S-EMCA   Click here for help

GtoPdb Ligand ID: 7048

Synonyms: 6α-ethyl-23(S)-methyl-cholic acid | INT-777 | INT777
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: S-EMCA (INT-777) is a potent and selective agonist of the G-protein-coupled bile acid receptor TGR5 (gene symbol GPBAR1) which is formally known as the GPBA receptor [3]. The GPBA receptor was historically identified as a metabolic regulator with roles in energy homeostasis, bile acid homeostasis, and glucose metabolism. More recently additional functions for the GPBA receptor such as regulation of the inflammatory response, cancer and liver regeneration have been described [1].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 5
Topological polar surface area 97.99
Molecular weight 450.33
XLogP 5.25
No. Lipinski's rules broken 1
Click here for help
Isomeric SMILES CC[C@H]1[C@@H](O)[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)[C@H](C[C@@H]2[C@@]2([C@H]1C[C@H](O)CC2)C)O)[C@@H](C[C@@H](C(=O)O)C)C
InChI InChI=1S/C27H46O5/c1-6-17-20-12-16(28)9-10-26(20,4)21-13-22(29)27(5)18(14(2)11-15(3)25(31)32)7-8-19(27)23(21)24(17)30/h14-24,28-30H,6-13H2,1-5H3,(H,31,32)/t14-,15+,16-,17-,18-,19+,20+,21+,22+,23+,24-,26+,27-/m1/s1
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2S,4R)-4-[(3R,5S,6R,7R,8R,9S,10S,12S,13R,14S,17R)-6-ethyl-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]-2-methylpentanoic acid
Synonyms Click here for help
6α-ethyl-23(S)-methyl-cholic acid | INT-777 | INT777
Database Links Click here for help
CAS Registry No. 1199796-29-6 (source: Scifinder)
ChEMBL Ligand CHEMBL567640
GtoPdb PubChem SID 178103627
PubChem CID 45483949
Search Google for chemical match using the InChIKey NPBCMXATLRCCLF-IRRLEISYSA-N
Search Google for chemicals with the same backbone NPBCMXATLRCCLF
Search UniChem for chemical match using the InChIKey NPBCMXATLRCCLF-IRRLEISYSA-N
Search UniChem for chemicals with the same backbone NPBCMXATLRCCLF