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Human Metabolome Database Version 3.5

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Showing metabocard for Picolinic acid (HMDB02243)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:43 -0600
Update Date 2013-02-08 17:11:38 -0700
HMDB ID HMDB02243
Secondary Accession Numbers None
Metabolite Identification
Common Name Picolinic acid
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 Link_out, 8473748 Link_out, 1701787 Link_out, 6694049 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Carboxypyridine
  2. 2-Methoxy-5-aminopyridine
  3. 2-Picolinic acid
  4. 2-Pyridinecarboxylic acid
  5. 4,5-Dehydropipecolic acid
  6. 5-Amino-2-fluoropyridine
  7. 5-Amino-2-methoxypyridine
  8. 5-Amino-2-Pyridinecarboxylic acid
  9. 5-Aminopicolinic acid
  10. 5-Aminopyridine-2-carboxylic acid
  11. 6-Methoxy-pyridin-3-ylamine
  12. a-Pyridinecarboxylic acid
  13. Acide picolique
  14. alpha-Picolinic acid
  15. alpha-Pyridinecarboxylic acid
  16. L-Baikiain
  17. O-Pyridinecarboxylic acid
  18. Phenyl-(2-pyridyl)acetonitrile
  19. Picolinate
  20. PLA
  21. Pyridine-2-carboxylic acid
  22. Pyridine-carboxylique-2
  23. Pyridinecarboxylic acid-(2)
Chemical Formula C6H5NO2
Average Molecular Weight 123.1094
Monoisotopic Molecular Weight 123.032028409
IUPAC Name pyridine-2-carboxylic acid
Traditional IUPAC Name picolinic acid
CAS Registry Number 98-98-6
SMILES OC(=O)C1=CC=CC=N1
InChI Identifier InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
InChI Key SIOXPEMLGUPBBT-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
  • Piperidine alkaloids(KEGG)
  • pyridinemonocarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Pyridine
  • Pyridine Carboxylic Acid
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 136.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 960 mg/mL at 20 °C Not Available
LogP 0.72 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 61.1 g/L ALOGPS
LogP 0.22 ALOGPS
LogP -0.67 ChemAxon
LogS -0.30 ALOGPS
pKa (strongest acidic) 0.99 ChemAxon
pKa (strongest basic) 5.53 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 50.19 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 30.79 ChemAxon
Polarizability 11.38 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (MX-1303)
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-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Prostate
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.299 +/- 0.034 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.31 (0.21-0.46) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
19.4 (7.2-37.6) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.36 (0.18-0.71) uM Adult (>18 years old) Both Circulatory system disorder Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.51 +/- 0.011 uM Adult (>18 years old) Not Specified control Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.36 +/- 0.04 uM Adult (>18 years old) Male amyotrophic lateral sclerosis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.37 +/- 0.06 uM Adult (>18 years old) Female amyotrophic lateral sclerosis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.35 +/- 0.07 uM Adult (>18 years old) Not Specified Sporadic amyotrophic lateral sclerosis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.60 +/- 0.21 uM Adult (>18 years old) Not Specified Familial amyotrophic lateral sclerosis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.30 +/- 0.06 uM Adult (>18 years old) Not Specified Amyotrophic lateral sclerosis (bulbar onset) Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022926
KNApSAcK ID Not Available
Chemspider ID 993 Link_out
KEGG Compound ID C10164 Link_out
BioCyc ID CPD-5062 Link_out
BiGG ID Not Available
Wikipedia Link Picolinic acid Link_out
NuGOwiki Link HMDB02243 Link_out
Metagene Link HMDB02243 Link_out
METLIN ID Not Available
PubChem Compound 1018 Link_out
PDB ID 6PC Link_out
ChEBI ID 28747 Link_out
References
Synthesis Reference Hagedorn, Scott R.; East, Anthony J.; Barer, Sol J. Production of picolinic acid and pyridine products by Pseudomonas. U.S. (1989), 11 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Dazzi C, Candiano G, Massazza S, Ponzetto A, Varesio L: New high-performance liquid chromatographic method for the detection of picolinic acid in biological fluids. J Chromatogr B Biomed Sci Appl. 2001 Feb 10;751(1):61-8. Pubmed: 11232856 Link_out
  2. Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. Pubmed: 2338430 Link_out
  3. 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