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

• ChemBase ID: 175295
• Molecular Formular: C20H28N2O13
• Molecular Mass: 504.44192
• Monoisotopic Mass: 504.15913897
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)Oc1ccc(cc1)[N+](=O)[O-])NC(=O)C)O[C@H]1O[C@H]([C@@H]([C@@H]([C@@H]1O)O)O)CO)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@H]1O)O[C@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O)NC(=O)C
• InChI: InChI=1S/C20H28N2O13/c1-8(25)21-13-18(35-20-17(29)16(28)14(26)11(6-23)34-20)15(27)12(7-24)33-19(13)32-10-4-2-9(3-5-10)22(30)31/h2-5,11-20,23-24,26-29H,6-7H2,1H3,(H,21,25)/t11-,12-,13-,14+,15+,16+,17-,18-,19+,20-/m1/s1
• InChIKey: INMOOBMAIAWVBW-MBOHZYJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: 4-Nitrophenyl 2-(Acetylamino)-2-deoxy-3-O-α-D-galactopyranosyl-α-D-galactopyranoside; Gal1-α-3GalNAc-α-PNP; 4-Nitrophenyl 2-(Acetamido)-2-deoxy-3-O-α-D-galactopyranosyl-α-D-galactopyranoside

Database IDs

• CAS Number: 1144040-14-1
• PubChem SID: 164231205
• PubChem CID: 71751076

CALCULATED PROPERTIES

• Acid pKa: 11.623808
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -2.7172747
• LogD (pH = 7.4): -2.717298
• Log P: -2.7172742
• Molar Refractivity: 111.0226 cm^3
• Polarizability: 44.714172 Å^3
• Polar Surface Area: 233.22 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N501005

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)