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

• ChemBase ID: 155873
• Molecular Formular: C18H25NO10
• Molecular Mass: 415.3918
• Monoisotopic Mass: 415.14784601
• SMILES: Cc1cc(=O)oc2c1ccc(c2)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C.O.O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@@H]([C@H]([C@@H]1O)O)NC(=O)C.O.O
• InChI: InChI=1S/C18H21NO8.2H2O/c1-8-5-14(22)26-12-6-10(3-4-11(8)12)25-18-15(19-9(2)21)17(24)16(23)13(7-20)27-18;;/h3-6,13,15-18,20,23-24H,7H2,1-2H3,(H,19,21);2*1H2/t13-,15-,16-,17-,18-;;/m1../s1
• InChIKey: PAVCYMSNMRWMAK-DMYIEBNJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]acetamide dihydrate
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-3-yl]acetamide dihydrate
• Synonyms: 4-Methylumbelliferyl-2-acetamido-2-deoxy-β-D-glucopyranoside; 4-Methylumbelliferyl N-acetyl-β-D-glucosaminide

Database IDs

• CAS Number: 37067-30-4(anhydrous)
• EC Number: 253-333-0
• MDL Number: MFCD00150977
• Beilstein Number: 1693397
• PubChem SID: 162250011; 24885953
• PubChem CID: 16218412

CALCULATED PROPERTIES

• Acid pKa: 11.977438
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.7769147
• LogD (pH = 7.4): -0.7769247
• Log P: -0.7769144
• Molar Refractivity: 91.0572 cm^3
• Polarizability: 36.148544 Å^3
• Polar Surface Area: 134.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble20 mg/mL, clear, colorless
• Fluorescence: λex 317 nm (pH 10.0); λex 365 nm; λem 445 nm in aqueous buffer pH 5.0 (after cleavage by β-N-acetylglucosaminidase)

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: ≥99.0% (TLC)
• Suitability: suitable for fluorescence
• Impurities: ≤0.1% free 4-methylumbelliferone
• Empirical Formula (Hill Notation): C18H21NO8

DETAILS

Sigma Aldrich - 69585

Other Notes
Assay of β-N-acetylhexosaminidase1