(2S,3R,4S,5S,6R)-5-acetamido-3-fluoro-4-hydroxy-6-[(1R,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 3824
• Molecular Formular: C11H18FNO8
• Molecular Mass: 311.2609232
• Monoisotopic Mass: 311.10164476
• SMILES: CC(=O)N[C@H]1[C@H](O)[C@@H](F)[C@@H](O[C@H]1[C@H](O)[C@@H](O)CO)C(=O)O
• Canonical SMILES: OC[C@@H]([C@H]([C@@H]1O[C@@H](C(=O)O)[C@@H]([C@H]([C@@H]1NC(=O)C)O)F)O)O
• InChI: InChI=1S/C11H18FNO8/c1-3(15)13-6-8(18)5(12)9(11(19)20)21-10(6)7(17)4(16)2-14/h4-10,14,16-18H,2H2,1H3,(H,13,15)(H,19,20)/t4-,5+,6-,7+,8+,9+,10+/m0/s1
• InChIKey: ZQJAHJWWLQMSQT-GEFQIMLOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-5-acetamido-3-fluoro-4-hydroxy-6-[(1R,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: @3-fluorosialic acid
• Synonyms: 3-Fluorosialic Acid

Database IDs

• PubChem SID: 46504998; 160967261
• PubChem CID: 46936922

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6948926
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.3397603
• LogD (pH = 7.4): -6.843531
• Log P: -3.535989
• Molar Refractivity: 62.0576 cm^3
• Polarizability: 25.434616 Å^3
• Polar Surface Area: 156.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.81
• LOG S: -0.57
• Solubility (Water): 8.33e+01 g/l

DETAILS

DrugBank - DB04211

Drug information: experimental