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Showing metabocard for Picolinic acid (HMDB0002243)

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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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002243 (Picolinic acid)

  Mrv1652305271900262D          

  9  9  0  0  0  0            999 V2000
   24.7030   -5.1933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4175   -6.4308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8465   -5.6058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1320   -5.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1320   -4.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8465   -3.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5609   -4.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5609   -5.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4175   -5.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for HMDB0002243 (Picolinic acid)

HMDB0002243
     RDKit          3D
Picolinic acid
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.4014    1.7102   -0.9951 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458    0.7046   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -0.1299    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6194    0.4237   -0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789   -0.6700    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1530   -0.9735    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0936   -0.1604    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6368    0.9236   -0.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3262    1.1956   -0.7555 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2075   -1.0504   -0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8938   -1.3295    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088   -1.8356    1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1738   -0.3576    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105    1.5493   -1.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  3 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
M  END
Download

3D SDF for HMDB0002243 (Picolinic acid)

  Mrv1652305271900262D          

  9  9  0  0  0  0            999 V2000
   24.7030   -5.1933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4175   -6.4308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8465   -5.6058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1320   -5.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1320   -4.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8465   -3.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5609   -4.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5609   -5.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4175   -5.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002243

> <DATABASE_NAME>
hmdb

> <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_KEY>
SIOXPEMLGUPBBT-UHFFFAOYSA-N

> <FORMULA>
C6H5NO2

> <MOLECULAR_WEIGHT>
123.1094

> <EXACT_MASS>
123.032028409

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
11.380969930377109

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridine-2-carboxylic acid

> <ALOGPS_LOGP>
0.22

> <JCHEM_LOGP>
-0.6513314798278669

> <ALOGPS_LOGS>
-0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9979485822657974

> <JCHEM_PKA_STRONGEST_BASIC>
5.517960982029459

> <JCHEM_POLAR_SURFACE_AREA>
50.19

> <JCHEM_REFRACTIVITY>
30.7853

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
picolinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002243 (Picolinic acid)

HMDB0002243
     RDKit          3D
Picolinic acid
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.4014    1.7102   -0.9951 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458    0.7046   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -0.1299    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6194    0.4237   -0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789   -0.6700    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1530   -0.9735    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0936   -0.1604    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6368    0.9236   -0.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3262    1.1956   -0.7555 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2075   -1.0504   -0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8938   -1.3295    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088   -1.8356    1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1738   -0.3576    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105    1.5493   -1.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  3 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
M  END
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PDB for HMDB0002243 (Picolinic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      46.112  -9.694   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      47.446 -12.004   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      50.113 -10.464   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      48.780  -9.694   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      48.780  -8.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      50.113  -7.384   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      51.447  -8.154   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      51.447  -9.694   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      47.446 -10.464   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    4    8                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7                                                       
CONECT    9    1    2    4                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0002243 (Picolinic acid)

COMPND    HMDB0002243
HETATM    1  O1  UNL     1       2.401   1.710  -0.995  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.046   0.705  -0.326  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.956  -0.130   0.279  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.619   0.424  -0.192  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.179  -0.670   0.534  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.153  -0.974   0.686  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.094  -0.160   0.095  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.637   0.924  -0.624  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.326   1.196  -0.755  1.00  0.00           N  
HETATM   10  H1  UNL     1       3.207  -1.050  -0.075  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.894  -1.329   1.011  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.509  -1.836   1.258  1.00  0.00           H  
HETATM   13  H4  UNL     1      -3.174  -0.358   0.186  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.411   1.549  -1.080  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    5    9
CONECT    5    6   11
CONECT    6    7    7   12
CONECT    7    8   13
CONECT    8    9    9   14
END
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SMILES for HMDB0002243 (Picolinic acid)

OC(=O)C1=CC=CC=N1
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INCHI for HMDB0002243 (Picolinic acid)

InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
Biological locationSource
ProcessNot Available
Role
Industrial application
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Abnormal Concentrations
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)Not Available
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 ]