Showing metabocard for Pyruvic acid (MMDBc0000083)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:29:45 UTC
Update Date2024-09-28 02:14:55 UTC
Metabolite IDMMDBc0000083
Metabolite Identification
Common NamePyruvic acid
DescriptionPyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures (From Stedman, 26th ed.). Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds). Pyruvic acid is found to be associated with Fumarase deficiency, which is an inborn error of metabolism. It is also a metabolite of Corynebacterium (PMID: 27872963 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46c4f01a38>


  Mrv1652309032023582D          

  6  5  0  0  0  0            999 V2000
    2.0928    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  4  2  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f46c4f01a38>

HMDB0000243
     RDKit          3D
Pyruvic acid
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.4948   -0.0189    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0968    0.4780   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926    1.6951    0.1124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9950   -0.4146   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -1.6555   -0.5104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428    0.1557   -0.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8284    0.2737    1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043    0.4053   -0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4394   -1.1250    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8494    0.2062    0.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  6 10  1  0
M  END
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3D SDF for #<Metabolite:0x00007f46c4f01a38>


  Mrv1652309032023582D          

  6  5  0  0  0  0            999 V2000
    2.0928    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  4  2  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000083

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)

> <INCHI_KEY>
LCTONWCANYUPML-UHFFFAOYSA-N

> <FORMULA>
C3H4O3

> <MOLECULAR_WEIGHT>
88.0621

> <EXACT_MASS>
88.016043994

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
7.310505872988212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopropanoic acid

> <ALOGPS_LOGP>
-0.38

> <JCHEM_LOGP>
0.06587395333333337

> <ALOGPS_LOGS>
0.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.93012330309767

> <JCHEM_PKA_STRONGEST_BASIC>
-9.583170381128017

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
17.9897

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f46c4f01a38>

HMDB0000243
     RDKit          3D
Pyruvic acid
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.4948   -0.0189    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0968    0.4780   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926    1.6951    0.1124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9950   -0.4146   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -1.6555   -0.5104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428    0.1557   -0.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8284    0.2737    1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043    0.4053   -0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4394   -1.1250    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8494    0.2062    0.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  6 10  1  0
M  END
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PDB for #<Metabolite:0x00007f46c4f01a38>

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0       3.907   0.385   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.574   1.925   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.240  -1.925   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.907  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.240  -0.385   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    4                                                            
CONECT    3    6                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    1    3    4                                                  
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for #<Metabolite:0x00007f46c4f01a38>

COMPND    HMDB0000243
HETATM    1  C1  UNL     1      -1.495  -0.019   0.188  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.097   0.478  -0.019  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.093   1.695   0.112  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.995  -0.415  -0.360  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.884  -1.655  -0.510  1.00  0.00           O  
HETATM    6  O3  UNL     1       2.243   0.156  -0.528  1.00  0.00           O  
HETATM    7  H1  UNL     1      -1.828   0.274   1.203  1.00  0.00           H  
HETATM    8  H2  UNL     1      -2.204   0.405  -0.535  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.439  -1.125   0.160  1.00  0.00           H  
HETATM   10  H4  UNL     1       2.849   0.206   0.288  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    3    4
CONECT    4    5    5    6
CONECT    6   10
END
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SMILES for #<Metabolite:0x00007f46c4f01a38>

CC(=O)C(O)=O
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INCHI for #<Metabolite:0x00007f46c4f01a38>

InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
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Synonyms
ValueSource
2-Ketopropionic acidChEBI
2-Oxopropanoic acidChEBI
2-OxopropansaeureChEBI
2-OxopropionsaeureChEBI
Acetylformic acidChEBI
Acide pyruviqueChEBI
alpha-Ketopropionic acidChEBI
alpha-OxopropionsaeureChEBI
BrenztraubensaeureChEBI
BTSChEBI
CH3COCOOHChEBI
Pyroracemic acidChEBI
2-OxopropanoateKegg
2-KetopropionateGenerator
AcetylformateGenerator
a-KetopropionateGenerator
a-Ketopropionic acidGenerator
alpha-KetopropionateGenerator
Α-ketopropionateGenerator
Α-ketopropionic acidGenerator
a-OxopropionsaeureGenerator
Α-oxopropionsaeureGenerator
PyroracemateGenerator
PyruvateGenerator
2-OxopropionateHMDB
2-Oxopropionic acidHMDB
Acid, pyruvicMeSH, HMDB
Pyruvic acidHMDB
alpha-Ketopropanoic acidHMDB
α-Ketopropanoic acidHMDB
Molecular FormulaC3H4O3
Average Mass88.0621
Monoisotopic Mass88.016043994
IUPAC Name2-oxopropanoic acid
Traditional Namepyruvic acid
CAS Registry Number127-17-3
SMILES
CC(=O)C(O)=O
InChI Identifier
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
InChI KeyLCTONWCANYUPML-UHFFFAOYSA-N