Record Information
Version1.0
Creation date2011-09-21 00:21:48 UTC
Update date2015-10-09 22:33:15 UTC
Primary IDFDB022926
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePicolinic acid
DescriptionPicolinic 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 Number98-98-6
Structure
Thumb
Synonyms
SynonymSource
2-CarboxypyridineChEBI
2-Picolinic acidChEBI
2-Pyridinecarboxylic acidChEBI
alpha-Picolinic acidChEBI
alpha-Pyridinecarboxylic acidChEBI
O-Pyridinecarboxylic acidChEBI
PYRIDINE-2-carboxylIC ACIDChEBI
2-PicolinateGenerator
2-PyridinecarboxylateGenerator
a-PicolinateGenerator
a-Picolinic acidGenerator
alpha-PicolinateGenerator
Α-picolinateGenerator
Α-picolinic acidGenerator
a-PyridinecarboxylateGenerator
a-Pyridinecarboxylic acidGenerator
alpha-PyridinecarboxylateGenerator
Α-pyridinecarboxylateGenerator
Α-pyridinecarboxylic acidGenerator
O-PyridinecarboxylateGenerator
PYRIDINE-2-carboxylateGenerator
PicolinateGenerator
2-Methoxy-5-aminopyridineHMDB
4,5-Dehydropipecolic acidHMDB
5-Amino-2-fluoropyridineHMDB
5-Amino-2-methoxypyridineHMDB
5-Amino-2-pyridinecarboxylic acidHMDB
5-Aminopicolinic acidHMDB
5-Aminopyridine-2-carboxylic acidHMDB
6-Methoxy-pyridin-3-ylamineHMDB
Acide picoliqueHMDB
L-BaikiainHMDB
Phenyl-(2-pyridyl)acetonitrileHMDB
PLAHMDB
Pyridine-carboxylique-2HMDB
Pyridinecarboxylic acid-(2)HMDB
Iron(III) picolinateHMDB
Zinc picolinateHMDB
Picolinic acid, sodium saltHMDB
2-Pyridine carboxylic acidHMDB
Calcium dipicolinate trihydrateHMDB
Picolinic acid, hydrochlorideHMDB
Chromium picolinateHMDB
2-methoxy-5-aminopyridinehmdb
5-amino-2-Pyridinecarboxylic acidhmdb
acide picoliquehmdb
o-Pyridinecarboxylic acidhmdb
Pyridine-2-carboxylic acidhmdb
α-picolinateGenerator
α-picolinic acidGenerator
α-pyridinecarboxylateGenerator
α-pyridinecarboxylic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility61.1 g/LALOGPS
logP0.22ALOGPS
logP-0.65ChemAxon
logS-0.3ALOGPS
pKa (Strongest Acidic)1ChemAxon
pKa (Strongest Basic)5.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.79 m³·mol⁻¹ChemAxon
Polarizability11.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H5NO2
IUPAC namepyridine-2-carboxylic acid
InChI IdentifierInChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
InChI KeySIOXPEMLGUPBBT-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC=CC=N1
Average Molecular Weight123.1094
Monoisotopic Molecular Weight123.032028409
Classification
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPicolinic acid, non-derivatized, GC-MS Spectrumsplash10-001r-0900000000-3d42fed18a7170ac902cSpectrum
GC-MSPicolinic acid, 1 TMS, GC-MS Spectrumsplash10-005i-4900000000-ceebd42c8dcc23fdf3e4Spectrum
GC-MSPicolinic acid, non-derivatized, GC-MS Spectrumsplash10-0fb9-9000000000-bab2bcb7bd27b0be1f51Spectrum
GC-MSPicolinic acid, non-derivatized, GC-MS Spectrumsplash10-001r-0900000000-3d42fed18a7170ac902cSpectrum
GC-MSPicolinic acid, non-derivatized, GC-MS Spectrumsplash10-005i-4900000000-ceebd42c8dcc23fdf3e4Spectrum
GC-MSPicolinic acid, non-derivatized, GC-MS Spectrumsplash10-001r-0900000000-7276adde2578b546a8f2Spectrum
Predicted GC-MSPicolinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i0-9400000000-7356d3453f3427cc9d89Spectrum
Predicted GC-MSPicolinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9500000000-5d9f84aec4ab264b04dbSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0adi-3900000000-7fac959b15471dc94406Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0e912cf3a3db8f8ee5dfSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-6d29f5dc4ddc1bb1adb5Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (MX-1303) , Positivesplash10-0fb9-9000000000-bab2bcb7bd27b0be1f51Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-05fr-0900000000-e169ce1e815eac2ad211Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-056s-9500000000-cd5fe946f692da4957caSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-004i-9000000000-927c599edd5deaf854f0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-004i-9000000000-1d63eb2db32cd991a084Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-219a58c586353210f1a3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-fe37c7a3e725d6a622fdSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05fs-4900000000-b85a7afe0ba03853cfbfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05fr-0900000000-59ec49f98e7a39b33252Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056s-9500000000-cd5fe946f692da4957caSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-927c599edd5deaf854f0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-1d63eb2db32cd991a084Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-219a58c586353210f1a3Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-3900000000-9fd4a6ac15261e2c8d8eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-b09ed1d66b009b4624eeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-a4d3409ab064e87942a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-ddbf2ed02e3b712aca5dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-7de5e81309a53ea848efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-8900000000-0143384039159388b6ebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-85d472523e404d49ec06Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID993
ChEMBL IDCHEMBL72628
KEGG Compound IDC10164
Pubchem Compound ID1018
Pubchem Substance IDNot Available
ChEBI ID28747
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02243
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID6PC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPicolinic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference