[(3S,4R)-3-(acetyloxy)-5-acetamido-4,6-dihydroxyoxan-2-yl]methyl acetate

• ChemBase ID: 159289
• Molecular Formular: C12H19NO8
• Molecular Mass: 305.28116
• Monoisotopic Mass: 305.11106657
• SMILES: [C@@H]1([C@@H](C(C(OC1COC(=O)C)O)NC(=O)C)O)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1C(COC(=O)C)OC(C([C@H]1O)NC(=O)C)O
• InChI: InChI=1S/C12H19NO8/c1-5(14)13-9-10(17)11(20-7(3)16)8(21-12(9)18)4-19-6(2)15/h8-12,17-18H,4H2,1-3H3,(H,13,14)/t8?,9?,10-,11-,12?/m1/s1
• InChIKey: ATDFUHJLTGDYJL-AWKVMXQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3S,4R)-3-(acetyloxy)-5-acetamido-4,6-dihydroxyoxan-2-yl]methyl acetate
• IUPAC Traditional name: [(3S,4R)-3-(acetyloxy)-5-acetamido-4,6-dihydroxyoxan-2-yl]methyl acetate
• Synonyms: 2-(Acetylamino)-2-deoxy-D-glucopyranose 4,6-Diacetate; (N,4-O,6-O)-Triacetyl-D-Glucosamine; N-Acetyl-D-Glucosamine 4,6-Diacetate

Database IDs

• PubChem SID: 162253424
• PubChem CID: 71312902

CALCULATED PROPERTIES

• Acid pKa: 11.601158
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.338324
• LogD (pH = 7.4): -2.33835
• Log P: -2.3383236
• Molar Refractivity: 65.3277 cm^3
• Polarizability: 27.107702 Å^3
• Polar Surface Area: 131.39 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A178225

A triacetylated analogue of D-Glucosamine (G514950).