acadesine   Click here for help

GtoPdb Ligand ID: 5133

Synonyms: AICA-riboside | AR-100 | SCH-900395
Compound class: Synthetic organic
2D Structure
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Physico-chemical Properties
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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
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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
1. Corton JM, Gillespie JG, Hawley SA, Hardie DG. (1995)
5-aminoimidazole-4-carboxamide ribonucleoside. A specific method for activating AMP-activated protein kinase in intact cells?.
Eur J Biochem, 229 (2): 558-65. [PMID:7744080]
2. Cuthbertson DJ, Babraj JA, Mustard KJ, Towler MC, Green KA, Wackerhage H, Leese GP, Baar K, Thomason-Hughes M, Sutherland C et al.. (2007)
5-aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside acutely stimulates skeletal muscle 2-deoxyglucose uptake in healthy men.
Diabetes, 56 (8): 2078-84. [PMID:17513706]
3. Daval M, Diot-Dupuy F, Bazin R, Hainault I, Viollet B, Vaulont S, Hajduch E, Ferré P, Foufelle F. (2005)
Anti-lipolytic action of AMP-activated protein kinase in rodent adipocytes.
J Biol Chem, 280 (26): 25250-7. [PMID:15878856]
4. Merrill GF, Kurth EJ, Hardie DG, Winder WW. (1997)
AICA riboside increases AMP-activated protein kinase, fatty acid oxidation, and glucose uptake in rat muscle.
Am J Physiol, 273 (6 Pt 1): E1107-12. [PMID:9435525]
5. Musi N, Goodyear LJ. (2002)
Targeting the AMP-activated protein kinase for the treatment of type 2 diabetes.
Curr Drug Targets Immune Endocr Metabol Disord, 2 (2): 119-27. [PMID:12476786]
6. Walker J, Jijon HB, Diaz H, Salehi P, Churchill T, Madsen KL. (2005)
5-aminoimidazole-4-carboxamide riboside (AICAR) enhances GLUT2-dependent jejunal glucose transport: a possible role for AMPK.
Biochem J, 385 (Pt 2): 485-91. [PMID:15367103]
7. Winder WW, Hardie DG. (1999)
AMP-activated protein kinase, a metabolic master switch: possible roles in type 2 diabetes.
Am J Physiol, 277 (1 Pt 1): E1-10. [PMID:10409121]