Showing NP-Card for Pyruvic acid (NP0000944)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:40:25 UTC
NP-MRD IDNP0000944
Secondary Accession NumbersNone
Natural Product Identification
Common NamePyruvic acid
DescriptionPyruvic acid or pyruvate is a simple alpha-keto acid. It is a three-carbon molecule containing a carboxylic acid group and a ketone functional group. Pyruvate is the simplest alpha-keto acid and according to official nomenclature by IUPAC, it is called alpha-keto propanoic acid. Like other keto acids, pyruvic acid can tautomerize from its ketone form to its enol form, containing a double bond and an alcohol. Pyruvate is found in all living organisms ranging from bacteria to plants to humans. It is intermediate compound in the metabolism of carbohydrates, proteins, and fats. Pyruvate is a key intermediate in several metabolic pathways throughout the cell. In particular, pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through a reaction with acetyl-CoA. Pyruvic acid supplies energy to cells through the citric acid cycle (TCA or Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking (lactic acid). In glycolysis, phosphoenolpyruvate (PEP) is converted to pyruvate by pyruvate kinase. This reaction is strongly exergonic and irreversible. In gluconeogenesis, it takes two enzymes, pyruvate carboxylase and PEP carboxykinase, to catalyze the reverse transformation of pyruvate to PEP. Pyruvic acid is also a metabolite of Corynebacterium (PMID: 27872963 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000944 (Pyruvic acid)

  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 NP0000944 (Pyruvic acid)

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 NP0000944 (Pyruvic acid)

  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>
NP0000944

> <DATABASE_NAME>
NP-MRD

> <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 NP0000944 (Pyruvic acid)

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 NP0000944 (Pyruvic acid)

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 NP0000944 (Pyruvic acid)

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 NP0000944 (Pyruvic acid)

CC(=O)C(O)=O
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INCHI for NP0000944 (Pyruvic acid)

InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
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View in JSmol
Synonyms
Chemical FormulaC3H4O3
Average Mass88.0621 Da
Monoisotopic Mass88.01604 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-06View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-07-25View Spectrum
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassAlpha-keto acids and derivatives
Direct ParentAlpha-keto acids and derivatives
Alternative Parents
Substituents
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point13.8 °CNot Available
Boiling Point164.00 to 166.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP-1.240 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility134 g/LALOGPS
logP-0.38ALOGPS
logP0.066ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.99 m³·mol⁻¹ChemAxon
Polarizability7.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000243
DrugBank IDDB00119
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031141
KNApSAcK IDC00001200
Chemspider ID1031
KEGG Compound IDC00022
BioCyc IDPYRUVATE
BiGG IDNot Available
Wikipedia LinkPyruvic_acid
METLIN IDNot Available
PubChem Compound1060
PDB IDNot Available
ChEBI ID32816
Good Scents IDrw1034261
References
General References