1-[(2R,3S,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 168966
• Molecular Formular: C9H11FN2O5
• Molecular Mass: 246.1924432
• Monoisotopic Mass: 246.06519968
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1ccc(=O)[nH]c1=O)CO)O)F
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)F)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H11FN2O5/c10-6-7(15)4(3-13)17-8(6)12-2-1-5(14)11-9(12)16/h1-2,4,6-8,13,15H,3H2,(H,11,14,16)/t4-,6+,7?,8-/m1/s1
• InChIKey: UIYWFOZZIZEEKJ-JDNPWWSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3S,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3S,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 2'-Deoxy-2'-fluorouridine; Fioluridine; 2'-Fluoro-2'-deoxyuridine

Database IDs

• CAS Number: 784-71-4
• PubChem SID: 162263098
• PubChem CID: 44629873

CALCULATED PROPERTIES

• Acid pKa: 9.4506035
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.5241984
• LogD (pH = 7.4): -1.5279545
• Log P: -1.5241504
• Molar Refractivity: 50.8735 cm^3
• Polarizability: 20.073658 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F590275

A component incorporated into therapeutic oligonucleotides to combat prostate and breast cancer.

REFERENCES

• Johar, M. et al.; J. Med. Chem. 50, 3696 (2007)
• Sioud, M. et al.; Eur. J. Immunol. 36, 1222 (2006)