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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-17 15:42:35 UTC
NP-MRD IDNP0000661
Secondary Accession NumbersNone
Natural Product Identification
Common NameUrsodeoxycholic acid
DescriptionUrsodeoxycholic acid, also known as ursodeoxycholate or acid deoxyursocholic, 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. Ursodeoxycholic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Thumb
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 Mass392.5720 Da
Monoisotopic Mass392.29266 Da
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
CAS Registry Number128-13-2
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 Identifier
InChI=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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Myocastor coypusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Selenarctos thibetanus-
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Bos taurus domesticus GMELINKNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203 °CNot Available
Boiling Point547.10 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.02 mg/mLNot Available
LogP3.00Roda, A., Minutello, A., Angellotti, M. A., & Fini, A. (1990). Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. Journal of lipid research, 31(8), 1433-1443.
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000946
DrugBank IDDB01586
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022332
KNApSAcK IDC00032464
Chemspider ID29131
KEGG Compound IDC07880
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUrsodiol
METLIN ID5893
PubChem Compound31401
PDB IDNot Available
ChEBI ID9907
Good Scents IDrw1296231
References
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 ]