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

• ChemBase ID: 133055
• Molecular Formular: C18H21NO8
• Molecular Mass: 379.36124
• Monoisotopic Mass: 379.12671664
• SMILES: Cc1cc(=O)oc2c1ccc(c2)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)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)O)NC(=O)C
• InChI: InChI=1S/C18H21NO8/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)/t13-,15-,16-,17-,18-/m1/s1
• InChIKey: QCTHLCFVVACBSA-JVNHZCFISA-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
• 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
• Synonyms: 4-Methylumbelliferyl-2-acetamido-2-deoxy-β-D-gluco-pyrano-side; 4-Methylumbelliferyl N-acetyl-β-D-glucosaminide; 4-Methylumbelliferyl-N-acetyl-β-D-glucosaminide; GlcNAc1-b-4MU; 4-Methylumbelliferyl 2-Acetamido-2-deoxy-β-D-glucopyranoside

Database IDs

• CAS Number: 37067-30-4
• EC Number: 253-333-0
• MDL Number: MFCD00065481
• PubChem SID: 162227332; 24896605
• PubChem CID: 2733787

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: DMSO; Warm Water
• Apperance: White Crystalline Solid
• Melting Point: 212-214°C

Safety Information

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

Product Information

• Classification: Rare Genuine Natural Compounds

DETAILS

Sigma Aldrich - M2133

Substrates
Fluorogenic substrate for β-N-acetylhexosaminidase

Toronto Research Chemicals - M334000

Fluorogenic substrate used for the assay of b-Acetylglucosaminidase. A fluorogenic substrate used for the diagnosis of GM2 gangliosidoses in leukocytes. Genetic defects in human b-hexosaminidase isozymes (Hex A & Hex B) result in various clinical and bioc

REFERENCES

• Biochem. J., 78, 151 (1961)