4-Nitrophenyl β-D-Glucuronide [Substrate for β-Glucuronidase] - ≥98%(HPLC) , CAS No.10344-94-2

CAS: 10344-94-2 Cat. No.: N159658 Molecular Weight: 315.23

GRADE & PURITY ≥98%(HPLC)

Synonyms

4-nitrophenyl-beta-D-glucuronide | (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acid | 3aminoquinuclidine dihydrochloride | p-nitrophenyl beta-d-glucuronide | 4-Nitrophenyl -D-glucuronide | b-D-Glucopyranosiduronic acid,4-nitroph

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

4-Nitrophenyl β-D-glucuronide has been used as substrate in acetate buffer to measure β-glucuronidase

Specifications

Synonyms

4-nitrophenyl-beta-D-glucuronide | (2S, 3S, 4S, 5R, 6S)-3, 4, 5-trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acid | 3aminoquinuclidine dihydrochloride | p-nitrophenyl beta-d-glucuronide | 4-Nitrophenyl -D-glucuronide | b-D-Glucopyranosiduronic acid, 4-nitroph

Specifications & Purity

≥98%(HPLC)

Storage

Protected from light, 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%(HPLC)

Names and Identifiers

• Pubchem Sid: 504755615
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504755615
• Canonical Smiles: C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)C(=O)O)O)O)O
• IUPAC Name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acid
• InChIKey: QSUILVWOWLUOEU-GOVZDWNOSA-N
• INCHI: 1S/C12H13NO9/c14-7-8(15)10(11(17)18)22-12(9(7)16)21-6-3-1-5(2-4-6)13(19)20/h1-4,7-10,12,14-16H,(H,17,18)/t7-,8-,9+,10-,12+/m0/s1
• Isomeric SMILES: C1=CC(=CC=C1[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
• Molecular Weight: 315.23
• Reaxy-Rn: 25079465
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25079465&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: O-glucuronides O-glycosyl compounds Nitrobenzenes Phenoxy compounds Phenol ethers Nitroaromatic compounds Beta hydroxy acids and derivatives Pyrans Monosaccharides Oxanes Secondary alcohols Acetals Propargyl-type 1,3-dipolar organic compounds Carboxylic acids Monocarboxylic acids and derivatives Polyols Organic oxoazanium compounds Oxacyclic compounds Carbonyl compounds Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - 1-o-glucuronide - O-glucuronide - Glucuronic acid or derivatives - O-glycosyl compound - Nitrobenzene - Phenoxy compound - Nitroaromatic compound - Phenol ether - Beta-hydroxy acid - Monocyclic benzene moiety - Hydroxy acid - Monosaccharide - Oxane - Pyran - Benzenoid - Organic nitro compound - C-nitro compound - Secondary alcohol - Polyol - Organoheterocyclic compound - Acetal - Organic 1,3-dipolar compound - Organic oxoazanium - Oxacycle - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Carboxylic acid - Organonitrogen compound - Organopnictogen compound - Alcohol - Organic nitrogen compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• 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

Associated Targets(Human)

ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

Discover Target: ABCC2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

Discover Target: ABCC4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Gusb Beta-glucuronidase (17 Activities)

Discover Target: Gusb

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat sensitive;Moisture sensitive;Light sensitive
• Specific Rotation[α]: -102° (C=1,EtOH)
• Melt Point(°C): 93 °C
• Molecular Weight: 315.230 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 315.059 Da
• Monoisotopic Mass: 315.059 Da
• Topological Polar Surface Area: 162.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 417.000
• 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. Guanhua Xie, Jingna Yan, Anxia Lu, Jirui Kun, Bei Wang, Chengda Song, Huarong Tong, Qing Meng.  (2021)  Characterizing relationship between chemicals and in vitro bioactivities of teas made by six typical processing methods using a single Camellia sinensis cultivar, Meizhan.  Bioengineered,      [PMID:33904375] [10.1080/21655979.2021.1903237]

2. Qinqin Zhao, Liwei Gao, Nuo Xu, Xiuting Zhang, Yuqi Qin, Yinbo Qu, Guodong Liu.  (2025)  An l-fucose-responsive transcription factor cross-regulates the expression of a diverse array of carbohydrate-active enzymes in Trichoderma reesei.  PLoS Genetics,  21  (8): (e1011815).  [PMID:40788923] [10.1371/journal.pgen.1011815]