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Showing NP-Card for Picolinic acid (NP0000706)

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Record Information
Version1.0
Created at2006-05-22 14:17:43 UTC
Updated at2021-10-07 20:40:47 UTC
NP-MRD IDNP0000706
Secondary Accession NumbersNone
Natural Product 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 NP0000706 (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
Download

3D MOL for NP0000706 (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 NP0000706 (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>
NP0000706

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000706 (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

PDB for NP0000706 (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
Download

3D PDB for NP0000706 (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 NP0000706 (Picolinic acid)

OC(=O)C1=CC=CC=N1
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INCHI for NP0000706 (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 Assignments
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 Mass123.1094 Da
Monoisotopic Mass123.03203 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pyricularia oryzae-
Russula subnigricansLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Species Where Detected
Species NameSourceReference
Fusarium lateritiumKNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
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
HMDB IDHMDB0002243
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1274841
References
General References
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