[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)oxolan-2-yl]methyl acetate

• ChemBase ID: 160515
• Molecular Formular: C15H20N4O8
• Molecular Mass: 384.3413
• Monoisotopic Mass: 384.12811362
• SMILES: c1(c(ncn1[C@H]1[C@@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)C(=O)N)N
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@H]1n1cnc(c1N)C(=O)N)COC(=O)C
• InChI: InChI=1S/C15H20N4O8/c1-6(20)24-4-9-11(25-7(2)21)12(26-8(3)22)15(27-9)19-5-18-10(13(19)16)14(17)23/h5,9,11-12,15H,4,16H2,1-3H3,(H2,17,23)/t9-,11-,12-,15-/m1/s1
• InChIKey: ZGVQACKXOOWCLS-SDBHATRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(5-amino-4-carbamoylimidazol-1-yl)oxolan-2-yl]methyl acetate
• Synonyms: 5-Amino-1-β-D-ribofuranosyl-imidazole-4-carboxamide 2',3',5'-Triacetate; AICAR-Tri-O-Acetate; NSC 157736; 5-Amino-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-imidazole-4-carboxamide

Database IDs

• CAS Number: 23274-21-7
• PubChem SID: 162254650
• PubChem CID: 15592037

CALCULATED PROPERTIES

• Acid pKa: 14.394725
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.3094075
• LogD (pH = 7.4): -1.2359865
• Log P: -1.2349434
• Molar Refractivity: 85.7237 cm^3
• Polarizability: 34.02993 Å^3
• Polar Surface Area: 175.06 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Brown Semi Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere