Np mrd loader

Showing NP-Card for Kynurenic acid (NP0000852)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:18:49 UTC
NP-MRD IDNP0000852
Secondary Accession NumbersNone
Natural Product Identification
Common NameKynurenic acid
DescriptionKynurenic 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 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000852 (Kynurenic acid)


  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
Download

3D MOL for NP0000852 (Kynurenic acid)

HMDB0000715
     RDKit          3D
Kynurenic acid
 21 22  0  0  0  0  0  0  0  0999 V2000
    3.3355   -1.7534    0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1360   -0.6215    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    0.1022   -0.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639   -0.1445    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045    1.0893   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883    1.5033   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    2.6244   -1.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693    0.7233   -0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1758    1.1457   -0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2210    0.3440    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9070   -0.8997    0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061   -1.3035    0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631   -0.5189    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7296   -0.9026    0.4066 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0562   -0.2461   -0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459    1.6889   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334    2.1085   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2494    0.6621   -0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7423   -1.4991    0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -2.2576    1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505   -1.8447    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14  4  1  0
 13  8  1  0
  3 15  1  0
  5 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
 14 21  1  0
M  END
Download

3D SDF for NP0000852 (Kynurenic acid)


  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>
NP0000852

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000852 (Kynurenic acid)

HMDB0000715
     RDKit          3D
Kynurenic acid
 21 22  0  0  0  0  0  0  0  0999 V2000
    3.3355   -1.7534    0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1360   -0.6215    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    0.1022   -0.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639   -0.1445    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045    1.0893   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883    1.5033   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    2.6244   -1.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693    0.7233   -0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1758    1.1457   -0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2210    0.3440    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9070   -0.8997    0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061   -1.3035    0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631   -0.5189    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7296   -0.9026    0.4066 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0562   -0.2461   -0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459    1.6889   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334    2.1085   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2494    0.6621   -0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7423   -1.4991    0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -2.2576    1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505   -1.8447    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14  4  1  0
 13  8  1  0
  3 15  1  0
  5 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
 14 21  1  0
M  END
Download

PDB for NP0000852 (Kynurenic acid)

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
Download

3D PDB for NP0000852 (Kynurenic acid)

COMPND    HMDB0000715
HETATM    1  O1  UNL     1       3.335  -1.753   0.670  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.136  -0.622   0.158  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.233   0.102  -0.230  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.764  -0.145   0.006  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.504   1.089  -0.550  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.188   1.503  -0.675  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.081   2.624  -1.179  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.869   0.723  -0.263  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.176   1.146  -0.393  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.221   0.344   0.028  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.907  -0.900   0.586  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.606  -1.304   0.707  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.563  -0.519   0.294  1.00  0.00           C  
HETATM   14  N1  UNL     1       0.730  -0.903   0.407  1.00  0.00           N  
HETATM   15  H1  UNL     1       5.056  -0.246  -0.673  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.346   1.689  -0.868  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.433   2.109  -0.824  1.00  0.00           H  
HETATM   18  H4  UNL     1      -4.249   0.662  -0.068  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.742  -1.499   0.903  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.395  -2.258   1.137  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.951  -1.845   0.830  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5    5   14
CONECT    5    6   16
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10   17
CONECT   10   11   11   18
CONECT   11   12   19
CONECT   12   13   13   20
CONECT   13   14
CONECT   14   21
END
Download

SMILES for NP0000852 (Kynurenic acid)

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

INCHI for NP0000852 (Kynurenic acid)

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)
Download
View in JSmol
Synonyms
ValueSource
4-Hydroxy-2-chinolincarbonsaeureChEBI
4-Hydroxy-2-quinolinecarboxylic acidChEBI
4-Hydroxyquinaldic acidChEBI
4-Hydroxyquinaldinic acidChEBI
KynurenateChEBI
KynurensaeureChEBI
4-Hydroxy-2-quinolinecarboxylateGenerator
4-HydroxyquinaldateGenerator
4-HydroxyquinaldinateGenerator
2-Carboxy-4-hydroxyquinolineHMDB
4-Hydroxy-quinaldateHMDB
4-Hydroxy-quinaldic acidHMDB
4-Hydroxyquinoline-2-carboxylateHMDB
4-Hydroxyquinoline-2-carboxylic acidHMDB
Quinurenic acidHMDB
Acid, kynurenicHMDB
Chemical FormulaC10H7NO3
Average Mass189.1675 Da
Monoisotopic Mass189.04259 Da
IUPAC Name4-oxo-1,4-dihydroquinoline-2-carboxylic acid
Traditional Nameacid, kynurenic
CAS Registry Number492-27-3
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 KeyHCZHHEIFKROPDY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Ephedra pachycladaLOTUS Database
Ephedra pachyclada ssp.sinaicaKNApSAcK Database
Ephedra transitoriaLOTUS Database
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tripterygium wilfordiiKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point280 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.95 g/LALOGPS
logP1.16ALOGPS
logP1.58ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity52.32 m³·mol⁻¹ChemAxon
Polarizability18.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000715
DrugBank IDDB11937
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022200
KNApSAcK IDC00026453
Chemspider ID3712
KEGG Compound IDC01717
BioCyc IDKYNURENATE
BiGG ID38234
Wikipedia LinkKynurenic_acid
METLIN ID5683
PubChem Compound3845
PDB IDNot Available
ChEBI ID18344
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. Milart P, Sikorski R: [Kynurenic acid concentration in blood and urine during normal pregnancy]. Ginekol Pol. 1998 Dec;69(12):968-73. [PubMed:10224760 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. Muller N, Schwarz M: Schizophrenia as an inflammation-mediated dysbalance of glutamatergic neurotransmission. Neurotox Res. 2006 Oct;10(2):131-48. [PubMed:17062375 ]