N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide

• ChemBase ID: 133772
• Molecular Formular: C14H18N2O8
• Molecular Mass: 342.30132
• Monoisotopic Mass: 342.10631555
• SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1Oc1ccc(cc1)[N+](=O)[O-])CO)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)[N+](=O)[O-])[C@@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C14H18N2O8/c1-7(18)15-11-13(20)12(19)10(6-17)24-14(11)23-9-4-2-8(3-5-9)16(21)22/h2-5,10-14,17,19-20H,6H2,1H3,(H,15,18)/t10-,11-,12-,13-,14-/m1/s1
• InChIKey: OMRLTNCLYHKQCK-DHGKCCLASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• Synonyms: GlcNAc1-b-PNP; p-Nitrophenyl 2-Acetamido-2-deoxy-β-D-glucopyranoside; 4-Nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside; 4-Nitrophenyl N-acetyl-β-D-glucosaminide

Database IDs

• CAS Number: 3459-18-5
• EC Number: 222-398-7
• MDL Number: MFCD00063696
• Beilstein Number: 96193
• PubChem SID: 162228049; 24897896
• PubChem CID: 102416

CALCULATED PROPERTIES

• Acid pKa: 11.628232
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.94643915
• LogD (pH = 7.4): -0.9464615
• Log P: -0.9464386
• Molar Refractivity: 78.6093 cm^3
• Polarizability: 30.910494 Å^3
• Polar Surface Area: 154.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether; Ethyl Acetate; H2O: soluble5 mg/mL, clear, colorless to very faintly yellow; Methanol
• Apperance: Slightly Off-White Solid
• Melting Point: 201-202°C
• Optical Rotation: [α]20/D -15±2°, c = 0.5% in H2O

Safety Information

• Storage Condition: -20°C Freezer
• 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% (TLC); ≥99.0% (TLC)
• Suitability: suitable as substrate for N-acetyl-β-D-glucosaminidase test
• Impurities: ≤0.05% free 4-nitrophenol; ≤0.05% Free p-nitrophenol
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C14H18N2O8

DETAILS

Sigma Aldrich - N9376

包装
1 g in poly bottle
100, 250, 500 mg in poly bottle
Substrates
Chromogenic substrate for N-acetyl-glucosaminidase.

Sigma Aldrich - 73606

Other Notes
Chromogenic substrate for N-acetyl glucosaminidase1,2

Toronto Research Chemicals - N502000

Useful substrate for the rapid colorimetric assay of N-Acetyl-beta-glucosaminidase in human urine.

REFERENCES

• Muruhn, D.: Clin. Chim. Acta, 73, 453 (1976)