N-(6-{[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4,5-trihydroxy-1-oxohexan-2-yl)acetamide

• ChemBase ID: 131971
• Molecular Formular: C16H28N2O11
• Molecular Mass: 424.40032
• Monoisotopic Mass: 424.16930973
• SMILES: CC(=O)NC1C(C(C(OC1OCC(C(C(C(C=O)NC(=O)C)O)O)O)CO)O)O
• Canonical SMILES: O=CC(C(C(C(COC1OC(CO)C(C(C1NC(=O)C)O)O)O)O)O)NC(=O)C
• InChI: InChI=1S/C16H28N2O11/c1-6(21)17-8(3-19)12(24)13(25)9(23)5-28-16-11(18-7(2)22)15(27)14(26)10(4-20)29-16/h3,8-16,20,23-27H,4-5H2,1-2H3,(H,17,21)(H,18,22)
• InChIKey: INPSEHNBUMPUQB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(6-{[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4,5-trihydroxy-1-oxohexan-2-yl)acetamide
• IUPAC Traditional name: N-(6-{[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4,5-trihydroxy-1-oxohexan-2-yl)acetamide
• Synonyms: β-D-GlcNAc-(1→6)-D-GlcNAc; 2-Acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose

Database IDs

• CAS Number: 35385-05-8
• MDL Number: MFCD00058463
• PubChem SID: 162226248
• PubChem CID: 4349547

CALCULATED PROPERTIES

• Acid pKa: 11.428474
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -5.915267
• LogD (pH = 7.4): -5.915305
• Log P: -5.9152665
• Molar Refractivity: 91.9615 cm^3
• Polarizability: 37.558872 Å^3
• Polar Surface Area: 215.11 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - A3919

Application
Reference compound for the study of 2-amino-6-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose (β-D-GlcN-[1→6]-D-GlcN), the basic structure in E. coli Lipid A.