| Record Information |
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| Version | 2.0 |
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| Creation Date | 2014-08-29 05:48:00 UTC |
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| Update Date | 2014-12-24 20:26:40 UTC |
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| Accession Number | T3D4160 |
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| Identification |
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| Common Name | Kynurenic acid |
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| Class | Small Molecule |
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| Description | Kynurenic acid is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
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. (1, 2). |
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| Compound Type | - Amide
- Ester
- Food Toxin
- Metabolite
- Natural Compound
- Organic Compound
- Uremic Toxin
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| Chemical Structure | |
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| Synonyms | | Synonym | | 2-Carboxy-4-hydroxyquinoline | | 4-Hydroxy-2-Quinolinecarboxylic acid | | 4-Hydroxy-Quinaldate | | 4-Hydroxy-Quinaldic acid | | 4-Hydroxyquinaldate | | 4-Hydroxyquinaldic acid | | 4-Hydroxyquinaldinate | | 4-Hydroxyquinaldinic acid | | 4-Hydroxyquinoline-2-carboxylate | | 4-Hydroxyquinoline-2-carboxylic acid | | Kynurenate | | Quinurenic acid |
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| Chemical Formula | C10H7NO3 |
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| Average Molecular Mass | 189.168 g/mol |
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| Monoisotopic Mass | 189.043 g/mol |
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| CAS Registry Number | 492-27-3 |
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| IUPAC Name | 4-oxo-1,4-dihydroquinoline-2-carboxylic acid |
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| Traditional Name | acid, kynurenic |
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| SMILES | OC(=O)C1=CC(=O)C2=CC=CC=C2N1 |
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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 | InChIKey=HCZHHEIFKROPDY-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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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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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Endogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | - Brain
- Epidermis
- Fibroblasts
- Prostate
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| Pathways | |
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| Applications | |
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| Biological Roles | |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 280°C | | Boiling Point | Not Available | | Solubility | Not Available | | LogP | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0159-1985000000-f1c74ffc481c3d0faaa2 | 2014-06-16 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0159-3895000000-6ba2750c5a9d9754abcc | 2014-06-16 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0159-0498000000-3db9df2c3d8456d7ba63 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-1985000000-f1c74ffc481c3d0faaa2 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0159-3895000000-6ba2750c5a9d9754abcc | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-1895000000-e25b66b0b42d1928cc67 | 2017-09-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-02ga-1900000000-8c67ab2acdc02b88af2b | 2016-09-22 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9740000000-a7c5c056d48055e0d44f | 2017-10-06 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0900000000-7a5c54ced5b83f291e67 | 2012-07-24 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-0900000000-e6b451ee354ed2717160 | 2012-07-24 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9500000000-887e5157431b2908f31e | 2012-07-24 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0006-1900000000-06f7059894cc245cb344 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0006-0900000000-89a88f44f08b8b68d5c1 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-014l-0900000000-3a256522dd8694fe04c0 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000f-0900000000-a4b194b85fef656b9b65 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-7862c532805b6036dc67 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-5fe3171fdaece30b78c8 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-df3b5b36289798800ad8 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-d4c11672b9479b2cd4b6 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-89a88f44f08b8b68d5c1 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0006-0900000000-9c26ffa9c04aa03d60f5 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0006-0900000000-6a8662ef19d900499a55 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0006-0900000000-d69a430b0eb34f38ad54 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0006-0900000000-d0ef7c769d4985e85667 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01ox-0900000000-2a593c8017254be4a387 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01ox-0900000000-59f3559c0b95c9411d2c | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-02tc-0900000000-57dbbfb8e12c60951d77 | 2017-09-14 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0900000000-878dcda0ee5ec971fa72 | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0900000000-92fe5294ec4a771f14e0 | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-1900000000-fa8b36fb6db8e403b711 | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-9cede81ef6dfc45f5f7a | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000f-0900000000-0d5cf046565b518442d5 | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-2900000000-2c420ff1e59666527005 | 2016-09-12 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | Not Available | 2014-09-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | Not Available | 2016-10-22 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | Not Available | 2016-10-22 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | 2012-12-05 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Endogenous, Ingestion, Dermal (contact) |
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| Mechanism of Toxicity | Uremic toxins such as kynurenic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (4). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (5). |
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| Metabolism | Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces. |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Naturally produced by the body (endogenous). |
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| Minimum Risk Level | Not Available |
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| Health Effects | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
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| Symptoms | As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. |
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| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB00715 |
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| PubChem Compound ID | 3845 |
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| ChEMBL ID | CHEMBL299155 |
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| ChemSpider ID | 3712 |
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| KEGG ID | C01717 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 18344 |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | KYA |
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| ACToR ID | Not Available |
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| Wikipedia Link | Kynurenic acid |
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| References |
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| Synthesis Reference | Stone, T. W. Development and therapeutic potential of kynurenic acid and kynurenine derivatives for neuroprotection. Trends in Pharmacological Sciences (2000), 21(4), 149-154. |
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| MSDS | Link |
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| General References | - Muller N, Schwarz M: Schizophrenia as an inflammation-mediated dysbalance of glutamatergic neurotransmission. Neurotox Res. 2006 Oct;10(2):131-48. [17062375 ]
- Kepplinger B, Baran H, Kainz A, Ferraz-Leite H, Newcombe J, Kalina P: Age-related increase of kynurenic acid in human cerebrospinal fluid - IgG and beta2-microglobulin changes. Neurosignals. 2005;14(3):126-35. [16088227 ]
- Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [22626821 ]
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. [22419041 ]
- Parada-Turska J, Rzeski W, Zgrajka W, Majdan M, Kandefer-Szerszen M, Turski W: Kynurenic acid, an endogenous constituent of rheumatoid arthritis synovial fluid, inhibits proliferation of synoviocytes in vitro. Rheumatol Int. 2006 Mar;26(5):422-6. Epub 2005 Oct 12. [16220290 ]
- Amirkhani A, Heldin E, Markides KE, Bergquist J: Quantitation of tryptophan, kynurenine and kynurenic acid in human plasma by capillary liquid chromatography-electrospray ionization tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 25;780(2):381-7. [12401365 ]
- Ilzecka J, Kocki T, Stelmasiak Z, Turski WA: Endogenous protectant kynurenic acid in amyotrophic lateral sclerosis. Acta Neurol Scand. 2003 Jun;107(6):412-8. [12757473 ]
- Bapurao S, Krishnaswamy K: Vitamin B6 nutritional status of pellagrins and their leucine tolerance. Am J Clin Nutr. 1978 May;31(5):819-24. [206127 ]
- Nilsson LK, Nordin C, Jonsson EG, Engberg G, Linderholm KR, Erhardt S: Cerebrospinal fluid kynurenic acid in male and female controls - correlation with monoamine metabolites and influences of confounding factors. J Psychiatr Res. 2007 Jan-Feb;41(1-2):144-51. Epub 2006 Jan 24. [16434056 ]
- Milart P, Sikorski R: [Kynurenic acid concentration in blood and urine during normal pregnancy]. Ginekol Pol. 1998 Dec;69(12):968-73. [10224760 ]
- Moroni F, Russi P, Lombardi G, Beni M, Carla V: Presence of kynurenic acid in the mammalian brain. J Neurochem. 1988 Jul;51(1):177-80. [3379401 ]
- Turski WA, Nakamura M, Todd WP, Carpenter BK, Whetsell WO Jr, Schwarcz R: Identification and quantification of kynurenic acid in human brain tissue. Brain Res. 1988 Jun 28;454(1-2):164-9. [3409000 ]
- Medana IM, Hien TT, Day NP, Phu NH, Mai NT, Chu'ong LV, Chau TT, Taylor A, Salahifar H, Stocker R, Smythe G, Turner GD, Farrar J, White NJ, Hunt NH: The clinical significance of cerebrospinal fluid levels of kynurenine pathway metabolites and lactate in severe malaria. J Infect Dis. 2002 Mar 1;185(5):650-6. Epub 2002 Feb 14. [11865422 ]
- Connick JH, Carla V, Moroni F, Stone TW: Increase in kynurenic acid in Huntington's disease motor cortex. J Neurochem. 1989 Mar;52(3):985-7. [2521895 ]
- Swartz KJ, Matson WR, MacGarvey U, Ryan EA, Beal MF: Measurement of kynurenic acid in mammalian brain extracts and cerebrospinal fluid by high-performance liquid chromatography with fluorometric and coulometric electrode array detection. Anal Biochem. 1990 Mar;185(2):363-76. [2339792 ]
- Baran H, Cairns N, Lubec B, Lubec G: Increased kynurenic acid levels and decreased brain kynurenine aminotransferase I in patients with Down syndrome. Life Sci. 1996;58(21):1891-9. [8637415 ]
- Medana IM, Day NP, Salahifar-Sabet H, Stocker R, Smythe G, Bwanaisa L, Njobvu A, Kayira K, Turner GD, Taylor TE, Hunt NH: Metabolites of the kynurenine pathway of tryptophan metabolism in the cerebrospinal fluid of Malawian children with malaria. J Infect Dis. 2003 Sep 15;188(6):844-9. Epub 2003 Sep 9. [12964115 ]
- Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. [1422788 ]
- Beal MF, Matson WR, Storey E, Milbury P, Ryan EA, Ogawa T, Bird ED: Kynurenic acid concentrations are reduced in Huntington's disease cerebral cortex. J Neurol Sci. 1992 Mar;108(1):80-7. [1385624 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [19212411 ]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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