4-amino-1-[(2R,4S,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

• ChemBase ID: 165924
• Molecular Formular: C9H12FN3O4
• Molecular Mass: 245.2076832
• Monoisotopic Mass: 245.0811841
• SMILES: [C@H]1(C([C@@H](O[C@@H]1CO)n1c(=O)nc(cc1)N)F)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)F)n1ccc(nc1=O)N
• InChI: InChI=1S/C9H12FN3O4/c10-6-7(15)4(3-14)17-8(6)13-2-1-5(11)12-9(13)16/h1-2,4,6-8,14-15H,3H2,(H2,11,12,16)/t4-,6?,7+,8-/m1/s1
• InChIKey: NVZFZMCNALTPBY-PDVZPSIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4S,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,4S,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• Synonyms: 2'-Deoxy-2'-fluorocytidine; 2'-Fluoro-2'-deoxy-β-D-ribofuranosylcytosine; 2'-Fluoro-2'-deoxycytidine; NSC 529432; 2'-Deoxy-2'-fluoro Cytidine

Database IDs

• CAS Number: 10212-20-1
• PubChem SID: 162260057
• PubChem CID: 71168154

CALCULATED PROPERTIES

• Acid pKa: 12.71969
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.9064263
• LogD (pH = 7.4): -1.9064276
• Log P: -1.9064255
• Molar Refractivity: 52.8527 cm^3
• Polarizability: 20.647964 Å^3
• Polar Surface Area: 108.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D232945

2'-Deoxy-2'-fluorocytidine is a potent inhibitor of the subgenomic hepatitis C virus replicon in Huh-7 cells. 2'-Deoxy-2'-fluorocytidine has been shown to inhibit Borna Disease virus replication and spread.

REFERENCES

• Stuyver, L.J. et al.: Antimicrob. Agents Chemother., 48, 651 (2004)
• Bajramovic, J.J. et al.: Antiomicrob. Agents Chemother., 48, 1422 (2004)