acadesine   Click here for help

GtoPdb Ligand ID: 5133

Synonyms: AICA-riboside | AR-100 | SCH-900395
Compound class: Synthetic organic

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key RTRQQBHATOEIAF-UUOKFMHZSA-N
References
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]