Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2023-02-21 17:16:17 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?1676999777
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) picolinateMeSH, HMDB
Zinc picolinateMeSH, HMDB
Picolinic acid, sodium saltMeSH, HMDB
2-Pyridine carboxylic acidMeSH, HMDB
Calcium dipicolinate trihydrateMeSH, HMDB
Picolinic acid, hydrochlorideMeSH, HMDB
Chromium picolinateMeSH, 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 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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular 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)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.63431661259
DarkChem[M-H]-117.96531661259
DeepCCS[M+H]+120.4830932474
DeepCCS[M-H]-117.15530932474
DeepCCS[M-2H]-153.96330932474
DeepCCS[M+Na]+129.04430932474
AllCCS[M+H]+124.732859911
AllCCS[M+H-H2O]+119.832859911
AllCCS[M+NH4]+129.332859911
AllCCS[M+Na]+130.632859911
AllCCS[M-H]-120.432859911
AllCCS[M+Na-2H]-122.432859911
AllCCS[M+HCOO]-124.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Picolinic acidOC(=O)C1=CC=CC=N12137.1Standard polar33892256
Picolinic acidOC(=O)C1=CC=CC=N11183.8Standard non polar33892256
Picolinic acidOC(=O)C1=CC=CC=N11193.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Picolinic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=N11291.3Semi standard non polar33892256
Picolinic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=N11511.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Picolinic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001r-0900000000-3d42fed18a7170ac902c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Picolinic acid GC-MS (1 TMS)splash10-005i-4900000000-ceebd42c8dcc23fdf3e42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Picolinic acid EI-B (Non-derivatized)splash10-0fb9-9000000000-bab2bcb7bd27b0be1f512017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Picolinic acid GC-EI-TOF (Non-derivatized)splash10-001r-0900000000-3d42fed18a7170ac902c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Picolinic acid GC-MS (Non-derivatized)splash10-005i-4900000000-ceebd42c8dcc23fdf3e42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Picolinic acid GC-EI-TOF (Non-derivatized)splash10-001r-0900000000-7276adde2578b546a8f22017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Picolinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-9400000000-7356d3453f3427cc9d892017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Picolinic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9500000000-5d9f84aec4ab264b04db2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Picolinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0adi-3900000000-7fac959b15471dc944062012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004i-9000000000-0e912cf3a3db8f8ee5df2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0fb9-9000000000-6d29f5dc4ddc1bb1adb52012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid EI-B (MX-1303) , Positive-QTOFsplash10-0fb9-9000000000-bab2bcb7bd27b0be1f512012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-05fr-0900000000-e169ce1e815eac2ad2112012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-056s-9500000000-cd5fe946f692da4957ca2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-004i-9000000000-927c599edd5deaf854f02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-004i-9000000000-1d63eb2db32cd991a0842012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-004i-9000000000-219a58c586353210f1a32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-fe37c7a3e725d6a622fd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QTOF , positive-QTOFsplash10-05fs-4900000000-b85a7afe0ba03853cfbf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ , positive-QTOFsplash10-05fr-0900000000-59ec49f98e7a39b332522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ , positive-QTOFsplash10-056s-9500000000-cd5fe946f692da4957ca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ , positive-QTOFsplash10-004i-9000000000-927c599edd5deaf854f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ , positive-QTOFsplash10-004i-9000000000-1d63eb2db32cd991a0842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid LC-ESI-QQ , positive-QTOFsplash10-004i-9000000000-219a58c586353210f1a32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid , positive-QTOFsplash10-00di-3900000000-9fd4a6ac15261e2c8d8e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid 40V, Negative-QTOFsplash10-02t9-9600000000-bc378bb03dd26ace9a392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Picolinic acid 10V, Positive-QTOFsplash10-00di-0900000000-fe37c7a3e725d6a622fd2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Picolinic acid 10V, Positive-QTOFsplash10-00di-0900000000-b09ed1d66b009b4624ee2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Picolinic acid 20V, Positive-QTOFsplash10-00di-1900000000-a4d3409ab064e87942a92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Picolinic acid 40V, Positive-QTOFsplash10-0udi-9000000000-ddbf2ed02e3b712aca5d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Picolinic acid 10V, Negative-QTOFsplash10-00di-2900000000-7de5e81309a53ea848ef2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Picolinic acid 20V, Negative-QTOFsplash10-00fr-8900000000-0143384039159388b6eb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Picolinic acid 40V, Negative-QTOFsplash10-004i-9000000000-85d472523e404d49ec062015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB022926
KNApSAcK IDC00002063
Chemspider ID993
KEGG Compound IDC10164
BioCyc IDPICOLINATE
BiGG IDNot Available
Wikipedia LinkPicolinic_acid
METLIN IDNot Available
PubChem Compound1018
PDB IDNot Available
ChEBI ID28747
Food Biomarker OntologyNot Available
VMH IDC10164
MarkerDB IDMDB00000386
Good Scents IDrw1274841
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 ]