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

• ChemBase ID: 175282
• 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)OC[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)Oc1ccc(cc1)[N+](=O)[O-])NC(=O)C)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-NMEFWLLUSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 235752-73-5
• PubChem SID: 164231192
• PubChem CID: 71307207

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

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Crystalline Solid
• Melting Point: 286°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N499100

Acetylgalactosaminidase sequence substrate Clostridium Bifidobacterium.

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)