5-amino-1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl](4,5-13C2,3-15N)-1H-imidazole-4-carboxamide

• ChemBase ID: 160202
• Molecular Formular: C9H14N4O5
• Molecular Mass: 261.20997857
• Monoisotopic Mass: 261.10016414
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c[15n][13c]([13c]1N)C(=O)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1c[15n][13c]([13c]1N)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/i4+1,7+1,12+1
• InChIKey: RTRQQBHATOEIAF-OJSSWAJASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl](4,5-^1^3C₂,3-^1^5N)-1H-imidazole-4-carboxamide
• IUPAC Traditional name: 5-amino-1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl](4,5-^1^3C₂,3-^1^5N)imidazole-4-carboxamide
• Synonyms: 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranoside-13C2,15N; AICAR-13C2,15N; Acadesine-13C2,15N; 5-Amino-4-imidazolecarboxamide Riboside-13C2,15N; Arasine-13C2,15N; GP 1-110-13C2,15N; NSC 105823-13C2,15N; 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranoside-13C2,15N

Database IDs

• PubChem SID: 162254337
• PubChem CID: 71313279

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; Methanol
• Apperance: White Solid
• Melting Point: 187-192°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A611702

A labelled nucleoside analogue that is able to enter nucleoside pools and is able to significantly increase levels of adenosine during periods of ATP breakdown. Adenosine-regulating agents (ARAs) have been recognized for therapeutic potential in myocardi

REFERENCES

• Mullane, K., et al.: Trends Cardiovasc Med., 3, 227 (1993)
• Browne, G.J., et al.: J. Biol. Chem., 279, 13, 12220 (2004)