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

• ChemBase ID: 175311
• Molecular Formular: C20H24N2O11
• Molecular Mass: 468.41136
• Monoisotopic Mass: 468.1380096
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)Oc1ccc(cc1)[N+](=O)[O-])NC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@@H](Oc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C20H24N2O11/c1-10(23)21-17-19(31-13(4)26)18(30-12(3)25)16(9-29-11(2)24)33-20(17)32-15-7-5-14(6-8-15)22(27)28/h5-8,16-20H,9H2,1-4H3,(H,21,23)/t16-,17-,18-,19-,20-/m1/s1
• InChIKey: IMQGAARHTLJIRK-LASHMREHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-5-acetamido-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-5-acetamido-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate
• Synonyms: p-Nitrophenyl 2-Acetamido-2-deoxy-β-D-glucopyranoside, 3,4,6-Triacetate; p-Nitrophenyl 2-Acetamido-2-deoxy-β-D-glucopyranoside Triacetate; p-Nitrophenyl 2-Acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranoside

Database IDs

• CAS Number: 13089-27-5
• PubChem SID: 164231221
• PubChem CID: 10367344

CALCULATED PROPERTIES

• Acid pKa: 11.737751
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 0.37693718
• LogD (pH = 7.4): 0.37691996
• Log P: 0.37693763
• Molar Refractivity: 106.0638 cm^3
• Polarizability: 42.481533 Å^3
• Polar Surface Area: 172.28 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Light Brown Solid

DETAILS

Toronto Research Chemicals - N502200

Useful substrate for the rapid colorimetric assay of N-Acetyl-beta-glucosaminidase in human urine.