Showing Compound Kynurenic acid (FDB022200)

Record Information

Version

1.0

Creation date

2011-09-21 00:09:59 UTC

Update date

2015-10-09 22:28:01 UTC

Primary ID

FDB022200

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Kynurenic acid

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]

CAS Number

492-27-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
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

Predicted Properties

Property	Value	Source
Water Solubility	0.95 g/L	ALOGPS
logP	1.16	ALOGPS
logP	1.58	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	52.32 m³·mol⁻¹	ChemAxon
Polarizability	18.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H7NO3

IUPAC name

4-oxo-1,4-dihydroquinoline-2-carboxylic acid

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)

InChI Key

HCZHHEIFKROPDY-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C1=CC(=O)C2=CC=CC=C2N1

Average Molecular Weight

189.1675

Monoisotopic Molecular Weight

189.042593095

Classification

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monohydroxyquinoline (CHEBI:18344 )
quinolinemonocarboxylic acid (CHEBI:18344 )

Ontology

Dermal

Enteral:

Ingestion

Source:

Endogenous

Biological location:

Tissue and substructures:

Epidermis

Organ and components:

Cell and elements:

Cell:

Fibroblast

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
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

MS/MS

Type	Description	Splash Key	View
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

NMR

Type	Description	View
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