Showing metabocard for Picolinic acid (MMDBc0000411)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:37:09 UTC
Update Date2024-10-09 15:49:09 UTC
Metabolite IDMMDBc0000411
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb714f8310>


  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 #<Metabolite:0x00007fdb714f8310>

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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3D SDF for #<Metabolite:0x00007fdb714f8310>


  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>
MMDBc0000411

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fdb714f8310>

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 #<Metabolite:0x00007fdb714f8310>

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 #<Metabolite:0x00007fdb714f8310>

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 #<Metabolite:0x00007fdb714f8310>

OC(=O)C1=CC=CC=N1
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INCHI for #<Metabolite:0x00007fdb714f8310>

InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
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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
Molecular FormulaC6H5NO2
Average Mass123.1094
Monoisotopic Mass123.032028409
IUPAC Namepyridine-2-carboxylic acid
Traditional Namepicolinic acid
CAS Registry NumberNot Available
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