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

• ChemBase ID: 119592
• Molecular Formular: C10H12N4O3
• Molecular Mass: 236.22728
• Monoisotopic Mass: 236.09094026
• SMILES: n1(c2c(nc1)c(ncn2)O)[C@@H]1O[C@@H](CC1)CO
• Canonical SMILES: OC[C@@H]1CC[C@@H](O1)n1cnc2c1ncnc2O
• InChI: InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1
• InChIKey: BXZVVICBKDXVGW-NKWVEPMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol
• IUPAC Traditional name: 2',3' dideoxyinosine; 9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol
• Synonyms: Didanosine; 9-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-ol; 2',3'-Dideoxy-1,9-dihydro-9-beta- D -ribofuranosyl-6 H -purin-6-one; 2',3'-Dideoxyinosine; Videx; Didanosine

Database IDs

• CAS Number: 69655-05-6
• MDL Number: MFCD00077728
• PubChem SID: 162107686
• PubChem CID: 50599

CALCULATED PROPERTIES

• Acid pKa: 11.677703
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.043686293
• LogD (pH = 7.4): 0.043664996
• Log P: 0.04368759
• Molar Refractivity: 58.1715 cm^3
• Polarizability: 22.693178 Å^3
• Polar Surface Area: 93.29 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Cell proliferation inhibitor; Reverse Transcriptase inhibitor

Product Information

• Purity: 98%
• Application(s): Antiviral agent; Nucleoside transporter substrate.; Potentially of use against HIV infection and used in combination with other antiretroviral drug therapy as part of highly active

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 215B, (nmr)
• Mitsuya, H. et al., Proc. Natl. Acad. Sci. U.S.A., 1986, 83, 1911, (pharmacol)
• Ray, G. et al., Anal. Lett., 1987, 20, 1815, (hplc)
• Ahluwalia, G. et al., Biochem. Pharmacol., 1987, 36, 3797
• Hao, Z. et al., Mol. Pharmacol., 1988, 34, 431, (pharmacol)
• Chu, C.K. et al., J.O.C., 1989, 54, 2217, (synth, pmr)
• McGowan, J.J. et al., Rev. Infect. Dis., 1990, 12, S513, (rev, antiretroviral props)
• Shelton, M.J. et al., Ann. Pharmacother., 1992, 26, 660, (rev)
• Wu, X. et al., J. Biol. Chem., 1992, 267, 8813-8818, (pharmacol)
• Bhat, V. et al., Synth. Commun., 1992, 22, 1481, (synth, pmr, uv)
• Nassar, M.N. et al., Anal. Profiles Drug Subst., 1993, 22, 185, (rev)