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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2019-04-01 19:20:02 UTC
HMDB IDHMDB0002243
Secondary Accession Numbers
  • HMDB02243
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
Data?1547234211
Synonyms
ValueSource
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
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 KeySIOXPEMLGUPBBT-UHFFFAOYSA-N
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.
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:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.79 m³·mol⁻¹ChemAxon
Polarizability11.38 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001r-0900000000-3d42fed18a7170ac902cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005i-4900000000-ceebd42c8dcc23fdf3e4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9000000000-bab2bcb7bd27b0be1f51JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001r-0900000000-3d42fed18a7170ac902cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005i-4900000000-ceebd42c8dcc23fdf3e4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001r-0900000000-7276adde2578b546a8f2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-9400000000-7356d3453f3427cc9d89JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9500000000-5d9f84aec4ab264b04dbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0adi-3900000000-7fac959b15471dc94406JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0e912cf3a3db8f8ee5dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-6d29f5dc4ddc1bb1adb5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (MX-1303) , Positivesplash10-0fb9-9000000000-bab2bcb7bd27b0be1f51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-05fr-0900000000-e169ce1e815eac2ad211JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-056s-9500000000-cd5fe946f692da4957caJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-004i-9000000000-927c599edd5deaf854f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-004i-9000000000-1d63eb2db32cd991a084JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-219a58c586353210f1a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-fe37c7a3e725d6a622fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05fs-4900000000-b85a7afe0ba03853cfbfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05fr-0900000000-59ec49f98e7a39b33252JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056s-9500000000-cd5fe946f692da4957caJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-927c599edd5deaf854f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-1d63eb2db32cd991a084JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-219a58c586353210f1a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-3900000000-9fd4a6ac15261e2c8d8eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-b09ed1d66b009b4624eeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-a4d3409ab064e87942a9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-ddbf2ed02e3b712aca5dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-7de5e81309a53ea848efJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-8900000000-0143384039159388b6ebJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-85d472523e404d49ec06JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0337 uMInfant (0-1 year old)FemaleNicotinamide Adenine Dinucleotide Deficiency details
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
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Nicotinamide Adenine Dinucleotide Deficiency
  1. Shi H, Enriquez A, Rapadas M, Martin EMMA, Wang R, Moreau J, Lim CK, Szot JO, Ip E, Hughes JN, Sugimoto K, Humphreys DT, McInerney-Leo AM, Leo PJ, Maghzal GJ, Halliday J, Smith J, Colley A, Mark PR, Collins F, Sillence DO, Winlaw DS, Ho JWK, Guillemin GJ, Brown MA, Kikuchi K, Thomas PQ, Stocker R, Giannoulatou E, Chapman G, Duncan EL, Sparrow DB, Dunwoodie SL: NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552. doi: 10.1056/NEJMoa1616361. [PubMed:28792876 ]
Amyotrophic lateral sclerosis
  1. Chen Y, Stankovic R, Cullen KM, Meininger V, Garner B, Coggan S, Grant R, Brew BJ, Guillemin GJ: The kynurenine pathway and inflammation in amyotrophic lateral sclerosis. Neurotox Res. 2010 Aug;18(2):132-42. doi: 10.1007/s12640-009-9129-7. Epub 2009 Nov 18. [PubMed:19921535 ]
Sporadic amyotrophic lateral sclerosis
  1. Chen Y, Stankovic R, Cullen KM, Meininger V, Garner B, Coggan S, Grant R, Brew BJ, Guillemin GJ: The kynurenine pathway and inflammation in amyotrophic lateral sclerosis. Neurotox Res. 2010 Aug;18(2):132-42. doi: 10.1007/s12640-009-9129-7. Epub 2009 Nov 18. [PubMed:19921535 ]
Familial amyotrophic lateral sclerosis
  1. Chen Y, Stankovic R, Cullen KM, Meininger V, Garner B, Coggan S, Grant R, Brew BJ, Guillemin GJ: The kynurenine pathway and inflammation in amyotrophic lateral sclerosis. Neurotox Res. 2010 Aug;18(2):132-42. doi: 10.1007/s12640-009-9129-7. Epub 2009 Nov 18. [PubMed:19921535 ]
Associated OMIM IDs
  • 105400 (Amyotrophic lateral sclerosis)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022926
KNApSAcK IDC00002063
Chemspider ID993
KEGG Compound IDC10164
BioCyc IDCPD-5062
BiGG IDNot Available
Wikipedia LinkPicolinic_acid
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. doi: 10.1038/nature07762. [PubMed: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. [PubMed:11232856 ]
  3. Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:6694049 ]