9-[(2R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 165978
• Molecular Formular: C10H12N4O4
• Molecular Mass: 252.22668
• Monoisotopic Mass: 252.08585488
• SMILES: [nH]1cnc2c(c1=O)ncn2[C@H]1C(C[C@H](O1)CO)O
• Canonical SMILES: OC[C@@H]1CC([C@@H](O1)n1cnc2c1nc[nH]c2=O)O
• InChI: InChI=1S/C10H12N4O4/c15-2-5-1-6(16)10(18-5)14-4-13-7-8(14)11-3-12-9(7)17/h3-6,10,15-16H,1-2H2,(H,11,12,17)/t5-,6?,10+/m0/s1
• InChIKey: RPZDLTVHZJHPAW-GZRQHRFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 9-[(2R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: 1,9-Dihydro-9-(3’-deoxy-β-D-ribofuranosyl)-6H-purin-6-one; 3'-Deoxyinosine

Database IDs

• CAS Number: 13146-72-0
• PubChem SID: 162260111
• PubChem CID: 57135916

CALCULATED PROPERTIES

• Acid pKa: 8.933947
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.7883899
• LogD (pH = 7.4): -1.799316
• Log P: -1.7882434
• Molar Refractivity: 60.2347 cm^3
• Polarizability: 22.450644 Å^3
• Polar Surface Area: 108.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D239760

An Inosine (I661000) analog with potential use as an antileishmanial drug. Used as an inhibiting agent in studies of Trypanosoma cruzi growth inside host cells in vitro. An impurity of the antiviral drug 2’,3’-Dideoxyinosine (D440950).

REFERENCES

• Morishige, K. et al.: Exp. Parasitol., 80, 665 (1995)
• Aoki, T. et al.: Adv. Exp. Med. Biol., 370, 499 (1995)