tauroursodeoxycholic acid   Click here for help

GtoPdb Ligand ID: 4746

Abbreviated name: TUDA
Synonyms: tauroursodeoxycholate | taurursodiol | TUDCA | UR 906 | ursodoxicoltaurine (INN)
PDB Ligand Immunopharmacology Ligand
Compound class: Metabolite or derivative
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 [1].
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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
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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Click here for structure editor
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 CDK toolkit. 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
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.

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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
References
1. Cao SS, Zimmermann EM, Chuang BM, Song B, Nwokoye A, Wilkinson JE, Eaton KA, Kaufman RJ. (2013)
The unfolded protein response and chemical chaperones reduce protein misfolding and colitis in mice.
Gastroenterology, 144 (5): 989-1000.e6. [PMID:23336977]
2. Meier PJ, Eckhardt U, Schroeder A, Hagenbuch B, Stieger B. (1997)
Substrate specificity of sinusoidal bile acid and organic anion uptake systems in rat and human liver.
Hepatology, 26 (6): 1667-77. [PMID:9398014]
3. Paganoni S, Hendrix S, Dickson SP, Knowlton N, Macklin EA, Berry JD, Elliott MA, Maiser S, Karam C, Caress JB et al.. (2021)
Long-term survival of participants in the CENTAUR trial of sodium phenylbutyrate-taurursodiol in amyotrophic lateral sclerosis.
Muscle Nerve, 63 (1): 31-39. [PMID:33063909]
4. Paganoni S, Macklin EA, Hendrix S, Berry JD, Elliott MA, Maiser S, Karam C, Caress JB, Owegi MA, Quick A et al.. (2020)
Trial of Sodium Phenylbutyrate-Taurursodiol for Amyotrophic Lateral Sclerosis.
N Engl J Med, 383 (10): 919-930. [PMID:32877582]
5. Wang W, Zhao J, Gui W, Sun D, Dai H, Xiao L, Chu H, Du F, Zhu Q, Schnabl B et al.. (2018)
Tauroursodeoxycholic acid inhibits intestinal inflammation and barrier disruption in mice with non-alcoholic fatty liver disease.
Br J Pharmacol, 175 (3): 469-484. [PMID:29139555]
6. Zangerolamo L, Vettorazzi JF, Rosa LRO, Carneiro EM, Barbosa HCL. (2021)
The bile acid TUDCA and neurodegenerative disorders: An overview.
Life Sci, 272: 119252. [PMID:33636170]