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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:36 UTC
Update Date2022-03-07 02:53:03 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?1563862151
Synonyms
ValueSource
Ethyl pyruvic acidGenerator
2-oxo-Propionic acid ethyl esterHMDB
2-oxo-Propionate ethyl esterHMDB
Ethyl 2-oxopropanoateHMDB
Ethyl 2-oxopropionateHMDB
Ethyl pyroracemateHMDB
FEMA 2457HMDB
Propanoic acid, 2-oxo-, ethyl esterHMDB
Pyruvic acid ethyl esterHMDB
Pyruvic acid, ethyl esterHMDB
2-Oxopropanoic acid ethyl esterHMDB
2-Oxopropionic acid ethyl esterHMDB
Ethyl methylglyoxylateHMDB
Methyl ethoxycarbonyl ketoneHMDB
NSC 48386HMDB
Ethyl 2-oxopropanoic acidHMDB
Ethyl pyruvateHMDB, MeSH
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
Disposition

Source

Route of exposure

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
PropertyValueSource
Water Solubility86.8 g/LALOGPS
logP0.24ALOGPS
logP0.8ChemAxon
logS-0.57ALOGPS
pKa (Strongest Acidic)16.9ChemAxon
pKa (Strongest Basic)-7.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.51 m³·mol⁻¹ChemAxon
Polarizability11.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.52731661259
DarkChem[M-H]-119.92931661259
DeepCCS[M+H]+127.04330932474
DeepCCS[M-H]-125.02530932474
DeepCCS[M-2H]-160.99530932474
DeepCCS[M+Na]+135.43430932474
AllCCS[M+H]+128.232859911
AllCCS[M+H-H2O]+124.032859911
AllCCS[M+NH4]+132.132859911
AllCCS[M+Na]+133.332859911
AllCCS[M-H]-125.932859911
AllCCS[M+Na-2H]-129.232859911
AllCCS[M+HCOO]-132.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl pyruvateCCOC(=O)C(C)=O1117.2Standard polar33892256
Ethyl pyruvateCCOC(=O)C(C)=O695.6Standard non polar33892256
Ethyl pyruvateCCOC(=O)C(C)=O791.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethyl pyruvate,1TMS,isomer #1C=C(O[Si](C)(C)C)C(=O)OCC1064.5Semi standard non polar33892256
Ethyl pyruvate,1TMS,isomer #1C=C(O[Si](C)(C)C)C(=O)OCC1036.8Standard non polar33892256
Ethyl pyruvate,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=O)OCC1262.9Semi standard non polar33892256
Ethyl pyruvate,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=O)OCC1206.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethyl pyruvate EI-B (Non-derivatized)splash10-0006-9000000000-6b9687c0790faebef4062017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pyruvate CI-B (Non-derivatized)splash10-014i-4900000000-e148aa184db0bb5b7c162017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pyruvate EI-B (Non-derivatized)splash10-0006-9000000000-ceddbed69eabcd4ec0282017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pyruvate EI-B (Non-derivatized)splash10-0006-9000000000-980c9b02bf8c3edc429d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pyruvate EI-B (Non-derivatized)splash10-0006-9000000000-6b9687c0790faebef4062018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pyruvate CI-B (Non-derivatized)splash10-014i-4900000000-e148aa184db0bb5b7c162018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pyruvate EI-B (Non-derivatized)splash10-0006-9000000000-ceddbed69eabcd4ec0282018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pyruvate EI-B (Non-derivatized)splash10-0006-9000000000-980c9b02bf8c3edc429d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl pyruvate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 10V, Positive-QTOFsplash10-014i-3900000000-b3d7dafb3c580788a19b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 20V, Positive-QTOFsplash10-014m-9400000000-cabf5986bb33963f8a9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 40V, Positive-QTOFsplash10-0006-9000000000-fcf009856dd03d6e95912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 10V, Negative-QTOFsplash10-014i-2900000000-d4e74fcda0630e3d63482016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 20V, Negative-QTOFsplash10-014i-9800000000-3d4350790429a1d48d622016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 40V, Negative-QTOFsplash10-000f-9000000000-7d056c4cafa9bf19c9642016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 10V, Negative-QTOFsplash10-014i-4900000000-7e5d0e72cf4edb63e93f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 20V, Negative-QTOFsplash10-01bc-9400000000-60ed71a20b38254d3af02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 40V, Negative-QTOFsplash10-0006-9000000000-b13a80a659a7717e73c62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 10V, Positive-QTOFsplash10-006x-9000000000-c64b43d469c46d463ff62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 20V, Positive-QTOFsplash10-0006-9000000000-315cd46229a2be49ed9e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pyruvate 40V, Positive-QTOFsplash10-0006-9000000000-271d9ea25bd54e252a582021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
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

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