(4R,5S)-5-fluoro-6-(hydroxymethyl)oxane-2,3,4-triol

• ChemBase ID: 165934
• Molecular Formular: C6H11FO5
• Molecular Mass: 182.1469432
• Monoisotopic Mass: 182.05905167
• SMILES: [C@@H]1([C@@H](C(C(OC1CO)O)O)O)F
• Canonical SMILES: OCC1OC(O)C([C@H]([C@@H]1F)O)O
• InChI: InChI=1S/C6H11FO5/c7-3-2(1-8)12-6(11)5(10)4(3)9/h2-6,8-11H,1H2/t2?,3-,4+,5?,6?/m1/s1
• InChIKey: FIHYONSINSKFAH-DLABPRKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-5-fluoro-6-(hydroxymethyl)oxane-2,3,4-triol
• IUPAC Traditional name: (4R,5S)-5-fluoro-6-(hydroxymethyl)oxane-2,3,4-triol
• Synonyms: 4-Deoxy-4-fluoro-D-mannose; 4-Deoxy-4-fluoro-D-glucose

Database IDs

• CAS Number: 29218-07-3; 87764-47-4
• PubChem SID: 162260067
• PubChem CID: 71315463

CALCULATED PROPERTIES

• Acid pKa: 11.295285
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.041448
• LogD (pH = 7.4): -2.0415027
• Log P: -2.0414474
• Molar Refractivity: 34.2313 cm^3
• Polarizability: 14.3448515 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Crystalline Solid
• Melting Point: 189-190°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D235300

Shown to be metabolized in yeast. Also shown to interfere with the glycosylation of viral G-protein in vesicular-stomatitis-virus-infected BHK cells.

REFERENCES

• Biochem. J., 209 (3)
• 677-685 (3)
• J. Biol. Chem., 259, 1027-1030 (1984)