chenodeoxycholic acid   

GtoPdb Ligand ID: 608

Abbreviated name: CDCA
Synonyms: Chenix® | chenodeoxycholate | Chenodiol® | Leadiant® (formerly Chenodeoxycholic acid sigma-tau)
chenodeoxycholic acid is an approved drug (FDA (1983), EMA (2017))
Comment: Farnesoid X receptor (bile acid receptor FXR) agonist
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 77.76
Molecular weight 392.29
XLogP 6.18
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OC1CCC2(C(C1)CC(C1C2CCC2(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]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)O)C
InChI InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChI Key RUDATBOHQWOJDD-BSWAIDMHSA-N
Classification
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1983), EMA (2017))
IUPAC Name
(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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
International Nonproprietary Names
INN number INN
4391 chenodeoxycholic acid
Synonyms
Chenix® | chenodeoxycholate | Chenodiol® | Leadiant® (formerly Chenodeoxycholic acid sigma-tau)
Database Links
CAS Registry No. 474-25-9
ChEBI CHEBI:16755
ChEMBL Ligand CHEMBL240597
DrugBank Ligand DB06777
DrugCentral Ligand 4361
GtoPdb PubChem SID 135651455
NURSA Ligand 10.1621/H7NZZJBHW4
PubChem CID 10133
RCSB PDB Ligand JN3
Search Google for chemical match using the InChIKey RUDATBOHQWOJDD-BSWAIDMHSA-N
Search Google for chemicals with the same backbone RUDATBOHQWOJDD
Search PubMed clinical trials chenodeoxycholic acid
Search PubMed titles chenodeoxycholic acid
Search PubMed titles/abstracts chenodeoxycholic acid
Search UniChem for chemical match using the InChIKey RUDATBOHQWOJDD-BSWAIDMHSA-N
Search UniChem for chemicals with the same backbone RUDATBOHQWOJDD
SynPHARM 6410 (in complex with Farnesoid X receptor)
Wikipedia Chenodeoxycholic_acid