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tauroursodeoxycholic acid   Click here for help

GtoPdb Ligand ID: 4746

Abbreviated name: TUDA
Synonyms: Relyvrio® (sodium phenylbutyrate + taurursodiol) | tauroursodeoxycholate | taurursodiol | TUDCA | UR 906 | ursodoxicoltaurine (INN)
Approved drug PDB Ligand Immunopharmacology Ligand
tauroursodeoxycholic acid is an approved drug (FDA (2022))
Compound class: Metabolite
Comment: Tauroursodeoxycholic acid (TUDCA) is a conjugated bile acid derivative. Evidence suggests that it acts as a chemical chaperone and facilitates protein folding within the endoplasmic reticulum [2].

tauroursodeoxycholic 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 7
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 132.31
Molecular weight 499.3
XLogP 4.86
No. Lipinski's rules broken 0

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)NCCS(=O)(=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)NCCS(=O)(=O)O)C)C)O)C
InChI InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1
InChI Key BHTRKEVKTKCXOH-LBSADWJPSA-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. US FDA (2022)
Withdrawn drug? Yes
IUPAC Name Click here for help
2-[(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]pentanamido]ethane-1-sulfonic acid
International Nonproprietary Names Click here for help
INN number INN
11388 ursodoxicoltaurine
Synonyms Click here for help
Relyvrio® (sodium phenylbutyrate + taurursodiol) | tauroursodeoxycholate | taurursodiol | TUDCA | UR 906 | ursodoxicoltaurine (INN)
Database Links Click here for help
CAS Registry No. 14605-22-2 (source: Scifinder)
ChEMBL Ligand CHEMBL272427
GtoPdb PubChem SID 178101456
LIPID MAPS LMST05040015
PubChem CID 9848818
RCSB PDB Ligand 5D5
Search Google for chemical match using the InChIKey BHTRKEVKTKCXOH-LBSADWJPSA-N
Search Google for chemicals with the same backbone BHTRKEVKTKCXOH
Search PubMed clinical trials ursodoxicoltaurine
Search PubMed titles ursodoxicoltaurine
Search PubMed titles/abstracts ursodoxicoltaurine
UniChem Compound Search for chemical match using the InChIKey BHTRKEVKTKCXOH-LBSADWJPSA-N
UniChem Connectivity Search for chemical match using the InChIKey BHTRKEVKTKCXOH-LBSADWJPSA-N
Wikipedia Tauroursodeoxycholic_acid

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MedChemExpress
Tauroursodeoxycholate (links to external site)
Cat. No. HY-19696