Showing metabocard for Pyrazinic acid (MMDBc0029680)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:37:17 UTC
Update Date2024-04-30 19:40:35 UTC
Metabolite IDMMDBc0029680
Metabolite Identification
Common NamePyrazinic acid
DescriptionPyrazinic acid is a member of the chemical class known as Pyrazines. These are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Pyrazinamide (PZA), an analog of nicotinamide, is a prodrug that requires conversion to the bactericidal compound pyrazinoic acid (POA) by the bacterial pyrazinamidase (PZase) activity of nicotinamidase to show activity against Mycobacterium tuberculosis. (PMID 10049264 )
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fed14278ea0>

Structure #1
  Mrv0541 02241206232D          

  9  9  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fed14278ea0>

HMDB0059734
     RDKit          3D
Pyrazin-2-carboxylic acid
 13 13  0  0  0  0  0  0  0  0999 V2000
    2.0075   -0.4317   -2.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7693   -0.5580   -0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322   -1.1030   -0.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4628   -0.1111   -0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1210   -0.2124    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0742    0.2024    1.4523 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020    0.7348    0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589    0.8372   -0.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4564    0.4209   -1.1340 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885   -1.4776    0.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084   -0.6258    1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9747    1.0761    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3234    1.2483   -1.4442 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
  7 12  1  0
  8 13  1  0
M  END
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3D SDF for #<Metabolite:0x00007fed14278ea0>

Structure #1
  Mrv0541 02241206232D          

  9  9  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029680

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=CN=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)

> <INCHI_KEY>
NIPZZXUFJPQHNH-UHFFFAOYSA-N

> <FORMULA>
C5H4N2O2

> <MOLECULAR_WEIGHT>
124.0975

> <EXACT_MASS>
124.027277382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
10.71902388297032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyrazine-2-carboxylic acid

> <ALOGPS_LOGP>
-0.52

> <JCHEM_LOGP>
-0.41866580433333334

> <ALOGPS_LOGS>
-0.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4400522909719355

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9605520090943677

> <JCHEM_POLAR_SURFACE_AREA>
63.08

> <JCHEM_REFRACTIVITY>
28.6284

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrazinoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fed14278ea0>

HMDB0059734
     RDKit          3D
Pyrazin-2-carboxylic acid
 13 13  0  0  0  0  0  0  0  0999 V2000
    2.0075   -0.4317   -2.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7693   -0.5580   -0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322   -1.1030   -0.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4628   -0.1111   -0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1210   -0.2124    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0742    0.2024    1.4523 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020    0.7348    0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589    0.8372   -0.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4564    0.4209   -1.1340 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885   -1.4776    0.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084   -0.6258    1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9747    1.0761    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3234    1.2483   -1.4442 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
  7 12  1  0
  8 13  1  0
M  END
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PDB for #<Metabolite:0x00007fed14278ea0>

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    4    6                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    8    9                                                  
CONECT    6    1    3                                                       
CONECT    7    2    4                                                       
CONECT    8    5                                                            
CONECT    9    5                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for #<Metabolite:0x00007fed14278ea0>

COMPND    HMDB0059734
HETATM    1  O1  UNL     1       2.007  -0.432  -2.033  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.769  -0.558  -0.806  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.732  -1.103  -0.000  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.463  -0.111  -0.301  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.121  -0.212   1.023  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.074   0.202   1.452  1.00  0.00           N  
HETATM    7  C4  UNL     1      -2.002   0.735   0.636  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.659   0.837  -0.697  1.00  0.00           C  
HETATM    9  N2  UNL     1      -0.456   0.421  -1.134  1.00  0.00           N  
HETATM   10  H1  UNL     1       2.588  -1.478   0.925  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.808  -0.626   1.731  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.975   1.076   0.965  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.323   1.248  -1.444  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
CONECT    7    8   12
CONECT    8    9    9   13
END
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SMILES for #<Metabolite:0x00007fed14278ea0>

OC(=O)C1=CN=CC=N1
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INCHI for #<Metabolite:0x00007fed14278ea0>

InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)
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Synonyms
ValueSource
2-CarboxypyrazineChEBI
2-Pyrazinecarboxylic acidChEBI
Paradiazinecarboxylic acidChEBI
Pyrazinecarboxylic acidChEBI
Pyrazinemonocarboxylic acidChEBI
Pyrazinic acidChEBI
Pyrazinoic acidChEBI
2-PyrazinecarboxylateGenerator
ParadiazinecarboxylateGenerator
PyrazinecarboxylateGenerator
PyrazinemonocarboxylateGenerator
PyrazinateGenerator
PyrazinoateGenerator
Pyrazin-2-carboxylateGenerator
Pyrazine-2-carboxylic acidMeSH
Pyrazine-2-carboxylateGenerator
Molecular FormulaC5H4N2O2
Average Mass124.0975
Monoisotopic Mass124.027277382
IUPAC Namepyrazine-2-carboxylic acid
Traditional Namepyrazinoic acid
CAS Registry Number98-97-5
SMILES
OC(=O)C1=CN=CC=N1
InChI Identifier
InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)
InChI KeyNIPZZXUFJPQHNH-UHFFFAOYSA-N