2-chloro-9-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 164347
• Molecular Formular: C10H11ClN4O5
• Molecular Mass: 302.67114
• Monoisotopic Mass: 302.04179715
• SMILES: [nH]1c(nc2c(c1=O)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O)Cl
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1nc(Cl)[nH]c2=O
• InChI: InChI=1S/C10H11ClN4O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H,13,14,19)/t3-,5+,6?,9-/m1/s1
• InChIKey: NDSPCQCIHGSYAS-ACJOCUEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-9-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-chloro-9-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: 2-CIDO; 2-Chloroinosine

Database IDs

• CAS Number: 13276-43-2
• PubChem SID: 162258482
• PubChem CID: 71314746

CALCULATED PROPERTIES

• Acid pKa: 7.046837
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.4338713
• LogD (pH = 7.4): -1.8362856
• Log P: -1.4231126
• Molar Refractivity: 66.5353 cm^3
• Polarizability: 25.119776 Å^3
• Polar Surface Area: 129.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Tan Solid
• Melting Point: >140°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C367150

Halogenated nucleoside.

REFERENCES

• Sodum, R., et al.: Chem. Res. Toxicol., 11, 1453 (1998)