1.0 2011-09-21 00:21:48 UTC 2025-11-19 02:42:49 UTC FDB022926 Picolinic acid 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] 2-Carboxypyridine 2-methoxy-5-aminopyridine 2-Picolinic acid 2-Pyridinecarboxylate 2-Pyridinecarboxylic acid 4,5-Dehydropipecolic acid 5-Amino-2-fluoropyridine 5-Amino-2-methoxypyridine 5-amino-2-Pyridinecarboxylic acid 5-Aminopicolinic acid 5-Aminopyridine-2-carboxylic acid 6-Methoxy-pyridin-3-ylamine a-Picolinate a-Picolinic acid a-Pyridinecarboxylate a-Pyridinecarboxylic acid acide picolique alpha-Picolinate alpha-Picolinic acid alpha-Pyridinecarboxylate alpha-Pyridinecarboxylic acid L-Baikiain O-Pyridinecarboxylate o-Pyridinecarboxylic acid Phenyl-(2-pyridyl)acetonitrile Picolinate PLA PYRIDINE-2-carboxylate Pyridine-2-carboxylic acid Pyridine-carboxylique-2 Pyridinecarboxylic acid-(2) α-picolinate α-picolinic acid α-pyridinecarboxylate α-pyridinecarboxylic acid C6H5NO2 123.1094 123.032028409 pyridine-2-carboxylic acid picolinic acid 98-98-6 OC(=O)C1=CC=CC=N1 InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) SIOXPEMLGUPBBT-UHFFFAOYSA-N belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Pyridinecarboxylic acids Organic compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids and derivatives Aromatic heteromonocyclic compounds Azacyclic compounds Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Aromatic heteromonocyclic compound Azacycle Carboxylic acid Carboxylic acid derivative Heteroaromatic compound Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyridine carboxylic acid Piperidine alkaloids pyridinemonocarboxylic acid Solid logp 0.22 ALOGPS logs -0.30 ALOGPS solubility 6.11e+01 g/l ALOGPS logp -0.65 ChemAxon pka_strongest_acidic 1 ChemAxon pka_strongest_basic 5.52 ChemAxon iupac pyridine-2-carboxylic acid ChemAxon average_mass 123.1094 ChemAxon mono_mass 123.032028409 ChemAxon smiles OC(=O)C1=CC=CC=N1 ChemAxon formula C6H5NO2 ChemAxon inchi InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) ChemAxon inchikey SIOXPEMLGUPBBT-UHFFFAOYSA-N ChemAxon polar_surface_area 50.19 ChemAxon refractivity 30.79 ChemAxon polarizability 11.38 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 811 Specdb::CMs 1057 Specdb::CMs 21361 Specdb::CMs 26855 Specdb::CMs 30435 Specdb::CMs 31404 Specdb::CMs 32028 Specdb::CMs 38338 Specdb::CMs 164778 Specdb::MsIr 1707 Specdb::MsIr 1708 Specdb::MsIr 1709 Specdb::NmrTwoD 1807 Specdb::MsMs 2043 Specdb::MsMs 2044 Specdb::MsMs 2045 Specdb::MsMs 5751 Specdb::MsMs 5752 Specdb::MsMs 5753 Specdb::MsMs 5754 Specdb::MsMs 5755 Specdb::MsMs 5756 Specdb::MsMs 10217 Specdb::MsMs 10218 Specdb::MsMs 10219 Specdb::MsMs 16889 Specdb::MsMs 16890 Specdb::MsMs 16891 Specdb::MsMs 445166 Specdb::MsMs 445167 Specdb::MsMs 446742 Specdb::MsMs 446743 Specdb::MsMs 446744 Specdb::MsMs 446745 Specdb::MsMs 446746 Specdb::MsMs 451907 Specdb::MsMs 2228141 Specdb::MsMs 2252487 Specdb::NmrOneD 1868 Specdb::NmrOneD 115658 Specdb::NmrOneD 115659 Specdb::NmrOneD 115660 Specdb::NmrOneD 115661 Specdb::NmrOneD 115662 Specdb::NmrOneD 115663 Specdb::NmrOneD 115664 Specdb::NmrOneD 115665 Specdb::NmrOneD 115666 Specdb::NmrOneD 115667 Specdb::NmrOneD 115668 Specdb::NmrOneD 115669 Specdb::NmrOneD 115670 Specdb::NmrOneD 115671 Specdb::NmrOneD 115672 Specdb::NmrOneD 115673 Specdb::NmrOneD 115674 Specdb::NmrOneD 115675 Specdb::NmrOneD 115676 Specdb::NmrOneD 115677 HMDB02243 28747 6PC #<Reference:0x000055ce31721a78> #<Reference:0x000055ce31721820> #<Reference:0x000055ce31721550> #<Reference:0x000055ce31721320> #<Reference:0x000055ce317210c8> #<Reference:0x000055ce31720e48> #<Reference:0x000055ce31720c40> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823