fasiglifam   

GtoPdb Ligand ID: 6484

Synonyms: TAK 875 | TAK-875 | TAK875
Compound class: Synthetic organic
Comment: Fasiglifam is a positive allosteric modulator/partial agonist of the free fatty acid receptor 1 (FFA1, a.k.a. GPR40) [6]. In the presence of endogenous free fatty acids (FFAs) fasiglifam enhances insulin secretion, by binding to an allosteric site distinct from the orthosteric FFA binding site. On its own, it elicits a low level of insulin secretion. These findings indicate that fasiglifam acts cooperatively with FFAs to promote insulin secretion.
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 107.51
Molecular weight 524.19
XLogP 5.72
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES OC(=O)CC1COc2c1ccc(c2)OCc1cccc(c1)c1c(C)cc(cc1C)OCCCS(=O)(=O)C
Isomeric SMILES OC(=O)C[C@@H]1COc2c1ccc(c2)OCc1cccc(c1)c1c(C)cc(cc1C)OCCCS(=O)(=O)C
InChI InChI=1S/C29H32O7S/c1-19-12-25(34-10-5-11-37(3,32)33)13-20(2)29(19)22-7-4-6-21(14-22)17-35-24-8-9-26-23(15-28(30)31)18-36-27(26)16-24/h4,6-9,12-14,16,23H,5,10-11,15,17-18H2,1-3H3,(H,30,31)/t23-/m1/s1
InChI Key BZCALJIHZVNMGJ-HSZRJFAPSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-[(3S)-6-({3-[4-(3-methanesulfonylpropoxy)-2,6-dimethylphenyl]phenyl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid
International Nonproprietary Names
INN number INN
9651 fasiglifam
Synonyms
TAK 875 | TAK-875 | TAK875
Comments
Fasiglifam is a positive allosteric modulator/partial agonist of the free fatty acid receptor 1 (FFA1, a.k.a. GPR40) [6]. In the presence of endogenous free fatty acids (FFAs) fasiglifam enhances insulin secretion, by binding to an allosteric site distinct from the orthosteric FFA binding site. On its own, it elicits a low level of insulin secretion. These findings indicate that fasiglifam acts cooperatively with FFAs to promote insulin secretion.
Database Links
CAS Registry No. 1000413-72-8 (source: Scifinder)
ChEMBL Ligand CHEMBL1829174
GtoPdb PubChem SID 178103098
PubChem CID 24857286
RCSB PDB Ligand 2YB
Search Google for chemical match using the InChIKey BZCALJIHZVNMGJ-HSZRJFAPSA-N
Search Google for chemicals with the same backbone BZCALJIHZVNMGJ
Search PubMed clinical trials fasiglifam
Search PubMed titles fasiglifam
Search PubMed titles/abstracts fasiglifam
Search UniChem for chemical match using the InChIKey BZCALJIHZVNMGJ-HSZRJFAPSA-N
Search UniChem for chemicals with the same backbone BZCALJIHZVNMGJ
SynPHARM 78362 (in complex with FFA1 receptor)