N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 174507
• Molecular Formular: C26H34N2O13
• Molecular Mass: 582.55376
• Monoisotopic Mass: 582.20608916
• SMILES: O1[C@@H](O[C@@H]2[C@@H](O[C@@H](Oc3cc4c(cc3)c(cc(=O)o4)C)[C@H]([C@H]2O)NC(=O)C)CO)[C@H]([C@H]([C@@H]([C@@H]1CO)O)O)NC(=O)C
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1NC(=O)C)O)O)O)NC(=O)C
• InChI: InChI=1S/C26H34N2O13/c1-10-6-18(33)38-15-7-13(4-5-14(10)15)37-25-20(28-12(3)32)23(36)24(17(9-30)40-25)41-26-19(27-11(2)31)22(35)21(34)16(8-29)39-26/h4-7,16-17,19-26,29-30,34-36H,8-9H2,1-3H3,(H,27,31)(H,28,32)/t16-,17-,19-,20-,21-,22-,23-,24-,25-,26+/m1/s1
• InChIKey: UPSFMJHZUCSEHU-JYGUBCOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; N-[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; N-[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-3-yl]acetamide
• Synonyms: 4-Mu-chitobiose; [(4-Methylumbelliferyl)-N-acetylglucosamine]-4,1-N-acetylglucosamine; 7-[[2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-2-deoxy-β-D-glucopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one; 4-Methylumbelliferyl Di-N-Acetyl-β-D-chitobiose; GlcNAc1-b-4GlcNAc1-b-4GlcNAc1-b-4MU; 4-Methylumbelliferyl β-D-N,N',N''-Triacetylchitotrioside

Database IDs

• CAS Number: 53643-13-3; 53643-12-2
• PubChem SID: 164230417
• PubChem CID: 171284

CALCULATED PROPERTIES

• Acid pKa: 11.748206
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -2.8357856
• LogD (pH = 7.4): -2.8358028
• Log P: -2.8357852
• Molar Refractivity: 134.5718 cm^3
• Polarizability: 54.19327 Å^3
• Polar Surface Area: 222.57 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 1:1 Sparingly; D2O:Methanol; DMSO
• Apperance: White Crystalline Solid; White Solid
• Melting Point: 222-225°C (dec.); 256-257°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M337500

A fluorogenic substrate of uniform, characterized structure for assays of lysozyme.

REFERENCES

• Yang, Y., et al.: J. Biochem., 87, 1003 (1980)