N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(propan-2-yloxy)oxan-3-yl]acetamide

• ChemBase ID: 171855
• Molecular Formular: C11H21NO6
• Molecular Mass: 263.28754
• Monoisotopic Mass: 263.1368874
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)OC(C)C)NC(=O)C)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](OC(C)C)[C@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C11H21NO6/c1-5(2)17-11-8(12-6(3)14)10(16)9(15)7(4-13)18-11/h5,7-11,13,15-16H,4H2,1-3H3,(H,12,14)/t7-,8-,9-,10-,11-/m1/s1
• InChIKey: CSHJQINNMOQHDM-ISUQUUIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(propan-2-yloxy)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-isopropoxyoxan-3-yl]acetamide
• Synonyms: 1-Methylethyl 2-(Acetylamino)-2-deoxy-β-D-glucopyranoside; Isopropyl N-Acetyl-β-D-glucosamine(α/β-Mixture)

Database IDs

• CAS Number: 78341-33-0
• PubChem SID: 164227765
• PubChem CID: 7573802

CALCULATED PROPERTIES

• Acid pKa: 12.382926
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.8040652
• LogD (pH = 7.4): -1.804069
• Log P: -1.8040649
• Molar Refractivity: 60.9433 cm^3
• Polarizability: 24.894478 Å^3
• Polar Surface Area: 108.25 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I823900

Used in the chemical synthesis of N-acetylglucosamine derivatives as glycosyl acceptors by the Mesorhizobium loti chitin oligosaccharide synthase NodC.

REFERENCES

• Kamst, E., et al.: J. Bacteriol., 177, 6282 (1995)
• Mergaert, P., et al.: J. Biol. Chem., 270, 29217 (1995)
• Kamst, E., et al.: Biochemistry, 38, 4045 (1995)