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

• ChemBase ID: 179111
• Molecular Formular: C22H24F3NO11
• Molecular Mass: 535.4212696
• Monoisotopic Mass: 535.13014525
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@](O1)(Oc1ccc2c(c1)oc(=O)cc2C(F)(F)F)C(=O)OC)O)NC(=O)C)C([C@@H](CO)O)O
• Canonical SMILES: OC[C@H](C([C@@H]1O[C@@](C[C@H]([C@H]1NC(=O)C)O)(Oc1ccc2c(c1)oc(=O)cc2C(F)(F)F)C(=O)OC)O)O
• InChI: InChI=1S/C22H24F3NO11/c1-9(28)26-17-13(29)7-21(20(33)34-2,37-19(17)18(32)14(30)8-27)36-10-3-4-11-12(22(23,24)25)6-16(31)35-15(11)5-10/h3-6,13-14,17-19,27,29-30,32H,7-8H2,1-2H3,(H,26,28)/t13-,14+,17+,18?,19+,21+/m0/s1
• InChIKey: UEBOHHUZMLBUHI-KPPVFQKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]oxy}-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]oxy}-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: N-Acetyl-2-O-[2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-α-neuraminic Acid Methyl Ester; 4-Trifluoromethylumbelliferyl α-D-N-Acetylneuraminate Methyl Ester

Database IDs

• PubChem SID: 164235021
• PubChem CID: 71752769

CALCULATED PROPERTIES

• Molar Refractivity: 113.5155 cm^3
• Polarizability: 44.592545 Å^3
• Polar Surface Area: 181.08 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 12.433187
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.609957
• LogD (pH = 7.4): -0.6099601
• Log P: -0.6099563

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - T792020

An intermediate for the synthesis of a fluorogenic substrate used to measure sialidase activity.

REFERENCES

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