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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
Data?1677000623
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
DispositionNot Available
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 Solubility16.6 g/LALOGPS
logP-0.06ALOGPS
logP0.42ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)14.65ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity38.42 m³·mol⁻¹ChemAxon
Polarizability16.43 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]+141.80431661259
DarkChem[M-H]-137.05331661259
DeepCCS[M+H]+129.30830932474
DeepCCS[M-H]-125.47330932474
DeepCCS[M-2H]-162.85830932474
DeepCCS[M+Na]+138.39830932474
AllCCS[M+H]+139.532859911
AllCCS[M+H-H2O]+135.732859911
AllCCS[M+NH4]+143.132859911
AllCCS[M+Na]+144.132859911
AllCCS[M-H]-136.732859911
AllCCS[M+Na-2H]-138.332859911
AllCCS[M+HCOO]-140.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dimethyl 2-oxoglutarateCOC(=O)CCC(=O)C(=O)OC1798.2Standard polar33892256
Dimethyl 2-oxoglutarateCOC(=O)CCC(=O)C(=O)OC1062.7Standard non polar33892256
Dimethyl 2-oxoglutarateCOC(=O)CCC(=O)C(=O)OC1249.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dimethyl 2-oxoglutarate,1TMS,isomer #1COC(=O)CC=C(O[Si](C)(C)C)C(=O)OC1442.1Semi standard non polar33892256
Dimethyl 2-oxoglutarate,1TMS,isomer #1COC(=O)CC=C(O[Si](C)(C)C)C(=O)OC1350.3Standard non polar33892256
Dimethyl 2-oxoglutarate,1TMS,isomer #1COC(=O)CC=C(O[Si](C)(C)C)C(=O)OC1888.0Standard polar33892256
Dimethyl 2-oxoglutarate,1TBDMS,isomer #1COC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)OC1639.6Semi standard non polar33892256
Dimethyl 2-oxoglutarate,1TBDMS,isomer #1COC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)OC1557.6Standard non polar33892256
Dimethyl 2-oxoglutarate,1TBDMS,isomer #1COC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)OC2007.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dimethyl 2-oxoglutarate GC-MS (Non-derivatized) - 70eV, Positivesplash10-05n0-9400000000-6905e18ab68786fb03da2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimethyl 2-oxoglutarate 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 - Dimethyl 2-oxoglutarate 10V, Positive-QTOFsplash10-004l-0900000000-614c0d6eaf9d66c3f1d82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 20V, Positive-QTOFsplash10-0553-7900000000-350d4a3a3c24c42430612017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 40V, Positive-QTOFsplash10-0a4i-9000000000-df8cc85d03a449cc68ce2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 10V, Negative-QTOFsplash10-00dl-0900000000-43653259adc4cbb67bd02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 20V, Negative-QTOFsplash10-022c-3900000000-4994f41ae55738c9992d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 40V, Negative-QTOFsplash10-01q9-9300000000-799dbcd2007d5472dec22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 10V, Positive-QTOFsplash10-0673-9700000000-f096a10d10759c66afaa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 20V, Positive-QTOFsplash10-0a4i-9000000000-c5ab16829e2a89ef2f2e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 40V, Positive-QTOFsplash10-0a4i-9000000000-a7fc60e92af3833ccdc02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 10V, Negative-QTOFsplash10-0006-2900000000-eb76ed03f395cbfd044a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 20V, Negative-QTOFsplash10-01qc-9600000000-cb244dc8f2e317de34302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 40V, Negative-QTOFsplash10-0006-9000000000-a5ac7931654b0dd89d2b2021-09-22Wishart 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 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 ]