A-769662   Click here for help

GtoPdb Ligand ID: 10069

Synonyms: A769662
PDB Ligand
Compound class: Synthetic organic
Comment: A-769662 is a small molecule activator of AMP-activated protein kinase (AMPK). Its chemical structure was originally disclosed by Cool et al. (2006) [1], in which it was used to demonstrate that AMPK activation is a feasible approach for the treatment of the metabolic syndrome and type 2 diabetes. A-769662 activates AMPK both allosterically (as evidenced by its ability to activate a mutant AMPK γ subunit that is resistant to endogenous AMP-induced activation) and by inhibiting dephosphorylation of AMPK on Thr172 [3]. A-769662 is suitable as as experimental tool to understand the physiological roles of AMPK in vitro and in vivo. Use of A-769662 has also confirmed AMPK's role as an autophagy target, whose activation is able to ameliorate neurodegeneration in animal models [4]. AMPK activation induces autophagy in an mTOR-independent manner, so limits the risk of the potentially detrimental effects that mTOR inhibition may have on important cellular pathways in addition to autophagy.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 125.35
Molecular weight 360.06
XLogP 4.39
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES N#Cc1c(=O)[nH]c2c(c1O)c(cs2)c1ccc(cc1)c1ccccc1O
Isomeric SMILES N#Cc1c(=O)[nH]c2c(c1O)c(cs2)c1ccc(cc1)c1ccccc1O
InChI InChI=1S/C20H12N2O3S/c21-9-14-18(24)17-15(10-26-20(17)22-19(14)25)12-7-5-11(6-8-12)13-3-1-2-4-16(13)23/h1-8,10,23H,(H2,22,24,25)
InChI Key CTESJDQKVOEUOY-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-hydroxy-3-[4-(2-hydroxyphenyl)phenyl]-6-oxo-7H-thieno[2,3-b]pyridine-5-carbonitrile
Synonyms Click here for help
A769662
Database Links Click here for help
BindingDB Ligand 50242401
CAS Registry No. 844499-71-4 (source: PubChem)
ChEMBL Ligand CHEMBL512504
GtoPdb PubChem SID 375973256
PubChem CID 54708532
RCSB PDB Ligand C1V
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Tocris
A 769662
Cat. No. 3336