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

• ChemBase ID: 175050
• Molecular Formular: C10H12N4O4
• Molecular Mass: 252.22668
• Monoisotopic Mass: 252.08585488
• SMILES: n1cnc2c(c1)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1ncnc2
• InChI: InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2/t6-,7+,8?,10-/m1/s1
• InChIKey: MRWXACSTFXYYMV-KIUGWDQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,5R)-2-(hydroxymethyl)-5-(purin-9-yl)oxolane-3,4-diol
• Synonyms: Purine-9-β-D-ribofuranoside; 9-β-D-Ribofuranosyl-9H-purine; Ribosyl-isopurine; Purinosine; NSC 65423; Nebularine

Database IDs

• CAS Number: 550-33-4
• PubChem SID: 164230960
• PubChem CID: 71750973

CALCULATED PROPERTIES

• Acid pKa: 12.454004
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.8643277
• LogD (pH = 7.4): -1.8565989
• Log P: -1.8564955
• Molar Refractivity: 58.1817 cm^3
• Polarizability: 23.381533 Å^3
• Polar Surface Area: 113.52 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: Beige Solid
• Melting Point: 173-175°C

Safety Information

• Storage Condition: -20°C Freezer, Under inert atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - N388500

Shown to have inhibitory effects against mouse Sarcoma 180 and mycobacteria.

REFERENCES

• Iwamura, H. and Hashizume, T.: J.O.C., 33, 5 1796 (1968)