[(2R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 178789
• Molecular Formular: C17H20N2O7S
• Molecular Mass: 396.4149
• Monoisotopic Mass: 396.09912199
• SMILES: c1(cn(c(=O)[nH]c1=O)[C@H]1CC(O)[C@@H](COS(=O)(=O)c2ccc(cc2)C)O1)C
• Canonical SMILES: OC1C[C@@H](O[C@@H]1COS(=O)(=O)c1ccc(cc1)C)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C17H20N2O7S/c1-10-3-5-12(6-4-10)27(23,24)25-9-14-13(20)7-15(26-14)19-8-11(2)16(21)18-17(19)22/h3-6,8,13-15,20H,7,9H2,1-2H3,(H,18,21,22)/t13?,14-,15-/m1/s1
• InChIKey: RSEWNGNFIIXLHN-JVIGXAJISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: [(2R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzenesulfonate
• Synonyms: 5'-(4-Methylbenzenesulfonate)thymidine; 5'-O-(p-Toluenesulfonyl)thymidine; 5'-O-Tosylthymidine; NSC 69443; 5'-Tosyl Thymidine

Database IDs

• CAS Number: 7253-19-2
• PubChem SID: 164234699
• PubChem CID: 46783117

CALCULATED PROPERTIES

• Acid pKa: 9.960286
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.4450432
• LogD (pH = 7.4): 1.443878
• Log P: 1.4450581
• Molar Refractivity: 93.3547 cm^3
• Polarizability: 37.543415 Å^3
• Polar Surface Area: 122.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T686500

A nucleoside analogue as inhibitors of thymidylate kinases.

REFERENCES

• Saito, H., et al.: J. Gen. Microbiol., 130, 1863 (1984)
• Sali, A., et al.: J. Mol. Biol., 234, 779 (1984)
• Blondin, C., et al.: Anal. Biochem., 220, 219 (1984)
• Lavie, A., et al.: Biochemistry, 37, 3677 (1984)
• Chenal-Francisque, V., et al.: Eur. J. Bioc