DL-Kynurenine - ≥95% , CAS No.343-65-7

CAS: 343-65-7 Cat. No.: R134932 Molecular Weight: 208.21 Beilstein Registry Number: 2697333 EC Number: 206-445-9

GRADE & PURITY ≥95%

Synonyms

.alpha.-2-diamino-.gamma.-oxobenzenebutyric acid | alpha,2-Diamino-gamma-oxobenzenebutanoic acid | Benzenebutanoic acid, alpha,2-diamino-gamma-oxo- | (+-)-Kynurenine | 2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid # | NCGC00095648-01 | Spectrum_001162 | SR

Storage

Room temperature

Shipped In

Normal

Overview

A tryptophan metabolite, and a precursor of kynurenic acid, which is an antagonist of N-methyl-aspartate receptor.

Specifications

Synonyms

.alpha.-2-diamino-.gamma.-oxobenzenebutyric acid | alpha, 2-Diamino-gamma-oxobenzenebutanoic acid | Benzenebutanoic acid, alpha, 2-diamino-gamma-oxo- | (+-)-Kynurenine | 2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid # | NCGC00095648-01 | Spectrum_001162 | SR

Specifications & Purity

≥95%

Storage

Room temperature

Shipped In

Normal

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504750422
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750422
• Canonical Smiles: C1=CC=C(C(=C1)C(=O)CC(C(=O)O)N)N
• IUPAC Name: 2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
• InChIKey: YGPSJZOEDVAXAB-UHFFFAOYSA-N
• INCHI: 1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)
• Isomeric SMILES: C1=CC=C(C(=C1)C(=O)CC(C(=O)O)N)N
• WGK Germany: 3
• Molecular Weight: 208.21
• Beilstein: 2697333
• Reaxy-Rn: 2697333
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2697333&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 Gamma-keto acids and derivatives Benzoyl derivatives Aryl alkyl ketones Aniline and substituted anilines Beta-amino ketones Vinylogous amides Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Butyrophenone - Alpha-amino acid - Alpha-amino acid or derivatives - Benzoyl - Aniline or substituted anilines - Aryl alkyl ketone - Gamma-keto acid - Monocyclic benzene moiety - Beta-aminoketone - Benzenoid - Keto acid - Vinylogous amide - Amino acid - Amino acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Primary aliphatic amine - Organonitrogen compound - Primary amine - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Amine - Organopnictogen compound - 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: substituted aniline - non-proteinogenic alpha-amino acid - aromatic ketone

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)

KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

Discover Target: KDM4E

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

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

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

Associated Targets(non-human)

Mapt Microtubule-associated protein tau (6 Activities)

Discover Target: Mapt

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

Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

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

fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

Discover Target: fba

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

ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

Discover Target: ffp

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

Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): ~235°C
• Molecular Weight: 208.210 g/mol
• XLogP3: -2.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 208.085 Da
• Monoisotopic Mass: 208.085 Da
• Topological Polar Surface Area: 106.000 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 255.000
• 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. Qixing Nie, Yonggan Sun, Mingzhi Li, Sheng Zuo, Chunhua Chen, Qiongni Lin, Shaoping Nie.  (2023)  Targeted modification of gut microbiota and related metabolites via dietary fiber.  CARBOHYDRATE POLYMERS,      [PMID:37321707] [10.1016/j.carbpol.2023.120986]

2. Zhuoting Liu, Yunfang Ping, Lumei Zhang, Jingran Zhang, Ann Van Schepdael, Xu Wang.  (2023)  Indoleamine 2,3 dioxygenase 1 immobilization on magnetic nanoparticles for screening inhibitors from coffee.  Food Chemistry-X,      [PMID:36845477] [10.1016/j.fochx.2023.100591]

3. Xiaoxu Cheng, Zifeng Pi, Zhong Zheng, Shu Liu, Fengrui Song, Zhiqiang Liu.  (2022)  Combined 16S rRNA gene sequencing and metabolomics to investigate the protective effects of Wu-tou decoction on rheumatoid arthritis in rats.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:35447521] [10.1016/j.jchromb.2022.123249]

4. Mengmeng Song, Xianjie Sheng, Genyi Ye, Zhuicheng Xu, Xinru Li, Tong Xie, Haishan Deng, An Kang.  (2022)  Selective enrichment of microbiota-derived tryptophan metabolites in mouse faeces based on molecularly imprinted solid-phase extraction for HPLC analysis.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:35182828] [10.1016/j.jpba.2022.114641]

5. Jia Yin, Yujie Song, Yaozhong Hu, Yuanyifei Wang, Bowei Zhang, Jin Wang, Xuemeng Ji, Shuo Wang.  (2021)  Dose-Dependent Beneficial Effects of Tryptophan and Its Derived Metabolites on Akkermansia In Vitro: A Preliminary Prospective Study.  Microorganisms,  9  (7): (1511).  [PMID:34361945] [10.3390/microorganisms9071511]

6. Yuanyuan Xia, Faqiong Zhao, Baizhao Zeng.  (2019)  A molecularly imprinted copolymer based electrochemical sensor for the highly sensitive detection of L-Tryptophan.  TALANTA,      [PMID:31514823] [10.1016/j.talanta.2019.120245]

7. Qixing Nie, Yonggan Sun, Wenbing Hu, Chunhua Chen, Qiongni Lin, Shaoping Nie.  (2024)  Glucomannan promotes Bacteroides ovatus to improve intestinal barrier function and ameliorate insulin resistance.  iMeta,      [PMID:38868507] [10.1002/imt2.163]

8. Wenjun Zhang, Chuntao Dong, Zhaosheng Li, Huina Shi, Yijun Xu, Mingchen Zhu.  (2024)  Serum targeted metabolomics uncovering specific amino acid signature for diagnosis of intrahepatic cholangiocarcinoma.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:39241676] [10.1016/j.jpba.2024.116457]

9. Kai Wang, Shufen Zhang, Yunxia Wang, Xiaomei Wu, Lijuan Wen, Tingting Meng, Xiangyu Jin, Sufen Li, Yiling Hong, Jia Ke, Yichong Xu, Hong Yuan, Fuqiang Hu.  (2024)  Taprenepag restores maternal–fetal interface homeostasis for the treatment of neurodevelopmental disorders.  Journal of Neuroinflammation,      [PMID:39609821] [10.1186/s12974-024-03300-7]

10. Sun Wen-Xing, Zhang Kai-Hui, Zhou Qian, Hu Song-Hua, Lin Yan, Xu Wei, Zhao Shi-Min, Yuan Yi-Yuan.  (2024)  Tryptophanylation of insulin receptor by WARS attenuates insulin signaling.  CELLULAR AND MOLECULAR LIFE SCIENCES,  81  (1): (1-15).  [PMID:38212570] [10.1007/s00018-023-05082-2]

11. Dan-Qian Chen, Gang Cao, Hua Chen, Dan Liu, Wei Su, Xiao-Yong Yu, Nosratola D. Vaziri, Xiu-Hua Liu, Xu Bai, Li Zhang, Ying-Yong Zhao.  (2017)  Gene and protein expressions and metabolomics exhibit activated redox signaling and wnt/β-catenin pathway are associated with metabolite dysfunction in patients with chronic kidney disease.  Redox Biology,      [PMID:28343144] [10.1016/j.redox.2017.03.017]