(2S,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-4-yl acetate

• ChemBase ID: 175284
• Molecular Formular: C16H20N2O9
• Molecular Mass: 384.338
• Monoisotopic Mass: 384.11688023
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)Oc1ccc(cc1)[N+](=O)[O-])NC(=O)C)OC(=O)C)O
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@@H]1O)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C16H20N2O9/c1-8(20)17-13-15(25-9(2)21)14(22)12(7-19)27-16(13)26-11-5-3-10(4-6-11)18(23)24/h3-6,12-16,19,22H,7H2,1-2H3,(H,17,20)/t12-,13-,14-,15-,16-/m1/s1
• InChIKey: USHWODHGXQXCCH-OXGONZEZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-4-yl acetate
• IUPAC Traditional name: (2S,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-4-yl acetate
• Synonyms: 4-Nitrophenyl 2-Acetamido-2-deoxy-3-O-acetyl-β-D-glucopyranoside; p-Nitrophenyl 2-Acetamido-2-deoxy-3-O-acetyl-β-D-glucopyranoside

Database IDs

• CAS Number: 23262-57-9
• PubChem SID: 164231194
• PubChem CID: 14775022

CALCULATED PROPERTIES

• Acid pKa: 11.658855
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.5053137
• LogD (pH = 7.4): -0.5053345
• Log P: -0.5053132
• Molar Refractivity: 87.7608 cm^3
• Polarizability: 34.76744 Å^3
• Polar Surface Area: 160.14 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO
• Apperance: Off-White Solid
• Melting Point: 185-187°C