Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:09:59 UTC |
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Update date | 2015-10-09 22:28:01 UTC |
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Primary ID | FDB022200 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Kynurenic acid |
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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] |
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CAS Number | 492-27-3 |
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Structure | |
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Synonyms | Synonym | Source |
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4-Hydroxy-2-chinolincarbonsaeure | ChEBI | 4-Hydroxy-2-quinolinecarboxylic acid | ChEBI | 4-Hydroxyquinaldic acid | ChEBI | 4-Hydroxyquinaldinic acid | ChEBI | Kynurenate | ChEBI | Kynurensaeure | ChEBI | 4-Hydroxy-2-quinolinecarboxylate | Generator | 4-Hydroxyquinaldate | Generator | 4-Hydroxyquinaldinate | Generator | 2-Carboxy-4-hydroxyquinoline | HMDB | 4-Hydroxy-quinaldate | HMDB | 4-Hydroxy-quinaldic acid | HMDB | 4-Hydroxyquinoline-2-carboxylate | HMDB | 4-Hydroxyquinoline-2-carboxylic acid | HMDB | Quinurenic acid | HMDB | Acid, kynurenic | MeSH, HMDB | 4-hydroxy-2-Quinolinecarboxylic acid | hmdb | 4-hydroxy-Quinaldate | hmdb | 4-hydroxy-Quinaldic acid | hmdb | Kynurenic acid | hmdb |
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Predicted Properties | |
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Chemical Formula | C10H7NO3 |
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IUPAC name | 4-oxo-1,4-dihydroquinoline-2-carboxylic acid |
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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) |
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InChI Key | HCZHHEIFKROPDY-UHFFFAOYSA-N |
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Isomeric SMILES | OC(=O)C1=CC(=O)C2=CC=CC=C2N1 |
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Average Molecular Weight | 189.1675 |
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Monoisotopic Molecular Weight | 189.042593095 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Quinolines and derivatives |
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Sub Class | Quinoline carboxylic acids |
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Direct Parent | Quinoline carboxylic acids |
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Alternative Parents | |
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Substituents | - Quinoline-2-carboxylic acid
- Dihydroquinolone
- Dihydroquinoline
- Pyridine carboxylic acid
- Pyridine carboxylic acid or derivatives
- Pyridine
- Benzenoid
- Heteroaromatic compound
- Vinylogous amide
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Azacycle
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Kynurenic acid, non-derivatized, GC-MS Spectrum | splash10-0159-1985000000-f1c74ffc481c3d0faaa2 | Spectrum | GC-MS | Kynurenic acid, 2 TMS, GC-MS Spectrum | splash10-0159-3895000000-6ba2750c5a9d9754abcc | Spectrum | GC-MS | Kynurenic acid, non-derivatized, GC-MS Spectrum | splash10-0159-0498000000-3db9df2c3d8456d7ba63 | Spectrum | GC-MS | Kynurenic acid, non-derivatized, GC-MS Spectrum | splash10-0159-1985000000-f1c74ffc481c3d0faaa2 | Spectrum | GC-MS | Kynurenic acid, non-derivatized, GC-MS Spectrum | splash10-0159-3895000000-6ba2750c5a9d9754abcc | Spectrum | GC-MS | Kynurenic acid, non-derivatized, GC-MS Spectrum | splash10-0159-1895000000-e25b66b0b42d1928cc67 | Spectrum | Predicted GC-MS | Kynurenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-02ga-1900000000-8c67ab2acdc02b88af2b | Spectrum | Predicted GC-MS | Kynurenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9740000000-a7c5c056d48055e0d44f | Spectrum | Predicted GC-MS | Kynurenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Kynurenic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Kynurenic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Kynurenic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0900000000-7a5c54ced5b83f291e67 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-0900000000-e6b451ee354ed2717160 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9500000000-887e5157431b2908f31e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0006-1900000000-06f7059894cc245cb344 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0006-0900000000-89a88f44f08b8b68d5c1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-014l-0900000000-3a256522dd8694fe04c0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000f-0900000000-a4b194b85fef656b9b65 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-7862c532805b6036dc67 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-5fe3171fdaece30b78c8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-df3b5b36289798800ad8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-d4c11672b9479b2cd4b6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-89a88f44f08b8b68d5c1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0006-0900000000-9c26ffa9c04aa03d60f5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0006-0900000000-6a8662ef19d900499a55 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-0006-0900000000-d69a430b0eb34f38ad54 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0006-0900000000-d0ef7c769d4985e85667 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01ox-0900000000-2a593c8017254be4a387 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01ox-0900000000-59f3559c0b95c9411d2c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-02tc-0900000000-57dbbfb8e12c60951d77 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0900000000-878dcda0ee5ec971fa72 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0900000000-92fe5294ec4a771f14e0 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-1900000000-fa8b36fb6db8e403b711 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-9cede81ef6dfc45f5f7a | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000f-0900000000-0d5cf046565b518442d5 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-2900000000-2c420ff1e59666527005 | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 3712 |
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ChEMBL ID | CHEMBL299155 |
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KEGG Compound ID | C01717 |
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Pubchem Compound ID | 3845 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18344 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00715 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 38234 |
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KNApSAcK ID | Not Available |
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HET ID | KYA |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Kynurenic acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Kynurenine--oxoglutarate transaminase 3 | CCBL2 | Q6YP21 | Kynurenine--oxoglutarate transaminase 1 | CCBL1 | Q16773 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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