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

• ChemBase ID: 158914
• Molecular Formular: C9H17NO6
• Molecular Mass: 235.23438
• Monoisotopic Mass: 235.10558727
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1CO)O)NC(=O)C)OC)O
• Canonical SMILES: CO[C@@H]1[C@H](NC(=O)C)C(O)O[C@H]([C@H]1O)CO
• InChI: InChI=1S/C9H17NO6/c1-4(12)10-6-8(15-2)7(13)5(3-11)16-9(6)14/h5-9,11,13-14H,3H2,1-2H3,(H,10,12)/t5-,6-,7-,8-,9?/m1/s1
• InChIKey: SXGSBXSSPNINRW-VARJHODCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-3-yl]acetamide
• Synonyms: 3-O-Methyl-N-acetyl-D-glucosamine; N-Acetyl-3-O-methyl-D-glucosamine; 2-Acetamido-2-deoxy-3-O-methyl-D-glucopyranose

Database IDs

• CAS Number: 94825-74-8
• PubChem SID: 162253049
• PubChem CID: 53230018

CALCULATED PROPERTIES

• Acid pKa: 11.628489
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.5774484
• LogD (pH = 7.4): -2.577473
• Log P: -2.577448
• Molar Refractivity: 51.7759 cm^3
• Polarizability: 21.269253 Å^3
• Polar Surface Area: 108.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 189-191°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A158375

Inhibitor of N-Acetylglucosamine kinase in the glucose metabolism pathway

REFERENCES

• Gerwig, G., et al.: J. Biol. Chem., 264, 1027 (1989)
• Zeitler, R., et al.: Eur. J. Biochem., 204, 1165 (1989)