Kynurenic Acid
PubChem CID: 3845
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| Compound Synonyms | kynurenic acid, 4-Hydroxyquinoline-2-carboxylic acid, 492-27-3, 13593-94-7, Transtorine, 4-oxo-1,4-dihydroquinoline-2-carboxylic acid, Kynurenate, Quinurenic acid, 1,4-Dihydro-4-oxoquinoline-2-carboxylic acid, 4-Hydroxyquinaldic acid, Kinurenic acid, Kynuronic acid, 4-Hydroxy-2-quinolincarboxylic acid, 2-Quinolinecarboxylic acid, 4-hydroxy-, 4-Hydroxy-2-quinolinecarboxylic acid, 4-Hydroxyquinaldinic acid, 4-oxo-1H-quinoline-2-carboxylic acid, Quinaldic acid, 4-hydroxy-, NSC 58973, KYNA, Kynurensaeure, CCRIS 4428, kynurenic-acid, CHEBI:18344, EINECS 207-751-5, NSC-58973, 4-Hydroxyquinaldate, 2-Carboxy-4-hydroxyquinoline, 4-hydroxy-Quinaldate, 4-Hydroxyquinaldinate, H030S2S85J, NSC58973, 4-hydroxy-Quinaldic acid, MFCD00006753, MFCD03197717, KYNURENIC ACID [MI], CHEMBL299155, DTXSID8075417, 4-Hydroxy-2-chinolincarbonsaeure, Acid, Kynurenic, 4-hydroxyquinoline-2-carboxylate, SR-01000075455, UNII-H030S2S85J, 4-Hydroxy-2-quinolinecarboxylic acid, 4-Hydroxy-quinaldic acid, 2-Carboxy-4-hydroxyquinoline, KYA, 4Hydroxyquinaldic acid, Spectrum_001116, Tocris-0223, 4Hydroxyquinaldinic acid, Quinaldic acid, 4hydroxy, Spectrum2_001342, Spectrum3_001390, Spectrum4_000814, Spectrum5_001318, Lopac-K-3375, Quinurenic acid, Kynurenate, Kynurenic acid (Standard), Biomol-NT_000229, bmse000410, Kynurenic acid, >=98%, 4-Oxo-1,4-dihydro-quinoline-2-carboxylic acid, Lopac0_000716, Oprea1_032085, SCHEMBL22979, BSPBio_002980, KBioGR_001327, KBioSS_001596, MLS002172436, DivK1c_000309, SPECTRUM1500688, 1,4-DIHYDRO-4-OXOQUINOLINE-2-CARBOXYLICACID, SPBio_001523, BPBio1_001350, GTPL2918, DTXCID5040675, 4Hydroxyquinoline2carboxylic acid, BDBM81975, HCZHHEIFKROPDY-UHFFFAOYSA-, HMS500P11, KBio1_000309, KBio2_001596, KBio2_004164, KBio2_006732, KBio3_002200, Quinaldic acid, 4hydroxy (8CI), NINDS_000309, 4-hydroxyquinolinium-2-carboxylate, HMS1736A10, HMS1921C20, HMS2269G22, HMS3262O13, HMS3266C13, HMS3411C03, HMS3675C03, HMS3885D20, Quinaldic acid, 4-hydroxy-(8CI), 2Quinolinecarboxylic acid, 4hydroxy, ALBB-014130, Kynurenic acid - Bio-X trade mark, Tox21_500716, BBL027606, BDBM50233945, CCG-39280, HB0362, PDSP1_000132, PDSP2_000131, s4719, STL294769, STL301826, 4-Hydroxy-quinoline-2-carboxylic acid, AKOS000118368, AKOS000277721, CS-W020664, DB11937, FK24817, GS-3763, HY-100806R, HY-W110662, LP00716, SB67494, SB67643, SDCCGSBI-0050694.P003, IDI1_000309, NSC_5280455, SMP1_000172, NCGC00015581-01, NCGC00015581-02, NCGC00015581-03, NCGC00015581-04, NCGC00015581-05, NCGC00015581-06, NCGC00015581-07, NCGC00015581-08, NCGC00015581-09, NCGC00015581-14, NCGC00024505-01, NCGC00024505-02, NCGC00024505-03, NCGC00024505-04, NCGC00024505-05, NCGC00024505-06, NCGC00024505-07, NCGC00261401-01, BK166244, CAS_492-27-3, SMR000112310, SY152524, DB-008408, DB-081634, HY-100806, 4-oxo-1,4-dihydroquinoline-2-carboxylicacid, CS-0168103, EU-0100716, H0303, NS00014859, EN300-13998, C01717, K 3375, S12153, AE-641/00585057, Q642217, SR-01000075455-1, SR-01000075455-3, BRD-K85872723-001-15-9, Z94602408, 6F535706-B297-4930-A3FC-7A2823830118, 207-751-5, 816-062-4, InChI=1/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) |
|---|---|
| Topological Polar Surface Area | 66.4 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 14.0 |
| Pathway Kegg Map Id | map00380 |
| 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] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 308.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Enzyme Uniprot Id | Q16773, Q6YP21 |
| Uniprot Id | Q16773, Q6YP21, Q7TSF2, Q9R1M7, P35439, P19490, Q63273, Q62795, n.a., Q03164, Q99714, B2RXH2, P33261, P00352, P10253, P28482, P15917, P15428, P08482, P06280, O75164, Q96KQ7, O15648, P83916, Q9UIF8, P05177, Q9UBT6, Q9HC97, O75496, Q9NUW8, P35869, P36544, Q16445, Q8TCU5, Q33BM1, Q9NPD5, Q9Y6L6, P27695, P0DTD1 |
| Iupac Name | 4-oxo-1H-quinoline-2-carboxylic acid |
| Prediction Hob | 1.0 |
| Class | Quinolines and derivatives |
| Target Id | NPT149, NPT48, NPT1038, NPT213, NPT94, NPT60, NPT282, NPT151, NPT501, NPT208, NPT1627, NPT155, NPT410 |
| Xlogp | 1.3 |
| Superclass | Organoheterocyclic compounds |
| Subclass | Quinoline carboxylic acids |
| Molecular Formula | C10H7NO3 |
| Prediction Swissadme | 0.0 |
| Inchi Key | HCZHHEIFKROPDY-UHFFFAOYSA-N |
| Fcsp3 | 0.0 |
| Logs | -2.585 |
| Rotatable Bond Count | 1.0 |
| State | Solid |
| Logd | 0.488 |
| Synonyms | 2-Carboxy-4-hydroxyquinoline, 4-Hydroxy-2-chinolincarbonsaeure, 4-Hydroxy-2-quinolinecarboxylate, 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, Kynurenic acid, Kynurensaeure, Quinurenic acid, 4-Hydroxy-2-quinolinecarboxylic acid, 4-Hydroxy-quinaldate, 4-Hydroxy-quinaldic acid, Acid, kynurenic |
| Substituent Name | Quinoline-2-carboxylic acid, Dihydroquinolone, Dihydroquinoline, Pyridine carboxylic acid or derivatives, Pyridine carboxylic acid, Benzenoid, Pyridine, Heteroaromatic compound, Vinylogous amide, Azacycle, Monocarboxylic acid or derivatives, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Aromatic alcohol, Organooxygen compound, Organonitrogen compound, Carbonyl group, Aromatic heteropolycyclic compound |
| Compound Name | Kynurenic Acid |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 189.043 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 189.043 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 189.17 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Esol | -3.189025428571429 |
| Inchi | 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) |
| Smiles | C1=CC=C2C(=C1)C(=O)C=C(N2)C(=O)O |
| Nring | 2.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Quinoline carboxylic acids |
- 1. Outgoing r'ship
FOUND_INto/from Hansenia Forbesii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Hansenia Weberbaueriana (Plant) Rel Props:Source_db:cmaup_ingredients - 3. Outgoing r'ship
FOUND_INto/from Ostericum Grosseserratum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Taraxacum Borealisinense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Taraxacum Coreanum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 6. Outgoing r'ship
FOUND_INto/from Taraxacum Mongolicum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 7. Outgoing r'ship
FOUND_INto/from Taraxacum Officinale (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 8. Outgoing r'ship
FOUND_INto/from Taraxacum Platycarpum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all