[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 178765
• Molecular Formular: C16H19N3O6S
• Molecular Mass: 381.40356
• Monoisotopic Mass: 381.09945634
• SMILES: [C@H]1(C[C@@H](O[C@@H]1COS(=O)(=O)c1ccc(cc1)C)n1c(=O)nc(cc1)N)O
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)OC[C@H]1O[C@H](C[C@H]1O)n1ccc(nc1=O)N
• InChI: InChI=1S/C16H19N3O6S/c1-10-2-4-11(5-3-10)26(22,23)24-9-13-12(20)8-15(25-13)19-7-6-14(17)18-16(19)21/h2-7,12-13,15,20H,8-9H2,1H3,(H2,17,18,21)/t12-,13-,15-/m1/s1
• InChIKey: IENUZDCEUIARIF-UMVBOHGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• Synonyms: 5'-(4-Methylbenzenesulfonate) 2'-Deoxycytidine; 5'-p-Toluenesulfonate 2'-Deoxycytidine; 5'-Tosyl-2'-deoxy Cytidine

Database IDs

• CAS Number: 27999-55-9
• PubChem SID: 164234675
• PubChem CID: 46783115

CALCULATED PROPERTIES

• Acid pKa: 13.988904
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.6672319
• LogD (pH = 7.4): 0.6672324
• Log P: 0.6672325
• Molar Refractivity: 90.9768 cm^3
• Polarizability: 36.33331 Å^3
• Polar Surface Area: 131.52 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T631600

A nucleoside used to synthesize vitamin B12 coenzyme analogs containing 2'-deoxynucleoside.

REFERENCES

• Krug, F., et al.: J. Biol. Chem., 248, 1203 (1973)
• Beard, W., et al.: Methods Enzymol., 262, 98 (1973)
• Sucato, C., et al.: Biochemistry, 46, 461 (1973)
• Jain, N., et al.: Chem. Res. Toxicol., 21, 445 (1973)