(2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-4-hydroxy-2-methoxyoxane-2-carboxylic acid

• ChemBase ID: 159367
• Molecular Formular: C14H23NO10
• Molecular Mass: 365.33312
• Monoisotopic Mass: 365.13219594
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@](O1)(C(=O)O)OC)O)NC(=O)C)[C@@H]([C@@H](COC(=O)C)O)O
• Canonical SMILES: CO[C@]1(C[C@@H](O)[C@H]([C@@H](O1)[C@@H]([C@@H](COC(=O)C)O)O)NC(=O)C)C(=O)O
• InChI: InChI=1S/C14H23NO10/c1-6(16)15-10-8(18)4-14(23-3,13(21)22)25-12(10)11(20)9(19)5-24-7(2)17/h8-12,18-20H,4-5H2,1-3H3,(H,15,16)(H,21,22)/t8-,9+,10+,11+,12+,14-/m0/s1
• InChIKey: NIEBVOWRRSQMQG-DZXXBYIOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-4-hydroxy-2-methoxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-4-hydroxy-2-methoxyoxane-2-carboxylic acid
• Synonyms: Methyl 5-(Acetylamino)-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonic Acid 9-Acetate; N-Acetyl-2-O-methyl-β-neuraminic Acid 9-Acetate

Database IDs

• CAS Number: 55717-57-2
• PubChem SID: 162253502
• PubChem CID: 71312954

CALCULATED PROPERTIES

• Acid pKa: 2.9023826
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -5.0305266
• LogD (pH = 7.4): -5.9648023
• Log P: -2.4796855
• Molar Refractivity: 77.6841 cm^3
• Polarizability: 31.97169 Å^3
• Polar Surface Area: 171.85 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A186705

N-Acetylneuraminic acid derivatives were required for the high affinity interaction of sialoglycoconjugates with the sialic acid-specific lectin from the slug Limax flavus.

REFERENCES

• Kiefel, M., et al.: J. Med. Chem., 39, 1314 (1996)
• Tihova, M., et al.: J. Mol. Biol., 314, 985 (1996)
• Ciarlet, M., et al.: J. Virol., 76, 1109 (1996)
• Wen, X., et al.: Biochemistry, 44, 6729 (1996)