FComEx: Kynurenic acid (PC000076)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:01 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000076

FoodDB Record

FDB022200

Chemical Information

Name

Kynurenic acid

Description

Kynurenic acid (KYNA) is a well-known endogenous antagonist of the glutamate ionotropic excitatory amino acid receptors N-methyl-D-aspartate (NMDA), alphaamino-3-hydroxy-5-methylisoxazole-4-propionic acid and kainate receptors and of the nicotine cholinergic subtype alpha 7 receptors. KYNA neuroprotective and anticonvulsive activities have been demonstrated in animal models of neurodegenerative diseases. Because of KYNA's neuromodulatory character, its involvement has been speculatively linked to the pathogenesis of a number of neurological conditions including those in the ageing process. Different patterns of abnormalities in various stages of KYNA metabolism in the CNS have been reported in Alzheimer's disease, Parkinson's disease and Huntington's disease. In HIV-1-infected patients and in patients with Lyme neuroborreliosis a marked rise of KYNA metabolism was seen. In the ageing process KYNA metabolism in the CNS of rats shows a characteristic pattern of changes throughout the life span. A marked increase of the KYNA content in the CNS occurs before the birth, followed by a dramatic decline on the day of birth. A low activity was seen during ontogenesis, and a slow and progressive enhancement occurs during maturation and ageing. This remarkable profile of KYNA metabolism alterations in the mammalian brain has been suggested to result from the development of the organisation of neuronal connections and synaptic plasticity, development of receptor recognition sites, maturation and ageing. There is significant evidence that KYNA can improve cognition and memory, but it has also been demonstrated that it interferes with working memory. Impairment of cognitive function in various neurodegenerative disorders is accompanied by profound reduction and/or elevation of KYNA metabolism. The view that enhancement of CNS KYNA levels could underlie cognitive decline is supported by the increased KYNA metabolism in Alzheimer's disease, by the increased KYNA metabolism in down's syndrome and the enhancement of KYNA function during the early stage of Huntington's disease. Kynurenic acid is the only endogenous N-methyl-D-aspartate (NMDA) receptor antagonist identified up to now, that mediates glutamatergic hypofunction. Schizophrenia is a disorder of dopaminergic neurotransmission, but modulation of the dopaminergic system by glutamatergic neurotransmission seems to play a key role. Despite the NMDA receptor antagonism, kynurenic acid also blocks, in lower doses, the nicotinergic acetycholine receptor, i.e., increased kynurenic acid levels can explain psychotic symptoms and cognitive deterioration. Kynurenic acid levels are described to be higher in the cerebrospinal fluid (CSF) and in critical central nervous system (CNS) regions of schizophrenics as compared to controls. (PMID: 17062375, 16088227) [HMDB]

CAS Number

492-27-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Carboxy-4-hydroxyquinoline	hmdb
4-Hydroxy-2-chinolincarbonsaeure	ChEBI
4-Hydroxy-2-quinolinecarboxylate	Generator
4-hydroxy-2-Quinolinecarboxylic acid	hmdb
4-hydroxy-Quinaldate	hmdb
4-hydroxy-Quinaldic acid	hmdb
4-Hydroxyquinaldate	hmdb
4-Hydroxyquinaldic acid	hmdb
4-Hydroxyquinaldinate	hmdb
4-Hydroxyquinaldinic acid	hmdb
4-Hydroxyquinoline-2-carboxylate	hmdb
4-Hydroxyquinoline-2-carboxylic acid	hmdb
Kynurenate	hmdb
Kynurenic acid	hmdb
Kynurensaeure	ChEBI
Quinurenic acid	hmdb

Chemical Formula

C10H7NO3

IUPAC name

4-oxo-1,4-dihydroquinoline-2-carboxylic acid

InChI Identifier

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)

InChI Key

HCZHHEIFKROPDY-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C1=CC(=O)C2=CC=CC=C2N1

Average Molecular Weight

189.1675

Monoisotopic Molecular Weight

189.042593095

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents