(2R,4R,5R)-2-(6,8-diamino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 159798
• Molecular Formular: C10H14N6O4
• Molecular Mass: 282.25596
• Monoisotopic Mass: 282.10765296
• SMILES: n1cnc2c(c1N)nc(n2[C@H]1C([C@H]([C@H](O1)CO)O)O)N
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1c(N)nc2c1ncnc2N
• InChI: InChI=1S/C10H14N6O4/c11-7-4-8(14-2-13-7)16(10(12)15-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,15)(H2,11,13,14)/t3-,5+,6?,9-/m1/s1
• InChIKey: DVGWFQILDUEEGX-ACJOCUEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-(6,8-diamino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-(6,8-diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 6,8-Diamino-9-β-D-ribofuranosyl- 9H-purine; NSC 90394; 8-Amino Adenosine

Database IDs

• CAS Number: 3868-33-5
• PubChem SID: 162253933
• PubChem CID: 45038103

CALCULATED PROPERTIES

• Acid pKa: 12.452203
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.298821
• LogD (pH = 7.4): -2.2365005
• Log P: -2.2356398
• Molar Refractivity: 67.3693 cm^3
• Polarizability: 25.708996 Å^3
• Polar Surface Area: 165.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: >185°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A580375

The purine nucleoside analog; has role in induction of apoptosis in multiple myeloma.

REFERENCES

• Yan, Y., et al.: J. Biol. Chem., 274, 31917 (1999)
• Chang, L., et al.: Nature, 410, 37 (1999)
• Gandhi, V., et al.: Cancer Res., 61, 5474 (1999)
• Ravandi, F., et al.: Clin. Cancer Res., 9, 535 (1999)