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

• ChemBase ID: 174493
• Molecular Formular: C30H35NO15
• Molecular Mass: 649.5966
• Monoisotopic Mass: 649.20066943
• SMILES: O(c1ccc2c(c1)oc(=O)cc2C)[C@@]1(C[C@H]([C@H]([C@@H](O1)[C@@H]([C@H](COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@]1(Oc2ccc3c(c2)oc(=O)cc3C)C[C@@H](OC(=O)C)[C@H]([C@@H](O1)[C@@H]([C@@H](OC(=O)C)COC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C30H35NO15/c1-14-10-25(37)44-22-11-20(8-9-21(14)22)45-30(29(38)39-7)12-23(41-17(4)34)26(31-15(2)32)28(46-30)27(43-19(6)36)24(42-18(5)35)13-40-16(3)33/h8-11,23-24,26-28H,12-13H2,1-7H3,(H,31,32)/t23-,24-,26+,27+,28+,30+/m0/s1
• InChIKey: ZCGDEQZBAJRSAJ-UIYRTWACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-[(4-methyl-2-oxochromen-7-yl)oxy]-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• Synonyms: N-Acetyl-2-O-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-4,7,8,9-tetraacetate-α-neuraminic Acid Methyl Ester; (4-Methylumbelliferyl)-N-acetyl-4,7,8,9-tetra-O-acetyl-α-D-neuraminic Acid, Methyl Ester

Database IDs

• CAS Number: 59361-08-9
• PubChem SID: 164230403
• PubChem CID: 14375505

CALCULATED PROPERTIES

• Acid pKa: 12.641127
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): 0.7901176
• LogD (pH = 7.4): 0.790116
• Log P: 0.7901182
• Molar Refractivity: 149.189 cm^3
• Polarizability: 60.44236 Å^3
• Polar Surface Area: 205.36 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Yellow Amorphous Solid
• Melting Point: 93-95°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M334220

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)