Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000096
Name: Quinolinic acid
Description:Quinolinic acid is a dicarboxylic acid. It may be prepared by the oxidation of quinoline, either electrochemically, or with acidic hydrogen peroxide. (Wikipedia)
  • 2,3-Pyridinedicarboxylate
  • 2,3-Pyridinedicarboxylic acid
  • 3,4-Pyridinedicarboxylate
  • 3,4-Pyridinedicarboxylic acid
  • Pyridin-2,3-dicarbonsaeure
  • Pyridine-2,3-carboxylate
  • Pyridine-2,3-carboxylic acid
  • Pyridine-2,3-dicarboxylate
  • Pyridine-2,3-dicarboxylic acid
  • Pyridine-3,4-dicarboxylate
  • Pyridine-3,4-dicarboxylic acid
  • Quinolinate
  • Quinolinic acid
Chemical Formula: C7H5NO4
Average Molecular Weight: 167.1189
Monoisotopic Molecular Weight: 167.021857653
CAS number: 89-00-9
IUPAC Name:pyridine-2,3-dicarboxylic acid
Traditional IUPAC Name: quinolinic acid
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct Parent Pyridinecarboxylic acids
Alternative Parents
  • Pyridine carboxylic acid
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: 190
Experimental Properties:
Water Solubility:11.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
Water Solubility4.07 mg/mLALOGPS
pKa (Strongest Acidic)0.29ChemAxon
pKa (Strongest Basic)5.26ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.49 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.04 m3·mol-1ChemAxon
Polarizability14.34 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0910000000-a8eacf1916c539d286b6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0910000000-64e9e4b901dd69dc90c5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-7910000000-0bb1a7ce8a5907feae21View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-4a6d37bd8578b50cf677View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-45dc448cbedc6465ad63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-2aa35085995bdc1801daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-d0eb03bdfeea6084e0dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0100-5900000000-7d59ce683134a6f33e8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00or-9700000000-c13d2a2f6361459932dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-016r-8900000000-d7f12324cf02b0023aedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00or-9600000000-d51ee74ca89d43da53b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-1900000000-a44a9d75afd871a62687View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4r-4900000000-1b71b709786880019164View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-5900000000-56f78a7bdb3c091573a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a6r-9500000000-8140904c5eb795e92371View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9100000000-1175e50dbd23fc2a9922View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-f9e1437d75c6f5b25d88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-ad80f96e7d85d594f6cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9300000000-57792ffddc2cccbd77b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0900000000-343bdc632cd1916d92c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-4900000000-c83c2058ae8923828aa6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00os-9100000000-840c225c8204e80727f2View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • 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
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  • 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
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  • 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
  • Power C, Johnson RT: HIV-1 associated dementia: clinical features and pathogenesis. Can J Neurol Sci. 1995 May;22(2):92-100. Pubmed: 7627922
  • 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
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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
Synthesis Reference: Akhmerova, 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)
External Links:
Pubchem Compound ID1066
Kegg IDC03722
ChemSpider ID1037
Wikipedia IDQuinolinic acid
Ligand ExpoNTM