S-EMCA   

GtoPdb Ligand ID: 7048

Synonyms: 6α-ethyl-23(S)-methyl-cholic acid | INT-777 | INT777
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].
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
Canonical SMILES CCC1C(O)C2C3CCC(C3(C)C(CC2C2(C1CC(O)CC2)C)O)C(CC(C(=O)O)C)C
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
InChI Key NPBCMXATLRCCLF-IRRLEISYSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(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
6α-ethyl-23(S)-methyl-cholic acid | INT-777 | INT777
Database Links
CAS Registry No. 1199796-29-6 (source: Scifinder)
ChEMBL Ligand CHEMBL567640
GtoPdb PubChem SID 178103627
PubChem CID 45483949
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