N-[(2R,3R,4R,5R,6R)-6-({[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4,5-dihydroxy-2-(4-nitrophenoxy)oxan-3-yl]acetamide

• ChemBase ID: 175283
• Molecular Formular: C22H31N3O13
• Molecular Mass: 545.49384
• Monoisotopic Mass: 545.18568807
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO[C@H]1O[C@H]([C@H]([C@@H]([C@@H]1NC(=O)C)O)O)CO)Oc1ccc(cc1)[N+](=O)[O-])NC(=O)C)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](OC[C@@H]2O[C@H](Oc3ccc(cc3)[N+](=O)[O-])[C@H]([C@H]([C@H]2O)O)NC(=O)C)[C@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C22H31N3O13/c1-9(27)23-15-19(31)17(29)13(7-26)37-21(15)35-8-14-18(30)20(32)16(24-10(2)28)22(38-14)36-12-5-3-11(4-6-12)25(33)34/h3-6,13-22,26,29-32H,7-8H2,1-2H3,(H,23,27)(H,24,28)/t13-,14-,15-,16-,17-,18+,19-,20-,21+,22+/m1/s1
• InChIKey: VQYVGLNPBRTHNR-VHMNXSECSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5R,6R)-6-({[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4,5-dihydroxy-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5R,6R)-6-({[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4,5-dihydroxy-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• Synonyms: 4-Nitrophenyl 2-(Acetylamino)-6-O-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl]-2-deoxy-α-D-galactopyranoside; GlcNAc1-α-6GalNAc-α-PNP; 4-Nitrophenyl 2-Acetamido-2-deoxy-(6-O-2-acetamido-2-deoxy-α-D-gluco-pyranosyl)-α-D-galactopyranoside

Database IDs

• PubChem SID: 164231193
• PubChem CID: 71751074

CALCULATED PROPERTIES

• Acid pKa: 11.510702
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -3.00531
• LogD (pH = 7.4): -3.0053396
• Log P: -3.0053093
• Molar Refractivity: 122.1239 cm^3
• Polarizability: 48.971577 Å^3
• Polar Surface Area: 242.09 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N499105

An analogue of p-nitrophenyl T-antigen as potential substrate for elucidation of the substrate specificity of endo-α-N-acetylgalactosaminidase.

REFERENCES

• Ashida, H., et al.: J. Biol. Chem., 276, 28226 (2001)
• Katayama, T., et al.: J. Bacteriol., 186, 4885 (2001)
• Anderson, K., et al.: J. Biol. Chem., 280, 7720 (2001)