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
Classification
Compound class Metabolite or derivative
Approved drug? Yes (EMA (2013), FDA (2015))
IUPAC Name
(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Synonyms
cholate | Cholbam® | Kolbam® | Orphacol&Reg;
Database Links
CAS Registry No. 81-25-4 (source: Scifinder)
ChEBI CHEBI:16359
ChEMBL Ligand CHEMBL205596
DrugBank Ligand DB02659
DrugCentral Ligand 3096
GtoPdb PubChem SID 135651459
PubChem CID 221493
RCSB PDB Ligand CHD
Search Google for chemical match using the InChIKey BHQCQFFYRZLCQQ-OELDTZBJSA-N
Search Google for chemicals with the same backbone BHQCQFFYRZLCQQ
Search UniChem for chemical match using the InChIKey BHQCQFFYRZLCQQ-OELDTZBJSA-N
Search UniChem for chemicals with the same backbone BHQCQFFYRZLCQQ
Wikipedia Cholic_acid