N-[(2S,3R,4R,5S,6R)-5-fluoro-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 158922
• Molecular Formular: C8H14FNO5
• Molecular Mass: 223.1988632
• Monoisotopic Mass: 223.08560077
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)O)NC(=O)C)O)F
• Canonical SMILES: OC[C@@H]1O[C@H](O)[C@H]([C@H]([C@@H]1F)O)NC(=O)C
• InChI: InChI=1S/C8H14FNO5/c1-3(12)10-6-7(13)5(9)4(2-11)15-8(6)14/h4-8,11,13-14H,2H2,1H3,(H,10,12)/t4-,5-,6-,7+,8+/m1/s1
• InChIKey: QAPRNMNSFDDVPY-YQXRAVKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-5-fluoro-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-5-fluoro-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: 2-(Acetylamino)-2,4-dideoxy-4-fluoro-α-D-glucopyranose; 2-Acetamido-2,4-dideoxy-4-fluoro-α-D-glucopyranose

Database IDs

• CAS Number: 129728-87-6
• PubChem SID: 162253057
• PubChem CID: 14560951

CALCULATED PROPERTIES

• Acid pKa: 11.463041
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.3294833
• LogD (pH = 7.4): -2.3295183
• Log P: -2.3294826
• Molar Refractivity: 45.3326 cm^3
• Polarizability: 18.56879 Å^3
• Polar Surface Area: 99.02 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol; Water
• Apperance: Off-White to Light Brown Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A158390

Inhibitor of hepatic glycosaminoglycan biosynthesis

REFERENCES

• Berkin, A., et al.: Carbohyd. Res., 326, 250 (2000)