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

• ChemBase ID: 174492
• Molecular Formular: C21H24NNaO11
• Molecular Mass: 489.40513
• Monoisotopic Mass: 489.12470487
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@](O1)(Oc1ccc2c(c1)oc(=O)cc2C)C(=O)[O-])O)NC(=O)C)[C@@H]([C@@H](CO)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)C(=O)[O-])O)O.[Na+]
• InChI: InChI=1S/C21H25NO11.Na/c1-9-5-16(27)31-15-6-11(3-4-12(9)15)32-21(20(29)30)7-13(25)17(22-10(2)24)19(33-21)18(28)14(26)8-23;/h3-6,13-14,17-19,23,25-26,28H,7-8H2,1-2H3,(H,22,24)(H,29,30);/q;+1/p-1/t13-,14+,17+,18+,19+,21+;/m0./s1
• InChIKey: NNNXBDLJYKMDAI-NLSRWXBQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-[(4-methyl-2-oxo-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-[(4-methyl-2-oxochromen-7-yl)oxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: Neu5Ac-α-4MU; 2'-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic Acid, Sodium Salt

Database IDs

• CAS Number: 76204-02-9
• PubChem SID: 164230402
• PubChem CID: 71750675

CALCULATED PROPERTIES

• Acid pKa: 2.814878
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.7484286
• LogD (pH = 7.4): -4.6131625
• Log P: -1.1202775
• Molar Refractivity: 118.651 cm^3
• Polarizability: 42.845554 Å^3
• Polar Surface Area: 194.91 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >156°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M334200

Used as a substrate in a fluorometric assay of neuraminidase.

REFERENCES

• Potier, M., et al.: Anal. Biochem., 94, 287 (1979)
• Myers, R.W., et al.: Anal. Biochem., 101, 166 (1980)