You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:26:41 UTC
HMDB IDHMDB00433
Secondary Accession NumbersNone
Metabolite Identification
Common Name1,3,7,12-Tetrahydroxycholan-24-oic acid
Description1,3,7,12-Tetrahydroxycholan-24-oic 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. 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. 1,3,7,12-Tetrahydroxy-Cholan-24-oate
  2. 1,3,7,12-Tetrahydroxy-Cholan-24-oic acid
  3. 1,3,7,12-Tetrahydroxycholan-24-oate
  4. 1,3,7,12-Tetrahydroxycholan-24-oic acid
  5. 1,3,7,12-Tetrahydroxycholanoate
  6. 1,3,7,12-Tetrahydroxycholanoic acid
  7. 1,3,7,12-Thca
  8. 1beta-Hydroxycholate
  9. 1beta-Hydroxycholic acid
  10. CA-1beta-ol
Chemical FormulaC24H40O6
Average Molecular Weight424.5708
Monoisotopic Molecular Weight424.282489012
IUPAC Name(4R)-4-[(1S,2S,10S,11S,14R,15R)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,10S,11S,14R,15R)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number63266-89-7
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(O)C[C@@]1([H])[C@@]2([H])C(O)CC2CC(O)CC(O)[C@]12C
InChI Identifier
InChI=1S/C24H40O6/c1-12(4-7-21(29)30)15-5-6-16-22-17(11-20(28)24(15,16)3)23(2)13(9-18(22)26)8-14(25)10-19(23)27/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13?,14?,15-,16+,17+,18?,19?,20?,22+,23+,24-/m1/s1
InChI KeyUYVVLXVBEQAATF-KBXJPTNGSA-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
  • 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 Solubility0.44ALOGPS
logP1.34ALOGPS
logP1.18ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity112.26 m3·mol-1ChemAxon
Polarizability48.24 Å3ChemAxon
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 IDFDB022043
KNApSAcK IDNot Available
Chemspider ID168471
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00433
Metagene LinkHMDB00433
METLIN ID5422
PubChem Compound194158
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  2. 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
  3. 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
  4. 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

General function:
Involved in binding
Specific function:
Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:
FABP6
Uniprot ID:
P51161
Molecular weight:
14371.2
References
  1. Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. Pubmed: 12486725

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular weight:
77402.2
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. Pubmed: 12196548
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular weight:
169341.1
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
General function:
Involved in bile acid:sodium symporter activity
Specific function:
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Molecular weight:
37697.4
References
  1. Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. Pubmed: 11447228
General function:
Involved in bile acid:sodium symporter activity
Specific function:
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:
SLC10A1
Uniprot ID:
Q14973
Molecular weight:
38118.64
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:
SLCO4A1
Uniprot ID:
Q96BD0
Molecular weight:
77192.5