FComEx: Picolinic acid (PC000891)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:15 UTC

Update date

2017-01-19 02:36:40 UTC

FoodComEx ID

PC000891

FoodDB Record

FDB022926

Chemical Information

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, 8473748, 1701787, 6694049) [HMDB]

CAS Number

98-98-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Carboxypyridine	hmdb
2-methoxy-5-aminopyridine	hmdb
2-Picolinic acid	hmdb
2-Pyridinecarboxylate	Generator
2-Pyridinecarboxylic acid	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
a-Picolinate	Generator
a-Picolinic acid	Generator
a-Pyridinecarboxylate	Generator
a-Pyridinecarboxylic acid	hmdb
acide picolique	hmdb
alpha-Picolinate	Generator
alpha-Picolinic acid	hmdb
alpha-Pyridinecarboxylate	Generator
alpha-Pyridinecarboxylic acid	hmdb
L-Baikiain	hmdb
O-Pyridinecarboxylate	Generator
o-Pyridinecarboxylic acid	hmdb
Phenyl-(2-pyridyl)acetonitrile	hmdb
Picolinate	hmdb
PLA	hmdb
PYRIDINE-2-carboxylate	Generator
Pyridine-2-carboxylic acid	hmdb
Pyridine-carboxylique-2	hmdb
Pyridinecarboxylic acid-(2)	hmdb
α-picolinate	Generator
α-picolinic acid	Generator
α-pyridinecarboxylate	Generator
α-pyridinecarboxylic acid	Generator

Chemical Formula

C6H5NO2

IUPAC name

pyridine-2-carboxylic acid

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

Isomeric SMILES

OC(=O)C1=CC=CC=N1

Average Molecular Weight

123.1094

Monoisotopic Molecular Weight

123.032028409

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents