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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-01-14 21:26:57 UTC
Update Date2023-02-21 17:30:23 UTC
HMDB IDHMDB0061388
Secondary Accession Numbers
  • HMDB61388
Metabolite Identification
Common NameDimethyl 2-oxoglutarate
DescriptionDimethyl 2-oxoglutarate 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. Dimethyl 2-oxoglutarate is an extremely weak basic (essentially neutral) compound (based on its pKa). Dimethyl-2-oxoglutarate (MOG) is a key intermediate in the Krebs cycle and an important nitrogen transporter in the metabolic pathways in biological processes (PMID: 19766063 ).
Structure
Thumb
Synonyms
ValueSource
Dimethyl 2-oxoglutaric acidGenerator
Dimethyl alpha-ketoglutarateMeSH
Chemical FormulaC7H10O5
Average Molecular Weight174.1513
Monoisotopic Molecular Weight174.05282343
IUPAC Name1,5-dimethyl 2-oxopentanedioate
Traditional Name1,5-dimethyl 2-oxopentanedioate
CAS Registry Number13192-04-6
SMILES
COC(=O)CCC(=O)C(=O)OC
InChI Identifier
InChI=1S/C7H10O5/c1-11-6(9)4-3-5(8)7(10)12-2/h3-4H2,1-2H3
InChI KeyTXIXSLPEABAEHP-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
  • Fatty acid ester
  • Fatty acid methyl ester
  • Alpha-keto acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Methyl ester
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25775
PDB IDNot Available
ChEBI IDNot Available
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. Willenborg M, Panten U, Rustenbeck I: Triggering and amplification of insulin secretion by dimethyl alpha-ketoglutarate, a membrane permeable alpha-ketoglutarate analogue. Eur J Pharmacol. 2009 Apr 1;607(1-3):41-6. doi: 10.1016/j.ejphar.2009.02.014. Epub 2009 Feb 20. [PubMed:19233162 ]
  2. Odegaard ML, Joseph JW, Jensen MV, Lu D, Ilkayeva O, Ronnebaum SM, Becker TC, Newgard CB: The mitochondrial 2-oxoglutarate carrier is part of a metabolic pathway that mediates glucose- and glutamine-stimulated insulin secretion. J Biol Chem. 2010 May 28;285(22):16530-7. doi: 10.1074/jbc.M109.092593. Epub 2010 Mar 31. [PubMed:20356834 ]
  3. Shah A, Diculescu VC, Qureshi R, Oliveira-Brett AM: Electrochemical behaviour of dimethyl-2-oxoglutarate on glassy carbon electrode. Bioelectrochemistry. 2010 Feb;77(2):145-50. doi: 10.1016/j.bioelechem.2009.07.012. Epub 2009 Aug 12. [PubMed:19766063 ]
  4. Doucette CD, Schwab DJ, Wingreen NS, Rabinowitz JD: alpha-Ketoglutarate coordinates carbon and nitrogen utilization via enzyme I inhibition. Nat Chem Biol. 2011 Oct 16;7(12):894-901. doi: 10.1038/nchembio.685. [PubMed:22002719 ]