Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:21:48 UTC |
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Update date | 2015-10-09 22:33:15 UTC |
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Primary ID | FDB022926 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Picolinic acid |
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Description | Picolinic acid is a metabolite of the tryptophan catabolism. Picolinic acid is produced under inflammatory conditions and a costimulus with interferon-gamma (IFNgamma) of macrophage (Mphi) effector functions, is a selective inducer of the Mphi inflammatory protein-1alpha (MIP-1alpha) and -1beta (MIPs), two chemokines/cytokines involved in the elicitation of the inflammatory reactions and in the development of the Th1 responses. IFNgamma and picolinic acid have reciprocal effects on the production of MIPs chemokines and the expression of their receptor. The concerted action of IFNgamma and picolinic acid on MIP-1alpha/beta chemokine/receptor system is likely to be of pathophysiological significance and to represent an important regulatory mechanism for leukocyte recruitment and distribution into damaged tissues during inflammatory responses. Picolinic acid has an effect on the production of L-arginine-derived reactive nitrogen intermediates in macrophages, by augmenting IFN-gamma-induced NO2- production, and acts synergistically with IFN-gamma in activating macrophages.
Children with acrodermatitis enteropathica (AE) are treated with oral zinc dipicolinate (zinc-PA). The concentration of picolinic acid in the plasma of asymptomatic children with AE was significantly less than that of normal children. However, oral treatment with PA alone is ineffective. The results support the hypothesis that the genetic defect in AE is in the tryptophan pathway, although the role of PA in zinc metabolism remains to be defined. (PMID: 15206716, 8473748, 1701787, 6694049) [HMDB] |
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CAS Number | 98-98-6 |
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Structure | |
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Synonyms | Synonym | Source |
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2-Carboxypyridine | ChEBI | 2-Picolinic acid | ChEBI | 2-Pyridinecarboxylic acid | ChEBI | alpha-Picolinic acid | ChEBI | alpha-Pyridinecarboxylic acid | ChEBI | O-Pyridinecarboxylic acid | ChEBI | PYRIDINE-2-carboxylIC ACID | ChEBI | 2-Picolinate | Generator | 2-Pyridinecarboxylate | Generator | a-Picolinate | Generator | a-Picolinic acid | Generator | alpha-Picolinate | Generator | Α-picolinate | Generator | Α-picolinic acid | Generator | a-Pyridinecarboxylate | Generator | a-Pyridinecarboxylic acid | Generator | alpha-Pyridinecarboxylate | Generator | Α-pyridinecarboxylate | Generator | Α-pyridinecarboxylic acid | Generator | O-Pyridinecarboxylate | Generator | PYRIDINE-2-carboxylate | Generator | Picolinate | Generator | 2-Methoxy-5-aminopyridine | HMDB | 4,5-Dehydropipecolic acid | HMDB | 5-amino-2-Fluoropyridine | HMDB | 5-amino-2-Methoxypyridine | HMDB | 5-amino-2-Pyridinecarboxylic acid | HMDB | 5-Aminopicolinic acid | HMDB | 5-Aminopyridine-2-carboxylic acid | HMDB | 6-Methoxy-pyridin-3-ylamine | HMDB | Acide picolique | HMDB | L-Baikiain | HMDB | Phenyl-(2-pyridyl)acetonitrile | HMDB | PLA | HMDB | Pyridine-carboxylique-2 | HMDB | Pyridinecarboxylic acid-(2) | HMDB | Iron(III) picolinate | MeSH, HMDB | Zinc picolinate | MeSH, HMDB | Picolinic acid, sodium salt | MeSH, HMDB | 2-Pyridine carboxylic acid | MeSH, HMDB | Calcium dipicolinate trihydrate | MeSH, HMDB | Picolinic acid, hydrochloride | MeSH, HMDB | Chromium picolinate | MeSH, HMDB | 2-methoxy-5-aminopyridine | hmdb | 5-Amino-2-fluoropyridine | hmdb | 5-Amino-2-methoxypyridine | hmdb | acide picolique | hmdb | o-Pyridinecarboxylic acid | hmdb | Pyridine-2-carboxylic acid | hmdb | α-picolinate | Generator | α-picolinic acid | Generator | α-pyridinecarboxylate | Generator | α-pyridinecarboxylic acid | Generator |
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Predicted Properties | |
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Chemical Formula | C6H5NO2 |
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IUPAC name | pyridine-2-carboxylic acid |
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InChI Identifier | InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) |
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InChI Key | SIOXPEMLGUPBBT-UHFFFAOYSA-N |
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Isomeric SMILES | OC(=O)C1=CC=CC=N1 |
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Average Molecular Weight | 123.1094 |
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Monoisotopic Molecular Weight | 123.032028409 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Pyridinecarboxylic acids and derivatives |
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Direct Parent | Pyridinecarboxylic acids |
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Alternative Parents | |
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Substituents | - Pyridine carboxylic acid
- Heteroaromatic compound
- Azacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Picolinic acid, non-derivatized, GC-MS Spectrum | splash10-001r-0900000000-3d42fed18a7170ac902c | Spectrum | GC-MS | Picolinic acid, 1 TMS, GC-MS Spectrum | splash10-005i-4900000000-ceebd42c8dcc23fdf3e4 | Spectrum | GC-MS | Picolinic acid, non-derivatized, GC-MS Spectrum | splash10-0fb9-9000000000-bab2bcb7bd27b0be1f51 | Spectrum | GC-MS | Picolinic acid, non-derivatized, GC-MS Spectrum | splash10-001r-0900000000-3d42fed18a7170ac902c | Spectrum | GC-MS | Picolinic acid, non-derivatized, GC-MS Spectrum | splash10-005i-4900000000-ceebd42c8dcc23fdf3e4 | Spectrum | GC-MS | Picolinic acid, non-derivatized, GC-MS Spectrum | splash10-001r-0900000000-7276adde2578b546a8f2 | Spectrum | Predicted GC-MS | Picolinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05i0-9400000000-7356d3453f3427cc9d89 | Spectrum | Predicted GC-MS | Picolinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05fr-9500000000-5d9f84aec4ab264b04db | Spectrum | Predicted GC-MS | Picolinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0adi-3900000000-7fac959b15471dc94406 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-9000000000-0e912cf3a3db8f8ee5df | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0fb9-9000000000-6d29f5dc4ddc1bb1adb5 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (MX-1303) , Positive | splash10-0fb9-9000000000-bab2bcb7bd27b0be1f51 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-05fr-0900000000-e169ce1e815eac2ad211 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-056s-9500000000-cd5fe946f692da4957ca | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-004i-9000000000-927c599edd5deaf854f0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-004i-9000000000-1d63eb2db32cd991a084 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-004i-9000000000-219a58c586353210f1a3 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0900000000-fe37c7a3e725d6a622fd | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-05fs-4900000000-b85a7afe0ba03853cfbf | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-05fr-0900000000-59ec49f98e7a39b33252 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-056s-9500000000-cd5fe946f692da4957ca | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9000000000-927c599edd5deaf854f0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9000000000-1d63eb2db32cd991a084 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9000000000-219a58c586353210f1a3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-00di-3900000000-9fd4a6ac15261e2c8d8e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-02t9-9600000000-bc378bb03dd26ace9a39 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-fe37c7a3e725d6a622fd | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-b09ed1d66b009b4624ee | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-1900000000-a4d3409ab064e87942a9 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9000000000-ddbf2ed02e3b712aca5d | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-2900000000-7de5e81309a53ea848ef | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00fr-8900000000-0143384039159388b6eb | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-85d472523e404d49ec06 | 2015-04-25 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 993 |
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ChEMBL ID | CHEMBL72628 |
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KEGG Compound ID | C10164 |
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Pubchem Compound ID | 1018 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28747 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB02243 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | 6PC |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Picolinic acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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