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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:02:14 UTC
Secondary Accession Numbers
  • HMDB00946
  • HMDB15525
Metabolite Identification
Common NameUrsodeoxycholic acid
DescriptionUrsodeoxycholic acid is an epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. [PubChem]
(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-Oic acidChEBI
3alpha,7beta-Dihydroxy-5beta-cholan-24-Oic acidChEBI
(3a,5b,7b)-3,7-Dihydroxycholan-24-Oic acidGenerator
(3α,5β,7β)-3,7-dihydroxycholan-24-Oic acidGenerator
3a,7b-Dihydroxy-5b-cholan-24-Oic acidGenerator
3α,7β-dihydroxy-5β-cholan-24-Oic acidGenerator
(3a,5b,7b)-3,7-Dihydroxy-cholan-24-Oic acidHMDB
3,7-Dihydroxycholan-24-Oic acidHMDB
3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acidHMDB
3-alpha,7-beta-Dihydroxycholanic acidHMDB
3-alpha,7-beta-Dioxycholanic acidHMDB
Urosdesoxycholic acidHMDB
Ursodexycholic acidHMDB
Acid, deoxyursocholicMeSH
Aventis brand OF ursodeoxycholic acidMeSH
Axcan brand OF ursodeoxycholic acidMeSH
Falk brand OF ursodeoxycholic acidMeSH
Farmasa brand OF ursodeoxycholic acidMeSH
Galen brand OF ursodeoxycholic acidMeSH
Orphan brand OF ursodeoxycholic acidMeSH
Sodium ursodeoxycholateMeSH
3 alpha,7 beta Dihydroxy 5 beta cholan 24 Oic acidMeSH
3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-Oic acidMeSH
Acid, ursodeoxycholicMeSH
Antigen brand OF ursodeoxycholic acidMeSH
CP Brand OF ursodeoxycholic acidMeSH
Heumann brand OF ursodeoxycholic acidMeSH
Niddapharm brand OF ursodeoxycholic acidMeSH
Norgine brand OF ursodeoxycholic acidMeSH
urso HeumannMeSH
Sanofi synthelabo brand OF ursodeoxycholic acidMeSH
Ursacholic acidMeSH
Ursodeoxycholate, sodiumMeSH
Acid, ursacholicMeSH
Deoxyursocholic acidMeSH
Estedi brand OF ursodeoxycholic acidMeSH
Provalis brand OF ursodeoxycholic acidMeSH
tramedico Brand OF ursodeoxycholic acidMeSH
Vita brand OF ursodeoxycholic acidMeSH
Zambon brand OF ursodeoxycholic acidMeSH
Chemical FormulaC24H40O4
Average Molecular Weight392.572
Monoisotopic Molecular Weight392.292659768
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional NameUrso
CAS Registry Number128-13-2
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physiological effect

Health effect:

  Health condition:


Biological Location:


  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

  Cell and elements:



Route of exposure:



Industrial application:

  Pharmaceutical industry:

Biological role:

  Molecular messenger:


Naturally occurring process:

  Biological process:

    Cellular process:

Physical Properties
Experimental Properties
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.02 mg/mLNot Available
LogP3.00RODA,A ET AL. (1990)
Predicted Properties
Water Solubility0.02 g/LALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.27 m³·mol⁻¹ChemAxon
Polarizability46.33 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rt-0419000000-6a92f910581240163a99View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1110390000-52bc66ab11fd14425d4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4l-3940000000-cf90a6f216d592e2ad4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-00di-0029000000-54929e08fef761ba2b28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-2911000000-eec2b269eeb08a30ac6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-997e61e986e67265241cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0009000000-81134947694f847d1c65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-1219000000-6a0ddebebacac090c27eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-efdaad69eee0ae934dd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1009000000-15b4edab9d05e4c3693aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-9291e69db3a3c47ecd97View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Adrenal Cortex
  • Bladder
  • Fetus
  • Fibroblasts
  • Gut
  • Intestine
  • Liver
  • Muscle
  • Placenta
PathwaysNot Available
No entries found
Normal Concentrations
BloodDetected and Quantified0.16 +/- 0.03 uMAdult (>18 years old)BothNormal details
FecesDetected and Quantified27.05 +/- 61.13 nmol/g of fecesNot SpecifiedNot Specified
FecesDetected but not Quantified Adult (>18 years old)Both
UrineDetected and Quantified0.022 (0.013-0.030) umol/mmol creatinineAdult (>18 years old)Both
Abnormal Concentrations
BloodDetected and Quantified1.7 (0.7-3.0) uMAdult (>18 years old)Both
Biliary cirrhosis
BloodDetected and Quantified24.5 (2.3-51.3) uMAdult (>18 years old)Both
Biliary cirrhosis
BloodDetected and Quantified0.48 +/- 0.16 uMAdult (>18 years old)Both
Cystic fibrosis
BloodDetected and Quantified0.61 +/- 0.27 uMChildren (1-13 years old)BothCystic fibrosis details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
UrineDetected and Quantified0.29 (0.056-0.98) umol/mmol creatinineAdult (>18 years old)Both
Biliary cirrhosis
UrineDetected and Quantified12.5 (0.7-53.9) umol/mmol creatinineAdult (>18 years old)Both
Biliary cirrhosis
Associated Disorders and Diseases
Disease References
Cystic fibrosis
  1. Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
Primary biliary cirrhosis
  1. Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. [PubMed:2621422 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022332
KNApSAcK IDNot Available
Chemspider ID29131
KEGG Compound IDC07880
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUrsodeoxycholic acid
PubChem Compound31401
PDB IDNot Available
ChEBI ID9907
Synthesis ReferenceSawada, Haruji; Kulprecha, Songsri; Nilubol, Naline; Yoshida, Toshiomi; Kinoshita, Shinichi; Taguchi, Hisaharu. Microbial production of ursodeoxycholic acid from lithocholic acid by Fusarium equiseti M41. Applied and Environmental Microbiology (1982), 44(6):1249-52
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
  2. Fiorucci S, Antonelli E, Morelli A: Nitric oxide and portal hypertension: a nitric oxide-releasing derivative of ursodeoxycholic acid that selectively releases nitric oxide in the liver. Dig Liver Dis. 2003 May;35 Suppl 2:S61-9. [PubMed:12846445 ]
  3. Meyers RL, Book LS, O'Gorman MA, Jackson WD, Black RE, Johnson DG, Matlak ME: High-dose steroids, ursodeoxycholic acid, and chronic intravenous antibiotics improve bile flow after Kasai procedure in infants with biliary atresia. J Pediatr Surg. 2003 Mar;38(3):406-11. [PubMed:12632357 ]
  4. Soderdahl G, Nowak G, Duraj F, Wang FH, Einarsson C, Ericzon BG: Ursodeoxycholic acid increased bile flow and affects bile composition in the early postoperative phase following liver transplantation. Transpl Int. 1998;11 Suppl 1:S231-8. [PubMed:9664985 ]
  5. Nobilis M, Pour M, Kunes J, Kopecky J, Kvetina J, Svoboda Z, Sladkova K, Vortel J: High-performance liquid chromatographic determination of ursodeoxycholic acid after solid phase extraction of blood serum and detection-oriented derivatization. J Pharm Biomed Anal. 2001 Mar;24(5-6):937-46. [PubMed:11248487 ]
  6. Hillaire S, Ballet F, Franco D, Setchell KD, Poupon R: Effects of ursodeoxycholic acid and chenodeoxycholic acid on human hepatocytes in primary culture. Hepatology. 1995 Jul;22(1):82-7. [PubMed:7601437 ]
  7. Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106. [PubMed:10766400 ]
  8. Hofmann AF: The continuing importance of bile acids in liver and intestinal disease. Arch Intern Med. 1999 Dec 13-27;159(22):2647-58. [PubMed:10597755 ]
  9. Eriksson LS, Olsson R, Glauman H, Prytz H, Befrits R, Ryden BO, Einarsson K, Lindgren S, Wallerstedt S, Weden M: Ursodeoxycholic acid treatment in patients with primary biliary cirrhosis. A Swedish multicentre, double-blind, randomized controlled study. Scand J Gastroenterol. 1997 Feb;32(2):179-86. [PubMed:9051880 ]
  10. Lindblad A, Glaumann H, Strandvik B: A two-year prospective study of the effect of ursodeoxycholic acid on urinary bile acid excretion and liver morphology in cystic fibrosis-associated liver disease. Hepatology. 1998 Jan;27(1):166-74. [PubMed:9425933 ]
  11. Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6. [PubMed:10781781 ]
  12. Geetha A, Surendran R: Effect of ursodeoxycholic acid on copper induced oxidation of low density lipoprotein. Pharmazie. 2005 Aug;60(8):609-13. [PubMed:16124405 ]
  13. Brites D: Intrahepatic cholestasis of pregnancy: changes in maternal-fetal bile acid balance and improvement by ursodeoxycholic acid. Ann Hepatol. 2002 Jan-Mar;1(1):20-8. [PubMed:15114292 ]
  14. Serrano MA, Brites D, Larena MG, Monte MJ, Bravo MP, Oliveira N, Marin JJ: Beneficial effect of ursodeoxycholic acid on alterations induced by cholestasis of pregnancy in bile acid transport across the human placenta. J Hepatol. 1998 May;28(5):829-39. [PubMed:9625319 ]
  15. Maton PN, Murphy GM, Dowling RH: Ursodeoxycholic acid treatment of gallstones. Dose-response study and possible mechanism of action. Lancet. 1977 Dec 24-31;2(8052-8053):1297-301. [PubMed:74722 ]
  16. Ikegami T, Matsuzaki Y, Al Rashid M, Ceryak S, Zhang Y, Bouscarel B: Enhancement of DNA topoisomerase I inhibitor-induced apoptosis by ursodeoxycholic acid. Mol Cancer Ther. 2006 Jan;5(1):68-79. [PubMed:16432164 ]
  17. Crosignani A, Setchell KD, Invernizzi P, Larghi A, Rodrigues CM, Podda M: Clinical pharmacokinetics of therapeutic bile acids. Clin Pharmacokinet. 1996 May;30(5):333-58. [PubMed:8743334 ]
  18. Baruch Y, Assy N, Weisbruch F, Reisner SA, Rinkevich D, Enat R, Blendis LM, Bomzon A: A pilot study on the hemodynamic effect of short-term ursodeoxycholic acid therapy in patients with stable liver cirrhosis. Am J Gastroenterol. 1999 Oct;94(10):3000-4. [PubMed:10520859 ]
  19. Marschall HU, Wagner M, Zollner G, Fickert P, Diczfalusy U, Gumhold J, Silbert D, Fuchsbichler A, Benthin L, Grundstrom R, Gustafsson U, Sahlin S, Einarsson C, Trauner M: Complementary stimulation of hepatobiliary transport and detoxification systems by rifampicin and ursodeoxycholic acid in humans. Gastroenterology. 2005 Aug;129(2):476-85. [PubMed:16083704 ]
  20. Guarino MP, Carotti S, Sarzano M, Alloni R, Vanni M, Grosso M, Sironi G, Maffettone PL, Cicala M: Short-term ursodeoxycholic acid treatment improves gallbladder bile turnover in gallstone patients: a randomized trial. Neurogastroenterol Motil. 2005 Oct;17(5):680-6. [PubMed:16185306 ]


General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
  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 ]


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:
Uniprot ID:
Molecular weight:
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:
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Molecular weight:
  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:
Uniprot ID:
Molecular weight:
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
Uniprot ID:
Molecular weight:
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
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Uniprot ID:
Molecular weight:
  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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
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
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