(2S,3S,5R)-2-{4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 164169
• Molecular Formular: C11H12ClN3O4
• Molecular Mass: 285.68368
• Monoisotopic Mass: 285.05163356
• SMILES: C1(O)[C@@H](CO)O[C@@H]([C@H]1O)n1c2c(c(ncn2)Cl)cc1
• Canonical SMILES: OC[C@H]1O[C@@H]([C@H](C1O)O)n1ccc2c1ncnc2Cl
• InChI: InChI=1S/C11H12ClN3O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2/t6-,7?,8+,11+/m1/s1
• InChIKey: BFDDOTZWMOKUCD-XUPSQLBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5R)-2-{4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2S,3S,5R)-2-{4-chloropyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 4-Chloro-7-α-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine; 6-Chloro-7-deazapurine-α-D-riboside

Database IDs

• CAS Number: 120401-32-3
• PubChem SID: 162258304
• PubChem CID: 46783438

CALCULATED PROPERTIES

• Acid pKa: 12.45567
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.2375031
• LogD (pH = 7.4): -0.2200015
• Log P: -0.21976979
• Molar Refractivity: 66.2238 cm^3
• Polarizability: 26.221851 Å^3
• Polar Surface Area: 100.63 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (sparingly)
• Apperance: White Solid
• Melting Point: 190-194°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C365181

An adenosine kinase inhibitor.

REFERENCES

• Dunn, D., et al.: Lancet, 353, 1829 (1999)
• El Kouni, M., et al.: Pharmacol. Ther., 99, 283 (1999)
• Tromp, R., et al.: J. Med. Chem., 47, 5441 (1999)
• Anderson, A., et al.: Drug Discovery Today, 10, 121 (1999)