(2R,3S,5R)-2-[6-hydroxy(4,5-13C2,7-15N)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 171640
• Molecular Formular: C10H12N4O5
• Molecular Mass: 271.20479857
• Monoisotopic Mass: 271.08451407
• SMILES: n1cn[13c]2[13c](c1O)[15n]cn2[C@H]1[C@H](C([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1c[15n][13c]2[13c]1ncnc2O
• InChI: InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6?,7+,10-/m1/s1/i5+1,8+1,13+1
• InChIKey: UGQMRVRMYYASKQ-RFFLEXJYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-[6-hydroxy(4,5-^1^3C₂,7-^1^5N)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-[6-hydroxy(4,5-^1^3C₂,7-^1^5N)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 1,9-Dihydro-9-β-D-ribofuranosyl-6H-purin-6-one-13C2,15N; 9-β-D-Ribofuranosylhypoxanthine-13C2,15N; Hypoxanthine 9-β-D-ribofuranoside-13C2,15N; Hypoxanthine Ribonucleoside-13C2,15N; Hypoxanthine Riboside-13C2,15N; (-)-Inosine-13C2,15N

Database IDs

• PubChem SID: 164227550
• PubChem CID: 71749497

CALCULATED PROPERTIES

• Acid pKa: 11.607877
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.5656046
• LogD (pH = 7.4): -1.5656298
• Log P: -1.5656033
• Molar Refractivity: 60.4761 cm^3
• Polarizability: 24.067204 Å^3
• Polar Surface Area: 133.75 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: White Solid
• Melting Point: 208-211°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I661002

Has neuroprotective properties improving axonal wiring. Has been used to treat stroke patients to restore neural function.

REFERENCES

• Vandemeulebroucke, A., et al.: Biochem., 49, 8999 (2010)
• Nestor, G., et al.: J. Agric. Food Chem., 58, 10799 (2010)