cholic acid   Click here for help

GtoPdb Ligand ID: 609

Abbreviated name: CA
Synonyms: cholate | Cholbam® | Kolbam® | Orphacol&Reg;
Approved drug PDB Ligand
cholic acid is an approved drug (EMA (2013), FDA (2015))
Comment: Cholic acid is a primary bile acid. Along with chenodeoxycholic acid, it is one of the two major bile acids synthesized from cholesterol in the liver.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 4
Topological polar surface area 97.99
Molecular weight 408.29
XLogP 4.09
No. Lipinski's rules broken 0
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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)O)C)C)O)C
InChI InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
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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]
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A G protein-coupled receptor responsive to bile acids.
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Identification of membrane-type receptor for bile acids (M-BAR).
Biochem Biophys Res Commun, 298 (5): 714-9. [PMID:12419312]
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Substrate specificity of sinusoidal bile acid and organic anion uptake systems in rat and human liver.
Hepatology, 26 (6): 1667-77. [PMID:9398014]
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Bile acids: natural ligands for an orphan nuclear receptor.
Science, 284 (5418): 1365-8. [PMID:10334993]
6. Wang H, Chen J, Hollister K, Sowers LC, Forman BM. (1999)
Endogenous bile acids are ligands for the nuclear receptor FXR/BAR.
Mol Cell, 3 (5): 543-53. [PMID:10360171]