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))
Compound class: Metabolite
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
SMILES / InChI / InChIKey
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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 Click here for help
Compound class Metabolite
Approved drug? Yes (EMA (2013), FDA (2015))
IUPAC Name Click here for help
(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 Click here for help
cholate | Cholbam® | Kolbam® | Orphacol&Reg;
Database Links Click here for help
Specialist databases
GPCRdb Ligand cholic acid
Other databases
CAS Registry No. 81-25-4 (source: Scifinder)
ChEBI CHEBI:16359
ChEMBL Ligand CHEMBL205596
DrugBank Ligand DB02659
DrugCentral Ligand 3096
GtoPdb PubChem SID 135651459
LIPID MAPS LMST04010001
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
UniChem Compound Search for chemical match using the InChIKey BHQCQFFYRZLCQQ-OELDTZBJSA-N
UniChem Connectivity Search for chemical match using the InChIKey BHQCQFFYRZLCQQ-OELDTZBJSA-N
Wikipedia Cholic_acid