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Human Metabolome Database Version 3.5

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Showing metabocard for Quinolinic acid (HMDB00232)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-13 17:07:24 -0600
HMDB ID HMDB00232
Secondary Accession Numbers None
Metabolite Identification
Common Name Quinolinic acid
Description Quinolinic 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C7H5NO4
Average Molecular Weight 167.1189
Monoisotopic Molecular Weight 167.021857653
IUPAC Name pyridine-2,3-dicarboxylic acid
Traditional IUPAC Name quinolinic acid
CAS Registry Number 89-00-9
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 Key GJAWHXHKYYXBSV-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
  • pyridinedicarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Pyridine
  • Pyridine Carboxylic Acid
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Nicotinate and nicotinamide metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 190 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 11.0 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 -0.54 ChemAxon
LogS -1.61 ALOGPS
pKa (strongest acidic) 0.29 ChemAxon
pKa (strongest basic) 5.26 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 87.49 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 38.04 ChemAxon
Polarizability 14.37 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Neuron
  • Brain
  • Prostate
  • Spleen
  • Central Nervous System
Pathways
Name SMPDB Link KEGG Link
Nicotinate and Nicotinamide Metabolism SMP00048 map00760 Link_out
Tryptophan Metabolism SMP00063 map00380 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.47 +/- 0.047 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.018 (0.012-0.024) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.023 +/- 0.002 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.02 +/- 0.002 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.022 +/- 0.0021 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.07 (0.05-0.10) uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.018 +/- 0.006 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.07 (0.05-0.10) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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0.67 +/- 1.34 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
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44.8 umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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2.5 +/- 1.1 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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5.2 (1.0-17.5) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
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44.8 (10.4-115.3) umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and Quantified
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13.2 (0.1-54.5) umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
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10.5 (4.8-26.2) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 2-6 years
Urine Detected and Quantified
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7.7 (4.3-13.7) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 6-10 years
Urine Detected and Quantified
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7.3 (2.4-13.2) umol/mmol creatinine Adult (>18 years old) Both Normal Children >10 years old
Urine Detected and Quantified
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3.9 (0.9-15.1) umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.00015 (0.00011-0.00019) uM Adult (>18 years old) Both Hepatic coma (fatal) Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.29 (0.17-0.41) uM Adult (>18 years old) Both Brain injury Brain oedema or injury
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.031 +/- 0.005 uM Adult (>18 years old) Not Specified Hydrocephalus Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.20 (0.12 - 0.75) uM Adult (>18 years old) Not Specified Intraventricular hemorrhage Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.28 +/- 0.082 uM Adult (>18 years old) Not Specified CNS Tumors Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1.08 +/- 0.54 uM Adult (>18 years old) Not Specified CNS Infections Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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3.78 +/- 0.88 uM Adult (>18 years old) Not Specified AIDS Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.8 (0.7-1.0) uM Adult (>18 years old) Not Specified Malaria Severe malaria
Cerebrospinal Fluid (CSF) Detected and Quantified
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6.10 (0.37-100.9) uM Not Specified Not Specified Tuberculosis Meningitis In children
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.10 (0-2.37) uM Not Specified Not Specified Anemia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.09 (0.07-0.11) uM Not Specified Not Specified Malaria Cerebral malaria in children
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.08 (0.04-0.16) uM Not Specified Not Specified Malaria Uncomplicated malaria in children
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.03 (0.01-0.13) uM Not Specified Not Specified Convulsions In children
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.04 +/- 0.01 uM Adult (>18 years old) Not Specified Familial amyotrophic lateral sclerosis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.04 +/- 0.00 uM Adult (>18 years old) Not Specified control Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.06 +/- 0.01 uM Adult (>18 years old) Female amyotrophic lateral sclerosis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.05 +/- 0.01 uM Adult (>18 years old) Not Specified Sporadic amyotrophic lateral sclerosis Not Available
Associated Disorders and Diseases
Disease References
Hepatic coma
  • 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 Link_out
    Traumatic brain injury
    • 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 Link_out
      Hydrocephalus
      • 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 Link_out
        Intraventricular hemorrhage
        • 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 Link_out
          CNS tumors
          • 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 Link_out
            CNS infections
            • 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 Link_out
              AIDS
              • 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 Link_out
                Malaria
                • 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 Link_out
                • 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 Link_out
                  Tuberculous meningitis
                  • 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 Link_out
                    Anemia
                    • 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 Link_out
                      Convulsion
                      • 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 Link_out
                        Associated OMIM IDs
                        DrugBank ID Not Available
                        Phenol Explorer Compound ID Not Available
                        Phenol Explorer Metabolite ID Not Available
                        FoodDB ID FDB021913
                        KNApSAcK ID Not Available
                        Chemspider ID 1037 Link_out
                        KEGG Compound ID C03722 Link_out
                        BioCyc ID QUINOLINATE Link_out
                        BiGG ID 42393 Link_out
                        Wikipedia Link Not Available
                        NuGOwiki Link HMDB00232 Link_out
                        Metagene Link HMDB00232 Link_out
                        METLIN ID 330 Link_out
                        PubChem Compound 1066 Link_out
                        PDB ID NTM Link_out
                        ChEBI ID 16675 Link_out
                        References
                        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)
                        General References
                        1. 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 Link_out
                        2. 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 Link_out
                        3. Kurup RK, Kurup PA: Hypothalamic digoxin, hemispheric chemical dominance, and Alzheimer's disease. Int J Neurosci. 2003 Mar;113(3):361-81. Pubmed: 12803139 Link_out
                        4. 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 Link_out
                        5. 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 Link_out
                        6. 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 Link_out
                        7. 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 Link_out
                        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 Link_out
                        9. 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 Link_out
                        10. Power C, Johnson RT: HIV-1 associated dementia: clinical features and pathogenesis. Can J Neurol Sci. 1995 May;22(2):92-100. Pubmed: 7627922 Link_out
                        11. 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 Link_out
                        12. 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 Link_out
                        13. 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 Link_out
                        14. 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 Link_out
                        15. 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 Link_out
                        16. 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 Link_out
                        17. 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 Link_out
                        18. 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 Link_out
                        19. 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 Link_out
                        20. 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 Link_out
                        21. 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 Link_out
                        Enzymes
                        Name: Nicotinate-nucleotide pyrophosphorylase [carboxylating]
                        Reactions:
                        • nicotinate D-ribonucleotide + diphosphate + CO2 = pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R03348]
                        Gene Name: QPRT
                        Uniprot ID: Q15274 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Kynurenine 3-monooxygenase
                        Reactions:
                        • L-kynurenine + NADPH + H+ + O2 = 3-hydroxy-L-kynurenine + NADP+ + H2O [RN:R01960]
                        Gene Name: KMO
                        Uniprot ID: O15229 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA