(2R,3R,4S,5R)-2-(6-amino-8-azido-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 160976
• Molecular Formular: C10H12N8O4
• Molecular Mass: 308.25348
• Monoisotopic Mass: 308.0981509
• SMILES: n1cnc2c(c1N)nc(n2[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)N=[N+]=[N-]
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(N=[N+]=[N-])nc2c1ncnc2N
• InChI: InChI=1S/C10H12N8O4/c11-7-4-8(14-2-13-7)18(10(15-4)16-17-12)9-6(21)5(20)3(1-19)22-9/h2-3,5-6,9,19-21H,1H2,(H2,11,13,14)/t3-,5-,6-,9-/m1/s1
• InChIKey: KYJLJOJCMUFWDY-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(6-amino-8-azido-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(6-amino-8-azidopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 8-Azidoadenosine; 8-Azido Adenosine

Database IDs

• CAS Number: 4372-67-2
• PubChem SID: 162255111
• PubChem CID: 160751

CALCULATED PROPERTIES

• Acid pKa: 12.45268
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -1.1517127
• LogD (pH = 7.4): -1.10108
• Log P: -0.9863443
• Molar Refractivity: 72.9565 cm^3
• Polarizability: 26.926247 Å^3
• Polar Surface Area: 168.97 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pink to pale Purple Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: Amber Vial, Refrigerator, Under Inert Atmosphere

REFERENCES

• Sawai, H., et al.: J. Med. Chem., 46, 4926 (2003)
• Polshakov, D., et al.: Biochem., 44, 11241 (2003)
• Long, M., et al.: Biochem. Pharmacol., 71, 1671 (2003)