sodium (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]oxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

• ChemBase ID: 179112
• Molecular Formular: C21H21F3NNaO11
• Molecular Mass: 543.3765196
• Monoisotopic Mass: 543.09643944
• SMILES: O(c1ccc2c(c1)oc(=O)cc2C(F)(F)F)[C@@]1(C[C@H]([C@H]([C@@H](O1)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)[O-].[Na+]
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](C[C@H]([C@H]1NC(=O)C)O)(Oc1ccc2c(c1)oc(=O)cc2C(F)(F)F)C(=O)[O-])O)O.[Na+]
• InChI: InChI=1S/C21H22F3NO11.Na/c1-8(27)25-16-12(28)6-20(19(32)33,36-18(16)17(31)13(29)7-26)35-9-2-3-10-11(21(22,23)24)5-15(30)34-14(10)4-9;/h2-5,12-13,16-18,26,28-29,31H,6-7H2,1H3,(H,25,27)(H,32,33);/q;+1/p-1/t12-,13+,16+,17+,18+,20+;/m0./s1
• InChIKey: BTQBNKHNJNDOSZ-KEIUTPEISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]oxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]oxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: CF3MU-Neu5Ac Sodium Salt; 4-Trifluoromethylumbelliferyl-α-D-N-acetylneuraminic Acid Sodium Salt

Database IDs

• PubChem SID: 164235022
• PubChem CID: 71752770

CALCULATED PROPERTIES

• Acid pKa: 3.2157838
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.018399
• LogD (pH = 7.4): -4.1984973
• Log P: -0.7558504
• Molar Refractivity: 119.5835 cm^3
• Polarizability: 42.457283 Å^3
• Polar Surface Area: 194.91 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Light Yellow Solid
• Melting Point: 161-163°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T792025

Used as a substrate in a fluorometric detection of poorly expressed natural and recombinant sialidases.

REFERENCES

• Engstler, M., et al.: Anal. Biochem., 250, 176 (1997)