Acetaminophen glucuronide (APAP-glu) - Moligand™, ≥99% , CAS No.16110-10-4

CAS: 16110-10-4 Cat. No.: A651386 Formula: C₁₄H₁₇NO₈ Molecular Weight: 327.29 EC Number: 694-366-4

GRADE & PURITY Moligand™, ≥99%

Synonyms

4-acetamidophenyl beta-delta-glucopyranosiduronic acid | 4-GLUCURONOSIDOACETANILIDE | DTXSID30936449 | (1,1'-biphenyl-4-yloxy)acetic acid | Acetaminophen glucuronide | 4-(acetylamino)phenyl beta-delta-glucopyranosiduronic acid | Acetaminophen D-glucuronid

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Acetaminophen glucuronide (APAP-glu) is an inactive glucuronide metabolite of Acetaminophen Acetaminophen is a selective cyclooxygenase-2 (COX-2) inhibitor and a potent hepatic N-acetyltransferase 2 (NAT2) inhibitor

In Vitro

Acetaminophen is metabolized in the liver mainly by glucuronidation and sulfation, thus generating the nontoxic metabolites, Acetaminophen glucuronide (APAP-glu). Acetaminophen glucuronide is a substrate for both canalicular Mrp2 and basolateral Mrp3 in rodents. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:Human Endogenous Metabolite

Specifications

Synonyms

4-acetamidophenyl beta-delta-glucopyranosiduronic acid | 4-GLUCURONOSIDOACETANILIDE | DTXSID30936449 | (1,1'-biphenyl-4-yloxy)acetic acid | Acetaminophen glucuronide | 4-(acetylamino)phenyl beta-delta-glucopyranosiduronic acid | Acetaminophen D-glucuronid

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Acetaminophen glucuronide (APAP-glu) is an inactive glucuronide metabolite of Acetaminophen (HY-66005). Acetaminophen is a selective cyclooxygenase-2 (COX-2) inhibitor and a potent hepatic N-acetyltransferase 2 (NAT2) inhibitor.

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC(=O)NC1=CC=C(C=C1)OC2C(C(C(C(O2)C(=O)O)O)O)O
• IUPAC Name: (2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• InChIKey: IPROLSVTVHAQLE-BYNIDDHOSA-N
• INCHI: 1S/C14H17NO8/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21)/t9-,10-,11+,12-,14+/m0/s1
• Isomeric SMILES: CC(=O)NC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
• Molecular Weight: 327.29

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 Phenoxy compounds Phenol ethers Beta hydroxy acids and derivatives Pyrans Oxanes Monosaccharides Secondary alcohols Propargyl-type 1,3-dipolar organic compounds Polyols Oxacyclic compounds Acetals Carboximidic acids Monocarboxylic acids and derivatives Carboxylic acids Hydrocarbon derivatives Organic oxides Carbonyl compounds Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - 1-o-glucuronide - O-glucuronide - Glucuronic acid or derivatives - O-glycosyl compound - Phenoxy compound - Phenol ether - Beta-hydroxy acid - Monocyclic benzene moiety - Hydroxy acid - Monosaccharide - Benzenoid - Pyran - Oxane - Secondary alcohol - Acetal - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Polyol - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Hydrocarbon derivative - Carbonyl group - Alcohol - Organic nitrogen compound - Organopnictogen compound - Organonitrogen compound - Organic oxide - 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: beta-D-glucosiduronic acid

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)

Homo sapiens (32628 Activities)

Explore this target

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

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Hygroscopic
• Melt Point(°C): 195-198°C
• Molecular Weight: 327.290 g/mol
• XLogP3: -0.800
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 327.095 Da
• Monoisotopic Mass: 327.095 Da
• Topological Polar Surface Area: 146.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 436.000
• 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. Yang Wenjuan, Tang Sidi, Xu Rubing, Zhang Lu, Zhou Zihao, Yang Yong, Li Yanyan, Xiang Haibo.  (2024)  LC-MS based metabolomics identification of natural metabolites against Fusarium oxysporum.  Frontiers in Plant Science,      [PMID:39290733] [10.3389/fpls.2024.1435963]