(2R,3R,5R)-5-[2,4-dioxo-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidin-1-yl]-2-[(4-methylbenzoyloxy)methyl]oxolan-3-yl 4-methylbenzoate

• ChemBase ID: 165913
• Molecular Formular: C25H24N2O7
• Molecular Mass: 467.44673263
• Monoisotopic Mass: 467.15577574
• SMILES: [15nH]1[13c](=O)[15n](ccc1=O)[C@H]1C[C@H]([C@H](O1)COC(=O)c1ccc(cc1)C)OC(=O)c1ccc(cc1)C
• Canonical SMILES: Cc1ccc(cc1)C(=O)OC[C@H]1O[C@H](C[C@H]1OC(=O)c1ccc(cc1)C)[15n]1ccc(=O)[15nH][13c]1=O
• InChI: InChI=1S/C25H24N2O7/c1-15-3-7-17(8-4-15)23(29)32-14-20-19(34-24(30)18-9-5-16(2)6-10-18)13-22(33-20)27-12-11-21(28)26-25(27)31/h3-12,19-20,22H,13-14H2,1-2H3,(H,26,28,31)/t19-,20-,22-/m1/s1/i25+1,26+1,27+1
• InChIKey: PHIPERUMORAWER-FIEPXANKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-5-[2,4-dioxo-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-2-[(4-methylbenzoyloxy)methyl]oxolan-3-yl 4-methylbenzoate
• IUPAC Traditional name: (2R,3R,5R)-5-[2,4-dioxo(2-^1^3C,1,3-^1^5N₂)-3H-pyrimidin-1-yl]-2-[(4-methylbenzoyloxy)methyl]oxolan-3-yl 4-methylbenzoate
• Synonyms: 2'-Deoxy-3',5'-di-O-p-toluoyl Uridine-13C,15N2

Database IDs

• PubChem SID: 162260046
• PubChem CID: 71315449

CALCULATED PROPERTIES

• Acid pKa: 9.705757
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.5028114
• LogD (pH = 7.4): 4.50072
• Log P: 4.5028386
• Molar Refractivity: 120.7813 cm^3
• Polarizability: 46.665146 Å^3
• Polar Surface Area: 111.24 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dimethyl Sulfoxide
• Apperance: Off-White Powder

DETAILS

Toronto Research Chemicals - D232897

2’-Deoxy-3’,5’-di-O-p-toluoyl Uridine is a substituted Uridine (U829910) used in the synthesis of Uridine analogs.

REFERENCES

• Balzarini, J., et al.: Biochim. Biophys. Acta., 1587, 287 (2002)
• Mathe, C., et al.: Antiviral Res., 71, 276 (2002)
• Weinberg, A., et al.: J. Clin. Virol., 38, 139 (2002)