CHEBI:16675 - quinolinic acid

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ChEBI Name quinolinic acid
ChEBI ID CHEBI:16675
Definition A pyridinedicarboxylic acid that is pyridine substituted by carboxy groups at positions 2 and 3. It is a metabolite of tryptophan.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:26418, CHEBI:44529, CHEBI:8663
Supplier Information No supplier information found for this compound.
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Quinolinic acid (abbreviated QUIN or QA), also known as pyridine-2,3-dicarboxylic acid, is a dicarboxylic acid with a pyridine backbone. It is a colorless solid. It is the biosynthetic precursor to niacin. Quinolinic acid is a downstream product of the kynurenine pathway, which metabolizes the amino acid tryptophan. It acts as an NMDA receptor agonist. Quinolinic acid has a potent neurotoxic effect. Studies have demonstrated that quinolinic acid may be involved in many psychiatric disorders, neurodegenerative processes in the brain, as well as other disorders. Within the brain, quinolinic acid is only produced by activated microglia and macrophages.
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Formula C7H5NO4
Net Charge 0
Average Mass 167.11890
Monoisotopic Mass 167.02186
InChI InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
InChIKey GJAWHXHKYYXBSV-UHFFFAOYSA-N
SMILES OC(=O)c1cccnc1C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: PubMed
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
NMDA receptor agonist
An excitatory amino acid agonist which binds to NMDA receptors and triggers a response.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Application(s): NMDA receptor agonist
An excitatory amino acid agonist which binds to NMDA receptors and triggers a response.
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ChEBI Ontology
Outgoing quinolinic acid (CHEBI:16675) has role Escherichia coli metabolite (CHEBI:76971)
quinolinic acid (CHEBI:16675) has role human metabolite (CHEBI:77746)
quinolinic acid (CHEBI:16675) has role mouse metabolite (CHEBI:75771)
quinolinic acid (CHEBI:16675) has role NMDA receptor agonist (CHEBI:64571)
quinolinic acid (CHEBI:16675) is a pyridinedicarboxylic acid (CHEBI:36112)
quinolinic acid (CHEBI:16675) is conjugate acid of quinolinate (CHEBI:132942)
quinolinic acid (CHEBI:16675) is conjugate acid of quinolinate(1−) (CHEBI:46828)
Incoming quinolinate (CHEBI:132942) is conjugate base of quinolinic acid (CHEBI:16675)
quinolinate(1−) (CHEBI:46828) is conjugate base of quinolinic acid (CHEBI:16675)
IUPAC Name
pyridine-2,3-dicarboxylic acid
Synonyms Sources
2,3-Pyridinedicarboxylic acid KEGG COMPOUND
Pyridine-2,3-dicarboxylate KEGG COMPOUND
Quinolinic acid KEGG COMPOUND
QUINOLINIC ACID PDBeChem
Manual Xrefs Databases
C00007381 KNApSAcK
C03722 KEGG COMPOUND
DB01796 DrugBank
HMDB0000232 HMDB
NTM PDBeChem
Quinolinic_acid Wikipedia
View more database links
Registry Numbers Types Sources
137110 Reaxys Registry Number Reaxys
201344 Gmelin Registry Number Gmelin
89-00-9 CAS Registry Number KEGG COMPOUND
89-00-9 CAS Registry Number ChemIDplus
Citations
Hartai Z, Klivenyi P, Janaky T, Penke B, Dux L, Vecsei L (2005)
Kynurenine metabolism in multiple sclerosis.
Acta neurologica Scandinavica 112, 93-96 [PubMed:16008534]
[show Abstract]
Obrenovitch TP (2001)
Quinolinic acid accumulation during neuroinflammation. Does it imply excitotoxicity?
Annals of the New York Academy of Sciences 939, 1-10 [PubMed:11462760]
[show Abstract]
Chiarugi A, Cozzi A, Ballerini C, Massacesi L, Moroni F (2001)
Kynurenine 3-mono-oxygenase activity and neurotoxic kynurenine metabolites increase in the spinal cord of rats with experimental allergic encephalomyelitis.
Neuroscience 102, 687-695 [PubMed:11226705]
[show Abstract]
Vogelgesang SA, Heyes MP, West SG, Salazar AM, Sfikakis PP, Lipnick RN, Klipple GL, Tsokos GC (1996)
Quinolinic acid in patients with systemic lupus erythematosus and neuropsychiatric manifestations.
The Journal of rheumatology 23, 850-855 [PubMed:8724297]
[show Abstract]
Last Modified
08 August 2016