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

• ChemBase ID: 175307
• Molecular Formular: C30H44N4O18
• Molecular Mass: 748.68636
• Monoisotopic Mass: 748.26506059
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)O[C@H]1[C@H]([C@@H](O[C@@H]([C@H]1NC(=O)C)Oc1ccc(cc1)[N+](=O)[O-])CO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1NC(=O)C)O)O)CO)O)NC(=O)C)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](O[C@H]2[C@@H](O)[C@H](CO[C@@H]3O[C@@H](CO)[C@H]([C@@H]([C@@H]3NC(=O)C)O)O)O[C@@H]([C@H]2NC(=O)C)Oc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C30H44N4O18/c1-11(37)31-19-25(43)22(40)16(8-35)49-28(19)47-10-18-24(42)27(52-29-20(32-12(2)38)26(44)23(41)17(9-36)50-29)21(33-13(3)39)30(51-18)48-15-6-4-14(5-7-15)34(45)46/h4-7,16-30,35-36,40-44H,8-10H2,1-3H3,(H,31,37)(H,32,38)(H,33,39)/t16-,17-,18-,19-,20-,21-,22-,23-,24+,25-,26-,27-,28-,29+,30+/m1/s1
• InChIKey: XLNAXKMQHIEVPS-LUBQLKINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5S,6R)-2-{[(2R,3R,4R,5R,6R)-3-acetamido-6-({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5-hydroxy-2-(4-nitrophenoxy)oxan-4-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5S,6R)-2-{[(2R,3R,4R,5R,6R)-3-acetamido-6-({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5-hydroxy-2-(4-nitrophenoxy)oxan-4-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: 4-Nitrophenyl O-2-(Acetylamino)-2-deoxy-β-D-glucopyranosyl-(1-3)-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1-6)]-2-(acetylamino)-2-deoxy-α-D-galactopyranoside; GlcNAcβ(1-3){GlcNAcβ(1-6)}GalNAcα(1-O)PNP; 4-Nitrophenyl 2-Acetamido-3,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-α-D-galactopyranoside

Database IDs

• CAS Number: 1144040-11-8
• PubChem SID: 164231217
• PubChem CID: 71751079

CALCULATED PROPERTIES

• Acid pKa: 11.405398
• H Acceptors: 18
• H Donor: 10
• LogD (pH = 5.5): -5.064181
• LogD (pH = 7.4): -5.0642185
• Log P: -5.0641804
• Molar Refractivity: 165.6385 cm^3
• Polarizability: 67.033745 Å^3
• Polar Surface Area: 330.11 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N502160

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)