acadesine   Click here for help

GtoPdb Ligand ID: 5133

Synonyms: AICA-riboside | AR-100 | SCH-900395
Compound class: Synthetic organic
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 3
Topological polar surface area 156.85
Molecular weight 258.1
XLogP -1.8
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OCC1OC(C(C1O)O)n1cnc(c1N)C(=O)N
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc(c1N)C(=O)N
InChI InChI=1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1
No information available.
Summary of Clinical Use Click here for help
It is postulated that activation of AMPK may have clinical potential for correcting defects in the insulin signaling cascade in patients with type 2 diabetes [5,7]. There are no active clinical trials registered on (May 2014)
Mechanism Of Action and Pharmacodynamic Effects Click here for help
5' AMP-activated protein kinase (AMPK) is a trimeric protein complex containing an α, a β, and a γ subunit. In humans there are genes for 2 α, 2 β and 3 γ protein isoforms. AMPK activation regulates many metabolic pathways, including hepatic ketogenesis, cholesterol synthesis, lipogenesis [3], triglyceride synthesis, adipocyte lipolysis, skeletal muscle fatty acid oxidation [4], and is potentially involved in insulin secretion and contraction-induced glucose uptake in muscle cells [2,6].