Ursodeoxycholic acid (CHEM021821)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:22 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021821
Identification
Common NameUrsodeoxycholic acid
ClassSmall Molecule
DescriptionUrsodeoxycholic acid is an epimer of . 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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-Oic acidChEBI
3alpha,7beta-Dihydroxy-5beta-cholan-24-Oic acidChEBI
ActigallChEBI
UrsodeoxycholateChEBI
UrsodiolChEBI
UrsoKegg
(3a,5b,7b)-3,7-Dihydroxycholan-24-OateGenerator
(3a,5b,7b)-3,7-Dihydroxycholan-24-Oic acidGenerator
(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-OateGenerator
(3Α,5β,7β)-3,7-dihydroxycholan-24-OateGenerator
(3Α,5β,7β)-3,7-dihydroxycholan-24-Oic acidGenerator
3a,7b-Dihydroxy-5b-cholan-24-OateGenerator
3a,7b-Dihydroxy-5b-cholan-24-Oic acidGenerator
3alpha,7beta-Dihydroxy-5beta-cholan-24-OateGenerator
3Α,7β-dihydroxy-5β-cholan-24-OateGenerator
3Α,7β-dihydroxy-5β-cholan-24-Oic acidGenerator
3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-Oic acidHMDB
Acid, deoxyursocholicHMDB
Acid, ursacholicHMDB
Acid, ursodeoxycholicHMDB
Cholit-ursanHMDB
CholofalkHMDB
DelursanHMDB
Deoxyursocholic acidHMDB
UrsocholHMDB
UrsogalHMDB
UrsoliteHMDB
UrsolvanHMDB
Urso heumannHMDB
UrsobilaneHMDB
UrsofalkHMDB
DestolitHMDB
Sodium ursodeoxycholateHMDB
Ursacholic acidHMDB
Ursodeoxycholate, sodiumHMDB
3 alpha,7 beta Dihydroxy 5 beta cholan 24 Oic acidHMDB
UrdoxHMDB
(3a,5b,7b)-3,7-Dihydroxy-cholan-24-OateHMDB
(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
AntigallHMDB
UrosdesoxycholateHMDB
Urosdesoxycholic acidHMDB
UrsodeoxycholicacidHMDB
UrsodexycholateHMDB
Ursodexycholic acidHMDB
Aventis brand OF ursodeoxycholic acidHMDB
Axcan brand OF ursodeoxycholic acidHMDB
Falk brand OF ursodeoxycholic acidHMDB
Farmasa brand OF ursodeoxycholic acidHMDB
Galen brand OF ursodeoxycholic acidHMDB
Orphan brand OF ursodeoxycholic acidHMDB
Antigen brand OF ursodeoxycholic acidHMDB
CP Brand OF ursodeoxycholic acidHMDB
Heumann brand OF ursodeoxycholic acidHMDB
Niddapharm brand OF ursodeoxycholic acidHMDB
Norgine brand OF ursodeoxycholic acidHMDB
Sanofi synthelabo brand OF ursodeoxycholic acidHMDB
Estedi brand OF ursodeoxycholic acidHMDB
Provalis brand OF ursodeoxycholic acidHMDB
Tramedico brand OF ursodeoxycholic acidHMDB
Vita brand OF ursodeoxycholic acidHMDB
Zambon brand OF ursodeoxycholic acidHMDB
Chemical FormulaC24H40O4
Average Molecular Mass392.572 g/mol
Monoisotopic Mass392.293 g/mol
CAS Registry Number128-13-2
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
InChI IdentifierInChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
InChI KeyRUDATBOHQWOJDD-UZVSRGJWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives 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
Substituents
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.01ALOGPS
logP3.71ChemAxon
logS-4.3ALOGPS
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
Polarizability46.42 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rt-0419000000-6a92f910581240163a99Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1110390000-52bc66ab11fd14425d4fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4l-3940000000-cf90a6f216d592e2ad4cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-00di-0029000000-54929e08fef761ba2b28Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-2911000000-eec2b269eeb08a30ac6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-997e61e986e67265241cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0009000000-81134947694f847d1c65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-1219000000-6a0ddebebacac090c27eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-efdaad69eee0ae934dd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1009000000-15b4edab9d05e4c3693aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-9291e69db3a3c47ecd97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7631731446db77938069Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0009000000-39e7e555dc6b36ada2afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1009000000-351c21e3dab693818b22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0019000000-56dc67f71a8507c1433fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3039000000-510702cae19e3906b6e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9550000000-7486a5f56afd302efa7eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01586
HMDB IDHMDB0000946
FooDB IDFDB022332
Phenol Explorer IDNot Available
KNApSAcK IDC00032464
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5893
PDB IDNot Available
Wikipedia LinkUrsodiol
Chemspider ID29131
ChEBI ID9907
PubChem Compound ID31401
Kegg Compound IDC07880
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sawada, 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
2. Geetha A, Surendran R: Effect of ursodeoxycholic acid on copper induced oxidation of low density lipoprotein. Pharmazie. 2005 Aug;60(8):609-13.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106.
13. 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.
14. 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.
15. Hofmann AF: The continuing importance of bile acids in liver and intestinal disease. Arch Intern Med. 1999 Dec 13-27;159(22):2647-58.
16. 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.
17. 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.
18. Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6.
19. 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.
20. 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.
21. 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.
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=14989050
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=17489439
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=24816727