9-[(3aS,4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ol

• ChemBase ID: 171906
• Molecular Formular: C13H16N4O5
• Molecular Mass: 308.28994
• Monoisotopic Mass: 308.11206963
• SMILES: n1cnc2c(c1O)ncn2[C@H]1[C@@H]2C([C@H](O1)CO)OC(O2)(C)C
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]2C1OC(O2)(C)C)n1cnc2c1ncnc2O
• InChI: InChI=1S/C13H16N4O5/c1-13(2)21-8-6(3-18)20-12(9(8)22-13)17-5-16-7-10(17)14-4-15-11(7)19/h4-6,8-9,12,18H,3H2,1-2H3,(H,14,15,19)/t6-,8?,9+,12-/m1/s1
• InChIKey: LIEKLUBCIPVWQD-WURNFRPNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(3aS,4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ol
• IUPAC Traditional name: 9-[(3aS,4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-ol
• Synonyms: 2',3'-O-(1-Methylethylidene)inosine; 2',3'-Isopropylideneinosine; NSC 29925; 2',3'-O-Isopropylideneinosine

Database IDs

• CAS Number: 2140-11-6
• PubChem SID: 164227816
• PubChem CID: 45039608

CALCULATED PROPERTIES

• Acid pKa: 11.6741
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.13682015
• LogD (pH = 7.4): 0.13679859
• Log P: 0.13682137
• Molar Refractivity: 72.6831 cm^3
• Polarizability: 28.949799 Å^3
• Polar Surface Area: 111.75 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Clear Colourless Solution at 200mg plus 4.0ml of Acetic Acid with Warming.; DMSO; Ethanol
• Apperance: White Solid
• Melting Point: 263-272°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I868500

An inosine derivative as antiviral, bactericidal, and antitumor agent for immunopotentiating uses.

REFERENCES

• Wilson, D., et al.: Biochemistry, 32, 1689 (1993)
• Marrone, T., et al.: J. Med. Chem., 39, 277 (1993)