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

• ChemBase ID: 160775
• Molecular Formular: C10H11FN4O5
• Molecular Mass: 286.2165432
• Monoisotopic Mass: 286.07134769
• SMILES: C1(O)[C@@H](CO)O[C@H]([C@H]1O)n1c2c(c(=O)[nH]c(n2)F)nc1
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1nc(F)[nH]c2=O
• InChI: InChI=1S/C10H11FN4O5/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: RHLSRGWIGPHHJW-VCXQEIDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-fluoro-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 9-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-fluoro-1H-purin-6-one
• Synonyms: 9-β-D-Arabinofuranosyl-2-fluoro-1,9-dihydro-6H-purin-6-one; 9-β-D-Arabinofuranosyl-2-fluorohypoxanthine

Database IDs

• CAS Number: 83480-48-2
• PubChem SID: 162254910
• PubChem CID: 46780470

CALCULATED PROPERTIES

• Acid pKa: 5.957464
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.8237194
• LogD (pH = 7.4): -2.5496254
• Log P: -1.7107018
• Molar Refractivity: 61.9003 cm^3
• Polarizability: 23.055119 Å^3
• Polar Surface Area: 129.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A763800

A major metabolite 9-β-D-arabinofuranosyl-2-fluoroadenine, an antitumor and antiviral agent.

REFERENCES

• Struck, R. F., et al.: Biochem. Pharmacol., 31, 1975 (1982)
• Avramis, V. I., et al.: Cancer Drug Delivery, 1, 1 (1982)