| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 2,3-Pyridinedicarboxylate
- 2,3-Pyridinedicarboxylic acid
- 3,4-Pyridinedicarboxylic acid
- Pyridin-2,3-dicarbonsaeure
- Pyridine-2,3-carboxylate
- Pyridine-2,3-dicarboxylate
- Pyridine-2,3-dicarboxylic acid
- Pyridine-3,4-dicarboxylic acid
- Quinolinate
- 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 |
|
| 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 |
|
| 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 |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.47 +/- 0.047 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.018 (0.012-0.024) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.023 +/- 0.002 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.02 +/- 0.002 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.022 +/- 0.0021 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.07 (0.05-0.10) uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.018 +/- 0.006 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.07 (0.05-0.10) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.67 +/- 1.34 umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
44.8 umol/mmol creatinine |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Urine compound detected by GC-MS
|
| Urine |
Detected and Quantified |
|
2.5 +/- 1.1 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
5.2 (1.0-17.5) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
urine by NMR
|
| Urine |
Detected and Quantified |
|
44.8 (10.4-115.3) umol/mmol creatinine |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
13.2 (0.1-54.5) umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
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 |
|
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 |
|
7.3 (2.4-13.2) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Children >10 years old
|
| Urine |
Detected and Quantified |
|
3.9 (0.9-15.1) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
by GC-MS
|
|
| Abnormal Concentrations |
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00015 (0.00011-0.00019) uM |
Adult (>18 years old) |
Both |
Hepatic coma (fatal) |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.29 (0.17-0.41) uM |
Adult (>18 years old) |
Both |
Brain injury |
Brain oedema or injury
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.031 +/- 0.005 uM |
Adult (>18 years old) |
Not Specified |
Hydrocephalus |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.20 (0.12 - 0.75) uM |
Adult (>18 years old) |
Not Specified |
Intraventricular hemorrhage |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.28 +/- 0.082 uM |
Adult (>18 years old) |
Not Specified |
CNS Tumors |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
1.08 +/- 0.54 uM |
Adult (>18 years old) |
Not Specified |
CNS Infections |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
3.78 +/- 0.88 uM |
Adult (>18 years old) |
Not Specified |
AIDS |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.8 (0.7-1.0) uM |
Adult (>18 years old) |
Not Specified |
Malaria |
Severe malaria
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
6.10 (0.37-100.9) uM |
Not Specified |
Not Specified |
Tuberculosis Meningitis |
In children
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.10 (0-2.37) uM |
Not Specified |
Not Specified |
Anemia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.09 (0.07-0.11) uM |
Not Specified |
Not Specified |
Malaria |
Cerebral malaria in children
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.08 (0.04-0.16) uM |
Not Specified |
Not Specified |
Malaria |
Uncomplicated malaria in children
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.03 (0.01-0.13) uM |
Not Specified |
Not Specified |
Convulsions |
In children
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.04 +/- 0.01 uM |
Adult (>18 years old) |
Not Specified |
Familial amyotrophic lateral sclerosis |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.04 +/- 0.00 uM |
Adult (>18 years old) |
Not Specified |
control |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.06 +/- 0.01 uM |
Adult (>18 years old) |
Female |
amyotrophic lateral sclerosis |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
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
|
| 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
|
| 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
|
| 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
|
| 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
|
| 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
|
| 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
|
| 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
- 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 |
- 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 |
- 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 |
- 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 |
|
| External Links |
| 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  |
| KEGG Compound ID |
C03722  |
| BioCyc ID |
QUINOLINATE  |
| BiGG ID |
42393  |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB00232  |
| Metagene Link |
HMDB00232  |
| METLIN ID |
330  |
| PubChem Compound |
1066  |
| PDB ID |
NTM  |
| ChEBI ID |
16675  |
| 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 |
- 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
- 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
- Kurup RK, Kurup PA: Hypothalamic digoxin, hemispheric chemical dominance, and Alzheimer's disease. Int J Neurosci. 2003 Mar;113(3):361-81.
Pubmed: 12803139
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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, 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
- 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
- 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
|