5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide

• ChemBase ID: 72806
• Molecular Formular: C9H14N4O5
• Molecular Mass: 258.23126
• Monoisotopic Mass: 258.09641957
• SMILES: O1[C@@H]([C@H]([C@H]([C@@H]1n1c(c(nc1)C(=O)N)N)O)O)CO
• Canonical 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
• InChIKey: RTRQQBHATOEIAF-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide
• IUPAC Traditional name: acadesine
• Synonyms: AICAR; AICA-riboside; Acadesine; 5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside; Acadesine; N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide; AICAR

Database IDs

• CAS Number: 2627-69-2
• EC Number: 220-097-5
• MDL Number: MFCD00869751
• PubChem SID: 162037727; 24724407
• PubChem CID: 17513

CALCULATED PROPERTIES

• Acid pKa: 12.449647
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.6328213
• LogD (pH = 7.4): -2.5593672
• Log P: -2.5583196
• Molar Refractivity: 58.2692 cm^3
• Polarizability: 22.46471 Å^3
• Polar Surface Area: 156.85 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: >7 mg/mL
• Apperance: tan powder
• Melting Point: 214-215 °C

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C9H14N4O5

DETAILS

Selleck Chemicals - S1802

Research Area: Cardiovascular Disease
Biological Activity:
Acadesine is an AMP-activated protein kinase activator which is used for the treatment of acute lymphoblastic leukemia and may have applications in treating other disorders such as diabetes. [1]

Sigma Aldrich - A9978

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
AICAR is a cell permeable activator of AMP-activated protein kinase (AMPK), a metabolic master regulator that is activated in times of reduced energy availability (high cellular AMP:ATP ratios) and serves to inhibit anabolic processes. In vivo, pharmacologic activation of AMPK with AICAR mimics exercise and triggers insulin-independent glucose uptake by skeletal muscle.

REFERENCES

• http://en.wikipedia.org/wiki/Acadesine