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Kynurenic acid

CAT: 0804-HY-100806-01Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-100806-01Size:100 mg
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Description
Kynurenic acid, an endogenous tryptophan metabolite, is a broad-spectrum antagonist targeting NMDA, glutamate, α7 nicotinic acetylcholine receptor. Kynurenic acid is also an agonist of GPR35/CXCR8.
CAS Number
492-27-3
Product Name Alternative
Quinurenic acid
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; CXCR; Endogenous Metabolite; GPR35 ; iGluR
Type
Natural Products
Related Pathways
Apoptosis; GPCR/G Protein; Immunology/Inflammation; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology; Neurological Disease; Endocrinology
Assay Protocol
https://www.medchemexpress.com/Kynurenic_acid.html
Purity
99.58
Solubility
0.1 M NaOH : 12.5 mg/mL (ultrasonic; adjust pH to 9 with NaOH) |DMSO : 9 mg/mL (ultrasonic; warming) |H2O : < 0.1 mg/mL (ultrasonic)
Smiles
O=C(C1=NC2=CC=CC=C2C(O)=C1)O
Molecular Formula
C10H7NO3
Molecular Weight
189.17
Precautions
H302, H315, H319, H335
References & Citations
[1]Wang J, et al. Kynurenic acid as a ligand for orphan G protein-coupled receptor GPR35. J Biol Chem. 2006 Aug 4;281 (31) :22021-8.|[2]Albuquerque EX, et al. Kynurenic acid as an antagonist of α7 nicotinic acetylcholine receptors in the brain: facts and challenges. Biochem Pharmacol. 2013 Apr 15;85 (8) :1027-32.|[3]Małaczewska J, et al. Effect of oral administration of kynurenic acid on the activity of the peripheral blood leukocytes in mice. Cent Eur J Immunol. 2014;39 (1) :6-13.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite; NMDA Receptor

Chemical Information

Kynurenic Acid

Kynurenic acid is a quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4. It has a role as a nicotinic antagonist, a NMDA receptor antagonist, a neuroprotective agent, a G-protein-coupled receptor agonist, a Saccharomyces cerevisiae metabolite and a human metabolite. It is a quinolinemonocarboxylic acid and a monohydroxyquinoline. It is a conjugate acid of a kynurenate.

CAS Number492-27-3
PubChem CID3845
IUPAC Name4-oxo-1H-quinoline-2-carboxylic acid
Molecular FormulaC10H7NO3
Molecular Weight189.17
XLogP1.3
Topological Polar Surface Area66.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Heavy Atom Count14
Formal Charge0
Complexity308
SMILES
C1=CC=C2C(=C1)C(=O)C=C(N2)C(=O)O
InChI
InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)
InChIKey
HCZHHEIFKROPDY-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Kynurenic Acid
CAS: 492-27-3
CID: 3845
Formula: C10H7NO3
MW: 189.17
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight189.17
XLogP31.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass189.042593085
Monoisotopic Mass189.042593085
Topological Polar Surface Area66.4 Ų
Heavy Atom Count14
Formal Charge0
Complexity308
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
M18648-01Kynurenic acid

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