1.02011-09-21 00:21:48 UTC2015-10-09 22:33:15 UTCFDB022926Picolinic acidPicolinic 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-Carboxypyridine2-methoxy-5-aminopyridine2-Picolinic acid2-Pyridinecarboxylate2-Pyridinecarboxylic acid4,5-Dehydropipecolic acid5-Amino-2-fluoropyridine5-Amino-2-methoxypyridine5-amino-2-Pyridinecarboxylic acid5-Aminopicolinic acid5-Aminopyridine-2-carboxylic acid6-Methoxy-pyridin-3-ylaminea-Picolinatea-Picolinic acida-Pyridinecarboxylatea-Pyridinecarboxylic acidacide picoliquealpha-Picolinatealpha-Picolinic acidalpha-Pyridinecarboxylatealpha-Pyridinecarboxylic acidL-BaikiainO-Pyridinecarboxylateo-Pyridinecarboxylic acidPhenyl-(2-pyridyl)acetonitrilePicolinatePLAPYRIDINE-2-carboxylatePyridine-2-carboxylic acidPyridine-carboxylique-2Pyridinecarboxylic acid-(2)α-picolinateα-picolinic acidα-pyridinecarboxylateα-pyridinecarboxylic acidC6H5NO2123.1094123.032028409pyridine-2-carboxylic acidpicolinic acid98-98-6OC(=O)C1=CC=CC=N1InChI=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 acidsOrganic compoundsOrganoheterocyclic compoundsPyridines and derivativesPyridinecarboxylic acids and derivativesAromatic heteromonocyclic compoundsAzacyclic compoundsCarboxylic acidsHeteroaromatic compoundsHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesOrganonitrogen compoundsOrganooxygen compoundsOrganopnictogen compoundsAromatic heteromonocyclic compoundAzacycleCarboxylic acidCarboxylic acid derivativeHeteroaromatic compoundHydrocarbon derivativeMonocarboxylic acid or derivativesOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPyridine carboxylic acidPiperidine alkaloidspyridinemonocarboxylic acidSolidlogp0.22logs-0.30solubility6.11e+01 g/llogp-0.65pka_strongest_acidic1pka_strongest_basic5.52iupacpyridine-2-carboxylic acidaverage_mass123.1094mono_mass123.032028409smilesOC(=O)C1=CC=CC=N1formulaC6H5NO2inchiInChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)inchikeySIOXPEMLGUPBBT-UHFFFAOYSA-Npolar_surface_area50.19refractivity30.79polarizability11.38rotatable_bond_count1acceptor_count3donor_count1physiological_charge-1formal_charge0Specdb::MsIr1707Specdb::MsIr1708Specdb::MsIr1709Specdb::CMs811Specdb::CMs1057Specdb::CMs21361Specdb::CMs26855Specdb::CMs30435Specdb::CMs31404Specdb::CMs32028Specdb::CMs38338Specdb::CMs164778Specdb::NmrTwoD1807Specdb::NmrOneD1868Specdb::NmrOneD115658Specdb::NmrOneD115659Specdb::NmrOneD115660Specdb::NmrOneD115661Specdb::NmrOneD115662Specdb::NmrOneD115663Specdb::NmrOneD115664Specdb::NmrOneD115665Specdb::NmrOneD115666Specdb::NmrOneD115667Specdb::NmrOneD115668Specdb::NmrOneD115669Specdb::NmrOneD115670Specdb::NmrOneD115671Specdb::NmrOneD115672Specdb::NmrOneD115673Specdb::NmrOneD115674Specdb::NmrOneD115675Specdb::NmrOneD115676Specdb::NmrOneD115677Specdb::MsMs2043Specdb::MsMs2044Specdb::MsMs2045Specdb::MsMs5751Specdb::MsMs5752Specdb::MsMs5753Specdb::MsMs5754Specdb::MsMs5755Specdb::MsMs5756Specdb::MsMs10217Specdb::MsMs10218Specdb::MsMs10219Specdb::MsMs16889Specdb::MsMs16890Specdb::MsMs16891Specdb::MsMs445166Specdb::MsMs445167Specdb::MsMs446742Specdb::MsMs446743Specdb::MsMs446744Specdb::MsMs446745Specdb::MsMs446746Specdb::MsMs451907Specdb::MsMs2228141Specdb::MsMs2252487HMDB02243287476PC#<Reference:0x0000555675ab3580>#<Reference:0x0000555675ab3350>#<Reference:0x0000555675ab30d0>#<Reference:0x0000555675ab2ea0>#<Reference:0x0000555675ab2c48>#<Reference:0x0000555675ab2a18>#<Reference:0x0000555675ab27e8>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823