9-[(2R,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 160678
• Molecular Formular: C10H10N4O4
• Molecular Mass: 250.2108
• Monoisotopic Mass: 250.07020482
• SMILES: [nH]1cnc2c(c1=O)ncn2[C@H]1C2[C@@H]([C@H](O1)CO)O2
• Canonical SMILES: OC[C@H]1O[C@H](C2[C@@H]1O2)n1cnc2c1nc[nH]c2=O
• InChI: InChI=1S/C10H10N4O4/c15-1-4-6-7(18-6)10(17-4)14-3-13-5-8(14)11-2-12-9(5)16/h2-4,6-7,10,15H,1H2,(H,11,12,16)/t4-,6-,7?,10-/m1/s1
• InChIKey: WDIGUIIOGAEQHN-CPTYKQRNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 9-[(2R,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-1H-purin-6-one
• Synonyms: 9-(2,3-Anhydro-β-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-one; 2',3'-Anhydroinosine

Database IDs

• CAS Number: 31766-13-9
• PubChem SID: 162254813
• PubChem CID: 71313424

CALCULATED PROPERTIES

• Acid pKa: 8.9339285
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.3169811
• LogD (pH = 7.4): -1.3279076
• Log P: -1.3168344
• Molar Refractivity: 57.8217 cm^3
• Polarizability: 21.821762 Å^3
• Polar Surface Area: 101.27 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A648370

An impurity of the antiviral drug 2’,3’-Dideoxyinosine (D440950).

REFERENCES

• Rao, D.V.N. et al.: J. Pharmac. Biomed.Anal., 45, 516 (2007)