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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:56:00 UTC

HMDB ID

HMDB0000715

Secondary Accession Numbers

HMDB00715

Metabolite Identification

Common 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 ). KYNA has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652305271900172D          

 14 15  0  0  0  0            999 V2000
   15.0250   -4.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0250   -3.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2780   -4.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2780   -2.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5407   -4.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5407   -3.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1127   -4.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8267   -4.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1127   -3.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8267   -2.9319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8267   -5.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3987   -2.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6847   -3.3452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3987   -2.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
  7  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  2  0  0  0  0
  9 12  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000715

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC(=O)C2=CC=CC=C2N1

> <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

> <FORMULA>
C10H7NO3

> <MOLECULAR_WEIGHT>
189.1675

> <EXACT_MASS>
189.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
18.04775467429836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-oxo-1,4-dihydroquinoline-2-carboxylic acid

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
1.5775564513333333

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.430451481237121

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1660666326673232

> <JCHEM_PKA_STRONGEST_BASIC>
-4.369517156660836

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
52.324000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acid, kynurenic

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      28.047  -7.816   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.047  -6.211   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.652  -8.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.652  -5.422   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.276  -7.782   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.276  -6.244   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.610  -7.782   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.943  -8.551   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.610  -6.244   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      23.943  -5.473   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      23.943 -10.092   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      21.278  -5.473   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      19.945  -6.244   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      21.278  -3.935   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    8                                                  
CONECT    6    4    5   10                                                  
CONECT    7    8    9                                                       
CONECT    8    7    5   11                                                  
CONECT    9    7   12   10                                                  
CONECT   10    6    9                                                       
CONECT   11    8                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	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

Chemical Formula

C₁₀H₇NO₃

Average Molecular Weight

189.1675

Monoisotopic Molecular Weight

189.042593095

IUPAC Name

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

Traditional Name

acid, kynurenic

CAS Registry Number

492-27-3

SMILES

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

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

Chemical Taxonomy

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

Physiological effect

Health effect

Observation

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)
Coma (HMDB: HMDB0000715)

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000715)
Psychosis (HMDB: HMDB0000715)

Tuberculous meningitis (HMDB: HMDB0000715)

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0000715)
Uremia (HMDB: HMDB0000715)
Chronic kidney disease (HMDB: HMDB0000715)

Circulatory system disorder

Blood and lymphatic system disorder

Erythrocytic disorder

Malaria (HMDB: HMDB0000715)

Anemia

Anemia (HMDB: HMDB0000715)

Cardiac disorder

Cardiovascular disease (HMDB: HMDB0000715)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8634758)
Cerebrospinal Fluid (CSF) (PMID: 16434056)
Cerebrospinal fluid (HMDB: HMDB0000715)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000715)

Fibroblasts (HMDB: HMDB0000715)

Organ

Tissue

Epithelium

Epidermis (HMDB: HMDB0000715)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27609529)

Cellular substructure

Cytoplasm (HMDB: HMDB0000715)
Extracellular (HMDB: HMDB0000715)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0000715)

Enteral

Ingestion (HMDB: HMDB0000715)

Source

Exogenous

Exogenous (HMDB: HMDB0000715)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000715)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (HMDB: HMDB0000715)
Tryptophan Metabolism (HMDB: HMDB0000715)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000715)

Biomarker

Uremia (MarkerDB: MDB00000232)
Malaria (MarkerDB: MDB00000232)

Neuroprotective agent (HMDB: HMDB0000715)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antinicotinic agent (HMDB: HMDB0000715)

Biological role

Human metabolite (HMDB: HMDB0000715)
NMDA receptor antagonist (HMDB: HMDB0000715)
G-protein-coupled receptor agonist (HMDB: HMDB0000715)
Waste product (PMID: 35448883)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	280 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	137.301	30932474
[M+H]+	Baker	140.987	30932474
[M+H]+	MetCCS_train_pos	136.997	30932474
[M-H]-	Not Available	134.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000328
[M+H]+	Not Available	137.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000328

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.311	31661259
DarkChem	[M-H]-	140.89	31661259
AllCCS	[M+H]+	139.198	32859911
AllCCS	[M-H]-	137.758	32859911
DeepCCS	[M+H]+	132.691	30932474
DeepCCS	[M-H]-	130.219	30932474
DeepCCS	[M-2H]-	165.726	30932474
DeepCCS	[M+Na]+	141.104	30932474
AllCCS	[M+H]+	139.2	32859911
AllCCS	[M+H-H2O]+	134.7	32859911
AllCCS	[M+NH4]+	143.4	32859911
AllCCS	[M+Na]+	144.6	32859911
AllCCS	[M-H]-	137.8	32859911
AllCCS	[M+Na-2H]-	137.8	32859911
AllCCS	[M+HCOO]-	138.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Kynurenic acid	OC(=O)C1=CC(=O)C2=CC=CC=C2N1	2487.0	Standard polar	33892256
Kynurenic acid	OC(=O)C1=CC(=O)C2=CC=CC=C2N1	1782.3	Standard non polar	33892256
Kynurenic acid	OC(=O)C1=CC(=O)C2=CC=CC=C2N1	2168.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Kynurenic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(=O)C2=CC=CC=C2[NH]1	2044.7	Semi standard non polar	33892256
Kynurenic acid,1TMS,isomer #2	C[Si](C)(C)N1C(C(=O)O)=CC(=O)C2=CC=CC=C21	2103.8	Semi standard non polar	33892256
Kynurenic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(=O)C2=CC=CC=C2N1[Si](C)(C)C	2150.9	Semi standard non polar	33892256
Kynurenic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(=O)C2=CC=CC=C2N1[Si](C)(C)C	2135.8	Standard non polar	33892256
Kynurenic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(=O)C2=CC=CC=C2N1[Si](C)(C)C	2267.1	Standard polar	33892256
Kynurenic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)C2=CC=CC=C2[NH]1	2290.7	Semi standard non polar	33892256
Kynurenic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(C(=O)O)=CC(=O)C2=CC=CC=C21	2319.0	Semi standard non polar	33892256
Kynurenic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	2554.6	Semi standard non polar	33892256
Kynurenic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	2530.4	Standard non polar	33892256
Kynurenic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	2516.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Kynurenic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-1985000000-f1c74ffc481c3d0faaa2	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kynurenic acid GC-MS (2 TMS)	splash10-0159-3895000000-6ba2750c5a9d9754abcc	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kynurenic acid EI-B (Non-derivatized)	splash10-0159-0498000000-3db9df2c3d8456d7ba63	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kynurenic acid GC-EI-TOF (Non-derivatized)	splash10-0159-1985000000-f1c74ffc481c3d0faaa2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kynurenic acid GC-MS (Non-derivatized)	splash10-0159-3895000000-6ba2750c5a9d9754abcc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kynurenic acid GC-EI-TOF (Non-derivatized)	splash10-0159-1895000000-e25b66b0b42d1928cc67	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ga-1900000000-8c67ab2acdc02b88af2b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9740000000-a7c5c056d48055e0d44f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0900000000-7a5c54ced5b83f291e67	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-0900000000-e6b451ee354ed2717160	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-9500000000-887e5157431b2908f31e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0006-1900000000-06f7059894cc245cb344	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0006-0900000000-89a88f44f08b8b68d5c1	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-qTof , Positive-QTOF	splash10-014l-0900000000-3a256522dd8694fe04c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , negative-QTOF	splash10-000f-0900000000-a4b194b85fef656b9b65	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , negative-QTOF	splash10-0006-0900000000-7862c532805b6036dc67	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , negative-QTOF	splash10-0006-0900000000-5fe3171fdaece30b78c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , negative-QTOF	splash10-0006-0900000000-df3b5b36289798800ad8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , negative-QTOF	splash10-0006-0900000000-d4c11672b9479b2cd4b6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , negative-QTOF	splash10-0006-0900000000-89a88f44f08b8b68d5c1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid Linear Ion Trap , negative-QTOF	splash10-0006-0900000000-9c26ffa9c04aa03d60f5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid Linear Ion Trap , negative-QTOF	splash10-0006-0900000000-6a8662ef19d900499a55	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid , negative-QTOF	splash10-0006-0900000000-d69a430b0eb34f38ad54	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , positive-QTOF	splash10-0006-0900000000-d0ef7c769d4985e85667	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , positive-QTOF	splash10-01ox-0900000000-2a593c8017254be4a387	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , positive-QTOF	splash10-01ox-0900000000-59f3559c0b95c9411d2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenic acid LC-ESI-QTOF , positive-QTOF	splash10-02tc-0900000000-57dbbfb8e12c60951d77	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenic acid 10V, Positive-QTOF	splash10-0006-0900000000-878dcda0ee5ec971fa72	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenic acid 20V, Positive-QTOF	splash10-0006-0900000000-92fe5294ec4a771f14e0	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenic acid 40V, Positive-QTOF	splash10-0006-1900000000-fa8b36fb6db8e403b711	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenic acid 10V, Negative-QTOF	splash10-000i-0900000000-9cede81ef6dfc45f5f7a	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenic acid 20V, Negative-QTOF	splash10-000f-0900000000-0d5cf046565b518442d5	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenic acid 40V, Negative-QTOF	splash10-0006-2900000000-2c420ff1e59666527005	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Brain
Epidermis
Fibroblasts
Placenta
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.023 +/- 0.010 uM	Adult (>18 years old)	Both	Normal	8634758	details
Blood	Detected and Quantified	0.03 +/- 0.007 uM	Adult (>18 years old)	Both	Normal	22626821	details
Blood	Detected and Quantified	<5.291 uM	Adult (>18 years old)	Both	Normal	12675874	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00106 +/- 0.00007 uM	Adult (>18 years old)	Male	Normal	26952797	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0040 +/- 0.00014 uM	Adult (>18 years old)	Not Specified	Normal	16088227	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.07 (0.06-0.08) uM	Adult (>18 years old)	Not Specified	Normal	11865422	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0019 (0.0017-0.0021) uM	Adult (>18 years old)	Female	Normal	16434056	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.001 (0.0009-0.0011) uM	Adult (>18 years old)	Male	Normal	16434056	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	5.232 +/- 0.546 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	1.34 +/- 0.30 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	16.508 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.73-1.1 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.53 (0.66-4.13) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Geigy Scientific ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22148915	details
Urine	Detected and Quantified	1.6 (0.8-4.2) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.62-0.86 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	4.94 (3.81-7.06) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	2.6(0.9-4.1) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.80 +/- 0.40 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00133 +/- 0.00009 uM	Adult (>18 years old)	Male	Schizophrenia	26952797	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.06 (0.06-0.07) uM	Adult (>18 years old)	Not Specified	Malaria	11865422	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.23 (0.18-8.40) uM	Not Specified	Not Specified	Anemia	12964115	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.21 (0.2-0.3) uM	Not Specified	Not Specified	Malaria	12964115	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.07 (0.0-34.1) uM	Not Specified	Not Specified	Tuberculous meningitis	12964115	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.05 (0.02-0.10) uM	Not Specified	Not Specified	Convulsions	12964115	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.05 (0.01-0.25) uM	Not Specified	Not Specified	Malaria	12964115	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Enthesitis-related arthritis	27786174	details
Urine	Detected and Quantified	1.881 +/- 0.513 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	20.976 +/- 3.813 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	117.043 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	22148915	details

Associated Disorders and Diseases

Disease References

Uremia
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. [PubMed:22626821 ]
Malaria
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. [PubMed:11865422 ] 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. [PubMed:12964115 ]
Anemia
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. [PubMed:12964115 ]
Tuberculous meningitis
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. [PubMed:12964115 ]
Convulsion
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. [PubMed:12964115 ]
Schizophrenia
Nilsson-Todd LK, Nordin C, Jonsson EG, Skogh E, Erhardt S: Cerebrospinal fluid kynurenic acid in male patients with schizophrenia - correlation with monoamine metabolites. Acta Neuropsychiatr. 2007 Feb;19(1):45-52. doi: 10.1111/j.1601-5215.2006.00170.x. [PubMed:26952797 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Colorectal cancer
Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28. [PubMed:22148915 ] Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

248310 (Malaria)
181500 (Schizophrenia)
266600 (Crohn's disease)
610247 (Eosinophilic esophagitis)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB11937

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18344

Food Biomarker Ontology

Not Available

VMH ID

KYNATE

MarkerDB ID

MDB00000232

Good Scents ID

Not Available

References

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:19212411 ]
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. [PubMed:11865422 ]
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. [PubMed: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. [PubMed:1422788 ]
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16434056 ]
Milart P, Sikorski R: [Kynurenic acid concentration in blood and urine during normal pregnancy]. Ginekol Pol. 1998 Dec;69(12):968-73. [PubMed: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. [PubMed: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. [PubMed:3409000 ]
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. [PubMed: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. [PubMed: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. [PubMed:8637415 ]
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. [PubMed:1385624 ]
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. [PubMed:16088227 ]
Muller N, Schwarz M: Schizophrenia as an inflammation-mediated dysbalance of glutamatergic neurotransmission. Neurotox Res. 2006 Oct;10(2):131-48. [PubMed:17062375 ]
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. [PubMed:22626821 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Kynurenine--oxoglutarate transaminase 1

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:: CCBL1
Uniprot ID:: Q16773
Molecular weight:: 47874.765

Enzyme Details

2. Aryl hydrocarbon receptor

General function:: Involved in transcription regulator activity
Specific function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:: AHR
Uniprot ID:: P35869
Molecular weight:: 96146.7

Enzyme Details

3. Kynurenine--oxoglutarate transaminase 3

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:: CCBL2
Uniprot ID:: Q6YP21
Molecular weight:: 51399.855

Showing metabocard for Kynurenic acid (HMDB0000715)

MOL for HMDB0000715 (Kynurenic acid)

3D MOL for HMDB0000715 (Kynurenic acid)

3D SDF for HMDB0000715 (Kynurenic acid)

3D-SDF for HMDB0000715 (Kynurenic acid)

PDB for HMDB0000715 (Kynurenic acid)

3D PDB for HMDB0000715 (Kynurenic acid)

SMILES for HMDB0000715 (Kynurenic acid)

INCHI for HMDB0000715 (Kynurenic acid)

Structure for HMDB0000715 (Kynurenic acid)

3D Structure for HMDB0000715 (Kynurenic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes