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

• ChemBase ID: 132675
• Molecular Formular: C34H47N3O18
• Molecular Mass: 785.74628
• Monoisotopic Mass: 785.28546168
• SMILES: Cc1cc(=O)oc2c1ccc(c2)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C)O)NC(=O)C)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[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1NC(=O)C)O)O)O)NC(=O)C
• InChI: InChI=1S/C34H47N3O18/c1-12-7-22(44)50-18-8-16(5-6-17(12)18)49-32-24(36-14(3)42)28(47)30(20(10-39)52-32)55-34-25(37-15(4)43)29(48)31(21(11-40)53-34)54-33-23(35-13(2)41)27(46)26(45)19(9-38)51-33/h5-8,19-21,23-34,38-40,45-48H,9-11H2,1-4H3,(H,35,41)(H,36,42)(H,37,43)/t19-,20-,21-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33+,34+/m1/s1
• InChIKey: BNYGKUQXGBVTRE-JFWBNMEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-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)-5-{[(2S,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-3-yl]acetamide
• Synonyms: 4-Methyl-7-coumarinyl-tri-N-acetyl-β-chitotrioside; 4-Methylumbelliferyl-N,N′,N″-triacetyl-β-chitotrioside; 4-Methylumbelliferyl β-D-N,N′,N′′-triacetylchitotrioside

Database IDs

• CAS Number: 53643-13-3
• MDL Number: MFCD00036892
• Beilstein Number: 5710839
• PubChem SID: 24897027; 162226952
• PubChem CID: 16219671

CALCULATED PROPERTIES

• Acid pKa: 11.607191
• H Acceptors: 17
• H Donor: 10
• LogD (pH = 5.5): -4.894656
• LogD (pH = 7.4): -4.89468
• Log P: -4.894656
• Molar Refractivity: 178.0864 cm^3
• Polarizability: 72.24753 Å^3
• Polar Surface Area: 310.59 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 365 nm; λem 445 nm in 0.1 M phosphate pH 7.0 (lysozyme)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 90%
• Grade: for fluorescence
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C34H47N3O18

DETAILS

Sigma Aldrich - M5639

Substrates
Fluorogenic substrate for endochitinases, peptidoglycan muramidase, and lysozyme.

Sigma Aldrich - 69615

Other Notes
Fluorogenic substrate for the assay of lysozyme1