9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 165977
• Molecular Formular: C10H12N4O4
• Molecular Mass: 252.22668
• Monoisotopic Mass: 252.08585488
• SMILES: [nH]1cnc2c(c1=O)ncn2[C@H]1C[C@H]([C@H](O1)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1nc[nH]c2=O
• InChI: InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6-,7-/m1/s1
• InChIKey: VGONTNSXDCQUGY-FSDSQADBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: 1,9-Dihydro-9-(2’-deoxy-β-D-ribofuranosyl)-6H-purin-6-one; 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one; Hypoxanthine Deoxyriboside; 2'-Deoxyinosine

Database IDs

• CAS Number: 890-38-0
• PubChem SID: 162260110
• PubChem CID: 7061348

CALCULATED PROPERTIES

• Acid pKa: 8.934634
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5780466
• LogD (pH = 7.4): -1.5889554
• Log P: -1.5778999
• Molar Refractivity: 59.8211 cm^3
• Polarizability: 22.45079 Å^3
• Polar Surface Area: 108.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D239755

An Inosine (I661000) analog with hypotensive activity. An impurity of the antiviral drug 2’,3’-Dideoxyinosine (D440950).

REFERENCES

• Maling, S.J. et al.: J. Appl. Biochem., 2, 130 (1980)
• Rao, D.V.N.S. et al.: J. Pharmac. Biomed. Anal., 45, 516 (1980)