[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-amino-8-bromo-6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methyl acetate

• ChemBase ID: 163072
• Molecular Formular: C16H18BrN5O8
• Molecular Mass: 488.24682
• Monoisotopic Mass: 487.03387456
• SMILES: [nH]1c(nc2c(c1=O)nc(n2[C@H]1[C@@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)Br)N
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@H]1n1c(Br)nc2c1nc(N)[nH]c2=O)COC(=O)C
• InChI: InChI=1S/C16H18BrN5O8/c1-5(23)27-4-8-10(28-6(2)24)11(29-7(3)25)14(30-8)22-12-9(19-15(22)17)13(26)21-16(18)20-12/h8,10-11,14H,4H2,1-3H3,(H3,18,20,21,26)/t8-,10-,11-,14-/m1/s1
• InChIKey: JLZCAXCVNVVXJL-IDTAVKCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-amino-8-bromo-6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-amino-8-bromo-6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• Synonyms: 8-Bromo-guanosine 2',3',5'-Triacetate; 2',3',5'-Tri-O-acetyl-8-bromoguanosine; NSC 174056; NSC 79210; 8-Bromo-2',3',5'-tri-O-acetylguanosine

Database IDs

• CAS Number: 15717-45-0
• PubChem SID: 162257207
• PubChem CID: 85067

CALCULATED PROPERTIES

• Acid pKa: 10.116221
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.31879735
• LogD (pH = 7.4): -0.3195131
• Log P: -0.31877485
• Molar Refractivity: 99.7004 cm^3
• Polarizability: 39.041313 Å^3
• Polar Surface Area: 173.43 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 200-204°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Kazmers, I.S., et al.: Science, 214, 1137 (1981)
• Chern, J-W., et al.: J. Med. Chem., 36, 1024 (1993)