Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:40 UTC
HMDB IDHMDB00328
Secondary Accession NumbersNone
Metabolite Identification
Common Name12-Ketodeoxycholic acid
Description12-Ketodeoxycholic 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. (3a,5b)-3-hydroxy-12-oxo-cholan-24-oate
  2. (3a,5b)-3-hydroxy-12-oxo-cholan-24-oic acid
  3. (3alpha,5beta)-3-hydroxy-12-oxo-cholan-24-oate
  4. (3alpha,5beta)-3-hydroxy-12-oxo-cholan-24-oic acid
  5. 12-Dehydrodeoxycholate
  6. 12-Dehydrodeoxycholic acid
  7. 12-Ketodeoxycholate
  8. 12-Ketodeoxycholic acid
  9. 12-Ketolithocholate
  10. 12-Ketolithocholic acid
  11. 12-Oxo-3a-hydroxy-5b-cholanate
  12. 12-Oxo-3a-hydroxy-5b-cholanic acid
  13. 12-Oxolithocholate
  14. 12-Oxolithocholic acid
  15. 3a-Hydroxy-12-oxo-5b-cholan-24-oate
  16. 3a-Hydroxy-12-oxo-5b-cholan-24-oic acid
  17. 3a-Hydroxy-12-oxo-5b-cholanate
  18. 3a-Hydroxy-12-oxo-5b-cholanic acid
  19. 3a-Hydroxy-12-oxo-5b-cholanoate
  20. 3a-Hydroxy-12-oxo-5b-cholanoic acid
Chemical FormulaC24H38O4
Average Molecular Weight390.5561
Monoisotopic Molecular Weight390.277009704
IUPAC Name(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number5130-29-0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O
InChI Identifier
InChI=1S/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1
InChI KeyCVNYHSDFZXHMMJ-VPUMZWJWSA-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 Keto Steroid
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Ketone
  • 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 solubility0.013 g/LALOGPS
logP3.78ALOGPS
logP4.35ChemAxon
logS-4.5ALOGPS
pKa (strongest acidic)4.56ChemAxon
pKa (strongest basic)-1.4ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area74.6ChemAxon
rotatable bond count4ChemAxon
refractivity108.37ChemAxon
polarizability45.52ChemAxon
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 IDFDB021953
KNApSAcK IDNot Available
Chemspider ID2338365
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00328
Metagene LinkHMDB00328
METLIN ID5317
PubChem Compound3080612
PDB IDNot Available
ChEBI ID803536
References
Synthesis ReferenceSuzuki, Yoshinori; Okamura, Akio; Shimomura, Kazuo; Suzuki, Tadayuki. Purification of bile acids. Jpn. Kokai Tokkyo Koho (1985), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Reddy B, Engle A, Katsifis S, Simi B, Bartram HP, Perrino P, Mahan C: Biochemical epidemiology of colon cancer: effect of types of dietary fiber on fecal mutagens, acid, and neutral sterols in healthy subjects. Cancer Res. 1989 Aug 15;49(16):4629-35. Pubmed: 2545348
  2. Barker GM, Radley S, Bain I, Davis A, Lawson AM, Keighley MR, Neoptolemos JP: Biliary bile acid profiles in patients with familial adenomatous polyposis before and after colectomy. Br J Surg. 1994 Mar;81(3):441-4. Pubmed: 8173925
  3. Andersen E, Karlaganis G, Sjovall J: Altered bile acid profiles in duodenal bile and urine in diabetic subjects. Eur J Clin Invest. 1988 Apr;18(2):166-72. Pubmed: 3133222
  4. 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
  5. 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
  6. 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
  7. 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