ursodeoxycholic acid   Click here for help

GtoPdb Ligand ID: 7104

Synonyms: Actigall® | UDCA
Approved drug
ursodeoxycholic acid is an approved drug (UK (2003))
Comment: Unfortunately ursodeoxycholic acid is found in large quantities in bear bile [1] and this results in the practice of 'farming' bears for bile extraction, in some east Asian countries.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 77.76
Molecular weight 392.29
XLogP 6.18
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC1CCC2(C(C1)CC(C1C2CCC2(C1CCC2C(CCC(=O)O)C)C)O)C
Isomeric SMILES O[C@@H]1CC[C@]2([C@@H](C1)C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)O)C
InChI 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 Key RUDATBOHQWOJDD-UZVSRGJWSA-N
References
1. Hagey LR, Crombie DL, Espinosa E, Carey MC, Igimi H, Hofmann AF. (1993)
Ursodeoxycholic acid in the Ursidae: biliary bile acids of bears, pandas, and related carnivores.
J Lipid Res, 34 (11): 1911-7. [PMID:8263415]
2. Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J. (2007)
Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: a population-based cohort study.
Hepatology, 46 (4): 1131-7. [PMID:17685473]