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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:30 UTC
Secondary Accession Numbers
  • HMDB04011
Metabolite Identification
Common NameTaurodeoxycholic acid
DescriptionTaurodeoxycholic acid is a bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. 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 ).
Taurodeoxycholic acidGenerator
Deoxytaurocholic acidHMDB
Sodium taurodeoxycholateHMDB
Sodium taurodeoxylateHMDB
Taurodeoxycholic acid sodium saltHMDB
Taurodeoxycholic acid sodium salt hydrateHMDB
Taurodesoxycholic acidHMDB
Chemical FormulaC26H45NO6S
Average Molecular Weight499.704
Monoisotopic Molecular Weight499.296758867
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
Traditional Nametaurodeoxycholate
CAS Registry Number516-50-7
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTaurinated bile acids and derivatives
Alternative Parents
  • Taurinated bile acid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 12-hydroxysteroid
  • 3-hydroxysteroid
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Food
  • Microbial
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
Experimental Properties
Melting Point204 - 208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility41 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0078 mg/mLALOGPS
pKa (Strongest Acidic)-0.94ChemAxon
pKa (Strongest Basic)0.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.93 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.6 m3·mol-1ChemAxon
Polarizability56.56 Å3ChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ikd-0047930000-8f9f65d8c1d3c8253501View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03g0-0950300000-d3a559bd8c5ccd049d7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9545740000-d9a7750b1b579bd2bb05View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Bile
  • Blood
  • Feces
Tissue Location
  • Intestine
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
Normal Concentrations
BileDetected and Quantified> 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.062 (0.000-0.177) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected and Quantified4.32 +/- 5.81 nmol/g of fecesNot SpecifiedNot Specified
Abnormal Concentrations
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hepatocellular carcinoma
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Liver Cirrhosis
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 IDFDB022304
KNApSAcK IDNot Available
Chemspider ID2015539
KEGG Compound IDC05463
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00896
Metagene LinkHMDB00896
PubChem Compound2733768
PDB IDNot Available
ChEBI ID9410
Synthesis ReferenceParenti, Massimo. Preparation of tauroursodesoxycholic acid dihydrate. Eur. Pat. Appl. (1990), 3 pp. CODEN: EPXXDW EP 400695 A2 19901205 CAN 114:82269 AN 1991:82269
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bloch CA, Watkins JB: Determination of conjugated bile acids in human bile and duodenal fluid by reverse-phase high-performance liquid chromatography. J Lipid Res. 1978 May;19(4):510-3. [659989 ]
  2. Foley DP, Collins BR, Magee JC, Platt JL, Katz E, Harland RC, Meyers WC, Chari RS: Bile acids in xenogeneic ex-vivo liver perfusion: function of xenoperfused livers and compatibility with human bile salts and porcine livers. Transplantation. 2000 Jan 27;69(2):242-8. [10670634 ]
  3. Bretagne JF, Vidon N, L'Hirondel C, Bernier JJ: Increased cell loss in the human jejunum induced by laxatives (ricinoleic acid, dioctyl sodium sulphosuccinate, magnesium sulphate, bile salts). Gut. 1981 Apr;22(4):264-9. [6165655 ]
  4. Leveau P, Wang X, Sun Z, Borjesson A, Andersson E, Andersson R: Severity of pancreatitis-associated gut barrier dysfunction is reduced following treatment with the PAF inhibitor lexipafant. Biochem Pharmacol. 2005 May 1;69(9):1325-31. [15826603 ]
  5. Burkard I, von Eckardstein A, Rentsch KM: Differentiated quantification of human bile acids in serum by high-performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Nov 5;826(1-2):147-59. Epub 2005 Sep 22. [16182619 ]
  6. Lim HJ, Kim SY, Lee WK: Isolation of cholesterol-lowering lactic acid bacteria from human intestine for probiotic use. J Vet Sci. 2004 Dec;5(4):391-5. [15613825 ]
  7. Muhlbauer M, Allard B, Bosserhoff AK, Kiessling S, Herfarth H, Rogler G, Scholmerich J, Jobin C, Hellerbrand C: Differential effects of deoxycholic acid and taurodeoxycholic acid on NF-kappa B signal transduction and IL-8 gene expression in colonic epithelial cells. Am J Physiol Gastrointest Liver Physiol. 2004 Jun;286(6):G1000-8. Epub 2004 Jan 15. [14726307 ]
  8. Pouwels MJ, Tack CJ, Span PN, Olthaar AJ, Sweep CG, Huvers FC, Lutterman JA, Hermus AR: Role of hexosamines in insulin resistance and nutrient sensing in human adipose and muscle tissue. J Clin Endocrinol Metab. 2004 Oct;89(10):5132-7. [15472217 ]
  9. Elkins CA, Mullis LB: Bile-mediated aminoglycoside sensitivity in Lactobacillus species likely results from increased membrane permeability attributable to cholic acid. Appl Environ Microbiol. 2004 Dec;70(12):7200-9. [15574918 ]
  10. Aubert E, Sbarra V, Le Petit-Thevenin J, Valette A, Lombardo D: Site-directed mutagenesis of the basic N-terminal cluster of pancreatic bile salt-dependent lipase. Functional significance. J Biol Chem. 2002 Sep 20;277(38):34987-96. Epub 2002 Jul 10. [12110666 ]
  11. Xie Q, Li GM, Zhou XQ, Liao D, Yu H, Guo Q: [Effect of Tauroursodeoxycholic acid on cytochrome C-mediated apoptosis in HepG2 cells] Zhonghua Gan Zang Bing Za Zhi. 2003 May;11(5):298-301. [12773247 ]
  12. 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. [11316487 ]
  13. 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. [16037564 ]
  14. 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. [12576301 ]
  15. 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. [11907135 ]