5-amino-1-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-6-yl}-1H-imidazole-4-carboxamide

• ChemBase ID: 131120
• Molecular Formular: C9H13N4O7P
• Molecular Mass: 320.195881
• Monoisotopic Mass: 320.05218541
• SMILES: c1nc(c(n1C1C(C2C(O1)COP(=O)(O2)O)O)N)C(=O)N
• Canonical SMILES: OC1C2OP(=O)(O)OCC2OC1n1cnc(c1N)C(=O)N
• InChI: InChI=1S/C9H13N4O7P/c10-7-4(8(11)15)12-2-13(7)9-5(14)6-3(19-9)1-18-21(16,17)20-6/h2-3,5-6,9,14H,1,10H2,(H2,11,15)(H,16,17)
• InChIKey: QQDWJBYNAORJHB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl}-1H-imidazole-4-carboxamide
• IUPAC Traditional name: 5-amino-1-{2,7-dihydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl}imidazole-4-carboxamide
• Synonyms: AICAR 3′:5′-monophosphate; N1-(β-D-3′:5′-Monophosphoribofuranosyl)-5-aminoimidazole-4-carboxamide; 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 3′:5′-cyclic-monophosphate,

Database IDs

• CAS Number: 35908-14-6
• EC Number: 252-787-7
• MDL Number: MFCD00057115
• PubChem SID: 162225398
• PubChem CID: 340730

CALCULATED PROPERTIES

• Acid pKa: 1.8322592
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -4.116121
• LogD (pH = 7.4): -4.1610184
• Log P: -3.7089765
• Molar Refractivity: 65.3631 cm^3
• Polarizability: 25.874771 Å^3
• Polar Surface Area: 172.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C