tauroursodeoxycholic acid   Click here for help

GtoPdb Ligand ID: 4746

Abbreviated name: TUDA
Synonyms: tauroursodeoxycholate | TUDCA
PDB Ligand Immunopharmacology Ligand
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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2D Structure
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Physico-chemical Properties
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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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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
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Compound class Metabolite or derivative
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
Synonyms Click here for help
tauroursodeoxycholate | TUDCA
Database Links Click here for help
CAS Registry No. 14605-22-2 (source: Scifinder)
ChEMBL Ligand CHEMBL272427
GtoPdb PubChem SID 178101456
PubChem CID 9848818
RCSB PDB Ligand 5D5
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Wikipedia Tauroursodeoxycholic_acid