GRADE & PURITY ≥98%

Synonyms

3-(3-Hydroxyanthraniloyl)alanine | 3-(3-hydroxyanthraniloyl)-alanine | alpha,2-Diamino-3-hydroxy-gamma-oxobenzenebutanoic acid | BPBio1_000576 | Prestwick3_000451 | 2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoicacid | Prestwick0_000451 | A815406 | DL-3

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

3-Hydroxy-DL-kynurenine is a tryptophan metabolite with a molecular weight corresponding to 224Da. It is a chromophore or hydrophilic yellow compound present in the lens of the eye. 3-Hydroxy-DL-kynurenine is synthesized from kynurenine by the action of enzyme kynurenine 3-monooxygenase (KMO). It is metabolized to 3-hydroxyanthranilic acid and xanthurenic acid in the presence of enzymes kynureninase and kynurenine aminotransferases, respectively.
Application
3-Hydroxy-DL-kynurenine has been used:
as a substrate for the recombinant human kynureninase assay
as a reference standard in tandem mass spectrometry (MS/MS) analysis
as a control for quantifying serum 3-Hydroxy-DL-kynurenine levels in diabetic retinopathy patients

Specifications

Synonyms

3-(3-Hydroxyanthraniloyl)alanine | 3-(3-hydroxyanthraniloyl)-alanine | alpha, 2-Diamino-3-hydroxy-gamma-oxobenzenebutanoic acid | BPBio1_000576 | Prestwick3_000451 | 2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoicacid | Prestwick0_000451 | A815406 | DL-3

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

3-Hydroxy-DL-kynurenine (3-HKYN) has antioxidant functionality and prevents lipid peroxidation in cerebral cortex. It may modulate synaptic neurotransmission. The levels of 3-HKYN is elevated in Huntington′s disease. However, its role in neurodegenerative

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.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504750348
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750348
• Canonical Smiles: C1=CC(=C(C(=C1)O)N)C(=O)CC(C(=O)O)N
• IUPAC Name: 2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
• InChIKey: VCKPUUFAIGNJHC-UHFFFAOYSA-N
• INCHI: 1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)
• Isomeric SMILES: C1=CC(=C(C(=C1)O)N)C(=O)CC(C(=O)O)N
• Alternate CAS: 484-78-6
• Molecular Weight: 224.21
• Reaxy-Rn: 2697635
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2697635&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Aryl ketones
            • Level7 Phenylketones
              • Level8 Alkyl-phenylketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Aryl ketones - Phenylketones
• Direct Parent: Alkyl-phenylketones
• Alternative Parents: Butyrophenones Alpha amino acids o-Aminophenols Aniline and substituted anilines Gamma-keto acids and derivatives Aryl alkyl ketones Benzoyl derivatives 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Beta-amino ketones Vinylogous amides Amino acids Monocarboxylic acids and derivatives Carboxylic acids Monoalkylamines Organopnictogen compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Butyrophenone - Alpha-amino acid - Alpha-amino acid or derivatives - Gamma-keto acid - O-aminophenol - Aryl alkyl ketone - Aniline or substituted anilines - Benzoyl - Aminophenol - Phenol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Keto acid - Beta-aminoketone - Monocyclic benzene moiety - Benzenoid - Vinylogous amide - Amino acid or derivatives - Amino acid - Carboxylic acid - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organonitrogen compound - Primary amine - Hydrocarbon derivative - Organopnictogen compound - Organic oxide - Organic nitrogen compound - Amine - Primary aliphatic amine - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
• External Descriptors: hydroxykynurenine

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)

KYNU Tchem Kynureninase (42 Activities)

Discover Target: KYNU

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

Associated Targets(non-human)

Slc1a5 Amino acid transporter (271 Activities)

Discover Target: Slc1a5

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly, Heated)
• Sensitivity: Hygroscopic
• Melt Point(°C): >195°C
• Molecular Weight: 224.210 g/mol
• XLogP3: -2.500
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 224.08 Da
• Monoisotopic Mass: 224.08 Da
• Topological Polar Surface Area: 127.000 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 282.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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. Zhuangzhuang Li, Baoyan Ding, Mustafa R. K. Ali, Lizhen Zhao, Xiaoling Zang, Zhihua Lv.  (2022)  Dual Effect of Tryptamine on Prostate Cancer Cell Growth Regulation: A Pilot Study.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  23  (19): (11087).  [PMID:36232383] [10.3390/ijms231911087]

2. Dezhen Wang, Xinru Wang, Ping Zhang, Yao Wang, Renke Zhang, Jin Yan, Zhiqiang Zhou, Wentao Zhu.  (2016)  The fate of technical-grade chlordane in mice fed a high-fat diet and its roles as a candidate obesogen.  ENVIRONMENTAL POLLUTION,      [PMID:28041837] [10.1016/j.envpol.2016.11.028]