(2S)-2-{[(3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

• ChemBase ID: 159290
• Molecular Formular: C19H32N2O13
• Molecular Mass: 496.46298
• Monoisotopic Mass: 496.19043909
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1CO)O)NC(=O)C)O[C@H](C)C(=O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1NC(=O)C)O)O)CO
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1NC(=O)C)O)O)O[C@@H](C(=O)O)C)NC(=O)C
• InChI: InChI=1S/C19H32N2O13/c1-6(17(28)29)31-16-12(21-8(3)25)18(30)32-10(5-23)15(16)34-19-11(20-7(2)24)14(27)13(26)9(4-22)33-19/h6,9-16,18-19,22-23,26-27,30H,4-5H2,1-3H3,(H,20,24)(H,21,25)(H,28,29)/t6-,9+,10+,11+,12+,13+,14+,15+,16+,18?,19-/m0/s1
• InChIKey: WQKIVDUWFNRJHE-NMSAXZLKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
• IUPAC Traditional name: (2S)-2-{[(3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
• Synonyms: N-Acetyl-4-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-muramic Acid; N-Acetyl-D-glucosaminyl-(1-4)-N-acetylmuramic Acid

Database IDs

• CAS Number: 41137-10-4
• PubChem SID: 162253425
• PubChem CID: 71312903

CALCULATED PROPERTIES

• Acid pKa: 3.4384646
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -6.64032
• LogD (pH = 7.4): -7.9824705
• Log P: -4.589571
• Molar Refractivity: 105.869 cm^3
• Polarizability: 43.66624 Å^3
• Polar Surface Area: 233.57 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Light Tan Solid
• Melting Point: 169-171°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A178230

The compound is effective in activating human monocytes with subsequent destruction of tumor cells.

REFERENCES

• Sharon, N., et al.: J. Biol. Chem., 241, 223 (1966)
• Valinger, Z., et al.: Biochim. Biophys. Acta, 701, 63 (1982)