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

• ChemBase ID: 164182
• Molecular Formular: C13H15ClN2O7
• Molecular Mass: 346.7204
• Monoisotopic Mass: 346.05677851
• SMILES: [C@@H]1(C[C@@H](O[C@@H]1COC(=O)C)n1c(=O)[nH]c(=O)c(c1)Cl)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1C[C@@H](O[C@@H]1COC(=O)C)n1cc(Cl)c(=O)[nH]c1=O
• InChI: InChI=1S/C13H15ClN2O7/c1-6(17)21-5-10-9(22-7(2)18)3-11(23-10)16-4-8(14)12(19)15-13(16)20/h4,9-11H,3,5H2,1-2H3,(H,15,19,20)/t9-,10+,11+/m0/s1
• InChIKey: VYGRPIVVXOHVEA-HBNTYKKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,5R)-3-(acetyloxy)-5-(5-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,5R)-3-(acetyloxy)-5-(5-chloro-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methyl acetate
• Synonyms: 5-Chloro-2'-deoxyuridine 3',5'-Diacetate; 5-Chloro-3',5'-di-O-acetyl-2'-deoxyuridine

Database IDs

• CAS Number: 6046-63-5
• PubChem SID: 162258317
• PubChem CID: 11002516

CALCULATED PROPERTIES

• Acid pKa: 7.972004
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.026986754
• LogD (pH = 7.4): -0.07333268
• Log P: 0.028432392
• Molar Refractivity: 74.1492 cm^3
• Polarizability: 29.854048 Å^3
• Polar Surface Area: 111.24 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate
• Apperance: White Crystalline Solid

DETAILS

Toronto Research Chemicals - C365236

A halogenated uridine derivative used in pharmaceutical compositions.

REFERENCES

• Brammer, K., et al.: Biochim. Biophys. Acta, 72, 217 (1963)
• Uesugi, S., et al.: Chem. Pharm. Bull., 26, 3040 (1978)