taurocholic acid   Click here for help

GtoPdb Ligand ID: 4547

Abbreviated name: TCA
Synonyms: taurocholate
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 8
Topological polar surface area 152.54
Molecular weight 515.29
XLogP 2.77
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC1CCC2(C(C1)CC(C1C2CC(O)C2(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]2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCCS(=O)(=O)O)C)C)O)C
InChI InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1
InChI Key WBWWGRHZICKQGZ-HZAMXZRMSA-N
References
1. Craddock AL, Love MW, Daniel RW, Kirby LC, Walters HC, Wong MH, Dawson PA. (1998)
Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter.
Am J Physiol, 274 (1 Pt 1): G157-69. [PMID:9458785]
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]