methyl (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

• ChemBase ID: 159381
• Molecular Formular: C12H21NO9
• Molecular Mass: 323.29644
• Monoisotopic Mass: 323.12163126
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@@](O1)(O)C(=O)OC)O)NC(=O)C)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](O)(C[C@H]([C@H]1NC(=O)C)O)C(=O)OC)O)O
• InChI: InChI=1S/C12H21NO9/c1-5(15)13-8-6(16)3-12(20,11(19)21-2)22-10(8)9(18)7(17)4-14/h6-10,14,16-18,20H,3-4H2,1-2H3,(H,13,15)/t6-,7+,8+,9+,10+,12-/m0/s1
• InChIKey: BKZQMWNJESHHSA-AGNBLMTLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: 5-(Acetylamino)-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic AcidMethyl Ester; N-Acetylneuraminic Acid Methyl Ester

Database IDs

• CAS Number: 22900-11-4
• PubChem SID: 162253516
• PubChem CID: 7173831

CALCULATED PROPERTIES

• Acid pKa: 9.561499
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.4180818
• LogD (pH = 7.4): -3.4210243
• Log P: -3.4180434
• Molar Refractivity: 68.5505 cm^3
• Polarizability: 28.28038 Å^3
• Polar Surface Area: 165.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 193.5-194.5°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A187250

Derivative of Neuraminic Acid

REFERENCES

• Oetke, C., et al.: J. Biol. Chem., 277, 6688 (2002)