(2R,4R,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 164621
• Molecular Formular: C10H11ClN4O4
• Molecular Mass: 286.67174
• Monoisotopic Mass: 286.04688253
• SMILES: n1cnc2c(c1Cl)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1ncnc2Cl
• InChI: InChI=1S/C10H11ClN4O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2/t4-,6+,7?,10-/m1/s1
• InChIKey: XHRJGHCQQPETRH-PKJMTWSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-(6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 6-Chloro-6-deaminoadenosine; 6-Chloro-9-β-D-ribofuranosyl-9H-purine; 6-Chloro-9-β-D-ribofuranosylpurine; 6-Chloronebularine; 6-Chloropurine 9-β-D-ribofuranoside; 6-Chloropurine riboside; 6-Chloropurine-D-riboside; 6-Chloropurinosine; 9-(β-D-Ribofuranosyl)-6-chloropurine; NSC 4910; 6-Chloropurine-9-β-D-ribofuranoside

Database IDs

• CAS Number: 5399-87-1
• PubChem SID: 162258756
• PubChem CID: 46781002

CALCULATED PROPERTIES

• Acid pKa: 12.454003
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.032419
• LogD (pH = 7.4): -1.0322793
• Log P: -1.0322737
• Molar Refractivity: 64.0478 cm^3
• Polarizability: 25.42824 Å^3
• Polar Surface Area: 113.52 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White to Off-White Solid
• Melting Point: 161-162°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C379900

A substrate for adenosine deaminase.

REFERENCES

• Mol. Pharmacol., 2, 574 (1966)