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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:01:05 UTC
Update Date2022-03-07 02:55:30 UTC
HMDB IDHMDB0037759
Secondary Accession Numbers
  • HMDB37759
Metabolite Identification
Common Name2-Methylene-4-oxopentanedioic acid
Description2-Methylene-4-oxopentanedioic acid, also known as 4-carboxy-2-oxo-4-pentenoate, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. 2-Methylene-4-oxopentanedioic acid exists in all living organisms, ranging from bacteria to humans. 2-Methylene-4-oxopentanedioic acid has been detected, but not quantified in, nuts. This could make 2-methylene-4-oxopentanedioic acid a potential biomarker for the consumption of these foods. 2-Methylene-4-oxopentanedioic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 2-Methylene-4-oxopentanedioic acid.
Structure
Data?1563863084
Synonyms
ValueSource
2-Methylidene-4-oxopentanedioic acidKegg
4-Carboxy-2-oxo-4-pentenoateKegg
2-Methylidene-4-oxopentanedioateGenerator
4-Carboxy-2-oxo-4-pentenoic acidGenerator
2-Methylene-4-oxopentanedioateGenerator
2-Methylene-4-oxoglutaric acidHMDB
g-Methylene-a-ketoglutaric acidHMDB
2-Methylene-4-oxo-pentanedioateGenerator
2-oxo-4-MethylenepentanedioateGenerator
Chemical FormulaC6H6O5
Average Molecular Weight158.1088
Monoisotopic Molecular Weight158.021523302
IUPAC Name2-methylidene-4-oxopentanedioic acid
Traditional Name4-methylene-2-oxoglutarate
CAS Registry NumberNot Available
SMILES
OC(=O)C(=C)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H6O5/c1-3(5(8)9)2-4(7)6(10)11/h1-2H2,(H,8,9)(H,10,11)
InChI KeyOARCEFMISOKEKI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Branched fatty acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Dicarboxylic acid or derivatives
  • Unsaturated fatty acid
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.27 g/LALOGPS
logP0.08ALOGPS
logP0.34ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.76ChemAxon
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.26 m³·mol⁻¹ChemAxon
Polarizability13 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
DeepCCS[M+H]+130.09230932474
DeepCCS[M-H]-126.26430932474
DeepCCS[M-2H]-163.56330932474
DeepCCS[M+Na]+139.10230932474
AllCCS[M+H]+135.232859911
AllCCS[M+H-H2O]+131.232859911
AllCCS[M+NH4]+138.932859911
AllCCS[M+Na]+140.032859911
AllCCS[M-H]-127.732859911
AllCCS[M+Na-2H]-129.532859911
AllCCS[M+HCOO]-131.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methylene-4-oxopentanedioic acidOC(=O)C(=C)CC(=O)C(O)=O2305.6Standard polar33892256
2-Methylene-4-oxopentanedioic acidOC(=O)C(=C)CC(=O)C(O)=O1341.0Standard non polar33892256
2-Methylene-4-oxopentanedioic acidOC(=O)C(=C)CC(=O)C(O)=O1463.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methylene-4-oxopentanedioic acid,1TMS,isomer #1C=C(CC(=O)C(=O)O)C(=O)O[Si](C)(C)C1460.2Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,1TMS,isomer #2C=C(CC(=O)C(=O)O[Si](C)(C)C)C(=O)O1429.9Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,1TMS,isomer #3C=C(C=C(O[Si](C)(C)C)C(=O)O)C(=O)O1565.9Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,2TMS,isomer #1C=C(CC(=O)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1549.5Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,2TMS,isomer #2C=C(C=C(O[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C1620.1Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,2TMS,isomer #3C=C(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O1595.9Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,3TMS,isomer #1C=C(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1611.5Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,3TMS,isomer #1C=C(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1564.7Standard non polar33892256
2-Methylene-4-oxopentanedioic acid,1TBDMS,isomer #1C=C(CC(=O)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1694.2Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,1TBDMS,isomer #2C=C(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1673.0Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,1TBDMS,isomer #3C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O1782.9Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,2TBDMS,isomer #1C=C(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1997.0Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,2TBDMS,isomer #2C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2073.7Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,2TBDMS,isomer #3C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2045.0Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,3TBDMS,isomer #1C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2263.7Semi standard non polar33892256
2-Methylene-4-oxopentanedioic acid,3TBDMS,isomer #1C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2110.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylene-4-oxopentanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03du-9400000000-81a3083c94780ee6323b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylene-4-oxopentanedioic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00y0-9620000000-3344cc5d1e92eee5e1a92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylene-4-oxopentanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylene-4-oxopentanedioic acid 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 - 2-Methylene-4-oxopentanedioic acid 10V, Positive-QTOFsplash10-0bt9-1900000000-17aef9adbe7e535d1ffa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 20V, Positive-QTOFsplash10-03xs-8900000000-7b5f27985e9bb72f81f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 40V, Positive-QTOFsplash10-014i-9100000000-52fdc268b6e52b7c1f2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-0b7020a966666da8b45d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 20V, Negative-QTOFsplash10-03xr-6900000000-e2547b7568b2bba091162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 40V, Negative-QTOFsplash10-014l-9100000000-86549e52114ff94d73c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 10V, Negative-QTOFsplash10-0900-3900000000-7650ff0d40f36ed5f00c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 20V, Negative-QTOFsplash10-014i-9100000000-0a89795103a146e120032021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 40V, Negative-QTOFsplash10-014l-9000000000-58868b223aba342f62c72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 10V, Positive-QTOFsplash10-0295-9500000000-66ebaa22cffbf3a55f132021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 20V, Positive-QTOFsplash10-00ko-9000000000-1afef919158b681142d52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 40V, Positive-QTOFsplash10-00ko-9000000000-21f482923176566f48422021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019205
KNApSAcK IDNot Available
Chemspider ID389673
KEGG Compound IDC06035
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440813
PDB IDNot Available
ChEBI ID1898
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .