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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:01:05 UTC
Update Date2019-07-23 06:24:44 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 or g-methylene-a-ketoglutaric acid, 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 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Methylene-4-oxopentanedioic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 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.
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
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

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
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03du-9400000000-81a3083c94780ee6323bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y0-9620000000-3344cc5d1e92eee5e1a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bt9-1900000000-17aef9adbe7e535d1ffaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xs-8900000000-7b5f27985e9bb72f81f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-52fdc268b6e52b7c1f2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-0b7020a966666da8b45dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-6900000000-e2547b7568b2bba09116Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9100000000-86549e52114ff94d73c6Spectrum
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 IDFDB016899
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 ID
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.. .