L-Kynurenine Hydrate - ≥98%(T) , CAS No.2922-83-0

CAS: 2922-83-0 Cat. No.: S138616 Molecular Weight: 208.22(as Anhydrous) Beilstein Registry Number: 14(4)1656

GRADE & PURITY ≥98%(T)

Synonyms

CCRIS 4425 | L-kynurenine | SCHEMBL20875 | KYN | AKOS016843487 | beta-Anthraniloyl-L-alanine, L-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid | DTXSID1074414 | 3-(2-aminobenzoyl)-L-alanine | (alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate | (

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

L-Kynurenine is a key intermediate in the breakdown pathway of tryptophan. L-Kynurenine is a substrate of kynureninase, KMO, and KAT associated with the suppression of antitumor immune responses. It has been shown to inhibit allogeneic T-cell proliferation and to increase malignant U87 glioma cell invasion into a collagen matrix.

Specifications

Synonyms

CCRIS 4425 | L-kynurenine | SCHEMBL20875 | KYN | AKOS016843487 | beta-Anthraniloyl-L-alanine, L-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid | DTXSID1074414 | 3-(2-aminobenzoyl)-L-alanine | (alphaS)-alpha, 2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate | (

Specifications & Purity

≥98%(T)

Biochemical and Physiological Mechanisms

Endogenous AhR agonist. L-Tryptophan metabolite. Suppresses allogeneic T cell proliferation. Centrally active.

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.

Action Type

AGONIST

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(T)

Names and Identifiers

• Pubchem Sid: 488188330
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488188330
• Canonical Smiles: C1=CC=C(C(=C1)C(=O)CC(C(=O)O)N)N
• IUPAC Name: (2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
• InChIKey: YGPSJZOEDVAXAB-QMMMGPOBSA-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)/t8-/m0/s1
• Isomeric SMILES: C1=CC=C(C(=C1)C(=O)C[C@@H](C(=O)O)N)N
• RTECS: CY9049700
• Molecular Weight: 208.22(as Anhydrous)
• Beilstein: 14(4)1656
• 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 L-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 - L-alpha-amino acid - Benzoyl - Gamma-keto acid - Aniline or substituted anilines - Aryl alkyl ketone - Monocyclic benzene moiety - Beta-aminoketone - Keto acid - Benzenoid - Vinylogous amide - Amino acid - Amino acid or derivatives - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Primary aliphatic amine - Amine - Hydrocarbon derivative - Organopnictogen compound - Organic oxide - Organic nitrogen compound - Organonitrogen compound - Primary 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: non-proteinogenic L-alpha-amino acid - kynurenine

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)

AHR Tclin Aryl hydrocarbon receptor (1071 Activities)

Discover Target: AHR

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

KYNU Tchem Kynureninase (42 Activities)

Discover Target: KYNU

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

IDO1 Tchem Indoleamine 2,3-dioxygenase (6650 Activities)

Discover Target: IDO1

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

RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

Discover Target: RGS4

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

Associated Targets(non-human)

Bacillus subtilis (32866 Activities)

Explore this target

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

• Sensitivity: air sensitive
• Specific Rotation[α]: -33° (C=0.4,H2O)
• Melt Point(°C): 219 °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: 1
• 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

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