[(2R,3S,5R)-3-(acetyloxy)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl acetate

• ChemBase ID: 166766
• Molecular Formular: C13H16N2O7
• Molecular Mass: 312.27534
• Monoisotopic Mass: 312.09575086
• SMILES: [C@@H]1(C[C@@H](O[C@@H]1COC(=O)C)n1c(=O)[nH]c(=O)cc1)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1C[C@@H](O[C@@H]1COC(=O)C)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C13H16N2O7/c1-7(16)20-6-10-9(21-8(2)17)5-12(22-10)15-4-3-11(18)14-13(15)19/h3-4,9-10,12H,5-6H2,1-2H3,(H,14,18,19)/t9-,10+,12+/m0/s1
• InChIKey: XCLQOCSQUSRPDH-HOSYDEDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,5R)-3-(acetyloxy)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,5R)-3-(acetyloxy)-5-(2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methyl acetate
• Synonyms: 3',5'-Diacetyl-2'-deoxyuridine; 2'-Deoxy-3',5'-di-O-acetyluridine; 1-(3',5'-Di-O-acetyl-2'-deoxy-β-D-ribofuranosyl)uracil; 3',5'-Di-O-acetyl-2'-deoxyuridine

Database IDs

• CAS Number: 13030-62-1
• PubChem SID: 162260899
• PubChem CID: 7075529

CALCULATED PROPERTIES

• Acid pKa: 9.705757
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.63238
• LogD (pH = 7.4): -0.6344714
• Log P: -0.63235325
• Molar Refractivity: 69.3579 cm^3
• Polarizability: 27.903975 Å^3
• Polar Surface Area: 111.24 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 99-101°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D324500

An antitumor carbocyclic nucleoside.

REFERENCES

• Gu, Y., et al.: J. Mol. Struc., 552, 17 (2000)
• Scheiner, S., et al.: J. Biol. Chem., 276, 9832 (2000)
• Thalacker, C., et al.: Org. Biomol. Chem., 3, 414 (2005)