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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-01-14 21:26:57 UTC

Update Date

2023-02-21 17:30:23 UTC

HMDB ID

HMDB0061388

Secondary Accession Numbers

HMDB61388

Metabolite Identification

Common Name

Dimethyl 2-oxoglutarate

Description

Dimethyl 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 14-JAN-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-14         0                                  
HETATM    1  C   UNK     0      -5.031  -0.374   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.705  -1.194   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.207  -0.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.970  -1.217   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.268  -0.218   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.557  -1.111   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.800  -0.208   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.210  -1.111   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.333  -0.259   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.207   1.235   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.557  -2.648   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.800   1.329   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    3                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Dimethyl 2-oxoglutaric acid	Generator
Dimethyl alpha-ketoglutarate	MeSH

Chemical Formula

C₇H₁₀O₅

Average Molecular Weight

174.1513

Monoisotopic Molecular Weight

174.05282343

IUPAC Name

1,5-dimethyl 2-oxopentanedioate

Traditional Name

1,5-dimethyl 2-oxopentanedioate

CAS Registry Number

13192-04-6

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 Key

TXIXSLPEABAEHP-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.6 g/L	ALOGPS
logP	-0.06	ALOGPS
logP	0.42	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	14.65	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	38.42 m³·mol⁻¹	ChemAxon
Polarizability	16.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.804	31661259
DarkChem	[M-H]-	137.053	31661259
DeepCCS	[M+H]+	129.308	30932474
DeepCCS	[M-H]-	125.473	30932474
DeepCCS	[M-2H]-	162.858	30932474
DeepCCS	[M+Na]+	138.398	30932474
AllCCS	[M+H]+	139.5	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.1	32859911
AllCCS	[M+Na]+	144.1	32859911
AllCCS	[M-H]-	136.7	32859911
AllCCS	[M+Na-2H]-	138.3	32859911
AllCCS	[M+HCOO]-	140.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dimethyl 2-oxoglutarate	COC(=O)CCC(=O)C(=O)OC	1798.2	Standard polar	33892256
Dimethyl 2-oxoglutarate	COC(=O)CCC(=O)C(=O)OC	1062.7	Standard non polar	33892256
Dimethyl 2-oxoglutarate	COC(=O)CCC(=O)C(=O)OC	1249.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dimethyl 2-oxoglutarate,1TMS,isomer #1	COC(=O)CC=C(O[Si](C)(C)C)C(=O)OC	1442.1	Semi standard non polar	33892256
Dimethyl 2-oxoglutarate,1TMS,isomer #1	COC(=O)CC=C(O[Si](C)(C)C)C(=O)OC	1350.3	Standard non polar	33892256
Dimethyl 2-oxoglutarate,1TMS,isomer #1	COC(=O)CC=C(O[Si](C)(C)C)C(=O)OC	1888.0	Standard polar	33892256
Dimethyl 2-oxoglutarate,1TBDMS,isomer #1	COC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)OC	1639.6	Semi standard non polar	33892256
Dimethyl 2-oxoglutarate,1TBDMS,isomer #1	COC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)OC	1557.6	Standard non polar	33892256
Dimethyl 2-oxoglutarate,1TBDMS,isomer #1	COC(=O)CC=C(O[Si](C)(C)C(C)(C)C)C(=O)OC	2007.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dimethyl 2-oxoglutarate GC-MS (Non-derivatized) - 70eV, Positive	splash10-05n0-9400000000-6905e18ab68786fb03da	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dimethyl 2-oxoglutarate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 10V, Positive-QTOF	splash10-004l-0900000000-614c0d6eaf9d66c3f1d8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 20V, Positive-QTOF	splash10-0553-7900000000-350d4a3a3c24c4243061	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 40V, Positive-QTOF	splash10-0a4i-9000000000-df8cc85d03a449cc68ce	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 10V, Negative-QTOF	splash10-00dl-0900000000-43653259adc4cbb67bd0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 20V, Negative-QTOF	splash10-022c-3900000000-4994f41ae55738c9992d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 40V, Negative-QTOF	splash10-01q9-9300000000-799dbcd2007d5472dec2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 10V, Positive-QTOF	splash10-0673-9700000000-f096a10d10759c66afaa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 20V, Positive-QTOF	splash10-0a4i-9000000000-c5ab16829e2a89ef2f2e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 40V, Positive-QTOF	splash10-0a4i-9000000000-a7fc60e92af3833ccdc0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 10V, Negative-QTOF	splash10-0006-2900000000-eb76ed03f395cbfd044a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 20V, Negative-QTOF	splash10-01qc-9600000000-cb244dc8f2e317de3430	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl 2-oxoglutarate 40V, Negative-QTOF	splash10-0006-9000000000-a5ac7931654b0dd89d2b	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25775

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]

Showing metabocard for Dimethyl 2-oxoglutarate (HMDB0061388)

MOL for HMDB0061388 (Dimethyl 2-oxoglutarate)

3D MOL for HMDB0061388 (Dimethyl 2-oxoglutarate)

3D SDF for HMDB0061388 (Dimethyl 2-oxoglutarate)

3D-SDF for HMDB0061388 (Dimethyl 2-oxoglutarate)

PDB for HMDB0061388 (Dimethyl 2-oxoglutarate)

3D PDB for HMDB0061388 (Dimethyl 2-oxoglutarate)

SMILES for HMDB0061388 (Dimethyl 2-oxoglutarate)

INCHI for HMDB0061388 (Dimethyl 2-oxoglutarate)

Structure for HMDB0061388 (Dimethyl 2-oxoglutarate)

3D Structure for HMDB0061388 (Dimethyl 2-oxoglutarate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra