MiMeDB: Showing metabocard for Kynurenic acid (MMDBc0000536)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:59 UTC

Update Date

2024-04-30 19:32:52 UTC

Metabolite ID

MMDBc0000536

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>
MMDBc0000536

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₀H₇NO₃

Average Mass

189.1675

Monoisotopic Mass

189.042593095

IUPAC Name

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

Traditional Name

acid, kynurenic

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
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)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Fibroblasts
Placenta
Prostate
Urine

Tissue Locations

Brain
Epidermis
Fibroblasts
Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192123	Kynurenine--oxoglutarate transaminase 1	Enzyme	Q16773	Homo sapiens
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo sapiens
MMDBp0195726	Kynurenine--oxoglutarate transaminase 3	Enzyme	Q6YP21	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001535	4-(2-Aminophenyl)-2,4-dioxobutanoic acid	Water	Not Available		VMH	15016471 16008534
MMDBr0003964	Oxoglutaric acid	L-Glutamic acid	Cysteine conjugate-beta lyase, cytoplasmic		VMH	10756023
MMDBr0003965	Oxoglutaric acid	L-Glutamic acid	Aminoadipate aminotransferase		VMH	10756023
MMDBr0005574	Oxoglutaric acid	Oxoglutaric acid	Solute carrier family 22 (organic anion transporter), member 6		VMH	30371894
MMDBr0005575	Kynurenic acid	Kynurenic acid	Not Available		VMH	30371894
MMDBr0017542	alpha-Ketoglutarate	Water	Aromatic amino acid aminotransferase 2	Amine group addition	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Anemia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	12964115
Convulsion		Association	Human Cerebrospinal Fluid (CSF)	HMDB	12964115
Malaria		Association	Human Cerebrospinal Fluid (CSF)	HMDB	12964115
Malaria	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	11865422
Schizophrenia	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	26952797
Tuberculous meningitis		Association	Human Cerebrospinal Fluid (CSF)	HMDB	12964115
Uremia	Increased	Association	Human Blood	HMDB	22626821
Eosinophilic esophagitis	Decreased	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis	Increased	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.23		0.18	8.40	uM	Not Specified	Not Specified	Anemia	HMDB	12964115
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.05		0.02	0.10	uM	Not Specified	Not Specified	Convulsions	HMDB	12964115
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.05		0.01	0.25	uM	Not Specified	Not Specified	Malaria	HMDB	12964115
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.06		0.06	0.07	uM	Adult (>18 years old)	Not Specified	Malaria	HMDB	11865422
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.21		0.2	0.3	uM	Not Specified	Not Specified	Malaria	HMDB	12964115
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00133	0.00009			uM	Adult (>18 years old)	Male	Schizophrenia	HMDB	26952797
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.07		0.0	34.1	uM	Not Specified	Not Specified	Tuberculous meningitis	HMDB	12964115
Human Blood	Detected and Quantified	0.80	0.40			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified	<5.291				uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.001		0.0009	0.0011	uM	Adult (>18 years old)	Male	Normal	HMDB	16434056
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00106	0.00007			uM	Adult (>18 years old)	Male	Normal	HMDB	26952797
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0019		0.0017	0.0021	uM	Adult (>18 years old)	Female	Normal	HMDB	16434056
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0040	0.00014			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	16088227
Human Blood	Detected and Quantified	0.023	0.010			uM	Adult (>18 years old)	Both	Normal	HMDB	8634758
Human Blood	Detected and Quantified	0.03	0.007			uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.07		0.06	0.08	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	11865422
Human Urine	Detected and Quantified			0.62	0.86	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.73	1.1	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified	1.6		0.8	4.2	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	2.6		0.9	4.1	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	1.881	0.513			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	20.976	3.813			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	16.508				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.232	0.546			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	1.34	0.30			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	1.53		0.66	4.13	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22827565
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22148915
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000715

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

References

Synthesis Reference

Not Available

General References

Bapurao S, Krishnaswamy K: Vitamin B6 nutritional status of pellagrins and their leucine tolerance. Am J Clin Nutr. 1978 May;31(5):819-24. doi: 10.1093/ajcn/31.5.819. [PubMed:206127 ]
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. doi: 10.1016/0022-510x(92)90191-m. [PubMed:1385624 ]
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. doi: 10.1093/brain/115.5.1249. [PubMed:1422788 ]
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. doi: 10.1016/0003-2697(90)90309-w. [PubMed:2339792 ]
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. doi: 10.1111/j.1471-4159.1989.tb02552.x. [PubMed:2521895 ]
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. doi: 10.1111/j.1471-4159.1988.tb04852.x. [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. doi: 10.1016/0006-8993(88)90815-3. [PubMed:3409000 ]
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. doi: 10.1016/0024-3205(96)00173-7. [PubMed:8637415 ]
Milart P, Sikorski R: [Kynurenic acid concentration in blood and urine during normal pregnancy]. Ginekol Pol. 1998 Dec;69(12):968-73. [PubMed:10224760 ]
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. doi: 10.1086/339009. Epub 2002 Feb 14. [PubMed:11865422 ]
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. doi: 10.1016/s1570-0232(02)00572-x. [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. doi: 10.1034/j.1600-0404.2003.00076.x. [PubMed:12757473 ]
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. doi: 10.1086/377583. Epub 2003 Sep 9. [PubMed:12964115 ]
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. doi: 10.1159/000086295. [PubMed:16088227 ]
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. doi: 10.1007/s00296-005-0057-4. Epub 2005 Oct 12. [PubMed:16220290 ]
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. doi: 10.1016/j.jpsychires.2005.12.001. Epub 2006 Jan 24. [PubMed:16434056 ]
Muller N, Schwarz M: Schizophrenia as an inflammation-mediated dysbalance of glutamatergic neurotransmission. Neurotox Res. 2006 Oct;10(2):131-48. doi: 10.1007/BF03033242. [PubMed:17062375 ]
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 ]
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 ]

Showing metabocard for Kynurenic acid (MMDBc0000536)

MOL for #<Metabolite:0x00007fd100009140>

3D MOL for #<Metabolite:0x00007fd100009140>

3D SDF for #<Metabolite:0x00007fd100009140>

3D-SDF for #<Metabolite:0x00007fd100009140>

PDB for #<Metabolite:0x00007fd100009140>

3D PDB for #<Metabolite:0x00007fd100009140>

SMILES for #<Metabolite:0x00007fd100009140>

INCHI for #<Metabolite:0x00007fd100009140>

Structure for #<Metabolite:0x00007fd100009140>

3D Structure for #<Metabolite:0x00007fd100009140>