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Record Information
Version3.6
Creation Date2006-05-22 14:17:43 UTC
Update Date2016-02-11 01:05:29 UTC
HMDB IDHMDB02243
Secondary Accession NumbersNone
Metabolite Identification
Common 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 ).
Structure
Thumb
Synonyms
ValueSource
2-CarboxypyridineChEBI
2-Pyridinecarboxylic acidChEBI
alpha-Picolinic acidChEBI
alpha-Pyridinecarboxylic acidChEBI
O-Pyridinecarboxylic acidChEBI
PYRIDINE-2-carboxylIC ACIDChEBI
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
2-Methoxy-5-aminopyridineHMDB
2-Picolinic acidHMDB
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
Chemical FormulaC6H5NO2
Average Molecular Weight123.1094
Monoisotopic Molecular Weight123.032028409
IUPAC Namepyridine-2-carboxylic acid
Traditional Namepicolinic acid
CAS Registry Number98-98-6
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 KeyInChIKey=SIOXPEMLGUPBBT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point136.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility960 mg/mL at 20 °CNot Available
LogP0.72HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility61.1 mg/mLALOGPS
logP0.22ALOGPS
logP-0.67ChemAxon
logS-0.3ALOGPS
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.79 m3·mol-1ChemAxon
Polarizability11.38 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-001r-0900000000-3d42fed18a7170ac902cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005i-4900000000-ceebd42c8dcc23fdf3e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0adi-3900000000-7fac959b15471dc94406View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0e912cf3a3db8f8ee5dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-6d29f5dc4ddc1bb1adb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (MX-1303) , Positivesplash10-0fb9-9000000000-bab2bcb7bd27b0be1f51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-05fr-0900000000-e169ce1e815eac2ad211View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-056s-9500000000-cd5fe946f692da4957caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-004i-9000000000-927c599edd5deaf854f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-004i-9000000000-1d63eb2db32cd991a084View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-219a58c586353210f1a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-b09ed1d66b009b4624eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-a4d3409ab064e87942a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-ddbf2ed02e3b712aca5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-7de5e81309a53ea848efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-8900000000-0143384039159388b6ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-85d472523e404d49ec06View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.299 +/- 0.034 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.31 (0.21-0.46) uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified1.65-10.28 umol/mmol creatinineAdult (>18 years old)BothNormal
    • RS Lord, et al.,...
details
UrineDetected and Quantified19.4 (7.2-37.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.36 (0.18-0.71) uMAdult (>18 years old)BothCirculatory system disorder details
Cerebrospinal Fluid (CSF)Detected and Quantified0.51 +/- 0.011 uMAdult (>18 years old)Not Specifiedcontrol details
Cerebrospinal Fluid (CSF)Detected and Quantified0.36 +/- 0.04 uMAdult (>18 years old)Maleamyotrophic lateral sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.37 +/- 0.06 uMAdult (>18 years old)Femaleamyotrophic lateral sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.35 +/- 0.07 uMAdult (>18 years old)Not SpecifiedSporadic amyotrophic lateral sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.60 +/- 0.21 uMAdult (>18 years old)Not SpecifiedFamilial amyotrophic lateral sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.30 +/- 0.06 uMAdult (>18 years old)Not SpecifiedAmyotrophic lateral sclerosis (bulbar onset) details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022926
KNApSAcK IDNot Available
Chemspider ID993
KEGG Compound IDC10164
BioCyc IDCPD-5062
BiGG IDNot Available
Wikipedia LinkPicolinic acid
NuGOwiki LinkHMDB02243
Metagene LinkHMDB02243
METLIN IDNot Available
PubChem Compound1018
PDB ID6PC
ChEBI ID28747
References
Synthesis ReferenceHagedorn, 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. 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. [19212411 ]
  2. 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. [11232856 ]
  3. Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [2338430 ]
  4. Bosco MC, Rapisarda A, Reffo G, Massazza S, Pastorino S, Varesio L: Macrophage activating properties of the tryptophan catabolite picolinic acid. Adv Exp Med Biol. 2003;527:55-65. [15206716 ]
  5. Melillo G, Cox GW, Radzioch D, Varesio L: Picolinic acid, a catabolite of L-tryptophan, is a costimulus for the induction of reactive nitrogen intermediate production in murine macrophages. J Immunol. 1993 May 1;150(9):4031-40. [8473748 ]
  6. Varesio L, Clayton M, Blasi E, Ruffman R, Radzioch D: Picolinic acid, a catabolite of tryptophan, as the second signal in the activation of IFN-gamma-primed macrophages. J Immunol. 1990 Dec 15;145(12):4265-71. [1701787 ]
  7. Krieger I, Cash R, Evans GW: Picolinic acid in acrodermatitis enteropathica: evidence for a disorder of tryptophan metabolism. J Pediatr Gastroenterol Nutr. 1984;3(1):62-8. [6694049 ]