[(2R,3R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 178766
• Molecular Formular: C17H19N5O6S
• Molecular Mass: 421.42766
• Monoisotopic Mass: 421.10560435
• SMILES: [nH]1c(nc2c(c1=O)ncn2[C@H]1C[C@H]([C@H](O1)COS(=O)(=O)c1ccc(cc1)C)O)N
• Canonical SMILES: O[C@@H]1C[C@@H](O[C@@H]1COS(=O)(=O)c1ccc(cc1)C)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C17H19N5O6S/c1-9-2-4-10(5-3-9)29(25,26)27-7-12-11(23)6-13(28-12)22-8-19-14-15(22)20-17(18)21-16(14)24/h2-5,8,11-13,23H,6-7H2,1H3,(H3,18,20,21,24)/t11-,12-,13-/m1/s1
• InChIKey: QZERCZKEESOISM-JHJVBQTASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: [(2R,3R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• Synonyms: 5'-(4-Methylbenzenesulfonate) 2'-Deoxyguanosine; 5'-Tosyl-2'-deoxy Guanosine

Database IDs

• CAS Number: 109954-64-5
• PubChem SID: 164234676
• PubChem CID: 46783116

CALCULATED PROPERTIES

• Acid pKa: 10.158544
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 0.7584786
• LogD (pH = 7.4): 0.7578626
• Log P: 0.7585316
• Molar Refractivity: 101.0531 cm^3
• Polarizability: 39.14956 Å^3
• Polar Surface Area: 158.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T631700

A novel 2'-deoxycyclonucleosides used in synthesis of α,β-methylene-2'-deoxynucleoside 5'-triphosphates as noncleavable substrates for DNA polymerases.

REFERENCES

• Krug, F., et al.: J. Biol. Chem., 248, 1203 (1973)
• Ahn, J., et al.: Biochem. J., 331, 79 (1973)
• Sucato, C., et al.: Biochemistry, 46, 461 (1973)
• Liang, F., et al.: J. Med. Chem., 51, 6460 (1973)