1-[(3aS,4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-5-amino-1H-imidazole-4-carboxamide

• ChemBase ID: 160224
• Molecular Formular: C12H18N4O5
• Molecular Mass: 298.29512
• Monoisotopic Mass: 298.1277197
• SMILES: [C@H]12C([C@H](O[C@H]1n1cnc(c1N)C(=O)N)CO)OC(O2)(C)C
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]2C1OC(O2)(C)C)n1cnc(c1N)C(=O)N
• InChI: InChI=1S/C12H18N4O5/c1-12(2)20-7-5(3-17)19-11(8(7)21-12)16-4-15-6(9(16)13)10(14)18/h4-5,7-8,11,17H,3,13H2,1-2H3,(H2,14,18)/t5-,7?,8+,11-/m1/s1
• InChIKey: HUTXHGRHFXEXPQ-DWVWSIQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3aS,4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-5-amino-1H-imidazole-4-carboxamide
• IUPAC Traditional name: 1-[(3aS,4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-aminoimidazole-4-carboxamide
• Synonyms: 5-Amino-1-[2,3-O-(1-methylethylidene)-β-D-ribofuranosyl]-1H-imidazole-4-carboxamide; 5-Amino-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxamide

Database IDs

• CAS Number: 3676-69-5
• PubChem SID: 162254359
• PubChem CID: 71313289

CALCULATED PROPERTIES

• Acid pKa: 14.17805
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.9303821
• LogD (pH = 7.4): -0.8569384
• Log P: -0.85589504
• Molar Refractivity: 70.4762 cm^3
• Polarizability: 27.327763 Å^3
• Polar Surface Area: 134.85 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A611840

Protected 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranoside (A611700), a 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 (

REFERENCES

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