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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-13 23:07:24 UTC
HMDB IDHMDB00232
Secondary Accession NumbersNone
Metabolite Identification
Common NameQuinolinic acid
DescriptionQuinolinic acid is a metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS. Quinolinic acid (QUIN) is a product of tryptophan metabolism that can act as an endogenous brain excitotoxin when released by activated macrophages. (Valle et. al, Brain 127:1047 (2004)).
Structure
Thumb
Synonyms
  1. 2,3-Pyridinedicarboxylate
  2. 2,3-Pyridinedicarboxylic acid
  3. 3,4-Pyridinedicarboxylic acid
  4. Pyridin-2,3-dicarbonsaeure
  5. Pyridine-2,3-carboxylate
  6. Pyridine-2,3-dicarboxylate
  7. Pyridine-2,3-dicarboxylic acid
  8. Pyridine-3,4-dicarboxylic acid
  9. Quinolinate
  10. Quinolinic acid
Chemical FormulaC7H5NO4
Average Molecular Weight167.1189
Monoisotopic Molecular Weight167.021857653
IUPAC Namepyridine-2,3-dicarboxylic acid
Traditional IUPAC Namequinolinic acid
CAS Registry Number89-00-9
SMILES
OC(=O)C1=CC=CN=C1C(O)=O
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 KeyGJAWHXHKYYXBSV-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
  • pyridinedicarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Pyridine
  • Pyridine Carboxylic Acid
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Nicotinate and nicotinamide metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point190 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.07 g/LALOGPS
logP0.15ALOGPS
logP-0.54ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.29ChemAxon
pKa (Strongest Basic)5.26ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.49ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.04ChemAxon
Polarizability14.37ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Central Nervous System
  • Neuron
  • Prostate
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Nicotinate and Nicotinamide MetabolismSMP00048map00760
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.47 +/- 0.047 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.018 (0.012-0.024) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.023 +/- 0.002 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.02 +/- 0.002 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.022 +/- 0.0021 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.07 (0.05-0.10) uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.018 +/- 0.006 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.07 (0.05-0.10) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.67 +/- 1.34 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified44.8 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.5 +/- 1.1 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified5.2 (1.0-17.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified44.8 (10.4-115.3) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified13.2 (0.1-54.5) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified10.5 (4.8-26.2) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified7.7 (4.3-13.7) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified7.3 (2.4-13.2) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified3.9 (0.9-15.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.00015 (0.00011-0.00019) uMAdult (>18 years old)BothHepatic coma (fatal) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.29 (0.17-0.41) uMAdult (>18 years old)Both
Brain injury
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.031 +/- 0.005 uMAdult (>18 years old)Not SpecifiedHydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified0.20 (0.12 - 0.75) uMAdult (>18 years old)Not SpecifiedIntraventricular hemorrhage details
Cerebrospinal Fluid (CSF)Detected and Quantified0.28 +/- 0.082 uMAdult (>18 years old)Not SpecifiedCNS Tumors details
Cerebrospinal Fluid (CSF)Detected and Quantified1.08 +/- 0.54 uMAdult (>18 years old)Not SpecifiedCNS Infections details
Cerebrospinal Fluid (CSF)Detected and Quantified3.78 +/- 0.88 uMAdult (>18 years old)Not SpecifiedAIDS details
Cerebrospinal Fluid (CSF)Detected and Quantified0.8 (0.7-1.0) uMAdult (>18 years old)Not Specified
Malaria
details
Cerebrospinal Fluid (CSF)Detected and Quantified6.10 (0.37-100.9) uMNot SpecifiedNot Specified
Tuberculous meningitis
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.10 (0-2.37) uMNot SpecifiedNot SpecifiedAnemia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.09 (0.07-0.11) uMNot SpecifiedNot Specified
Malaria
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.08 (0.04-0.16) uMNot SpecifiedNot Specified
Malaria
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.03 (0.01-0.13) uMNot SpecifiedNot Specified
Convulsions
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.04 +/- 0.01 uMAdult (>18 years old)Not SpecifiedFamilial amyotrophic lateral sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.04 +/- 0.00 uMAdult (>18 years old)Not Specifiedcontrol details
Cerebrospinal Fluid (CSF)Detected and Quantified0.06 +/- 0.01 uMAdult (>18 years old)Femaleamyotrophic lateral sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.05 +/- 0.01 uMAdult (>18 years old)Not SpecifiedSporadic amyotrophic lateral sclerosis details
Associated Disorders and Diseases
Disease References
AIDS
  1. 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
Anemia
  1. 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
Traumatic brain injury
  1. 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
CNS infections
  1. 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
CNS tumors
  1. 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
Convulsion
  1. 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
Hepatic coma
  1. 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
Hydrocephalus
  1. 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
Intraventricular hemorrhage
  1. 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
Malaria
  1. 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
  2. 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
  1. 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
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021913
KNApSAcK IDNot Available
Chemspider ID1037
KEGG Compound IDC03722
BioCyc IDQUINOLINATE
BiGG ID42393
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00232
Metagene LinkHMDB00232
METLIN ID330
PubChem Compound1066
PDB IDNTM
ChEBI ID16675
References
Synthesis ReferenceAkhmerova, S. G.; Islamgulova, V. R.; Koksharov, V. G.; Sapozhnikov, Yu. E.; Manaeva, R. M. Methods of preparation of quinolinic acid. Bashkirskii Khimicheskii Zhurnal (2001), 8(2), 9-14.
Material Safety Data Sheet (MSDS)Download (PDF)
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. Pubmed: 19212411
  2. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  3. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. Kurup RK, Kurup PA: Hypothalamic digoxin, hemispheric chemical dominance, and Alzheimer's disease. Int J Neurosci. 2003 Mar;113(3):361-81. Pubmed: 12803139
  12. 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
  13. 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
  14. 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
  15. 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
  16. Power C, Johnson RT: HIV-1 associated dementia: clinical features and pathogenesis. Can J Neurol Sci. 1995 May;22(2):92-100. Pubmed: 7627922
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
QPRT
Uniprot ID:
Q15274
Molecular weight:
30815.28
Reactions
nicotinate beta-D-ribonucleotide + Pyrophosphate + CO(2) → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
nicotinate beta-D-ribonucleotide + Pyrophosphate + Carbon dioxide → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the hydroxylation of L-kynurenine (L-Kyn) to form 3-hydroxy-L-kynurenine (L-3OHKyn). Required for synthesis of quinolinic acid, a neurotoxic NMDA receptor antagonist and potential endogenous inhibitor of NMDA receptor signaling in axonal targeting, synaptogenesis and apoptosis during brain development. Quinolinic acid may also affect NMDA receptor signaling in pancreatic beta cells, osteoblasts, myocardial cells, and the gastrointestinal tract.
Gene Name:
KMO
Uniprot ID:
O15229
Molecular weight:
55809.445