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Showing NP-Card for acetylpyruvic acid (NP0276358)

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Record Information
Version2.0
Created at2022-09-09 00:26:34 UTC
Updated at2022-09-09 00:26:34 UTC
NP-MRD IDNP0276358
Secondary Accession NumbersNone
Natural Product Identification
Common Nameacetylpyruvic acid
DescriptionAcetylpyruvic acid, also known as 2,4-dioxopentanoate or 2,4-dioxovaleric acid, belongs to the class of organic compounds known as 3-acylpyruvic acids. 3-Acylpyruvic acids are compounds containing a pyruvic acid substituted at the 3-position by an acyl group. Acetylpyruvic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. acetylpyruvic acid was first documented in 1976 (PMID: 1254564). Based on a literature review very few articles have been published on acetylpyruvic acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0276358 (acetylpyruvic acid)


  Mrv1652309092202262D          

  9  8  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for NP0276358 (acetylpyruvic acid)

     RDKit          3D

 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.5773   -0.0556   -0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2281    0.0617    0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0564   -0.4057    1.6020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700    0.6812   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -0.2860   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9022   -1.3849    0.4354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3188    0.0893   -0.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4672    1.2178   -1.3137 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3470   -0.8084   -0.7153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1118   -0.9091    0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1354    0.8901   -0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5342   -0.3174   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104    0.9887   -1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1707    1.6055    0.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -1.3672    0.0613 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  1  0
  5  6  2  0
  5  7  1  0
  7  9  1  0
  7  8  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  4 14  1  0
  9 15  1  0
M  END
Download

3D SDF for NP0276358 (acetylpyruvic acid)


  Mrv1652309092202262D          

  9  8  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0276358

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O4/c1-3(6)2-4(7)5(8)9/h2H2,1H3,(H,8,9)

> <INCHI_KEY>
UNRQTHVKJQUDDF-UHFFFAOYSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.099

> <EXACT_MASS>
130.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.170031003123977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4-dioxopentanoic acid

> <JCHEM_LOGP>
0.28772792199999986

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.81648030169802

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.862650480446318

> <JCHEM_PKA_STRONGEST_BASIC>
-7.434947999963477

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
27.884900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
acetylpyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0276358 (acetylpyruvic acid)

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PDB for NP0276358 (acetylpyruvic acid)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0276358 (acetylpyruvic acid)
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SMILES for NP0276358 (acetylpyruvic acid)
CC(=O)CC(=O)C(O)=O
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INCHI for NP0276358 (acetylpyruvic acid)
InChI=1S/C5H6O4/c1-3(6)2-4(7)5(8)9/h2H2,1H3,(H,8,9)
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Synonyms
ValueSource
2,4-DioxopentanoateChEBI
2,4-Dioxovaleric acidChEBI
AcetylpyruvateChEBI
2,4-Dioxopentanoic acidGenerator
2,4-DioxovalerateGenerator
AcetopyruvateMeSH
Chemical FormulaC5H6O4
Average Mass130.0990 Da
Monoisotopic Mass130.02661 Da
IUPAC Name2,4-dioxopentanoic acid
Traditional Nameacetylpyruvic acid
CAS Registry NumberNot Available
SMILES
CC(=O)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-3(6)2-4(7)5(8)9/h2H2,1H3,(H,8,9)
InChI KeyUNRQTHVKJQUDDF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-acylpyruvic acids. 3-Acylpyruvic acids are compounds containing a pyruvic acid substituted at the 3-position by an acyl group.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassGamma-keto acids and derivatives  
Direct Parent3-Acylpyruvic acids  
Alternative Parents
Substituents
  • 3-acylpyruvic acid
    • 

  • 1,3-diketone
    • 

  • Short-chain keto acid
    • 

  • Alpha-keto acid
    • 

  • 1,3-dicarbonyl compound
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.29ChemAxon
pKa (Strongest Acidic)2.86ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.88 m³·mol⁻¹ChemAxon
Polarizability11.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID20603  
KEGG Compound IDC02132  
BioCyc IDCPD-612  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21919  
PDB IDNot Available
ChEBI ID2424  
Good Scents IDNot Available
References
General References
  1. Chapman PJ, Ribbons DW: Metabolism of resorcinylic compounds by bacteria: orcinol pathway in Pseudomonas putida. J Bacteriol. 1976 Mar;125(3):975-84. doi: 10.1128/jb.125.3.975-984.1976. [PubMed:1254564  ] 
  2. LOTUS database [Link]