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

• ChemBase ID: 173225
• Molecular Formular: C15H27NO11
• Molecular Mass: 397.37498
• Monoisotopic Mass: 397.15841069
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)O[C@H]1[C@H]([C@@H](O[C@H]([C@H]1O)OC)CO)O)NC(=O)C)O)O
• Canonical SMILES: CO[C@@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O[C@@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1NC(=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)/t6-,7-,8-,9-,10+,11-,12-,13+,14+,15-/m1/s1
• InChIKey: USJPBCYUZSGJII-MUHRKBNZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: Μethyl 3-O-[2-(Αcetylamino)-2-deoxy-β-D-glucopyranosyl]-β-D-galactopyranoside; 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
• PubChem SID: 164229135
• PubChem CID: 13940669

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

DETAILS

Toronto Research Chemicals - M275325

Used in the preparation of disaccharide mucin fragment and for the inhibition studies of rat lung lectin. It is a substrate for β-6-GlcNAc-transferase.

REFERENCES

• Khushi L., et al.: Eur J. Biochem., 157, 463 (1986)