4-Nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside - ≥98% , CAS No.3459-18-5

CAS: 3459-18-5 Cat. No.: N107918 Molecular Weight: 342.3 Beilstein Registry Number: 96193 EC Number: 222-398-7

GRADE & PURITY ≥98%

Synonyms

4-Nitrophenyl-2-acetamido-2-deoxy-beta-D-glucopyranoside | 4-Nitrophenyl2-acetamido-2-deoxy-beta-D-glucopyranoside | AKOS016015692 | EX-A7998K | p-Nitrophenyl-N-acetyl-.beta.-D-glucosaminide | UNII-GVY9AA7Y5C | 4-nitrophenyl 2-(acetylamino)-2-deoxy-beta-D

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

4-Nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside is a useful substrate for rapid colorimetric assay of N-acetyl-b-glucosaminidase activity in human urine. Chromogenic β-Glucosaminidase substrate yielding a yellow solution upon cleavage, employed particularly in yeasts and molds.
A substrate for rapid colorimetric assays in human urine

Specifications

Synonyms

4-Nitrophenyl-2-acetamido-2-deoxy-beta-D-glucopyranoside | 4-Nitrophenyl2-acetamido-2-deoxy-beta-D-glucopyranoside | AKOS016015692 | EX-A7998K | p-Nitrophenyl-N-acetyl-.beta.-D-glucosaminide | UNII-GVY9AA7Y5C | 4-nitrophenyl 2-(acetylamino)-2-deoxy-beta-D

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

4-nitrophenyl-n-acetyl-β-D-glucoside (NP-GlcNAc) is a widely used hexosidase substrate. Enzymatic action cleaved the glycoside bond and formed 4-phenolate (pNP), measured at 405 nm. NP-GlcNAc can also be used in combination with diethylaminoethyl-a-cyclod

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504756521
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756521
• Canonical Smiles: CC(=O)NC1C(C(C(OC1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O
• IUPAC Name: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• InChIKey: OMRLTNCLYHKQCK-DHGKCCLASA-N
• 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
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O
• WGK Germany: 3
• Molecular Weight: 342.3
• Beilstein: 96193
• Reaxy-Rn: 25358208
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25358208&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 N-acyl-alpha-hexosamines

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides
• Direct Parent: N-acyl-alpha-hexosamines
• Alternative Parents: Hexoses O-glycosyl compounds Nitrobenzenes Nitroaromatic compounds Phenoxy compounds Phenol ethers Oxanes Secondary alcohols Organic oxoazanium compounds Acetals Propargyl-type 1,3-dipolar organic compounds Carboximidic acids Oxacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic zwitterions Organic oxides Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: N-acyl-alpha-hexosamine - Hexose monosaccharide - Glycosyl compound - O-glycosyl compound - Nitrobenzene - Phenoxy compound - Nitroaromatic compound - Phenol ether - Monocyclic benzene moiety - Monosaccharide - Oxane - Benzenoid - C-nitro compound - Organic nitro compound - Secondary alcohol - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Carboximidic acid - Carboximidic acid derivative - Acetal - Oxacycle - Organic oxoazanium - Organic oxide - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Alcohol - Organonitrogen compound - Organic zwitterion - Primary alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (~5 g/l), DMSO, and ethanol
• Sensitivity: Heat sensitive
• Specific Rotation[α]: -15 ° (C=0.5, H2O)
• Melt Point(°C): 205°C
• Molecular Weight: 342.300 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 342.106 Da
• Monoisotopic Mass: 342.106 Da
• Topological Polar Surface Area: 154.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 449.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zhuoning Cao, Chengqiang Li, Hong Jiang, Francesco Secundo, Xiangzhao Mao.  (2025)  Molecular modification of a GH84 β-N-acetylglucosaminidase from Streptomyces violascens for synthesis of lacto-N-triose II using whey powder and chitin-derived N-acetyl chitobiose.  FOOD CHEMISTRY,      [PMID:39919427] [10.1016/j.foodchem.2025.143046]

2. Liu Yucan, Wang Baoyan, Hu Jing, Sun Hongwei, Lv Xintao, Qu Zhiming, Yang Xiaoyong, Wang Gang, Zhang Yanxiang, Zhang Shujun.  (2025)  Effect of Perfluorobutane Sulfonic Acid On Microbial Community and Functional Enzyme of Nitrogen Cycling in Coastal Sediment.  WATER AIR AND SOIL POLLUTION,  236  (12): (1-16).  [PMID:] [10.1007/s11270-025-08433-w]