents
  • 12 Hydroxy Steroid
  • 3 Hydroxy Steroid
  • 7 Hydroxy Steroid
  • Bicyclohexane
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
Direct ParentTrihydroxy 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 solubility0.074 g/LALOGPS
logP2.26ALOGPS
logP2.48ChemAxon
logS-3.7ALOGPS
pKa (strongest acidic)4.48ChemAxon
pKa (strongest basic)-0.16ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count4ChemAxon
polar surface area97.99ChemAxon
rotatable bond count4ChemAxon
refractivity110.79ChemAxon
polarizability46.99ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue Location
  • Gall Bladder
  • Intestine
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 IDFDB021939
KNApSAcK IDNot Available
Chemspider ID4446957
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00312
Metagene LinkHMDB00312
METLIN ID5301
PubChem Compound5283869
PDB IDNot Available
ChEBI ID36240
References
Synthesis ReferenceBatta, Ashok K.; Aggarwal, Suresht K.; Salen, Gerald; Shefer, Sarah. Selective reduction of oxo bile acids: synthesis of 3b-, 7b-, and 12b-hydroxy bile acids. Journal of Lipid Research (1991), 32(6), 977-83.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Borgstrom B, Krabisch L, Lindstrom M: Metabolism of cholate, 7 beta-hydroxy- and 12 beta-hydroxy-isocholates in the rat. Scand J Clin Lab Invest. 1986 Apr;46(2):177-82. Pubmed: 3715369
  2. Yamaga N, Ikebuchi J, Kohara H, Ogura Y, Yamada K: Analysis of bile acids in urine specimens from healthy humans: determination of several bile acids with beta-hydroxyl and carbonyl groups. J Biochem (Tokyo). 1996 Apr;119(4):725-30. Pubmed: 8743575
  3. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. Pubmed: 11316487
  4. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. Pubmed: 16037564
  5. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. Pubmed: 12576301
  6. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. Pubmed: 11907135

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