(2R,4R,5R)-2-[2-amino-6-(benzyloxy)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 161558
• Molecular Formular: C17H19N5O5
• Molecular Mass: 373.36326
• Monoisotopic Mass: 373.13861873
• SMILES: n1([C@H]2C([C@H]([C@H](O2)CO)O)O)cnc2c1nc(nc2OCc1ccccc1)N
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1nc(N)nc2OCc1ccccc1
• InChI: InChI=1S/C17H19N5O5/c18-17-20-14-11(15(21-17)26-7-9-4-2-1-3-5-9)19-8-22(14)16-13(25)12(24)10(6-23)27-16/h1-5,8,10,12-13,16,23-25H,6-7H2,(H2,18,20,21)/t10-,12+,13?,16-/m1/s1
• InChIKey: LWYXQHQQWVZSOQ-QEFZCKDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-[2-amino-6-(benzyloxy)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-[2-amino-6-(benzyloxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: O6-Benzylguanosine; 2-Amino-6-(benzyloxy)-9-β-D-ribofuranosyl-purine; 6-O-(Phenylmethyl)guanosine; O6-Benzyl Guanosine

Database IDs

• CAS Number: 4552-61-8
• PubChem SID: 162255693
• PubChem CID: 71313823

CALCULATED PROPERTIES

• Acid pKa: 12.453926
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 0.1544306
• LogD (pH = 7.4): 0.15461774
• Log P: 0.154624
• Molar Refractivity: 94.2174 cm^3
• Polarizability: 36.581486 Å^3
• Polar Surface Area: 148.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Beige Solid
• Melting Point: 135-138°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B278525

Protected Guanosine derivative.

REFERENCES

• Kokkinakis, D., et al.: Cancer Chemother. Pharmacol., 45, 69 (1998)
• Hebert, M., et al.: J. Biol. Chem., 273, 5557 (1998)