(2R,3R,5R)-5-[2-amino-6-(benzyloxy)-9H-purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 161481
• Molecular Formular: C17H19N5O4
• Molecular Mass: 357.36386
• Monoisotopic Mass: 357.14370411
• SMILES: n1c(nc2c(c1OCc1ccccc1)ncn2[C@H]1C[C@H]([C@H](O1)CO)O)N
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1nc(N)nc2OCc1ccccc1
• InChI: InChI=1S/C17H19N5O4/c18-17-20-15-14(16(21-17)25-8-10-4-2-1-3-5-10)19-9-22(15)13-6-11(24)12(7-23)26-13/h1-5,9,11-13,23-24H,6-8H2,(H2,18,20,21)/t11-,12-,13-/m1/s1
• InChIKey: MTEDBOAIQUHDQD-JHJVBQTASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-5-[2-amino-6-(benzyloxy)-9H-purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,3R,5R)-5-[2-amino-6-(benzyloxy)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: 2'-Deoxy-6-O-(phenylmethyl)guanosine; O6-Benzyl-2'-deoxyguanosine

Database IDs

• CAS Number: 129732-90-7
• PubChem SID: 162255616
• PubChem CID: 71313802

CALCULATED PROPERTIES

• Acid pKa: 13.88469
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.0552535
• LogD (pH = 7.4): 1.0552619
• Log P: 1.0552621
• Molar Refractivity: 92.7067 cm^3
• Polarizability: 35.919468 Å^3
• Polar Surface Area: 128.54 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B234700

Protected Deoxyguanosine.

REFERENCES

• Kokkinakis, D., et al.: Clin. Cancer Res., 9, 3801 (2003)
• Coulter, R., et al.: Chem. Res. Toxicol., 20, 1966 (2003)