Page last updated: 2024-12-06

8-hydroxy-2-quinolinecarboxylic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

8-hydroxy-2-quinolinecarboxylic acid, also known as kynurenic acid, is a naturally occurring compound found in humans and animals. It is a metabolite of the amino acid tryptophan and is produced in the liver. Kynurenic acid is a potent antagonist of the NMDA receptor, which is involved in learning and memory. It also has anti-inflammatory and neuroprotective properties. Kynurenic acid has been studied for its potential therapeutic use in conditions such as Alzheimer's disease, Parkinson's disease, and schizophrenia. It has also been investigated for its role in the pathogenesis of cancer, inflammatory bowel disease, and other diseases.'

Cross-References

ID SourceID
PubMed CID74079
CHEMBL ID1368601
CHEBI ID109435
SCHEMBL ID171491

Synonyms (57)

Synonym
quinaldic acid, 8-hydroxy-
brn 0146082
8-hydroxyquinaldic acid
MLS000849721-02
MLS-0146266.0001
EU-0033714
8-hydroxy-2-quinolinecarboxylic acid
smr000455739
MLS000849721 ,
OPREA1_440614 ,
8-hydroxy-2-quinolinecarboxylic acid, >=98.0% (gc)
55088_ALDRICH ,
CHEBI:109435
AKOS001591538
8-hydroxyquinoline-2-carboxylic acid
A809811
CHEMBL1368601
NCGC00246181-01
NCGC00246181-02
1571-30-8
ST086494 ,
5-22-05-00272 (beilstein handbook reference)
FT-0621540
8hc ,
SCHEMBL171491
H1658
8-hydroxy-quinoline-2-carboxylic acid
UHBIKXOBLZWFKM-UHFFFAOYSA-N
W-205807
TS-02668
quinolinecarboxylic acid, 8-hydroxy-
Q27188565
DTXSID00166211
4LV4
mfcd00168972
2-quinolinecarboxylic acid, 8-hydroxy-
us9394254, 5 (hca)
bdbm237136
bay32-5915
CS-0059230
bdbm382
cid_74079
8-oxidanylquinoline-2-carboxylic acid
bay 32-5915
bay32 5915
bay 32 5915
bay-32-5915
bay325915
8-hydroxyquinaldinic acid
8-hydroxyquinolinium-2-carboxylate
SB67486
F13965
HY-W067427
2-quinolinecarboxylicacid,8-hydroxy-
8-hydroxy quinoline-2-carboxylic acid
EBM66FCM33
SY081302
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
quinolinesA class of aromatic heterocyclic compounds each of which contains a benzene ring ortho fused to carbons 2 and 3 of a pyridine ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (12)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency22.15920.140911.194039.8107AID2451; AID2785; AID2787
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency12.58930.177814.390939.8107AID2147
phosphopantetheinyl transferaseBacillus subtilisPotency2.81840.141337.9142100.0000AID1490
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency3.54810.707912.194339.8107AID720542
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency10.00000.707936.904389.1251AID504333
glyceraldehyde-3-phosphate dehydrogenase isoform 1Homo sapiens (human)Potency100.00001.122011.187739.8107AID2795
histone-lysine N-methyltransferase 2A isoform 2 precursorHomo sapiens (human)Potency31.62280.010323.856763.0957AID2662
gemininHomo sapiens (human)Potency0.36630.004611.374133.4983AID624297
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency1.77830.00419.962528.1838AID2675
Glycoprotein hormones alpha chainHomo sapiens (human)Potency5.62344.46688.344810.0000AID624291
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutaminyl-peptide cyclotransferaseHomo sapiens (human)IC50 (µMol)203.00005.00005.00005.0000AID1893771
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
citrate synthase 2, partialSaccharomyces cerevisiae (brewer's yeast)EC50 (µMol)299.50001.07003.07785.7170AID488825
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
peptidyl-pyroglutamic acid biosynthetic process, using glutaminyl-peptide cyclotransferaseGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
protein modification processGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
zinc ion bindingGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
glutaminyl-peptide cyclotransferase activityGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular regionGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
specific granule lumenGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
extracellular exosomeGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
tertiary granule lumenGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
ficolin-1-rich granule lumenGlutaminyl-peptide cyclotransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1824268Inhibition of recombinant IMP-1 (unknown origin) using fluorocillin as substrate at 3 uM incubated for 30 mins by fluorescence based assay2022European journal of medicinal chemistry, Jan-15, Volume: 228Nitroxoline and its derivatives are potent inhibitors of metallo-β-lactamases.
AID566700Inhibition of human recombinant 5-lipoxygenase at 1 mM after 10 mins by fluorescence assay2011Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2
Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1824267Inhibition of recombinant IMP-1 (unknown origin) using fluorocillin as substrate at 10 uM incubated for 30 mins by fluorescence based assay2022European journal of medicinal chemistry, Jan-15, Volume: 228Nitroxoline and its derivatives are potent inhibitors of metallo-β-lactamases.
AID566706Inhibition of human recombinant MMP9 at 1 mM after 30 mins2011Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2
Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID566707Inhibition of mouse recombinant iNOS at 1 mM after 40 mins by colorimetric assay2011Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2
Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1451101Inhibition of Pseudomonas aeruginosa VIM2 expressed in Escherichia coli BL21(DE3) at 50 uM using chromacef as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by HTS assay relative to control2017Journal of medicinal chemistry, 09-14, Volume: 60, Issue:17
Dipicolinic Acid Derivatives as Inhibitors of New Delhi Metallo-β-lactamase-1.
AID1824263Inhibition of recombinant VIM-1 (unknown origin) using fluorocillin as substrate at 30 uM incubated for 30 mins by fluorescence based assay2022European journal of medicinal chemistry, Jan-15, Volume: 228Nitroxoline and its derivatives are potent inhibitors of metallo-β-lactamases.
AID1679133Zinc chelating activity mediated inhibition of Clostridium botulinum BoNT/A1 LC (1 to 425 residues) activity using SNAPtide as substrate at 1 mM incubated with enzyme for 30 mins followed by substrate addition and measured for 20 mins by FRET assay relati
AID1824264Inhibition of recombinant VIM-1 (unknown origin) using fluorocillin as substrate at 10 uM incubated for 30 mins by fluorescence based assay2022European journal of medicinal chemistry, Jan-15, Volume: 228Nitroxoline and its derivatives are potent inhibitors of metallo-β-lactamases.
AID566701Inhibition of recombinant anthrax lethal factor at 1 mM after 30 mins by fluorescence assay2011Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2
Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1824265Inhibition of recombinant VIM-1 (unknown origin) using fluorocillin as substrate at 3 uM incubated for 30 mins by fluorescence based assay2022European journal of medicinal chemistry, Jan-15, Volume: 228Nitroxoline and its derivatives are potent inhibitors of metallo-β-lactamases.
AID1824260Inhibition of recombinant NDM-1 (unknown origin) using fluorocillin as substrate at 30 uM incubated for 30 mins by fluorescence based assay2022European journal of medicinal chemistry, Jan-15, Volume: 228Nitroxoline and its derivatives are potent inhibitors of metallo-β-lactamases.
AID566699Inhibition of mushroom tyrosinase at 1 mM after 10 mins2011Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2
Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID566704Inhibition of human recombinant MMP3 at 1 mM after 30 mins2011Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2
Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID566702Inhibition of human recombinant MMP1 at 1 mM after 30 mins2011Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2
Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1824266Inhibition of recombinant IMP-1 (unknown origin) using fluorocillin as substrate at 30 uM incubated for 30 mins by fluorescence based assay2022European journal of medicinal chemistry, Jan-15, Volume: 228Nitroxoline and its derivatives are potent inhibitors of metallo-β-lactamases.
AID1824262Inhibition of recombinant NDM-1 (unknown origin) using fluorocillin as substrate at 3 uM incubated for 30 mins by fluorescence based assay2022European journal of medicinal chemistry, Jan-15, Volume: 228Nitroxoline and its derivatives are potent inhibitors of metallo-β-lactamases.
AID1451100Inhibition of Serratia marcescens IMP1 expressed in Escherichia coli BL21(DE3) at 50 uM using chromacef as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by HTS assay relative to control2017Journal of medicinal chemistry, 09-14, Volume: 60, Issue:17
Dipicolinic Acid Derivatives as Inhibitors of New Delhi Metallo-β-lactamase-1.
AID566705Inhibition of human recombinant MMP8 at 1 mM after 30 mins2011Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2
Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1893771Inhibition of recombinant human QC using H-Gln-AMC hydrobromide as fluorogenic substrate incubated for 6 hrs by fluorometric microplate reader analysis2022ACS medicinal chemistry letters, Sep-08, Volume: 13, Issue:9
2-Amino-1,3,4-thiadiazoles as Glutaminyl Cyclases Inhibitors Increase Phagocytosis through Modification of CD47-SIRPα Checkpoint.
AID566703Inhibition of human recombinant MMP2 at 1 mM after 30 mins2011Journal of medicinal chemistry, Jan-27, Volume: 54, Issue:2
Identifying chelators for metalloprotein inhibitors using a fragment-based approach.
AID1824261Inhibition of recombinant NDM-1 (unknown origin) using fluorocillin as substrate at 10 uM incubated for 30 mins by fluorescence based assay2022European journal of medicinal chemistry, Jan-15, Volume: 228Nitroxoline and its derivatives are potent inhibitors of metallo-β-lactamases.
AID1451102Inhibition of bacterial MBP-fused NDM1 expressed in Escherichia coli BL21(DE3) at 50 uM using chromacef as substrate preincubated for 10 mins followed by substrate addition measured after 20 mins by HTS assay relative to control2017Journal of medicinal chemistry, 09-14, Volume: 60, Issue:17
Dipicolinic Acid Derivatives as Inhibitors of New Delhi Metallo-β-lactamase-1.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2014Biochemistry, Jan-14, Volume: 53, Issue:1
A noncompetitive inhibitor for Mycobacterium tuberculosis's class IIa fructose 1,6-bisphosphate aldolase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (7.69)29.6817
2010's7 (53.85)24.3611
2020's5 (38.46)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.05

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.05 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.69 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.05)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]