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 hydrate

• ChemBase ID: 156586
• Molecular Formular: C26H36N2O14
• Molecular Mass: 600.56904
• Monoisotopic Mass: 600.21665384
• 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)O)NC(=O)C)O)NC(=O)C.O
• 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.O
• InChI: InChI=1S/C26H34N2O13.H2O/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);1H2/t16-,17-,19-,20-,21-,22-,23-,24-,25-,26+;/m1./s1
• InChIKey: ZUEHXULHIWTLAX-UAKKAWJESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 hydrate
• IUPAC Traditional name: 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 hydrate
• Synonyms: 4-Methylumbelliferyl-N,N′-diacetyl-β-D-chitobioside monohydrate

Database IDs

• CAS Number: 53643-12-2
• MDL Number: MFCD00149222
• Beilstein Number: 8602777
• PubChem SID: 162250723
• PubChem CID: 71312338

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: DMF: soluble10 mg/mL, clear, colorless
• Fluorescence: λex 330 nm; λem 375 nm in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C26H34N2O13

DETAILS

Sigma Aldrich - 69589

Other Notes
Binding to rice lectin1; Determination of lectin by fluorescence quenching2; Substrate for endochitinase3