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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:57 UTC
HMDB IDHMDB0000232
Secondary Accession Numbers
  • HMDB00232
Metabolite Identification
Common NameQuinolinic acid
DescriptionQuinolinic 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
Data?1676999678
Synonyms
ValueSource
2,3-Pyridinedicarboxylic acidChEBI
Pyridine-2,3-dicarboxylateChEBI
2,3-PyridinedicarboxylateGenerator
QuinolinateGenerator
Pyridine-2,3-dicarboxylic acidGenerator
3,4-Pyridinedicarboxylic acidHMDB
Pyridin-2,3-dicarbonsaeureHMDB
Pyridine-2,3-carboxylateHMDB
Quinolinic acidHMDB
Chemical FormulaC7H5NO4
Average Molecular Weight167.1189
Monoisotopic Molecular Weight167.021857653
IUPAC Namepyridine-2,3-dicarboxylic acid
Traditional 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
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point190 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker130.02930932474
[M+H]+Baker138.97630932474
[M-H]-Not Available128.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000464
[M+H]+Not Available134.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00000464
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.07 g/LALOGPS
logP0.15ALOGPS
logP-1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.31ChemAxon
pKa (Strongest Basic)5.74ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.49 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.04 m³·mol⁻¹ChemAxon
Polarizability14.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.04131661259
DarkChem[M-H]-129.64431661259
AllCCS[M+H]+134.82732859911
AllCCS[M-H]-127.77532859911
DeepCCS[M+H]+132.06730932474
DeepCCS[M-H]-128.2430932474
DeepCCS[M-2H]-165.4930932474
DeepCCS[M+Na]+141.02930932474
AllCCS[M+H]+134.832859911
AllCCS[M+H-H2O]+130.432859911
AllCCS[M+NH4]+139.032859911
AllCCS[M+Na]+140.232859911
AllCCS[M-H]-127.832859911
AllCCS[M+Na-2H]-128.732859911
AllCCS[M+HCOO]-129.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Quinolinic acidOC(=O)C1=CC=CN=C1C(O)=O2247.0Standard polar33892256
Quinolinic acidOC(=O)C1=CC=CN=C1C(O)=O1441.3Standard non polar33892256
Quinolinic acidOC(=O)C1=CC=CN=C1C(O)=O1624.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Quinolinic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CN=C1C(=O)O1696.6Semi standard non polar33892256
Quinolinic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C1=NC=CC=C1C(=O)O1698.4Semi standard non polar33892256
Quinolinic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CN=C1C(=O)O[Si](C)(C)C1715.9Semi standard non polar33892256
Quinolinic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CN=C1C(=O)O1918.9Semi standard non polar33892256
Quinolinic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=NC=CC=C1C(=O)O1932.5Semi standard non polar33892256
Quinolinic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CN=C1C(=O)O[Si](C)(C)C(C)(C)C2115.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Quinolinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0910000000-a8eacf1916c539d286b62014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinolinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0910000000-64e9e4b901dd69dc90c52014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinolinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-7910000000-0bb1a7ce8a5907feae212014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinolinic acid EI-B (Non-derivatized)splash10-05i0-9500000000-555e92ebc410fc53e92f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinolinic acid EI-B (Non-derivatized)splash10-0100-5900000000-3d726d602fec21fd8beb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinolinic acid GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-a8eacf1916c539d286b62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinolinic acid GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-64e9e4b901dd69dc90c52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinolinic acid GC-EI-TOF (Non-derivatized)splash10-006t-7910000000-0bb1a7ce8a5907feae212017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinolinic acid GC-EI-TOF (Non-derivatized)splash10-0002-1960000000-8197ee161fa149deabdd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinolinic acid GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-40d676712c981904799f2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinolinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4j-4900000000-40b629f8c2ff96d454dc2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinolinic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9680000000-e45ac969fff3f654bb492017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinolinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinolinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinolinic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinolinic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinolinic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinolinic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinolinic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0002-0900000000-4a6d37bd8578b50cf6772012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004i-9100000000-45dc448cbedc6465ad632012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9000000000-2aa35085995bdc1801da2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-014i-0900000000-d0eb03bdfeea6084e0db2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0100-5900000000-7d59ce683134a6f33e8d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-00or-9700000000-c13d2a2f6361459932db2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-016r-8900000000-d7f12324cf02b0023aed2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-00or-9600000000-d51ee74ca89d43da53b42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0udi-1900000000-a44a9d75afd871a626872012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0a4r-4900000000-1b71b7097868800191642012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0a4i-5900000000-56f78a7bdb3c091573a72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0a6r-9500000000-8140904c5eb795e923712012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-004i-9100000000-1175e50dbd23fc2a99222012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QTOF , negative-QTOFsplash10-00di-0900000000-9a963e41421edb0415612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QTOF , negative-QTOFsplash10-00di-0900000000-4c0c9b98c2ce00d0d2822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-d0eb03bdfeea6084e0db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ , negative-QTOFsplash10-0100-5900000000-4af865513d09a8bab44f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ , negative-QTOFsplash10-00or-9700000000-c13d2a2f6361459932db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinolinic acid LC-ESI-QQ , negative-QTOFsplash10-016r-8900000000-ff25a1c9823ecb0185492017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinolinic acid 10V, Positive-QTOFsplash10-014i-0900000000-f9e1437d75c6f5b25d882015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinolinic acid 20V, Positive-QTOFsplash10-014i-1900000000-ad80f96e7d85d594f6cb2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinolinic acid 40V, Positive-QTOFsplash10-0uk9-9300000000-57792ffddc2cccbd77b92015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinolinic acid 10V, Negative-QTOFsplash10-00xr-0900000000-343bdc632cd1916d92c92015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinolinic acid 20V, Negative-QTOFsplash10-00fr-4900000000-c83c2058ae8923828aa62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinolinic acid 40V, Negative-QTOFsplash10-00os-9100000000-840c225c8204e80727f22015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Brain
  • Neuron
  • Placenta
  • Prostate
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.599 +/- 0.299 uMAdult (>18 years old)Both
Normal
details
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
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 QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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 Quantified3.307 +/- 1.801 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified5.2 (1.0-17.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified18.29 (14.14-24.02) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0402 uMInfant (0-1 year old)FemaleNicotinamide Adenine Dinucleotide Deficiency details
BloodDetected and Quantified8.982 +/- 5.389 uMAdult (>18 years old)Both
Uremia
details
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
UrineDetected and Quantified8.519 +/- 5.876 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Nicotinamide Adenine Dinucleotide Deficiency
  1. Shi H, Enriquez A, Rapadas M, Martin EMMA, Wang R, Moreau J, Lim CK, Szot JO, Ip E, Hughes JN, Sugimoto K, Humphreys DT, McInerney-Leo AM, Leo PJ, Maghzal GJ, Halliday J, Smith J, Colley A, Mark PR, Collins F, Sillence DO, Winlaw DS, Ho JWK, Guillemin GJ, Brown MA, Kikuchi K, Thomas PQ, Stocker R, Giannoulatou E, Chapman G, Duncan EL, Sparrow DB, Dunwoodie SL: NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552. doi: 10.1056/NEJMoa1616361. [PubMed:28792876 ]
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Amyotrophic lateral sclerosis
  1. Chen Y, Stankovic R, Cullen KM, Meininger V, Garner B, Coggan S, Grant R, Brew BJ, Guillemin GJ: The kynurenine pathway and inflammation in amyotrophic lateral sclerosis. Neurotox Res. 2010 Aug;18(2):132-42. doi: 10.1007/s12640-009-9129-7. Epub 2009 Nov 18. [PubMed:19921535 ]
Sporadic amyotrophic lateral sclerosis
  1. Chen Y, Stankovic R, Cullen KM, Meininger V, Garner B, Coggan S, Grant R, Brew BJ, Guillemin GJ: The kynurenine pathway and inflammation in amyotrophic lateral sclerosis. Neurotox Res. 2010 Aug;18(2):132-42. doi: 10.1007/s12640-009-9129-7. Epub 2009 Nov 18. [PubMed:19921535 ]
Familial amyotrophic lateral sclerosis
  1. Chen Y, Stankovic R, Cullen KM, Meininger V, Garner B, Coggan S, Grant R, Brew BJ, Guillemin GJ: The kynurenine pathway and inflammation in amyotrophic lateral sclerosis. Neurotox Res. 2010 Aug;18(2):132-42. doi: 10.1007/s12640-009-9129-7. Epub 2009 Nov 18. [PubMed:19921535 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB01796
Phenol Explorer Compound IDNot Available
FooDB IDFDB031142
KNApSAcK IDC00007381
Chemspider ID144985
KEGG Compound IDC03722
BioCyc IDQUINOLINATE
BiGG IDNot Available
Wikipedia LinkQuinolinic_acid
METLIN IDNot Available
PubChem Compound1066
PDB IDNot Available
ChEBI ID16675
Food Biomarker OntologyNot Available
VMH IDQULN
MarkerDB IDMDB00000112
Good Scents IDNot Available
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. doi: 10.1038/nature07762. [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 ]
  22. 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 ]
  23. 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 ]
  24. 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 ]
  25. 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 ]
  26. Stone TW: Endogenous neurotoxins from tryptophan. Toxicon. 2001 Jan;39(1):61-73. doi: 10.1016/s0041-0101(00)00156-2. [PubMed:10936623 ]

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
Nicotinic acid mononucleotide + Pyrophosphate + CO(2) → Quinolinic acid + Phosphoribosyl pyrophosphatedetails
Nicotinic acid mononucleotide + 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