ursodeoxycholic acid   Click here for help

GtoPdb Ligand ID: 7104

Synonyms: Actigall® | UDCA
Approved drug
ursodeoxycholic acid is an approved drug (UK (2003))
Compound class: Metabolite
Comment: Ursodeoxycholic acid (UDCA) acts as an antagonist of the bile acid receptor farnesoid X receptor (FXR) [5].

SARS-CoV-2 and COVID-19: ACE2's presence on host cells confers susceptibility to SARS-CoV-2 infection. UDCA attenuates bile acid-induced, FXR-mediated upregulation of ACE2 expression in vitro and in vivo [1]. For this effect, UDCA has been proposed as a repurposing drug with antiviral potential against SARS-CoV-2. It is hypothesised that UDCA would reduce SARS-CoV-2 infection potential by lowering the number of ACE2 binding sites on relevant tissues. In support of this theory, a correlation between UDCA treatment for liver conditions and a lower risk of developing severe COVID-19 has been identified,

Ursodeoxycholic acid is found in large quantities in bear bile [2] and this results in the practice of 'farming' bears for bile extraction, in some 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
Classification Click here for help
Compound class Metabolite
Approved drug? Yes (UK (2003))
IUPAC Name Click here for help
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
International Nonproprietary Names Click here for help
INN number INN
4920 ursodeoxycholic acid
Synonyms Click here for help
Actigall® | UDCA
Database Links Click here for help
CAS Registry No. 128-13-2
ChEBI CHEBI:9907
ChEMBL Ligand CHEMBL1551
DrugBank Ligand DB01586
DrugCentral Ligand 2797
GtoPdb PubChem SID 178103681
PubChem CID 31401
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UniChem Compound Search for chemical match using the InChIKey RUDATBOHQWOJDD-UZVSRGJWSA-N
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Wikipedia Ursodeoxycholic acid