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CHEBI:63965 - 7-chlorokynurenic acid

ChEBI IDCHEBI:63965
ChEBI Name7-chlorokynurenic acid
Stars
DefinitionA quinolinemonocarboxylic acid that is quinaldic acid which is substituted by a hydroxy group at position 4 and by a chlorine at position 7. It is a potent NMDA glutamate receptor antagonist which antagonizes the strychnine-insensitive glycine site of the NMDA receptor. It also prevents neurodegeneration produced by quinolinic acid.
Last Modified25 February 2016
SubmitterGareth Owen
DownloadsMolfile
FormulaC10H6ClNO3
Net Charge0
Average Mass223.615
Monoisotopic Mass223.00362
SMILESO=C(O)c1cc(O)c2ccc(Cl)cc2n1
InChIInChI=1S/C10H6ClNO3/c11-5-1-2-6-7(3-5)12-8(10(14)15)4-9(6)13/h1-4H,(H,12,13)(H,14,15)
InChIKeyUAWVRVFHMOSAPU-UHFFFAOYSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
NMDA receptor antagonist  Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
Application:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
7-chlorokynurenic acid (CHEBI:63965) has role neuroprotective agent (CHEBI:63726)
7-chlorokynurenic acid (CHEBI:63965) has role NMDA receptor antagonist (CHEBI:60643)
7-chlorokynurenic acid (CHEBI:63965) is a organochlorine compound (CHEBI:36683)
7-chlorokynurenic acid (CHEBI:63965) is a quinolinemonocarboxylic acid (CHEBI:26512)
IUPAC Name 
7-chloro-4-hydroxyquinoline-2-carboxylic acid
Synonyms  Source
7-Cl-KYNAChEBI
7-CKAChEBI
7-chloro-4-hydroxy-2-carboxyquinolineChEBI
Manual XrefsDatabases
LSM-24944LINCS
Registry NumbersSources
Reaxys:185645Reaxys
CAS:18000-24-3ChemIDplus
Citations