[(2R,3S,5R)-3-(acetyloxy)-5-(2-acetamido-6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methyl acetate

• ChemBase ID: 178852
• Molecular Formular: C16H19N5O7
• Molecular Mass: 393.35136
• Monoisotopic Mass: 393.12844797
• SMILES: [nH]1c(nc2c(c1=O)ncn2[C@H]1C[C@@H]([C@H](O1)COC(=O)C)OC(=O)C)NC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1C[C@@H](O[C@@H]1COC(=O)C)n1cnc2c1nc(NC(=O)C)[nH]c2=O
• InChI: InChI=1S/C16H19N5O7/c1-7(22)18-16-19-14-13(15(25)20-16)17-6-21(14)12-4-10(27-9(3)24)11(28-12)5-26-8(2)23/h6,10-12H,4-5H2,1-3H3,(H2,18,19,20,22,25)/t10-,11+,12+/m0/s1
• InChIKey: RCOVGEMUNRNWBU-QJPTWQEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,5R)-3-(acetyloxy)-5-(2-acetamido-6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,5R)-3-(acetyloxy)-5-(2-acetamido-6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• Synonyms: N-Acetyl-2'-deoxy-guanosine 3',5'-Diacetate; 3',5',N2-Tri-O-acetyl 2'-Deoxyguanosine

Database IDs

• CAS Number: 193092-29-4
• PubChem SID: 164234762
• PubChem CID: 13096950

CALCULATED PROPERTIES

• Acid pKa: 9.037138
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.9920029
• LogD (pH = 7.4): -1.0006483
• Log P: -0.9918877
• Molar Refractivity: 90.8572 cm^3
• Polarizability: 35.123096 Å^3
• Polar Surface Area: 150.21 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Pale Brown Solid

DETAILS

Toronto Research Chemicals - T740000

Protected Deoxyguanosine.

REFERENCES

• Mounetou, E., et al.: J. Med. Chem., 40, 2902 (1997)
• Perrino, F., et al.: Chem. Res. Toxicol., 18, 1451 (1997)