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Showing metabocard for Ethyl pyruvate (HMDB0031643)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:36 UTC
Update Date2023-02-21 17:21:05 UTC
HMDB IDHMDB0031643
Secondary Accession Numbers
  • HMDB31643
Metabolite Identification
Common NameEthyl pyruvate
DescriptionEthyl pyruvate, also known as pyruvic acid ethyl ester or 2-oxo-propionate ethyl ester, belongs to the family of alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Ethyl pyruvate is soluble (in water) and an extremely weak acidic compound (based on its pKa). When given as a drug, ethyl pyruvate (known as CTI-01) inhibits the systemic release of cytokines (e.g. TNF-alpha and HMGB1), which promote the body's inflammatory response. The over-expression of these cytokines has been linked to diseases that occur in critical care settings, such as severe organ damage following cardiopulmonary bypass (CPB) and post-operative ileus following abdominal surgery (DrugBank). Ethyl pyruvate is a flavouring ingredient.
Structure
Data?1677000065
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031643 (Ethyl pyruvate)

      
  Mrv1652303121817512D          

  8  7  0  0  0  0            999 V2000
 9994.4065 9994.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1213 9994.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8343 9994.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5493 9994.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6921 9994.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9756 9994.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6921 9995.7930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4065 9993.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
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3D MOL for HMDB0031643 (Ethyl pyruvate)

HMDB0031643
     RDKit          3D
Ethyl pyruvate
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.4653    0.2092   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8228   -0.3188    0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4990    0.1008    1.0023 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -0.1692    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -0.8527   -0.9010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8423    0.3381    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    0.0376   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288    1.0303    1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -0.0498   -0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0119   -0.2403   -1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    1.3143   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3710    0.1471    1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9406   -1.4126    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015    0.4983   -1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8887    0.4414   -0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9807   -1.0735   -0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  7 14  1  0
  7 15  1  0
  7 16  1  0
M  END
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3D SDF for HMDB0031643 (Ethyl pyruvate)

      
  Mrv1652303121817512D          

  8  7  0  0  0  0            999 V2000
 9994.4065 9994.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1213 9994.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8343 9994.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5493 9994.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6921 9994.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9756 9994.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6921 9995.7930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4065 9993.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031643

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3/c1-3-8-5(7)4(2)6/h3H2,1-2H3

> <INCHI_KEY>
XXRCUYVCPSWGCC-UHFFFAOYSA-N

> <FORMULA>
C5H8O3

> <MOLECULAR_WEIGHT>
116.1152

> <EXACT_MASS>
116.047344122

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.441461285447454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 2-oxopropanoate

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
0.8019092973333335

> <ALOGPS_LOGS>
-0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.902741432171045

> <JCHEM_PKA_STRONGEST_BASIC>
-7.733586933688887

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
27.507400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 2-oxopropanoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0031643 (Ethyl pyruvate)

HMDB0031643
     RDKit          3D
Ethyl pyruvate
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.4653    0.2092   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8228   -0.3188    0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4990    0.1008    1.0023 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -0.1692    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -0.8527   -0.9010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8423    0.3381    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    0.0376   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288    1.0303    1.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -0.0498   -0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0119   -0.2403   -1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    1.3143   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3710    0.1471    1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9406   -1.4126    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015    0.4983   -1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8887    0.4414   -0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9807   -1.0735   -0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  7 14  1  0
  7 15  1  0
  7 16  1  0
M  END
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PDB for HMDB0031643 (Ethyl pyruvate)

HEADER    PROTEIN                                 12-MAR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-MAR-18         0                                  
HETATM    1  C   UNK     0    8656.2268656.506   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8657.5608657.275   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8658.8918656.506   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8660.2258657.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8654.8928657.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8653.5548656.506   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8654.8928658.814   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8656.2268654.966   0.000  0.00  0.00           O+0
CONECT    1    2    5    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    1    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0031643 (Ethyl pyruvate)

COMPND    HMDB0031643
HETATM    1  C1  UNL     1      -2.465   0.209  -0.335  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.823  -0.319   0.919  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.499   0.101   1.002  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.497  -0.169   0.099  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.219  -0.853  -0.901  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.842   0.338   0.317  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.904   0.038  -0.667  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.129   1.030   1.327  1.00  0.00           O  
HETATM    9  H1  UNL     1      -3.548  -0.050  -0.282  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.012  -0.240  -1.237  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.403   1.314  -0.316  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.371   0.147   1.790  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.941  -1.413   1.025  1.00  0.00           H  
HETATM   14  H6  UNL     1       2.602   0.498  -1.636  1.00  0.00           H  
HETATM   15  H7  UNL     1       3.889   0.441  -0.361  1.00  0.00           H  
HETATM   16  H8  UNL     1       2.981  -1.074  -0.745  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8    8
CONECT    7   14   15   16
END
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SMILES for HMDB0031643 (Ethyl pyruvate)

CCOC(=O)C(C)=O
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INCHI for HMDB0031643 (Ethyl pyruvate)

InChI=1S/C5H8O3/c1-3-8-5(7)4(2)6/h3H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H8O3
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
IUPAC Nameethyl 2-oxopropanoate
Traditional Nameethyl 2-oxopropanoate
CAS Registry Number617-35-6
SMILES
CCOC(=O)C(C)=O
InChI Identifier
InChI=1S/C5H8O3/c1-3-8-5(7)4(2)6/h3H2,1-2H3
InChI KeyXXRCUYVCPSWGCC-UHFFFAOYSA-N
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
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-50 °CNot Available
Boiling Point144.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility259000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.351 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05869
Phenol Explorer Compound IDNot Available
FooDB IDFDB008294
KNApSAcK IDC00050457
Chemspider ID11544
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12041
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004191
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Cheng BQ, Liu CT, Li WJ, Fan W, Zhong N, Zhang Y, Jia XQ, Zhang SZ: Ethyl pyruvate improves survival and ameliorates distant organ injury in rats with severe acute pancreatitis. Pancreas. 2007 Oct;35(3):256-61. [PubMed:17895847 ]
  2. Kou QY, Guan XD: [Effect of ethyl pyruvate on indices of tissue oxygenation and perfusion in dogs with septic shock]. Zhongguo Wei Zhong Bing Ji Jiu Yi Xue. 2008 Jan;20(1):34-6. [PubMed:18199399 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. Tumor necrosis factor
General function:
Involved in tumor necrosis factor receptor binding
Specific function:
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation
Gene Name:
TNF
Uniprot ID:
P01375
Molecular weight:
25644.1