NP-MRD: Showing NP-Card for Quinolinic acid (NP0001076)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-03 04:19:13 UTC

NP-MRD ID

NP0001076

Natural Product DOI

https://doi.org/10.57994/1674

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinolinic acid

Description

Quinolinic acid, also known as quinolinate, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. It is also classified as a pyridine-2,3-dicarboxylic acid, which is a dicarboxylic acid with a pyridine backbone. Quinolinic acid is a colorless solid. In plants, it is the biosynthetic precursor to nicotine. Quinolinic acid is found in all organisms, from microbes to plants to animals. Quinolinic acid can be biosynthesized via aspartic acid in plants. Oxidation of aspartate by the enzyme aspartate oxidase gives iminosuccinate, containing the two carboxylic acid groups that are found in quinolinic acid. Condensation of iminosuccinate with glyceraldehyde-3-phosphate, mediated by quinolinate synthase, affords quinolinic acid Quinolinic acid is also a downstream product of the kynurenine pathway, which metabolizes the amino acid tryptophan ((PMID: 22678511 ). The kynurenine/tryptophan degradation pathway is important for its production of the coenzyme nicotinamide adenine dinucleotide (NAD+) and produces several neuroactive intermediates including quinolinic acid, kynurenine (KYN), kynurenic acid (KYNA), 3-hydroxykynurenine (3-HK), and 3-hydroxyanthranilic acid (3-HANA). In animals quinolinic acid acts as an NMDA receptor agonist and has a possible role in neurodegenerative disorders (PMID: 22678511 ). It also acts as a neurotoxin, gliotoxin, proinflammatory mediator, and pro-oxidant molecule (PMID: 22248144 ). Quinolinic acid can act as an endogenous brain excitotoxin when released by activated macrophages (PMID: 15013955 ). Within the brain, quinolinic acid is only produced by activated microglia and macrophages. Quinolinic acid is unable to pass through the blood-brain barrier (BBB) and must be produced within the brain by microglial cells or macrophages that have passed the BBB (PMID: 22248144 ). While quinolinic acid cannot pass through the BBB, kynurenic acid, tryptophan and 3-hydroxykynurenine can and can subsequently act as precursors to the production of quinolinic acid in the brain (PMID: 22248144 ). Quinolinic acid has potent neurotoxic effects. Studies have demonstrated that quinolinic acid may be involved in many psychiatric disorders and neurodegenerative diseases in the brain including ALS, Alzheimer’s disease, brain ischemia, Parkinson’s disease, Huntington’s disease and AIDS-dementia. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS. Indeed, levels of quinolinic acid in the CSF of AIDS patients suffering from AIDS-dementia can be up to twenty times higher than normal (PMID: 10936623 ). Quinolinic acid levels are increased in the brains of children infected with a range of bacterial infections of the central nervous system (CNS), of poliovirus patients, and of Lyme disease with CNS involvement patients. In addition, raised quinolinic acid levels have been found in traumatic CNS injury patients, patients suffering from cognitive decline with ageing, hyperammonaemia patients, hypoglycaemia patients, and systemic lupus erythematosus patients. Quinolinic acid has also been detected, but not quantified in, several different foods, such as Ceylon cinnamons, pitanga, Oregon yampahs, red bell peppers, and durians. This could make quinolinic acid a potential biomarker for the consumption of these foods.

Structure

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


  Mrv1652306242117433D          

 17 17  0  0  0  0            999 V2000
   -2.5965   -0.2934   -0.8769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5404   -0.8953   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6379   -2.2611   -1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572   -0.4513   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065   -1.3920   -0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502   -1.0185    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309    0.2812    0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299    1.1508    0.5437 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0424    0.8278    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0304    1.8761    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2200    1.8314   -0.2013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6512    3.1715    0.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8048   -2.9048   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016   -2.4048   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8751   -1.7391    0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413    0.5456    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2547    3.6761    1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9  4  1  0  0  0  0
  3 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 15  1  0  0  0  0
  7 16  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=NC([H])=C([H])C([H])=C1C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)

> <INCHI_KEY>
GJAWHXHKYYXBSV-UHFFFAOYSA-N

> <FORMULA>
C7H5NO4

> <MOLECULAR_WEIGHT>
167.1189

> <EXACT_MASS>
167.021857653

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.34239790996518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridine-2,3-dicarboxylic acid

> <ALOGPS_LOGP>
0.15

> <JCHEM_LOGP>
-1.0261279053302073

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.095867548424451

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.30900716364465675

> <JCHEM_PKA_STRONGEST_BASIC>
5.743217331848265

> <JCHEM_POLAR_SURFACE_AREA>
87.49000000000001

> <JCHEM_REFRACTIVITY>
38.0415

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quinolinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.596  -0.293  -0.877  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.540  -0.895  -0.755  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.638  -2.261  -1.150  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.257  -0.451  -0.290  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.807  -1.392  -0.257  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.050  -1.018   0.179  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.231   0.281   0.578  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.230   1.151   0.544  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.042   0.828   0.114  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.030   1.876   0.131  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.220   1.831  -0.201  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.651   3.172   0.583  0.00  0.00           O+0
HETATM   13  H   UNK     0      -1.805  -2.905  -0.382  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.602  -2.405  -0.586  0.00  0.00           H+0
HETATM   15  H   UNK     0       2.875  -1.739   0.206  0.00  0.00           H+0
HETATM   16  H   UNK     0       3.241   0.546   0.922  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.255   3.676   1.242  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   13                                                       
CONECT    4    2    5    9                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10    4                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   17                                                       
CONECT   13    3                                                            
CONECT   14    5                                                            
CONECT   15    6                                                            
CONECT   16    7                                                            
CONECT   17   12                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
2,3-Pyridinedicarboxylic acid	ChEBI
Pyridine-2,3-dicarboxylate	ChEBI
2,3-Pyridinedicarboxylate	Generator
Pyridine-2,3-dicarboxylic acid	Generator
Quinolinate	Generator
3,4-Pyridinedicarboxylic acid	HMDB
Pyridin-2,3-dicarbonsaeure	HMDB
Pyridine-2,3-carboxylate	HMDB
Quinolinic acid	HMDB

Chemical Formula

C₇H₅NO₄

Average Mass

167.1189 Da

Monoisotopic Mass

167.02186 Da

IUPAC Name

pyridine-2,3-dicarboxylic acid

Traditional Name

quinolinic acid

CAS Registry Number

89-00-9

SMILES

[H]OC(=O)C1=NC([H])=C([H])C([H])=C1C(=O)O[H]

InChI Identifier

InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)

InChI Key

GJAWHXHKYYXBSV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2023-05-18	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	KNApSAcK Database	22123792
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Corydalis yanhusuo	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Nicotiana tabacum	KNApSAcK Database	22123792
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridinedicarboxylic acid (CHEBI:16675 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	190 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.07 g/L	ALOGPS
logP	0.15	ALOGPS
logP	-1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	0.31	ChemAxon
pKa (Strongest Basic)	5.74	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	38.04 m³·mol⁻¹	ChemAxon
Polarizability	14.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000232

DrugBank ID

DB01796

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Quinolinic_acid

METLIN ID

Not Available

PubChem Compound

1066

PDB ID

Not Available

ChEBI ID

16675

Good Scents ID

Not Available

References

General References

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 ]
Smythe GA, Poljak A, Bustamante S, Braga O, Maxwell A, Grant R, Sachdev P: ECNI GC-MS analysis of picolinic and quinolinic acids and their amides in human plasma, CSF, and brain tissue. Adv Exp Med Biol. 2003;527:705-12. [PubMed:15206793 ]
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, Achim CL, Wiley CA, Major EO, Saito K, Markey SP: Human microglia convert l-tryptophan into the neurotoxin quinolinic acid. Biochem J. 1996 Dec 1;320 ( Pt 2):595-7. [PubMed:8973572 ]
Heyes MP, Saito K, Lackner A, Wiley CA, Achim CL, Markey SP: Sources of the neurotoxin quinolinic acid in the brain of HIV-1-infected patients and retrovirus-infected macaques. FASEB J. 1998 Jul;12(10):881-96. [PubMed:9657528 ]
Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
Wolfensberger M, Amsler U, Cuenod M, Foster AC, Whetsell WO Jr, Schwarcz R: Identification of quinolinic acid in rat and human brain tissue. Neurosci Lett. 1983 Nov 11;41(3):247-52. [PubMed:6664615 ]
Kurup RK, Kurup PA: Hypothalamic digoxin, hemispheric chemical dominance, and Alzheimer's disease. Int J Neurosci. 2003 Mar;113(3):361-81. [PubMed:12803139 ]
Heyes MP, Wyler AR, Devinsky O, Yergey JA, Markey SP, Nadi NS: Quinolinic acid concentrations in brain and cerebrospinal fluid of patients with intractable complex partial seizures. Epilepsia. 1990 Mar-Apr;31(2):172-7. [PubMed:1690639 ]
Kurup RK, Kurup PA: Central role of hypothalamic digoxin in conscious perception, neuroimmunoendocrine integration, and coordination of cellular function: relation to hemispheric dominance. Int J Neurosci. 2002 Jun;112(6):705-39. [PubMed:12325312 ]
Moroni F, Lombardi G, Carla V, Lal S, Etienne P, Nair NP: Increase in the content of quinolinic acid in cerebrospinal fluid and frontal cortex of patients with hepatic failure. J Neurochem. 1986 Dec;47(6):1667-71. [PubMed:2430055 ]
Basile AS, Saito K, al-Mardini H, Record CO, Hughes RD, Harrison P, Williams R, Li Y, Heyes MP: The relationship between plasma and brain quinolinic acid levels and the severity of hepatic encephalopathy. Gastroenterology. 1995 Mar;108(3):818-23. [PubMed:7875484 ]
Power C, Johnson RT: HIV-1 associated dementia: clinical features and pathogenesis. Can J Neurol Sci. 1995 May;22(2):92-100. [PubMed:7627922 ]
Ellison DW, Beal MF, Mazurek MF, Malloy JR, Bird ED, Martin JB: Amino acid neurotransmitter abnormalities in Huntington's disease and the quinolinic acid animal model of Huntington's disease. Brain. 1987 Dec;110 ( Pt 6):1657-73. [PubMed:2892568 ]
Saito K, Markey SP, Heyes MP: Effects of immune activation on quinolinic acid and neuroactive kynurenines in the mouse. Neuroscience. 1992 Nov;51(1):25-39. [PubMed:1465184 ]
Heyes MP, Rubinow D, Lane C, Markey SP: Cerebrospinal fluid quinolinic acid concentrations are increased in acquired immune deficiency syndrome. Ann Neurol. 1989 Aug;26(2):275-7. [PubMed:2528321 ]
Heyes MP, Ellis RJ, Ryan L, Childers ME, Grant I, Wolfson T, Archibald S, Jernigan TL: Elevated cerebrospinal fluid quinolinic acid levels are associated with region-specific cerebral volume loss in HIV infection. Brain. 2001 May;124(Pt 5):1033-42. [PubMed:11335705 ]
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 ]
Schwarcz R, Bruno JP, Muchowski PJ, Wu HQ: Kynurenines in the mammalian brain: when physiology meets pathology. Nat Rev Neurosci. 2012 Jul;13(7):465-77. doi: 10.1038/nrn3257. [PubMed:22678511 ]
Guillemin GJ: Quinolinic acid, the inescapable neurotoxin. FEBS J. 2012 Apr;279(8):1356-65. doi: 10.1111/j.1742-4658.2012.08485.x. Epub 2012 Mar 27. [PubMed:22248144 ]
Valle M, Price RW, Nilsson A, Heyes M, Verotta D: CSF quinolinic acid levels are determined by local HIV infection: cross-sectional analysis and modelling of dynamics following antiretroviral therapy. Brain. 2004 May;127(Pt 5):1047-60. doi: 10.1093/brain/awh130. Epub 2004 Mar 10. [PubMed:15013955 ]
Stone TW: Endogenous neurotoxins from tryptophan. Toxicon. 2001 Jan;39(1):61-73. doi: 10.1016/s0041-0101(00)00156-2. [PubMed:10936623 ]

Showing NP-Card for Quinolinic acid (NP0001076)

MOL for NP0001076 (Quinolinic acid)

3D MOL for NP0001076 (Quinolinic acid)

3D SDF for NP0001076 (Quinolinic acid)

3D-SDF for NP0001076 (Quinolinic acid)

PDB for NP0001076 (Quinolinic acid)

3D PDB for NP0001076 (Quinolinic acid)

SMILES for NP0001076 (Quinolinic acid)

INCHI for NP0001076 (Quinolinic acid)

Structure for NP0001076 (Quinolinic acid)

3D Structure for NP0001076 (Quinolinic acid)