cholic acid   

GtoPdb Ligand ID: 609

Abbreviated name: CA
Synonyms: cholate | Cholbam® | Kolbam® | Orphacol&Reg;
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.
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
Canonical SMILES OC1CCC2(C(C1)CC(C1C2CC(O)C2(C1CCC2C(CCC(=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)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
InChI Key BHQCQFFYRZLCQQ-OELDTZBJSA-N
No information available.
Summary of Clinical Use
The EMA and FDA have approved cholic acid for the treatment of rare bile acid synthesis disorders in pediatric and adult patients. These disorders include those arising from defects in a single enzyme, and peroxisomal disorders including Zellweger spectrum disorders.
Mechanism Of Action and Pharmacodynamic Effects
In patients with defects in cholic acid synthesis due to functional enzyme deficiency, supplementation with cholic acid can help ensure correct levels of bile flow and aid absorption of fats and fat-soluable vitamins.
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