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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

ursodeoxycholic acid is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Metabolite
Approved drug? Yes (UK (2003))
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
LIPID MAPS LMST04010033
PubChem CID 31401
Search Google for chemical match using the InChIKey RUDATBOHQWOJDD-UZVSRGJWSA-N
Search Google for chemicals with the same backbone RUDATBOHQWOJDD
Search PubMed clinical trials ursodeoxycholic acid
Search PubMed titles ursodeoxycholic acid
Search PubMed titles/abstracts ursodeoxycholic acid
UniChem Compound Search for chemical match using the InChIKey RUDATBOHQWOJDD-UZVSRGJWSA-N
UniChem Connectivity Search for chemical match using the InChIKey RUDATBOHQWOJDD-UZVSRGJWSA-N
Wikipedia Ursodeoxycholic acid

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MedChemExpress
Ursodeoxycholic acid (links to external site)
Cat. No. HY-13771