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

• ChemBase ID: 168963
• Molecular Formular: C9H12FN3O5
• Molecular Mass: 261.2070832
• Monoisotopic Mass: 261.07609872
• SMILES: n1([C@H]2C([C@H]([C@H](O2)CO)O)O)cc(c(nc1=O)N)F
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cc(F)c(nc1=O)N
• InChI: InChI=1S/C9H12FN3O5/c10-3-1-13(9(17)12-7(3)11)8-6(16)5(15)4(2-14)18-8/h1,4-6,8,14-16H,2H2,(H2,11,12,17)/t4-,5+,6?,8-/m1/s1
• InChIKey: STRZQWQNZQMHQR-CAXIXURWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one
• Synonyms: 5F-C; 5-Fluoro Cytidine

Database IDs

• CAS Number: 2341-22-2
• PubChem SID: 162263095
• PubChem CID: 57416888

CALCULATED PROPERTIES

• Acid pKa: 12.553133
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.5980744
• LogD (pH = 7.4): -2.5980775
• Log P: -2.5980744
• Molar Refractivity: 54.7477 cm^3
• Polarizability: 21.37676 Å^3
• Polar Surface Area: 128.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 183-185°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F588875

5-Fluoropyrimidine nucleotides as probes of RNA structure using 19F-NMR spectroscopy.

REFERENCES

• Metzler, W., et al.: J. Magn. Reson., 76, 534 (1988)
• de Dios, A., et al.: Science, 260, 1491 (1988)
• Kulinski, T., et al.: J. Biol. Chem., 278, 38892 (1988)