1-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-6-yl]-5-amino-1H-imidazole-4-carboxamide

• ChemBase ID: 159602
• Molecular Formular: C9H13N4O7P
• Molecular Mass: 320.195881
• Monoisotopic Mass: 320.05218541
• SMILES: [C@@H]12[C@H](O[C@H]([C@@H]1O)n1c(c(nc1)C(=O)N)N)COP(=O)(O2)O
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc(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)/t3-,5-,6-,9-/m1/s1
• InChIKey: QQDWJBYNAORJHB-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl]-5-amino-1H-imidazole-4-carboxamide
• IUPAC Traditional name: 1-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl]-5-aminoimidazole-4-carboxamide
• Synonyms: 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 3’:5’-cyclic-monophosphate; 5-Amino-1-(3,5-O-phosphinico-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide; NSC 371796; AICAR 3',5'-Cyclic Phosphate

Database IDs

• CAS Number: 35908-14-6
• PubChem SID: 162253737
• PubChem CID: 29971151

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

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: >225°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A440500

A cyclic nucleotides with protein kinase and phosphodiesterase activity.

REFERENCES

• Fujii, T., et al.: Chem. Pharm. Bull., 19, 1368 (1971)
• Montgomery, J.A., et al.: J. Med. Chem., 15, 182 (1971)