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

• ChemBase ID: 178764
• Molecular Formular: C17H19N5O6S
• Molecular Mass: 421.42766
• Monoisotopic Mass: 421.10560435
• SMILES: n1cnc2c(c1N)ncn2[C@H]1C([C@H]([C@H](O1)COS(=O)(=O)c1ccc(cc1)C)O)O
• Canonical SMILES: O[C@H]1[C@@H](COS(=O)(=O)c2ccc(cc2)C)O[C@H](C1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C17H19N5O6S/c1-9-2-4-10(5-3-9)29(25,26)27-6-11-13(23)14(24)17(28-11)22-8-21-12-15(18)19-7-20-16(12)22/h2-5,7-8,11,13-14,17,23-24H,6H2,1H3,(H2,18,19,20)/t11-,13+,14?,17-/m1/s1
• InChIKey: CAXLRAROZXYOHH-NUKIEUHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: [(2R,3R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• Synonyms: 5'-(4-Methylbenzenesulfonate) 2'-Deoxyadenosine; 5'-p-Toluenesulfonate 2'-Deoxyadenosine; 5'-O-Tosyl-2'-deoxyadenosine; 5'-Tosyl-2'-deoxy Adenosine

Database IDs

• CAS Number: 6698-29-9
• PubChem SID: 164234674
• PubChem CID: 45040555

CALCULATED PROPERTIES

• Acid pKa: 12.456077
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): 0.35799438
• LogD (pH = 7.4): 0.4714819
• Log P: 0.47314784
• Molar Refractivity: 101.1383 cm^3
• Polarizability: 40.096695 Å^3
• Polar Surface Area: 162.68 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T631500

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

REFERENCES

• Ladd, J., et al.: J. Biol. Chem., 236, 2114 (1961)
• Smith, E., et al.: Nature, 194, 1175 (1961)
• Robins, M., et al.: Biochemistry, 5, 224 (1961)