(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 164863
• Molecular Formular: C10H11ClFN5O3
• Molecular Mass: 303.6774432
• Monoisotopic Mass: 303.05344514
• SMILES: n1c(nc2c(c1N)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)F)Cl
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)F)n1cnc2c1nc(Cl)nc2N
• InChI: InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4?,6+,9-/m1/s1
• InChIKey: WDDPHFBMKLOVOX-MRJHDXJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: 2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine; Clolar; Clofarabine

Database IDs

• CAS Number: 123318-82-1
• PubChem SID: 162258997
• PubChem CID: 16760208

CALCULATED PROPERTIES

• Acid pKa: 12.70945
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.29132771
• LogD (pH = 7.4): -0.29132396
• Log P: -0.29132175
• Molar Refractivity: 67.0021 cm^3
• Polarizability: 25.781265 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 228-231°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C586890

Second generation purine nucleoside analog; antimetabolite that inhibits DNA synthesis and resists deamination by adenosine deaminase. Antineoplastic.

REFERENCES

• Gandhi, V., et al.: Clin. Cancer Res., 9, 6335 (2003)
• Kantarjian, H., et al.: Blood, 102, 2379 (2003)
• Faderl, S., et al.: Cancer, 103, 1985 (2003)