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

• ChemBase ID: 153394
• Molecular Formular: C15H27NO11
• Molecular Mass: 397.37498
• Monoisotopic Mass: 397.15841069
• SMILES: CC(=O)NC1C(C(C(OC1OC1C(C(OC(C1O)OC)CO)O)CO)O)O
• Canonical SMILES: COC1OC(CO)C(C(C1O)OC1OC(CO)C(C(C1NC(=O)C)O)O)O
• InChI: InChI=1S/C15H27NO11/c1-5(19)16-8-11(22)9(20)6(3-17)25-14(8)27-13-10(21)7(4-18)26-15(24-2)12(13)23/h6-15,17-18,20-23H,3-4H2,1-2H3,(H,16,19)
• InChIKey: USJPBCYUZSGJII-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-{[3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)acetamide
• IUPAC Traditional name: N-(2-{[3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)acetamide
• Synonyms: β-D-GlcNAc-(1→3)-β-D-Gal-1→OMe; Methyl 3-O-(N-acetyl-β-D-glucosaminyl)-β-D-galactopyranoside

Database IDs

• CAS Number: 93253-17-9
• MDL Number: MFCD00070380
• PubChem SID: 24896569; 162247533
• PubChem CID: 4124

CALCULATED PROPERTIES

• Acid pKa: 11.913256
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -4.348284
• LogD (pH = 7.4): -4.348296
• Log P: -4.348284
• Molar Refractivity: 84.1892 cm^3
• Polarizability: 35.078526 Å^3
• Polar Surface Area: 187.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Empirical Formula (Hill Notation): C16H27NO11

DETAILS

Sigma Aldrich - M0775

Application
Used for the inhibition studies of rat lung lectin,1 Streptococcus pneumoniae, and H. influenzae.2
Substrates
Substrate for β-6-GlcNAc-transferase.3