Canmetcon
Record Information
Version1.0
Creation date2015-05-07 19:05:54 UTC
Update date2018-05-29 01:54:51 UTC
Primary IDFDB030357
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-oxoglutarate
DescriptionOxoglutaric acid, also known as alpha-ketoglutaric acid or 2-oxoglutarate, belongs to gamma-keto acids and derivatives class of compounds. Those are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Oxoglutaric acid is soluble (in water) and a moderately acidic compound (based on its pKa). Oxoglutaric acid can be synthesized from glutaric acid. Oxoglutaric acid can also be synthesized into oxalosuccinic acid and 2-oxoglutaryl-CoA. Oxoglutaric acid can be found in a number of food items such as yautia, kumquat, narrowleaf cattail, and common sage, which makes oxoglutaric acid a potential biomarker for the consumption of these food products. Oxoglutaric acid can be found primarily in most biofluids, including urine, cellular cytoplasm, breast milk, and feces. Oxoglutaric acid exists in all living species, ranging from bacteria to humans. In humans, oxoglutaric acid is involved in several metabolic pathways, some of which include alanine metabolism, beta-alanine metabolism, tyrosine metabolism, and glycogenosis, type IC. Oxoglutaric acid is also involved in several metabolic disorders, some of which include glycogenosis, type IA. von gierke disease, dihydropyrimidine dehydrogenase deficiency (DHPD), monoamine oxidase-a deficiency (MAO-A), and dimethylglycine dehydrogenase deficiency. Moreover, oxoglutaric acid is found to be associated with schizophrenia, 2-Ketoglutarate dehydrogenase complex deficiency, hyperinsulinism-hyperammonemia syndrome, and d-2-hydroxyglutaric aciduria. Ketoglutaric acid or oxoglutaric acid may refer to either of two chemical compounds: α-Ketoglutaric acid β-Ketoglutaric acid (acetonedicarboxylic acid) . The exact mechanisms of action for α-Ketoglutarate have not yet been elucidated. Some of α-Ketoglutarate’s actions include acting in the Krebs cycle as an intermediate, transamination reactions during the metabolism of amino acids, forming glutamic acid by combining with ammonia, and reducing nitrogen by combining with it as well. Concerning α-Ketoglutarate’s actions with ammonia, it is proposed that α-Ketoglutarate can help patients with propionic academia who have high levels of ammonia and low levels of glutamine/glutamate in their blood. Because endogenous glutamate/glutamine is produced from α-Ketoglutarate, propionic acidemia patients have impaired production of α-Ketoglutarate and supplementation of α-Ketoglutarate should improve the condition of these patients. Several other experimental studies have also shown that administration of α-Ketoglutarate in parenteral nutrition given to post-operative patients helped attenuate the decreased synthesis of muscle protein that is often seen after a surgery. This decreased muscle synthesis is speculated to be due to too low α-Ketoglutarate levels (DrugBank).
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
2-Ketoglutaric acidChEBI
alpha-Ketoglutaric acidChEBI
2-KetoglutarateGenerator
a-KetoglutarateGenerator
a-Ketoglutaric acidGenerator
alpha-KetoglutarateGenerator
Α-ketoglutarateGenerator
Α-ketoglutaric acidGenerator
OxoglutarateGenerator
2-oxo-1,5-PentanedioateHMDB
2-oxo-1,5-Pentanedioic acidHMDB
2-OxoglutarateHMDB
2-Oxoglutaric acidHMDB
2-OxopentanedioateHMDB
2-Oxopentanedioic acidHMDB
alpha-Ketoglutaric acid, calcium salt (2:1)HMDB
alpha-Ketoglutaric acid, sodium saltHMDB
Calcium alpha-ketoglutarateHMDB
alpha-Ketoglutaric acid, disodium saltHMDB
alpha-Ketoglutaric acid, monosodium saltHMDB
Calcium ketoglutarateHMDB
alpha-Ketoglutaric acid, diammonium saltHMDB
alpha-Ketoglutaric acid, dipotassium saltHMDB
alpha-Ketoglutaric acid, monopotassium saltHMDB
alpha-Ketoglutaric acid, potassium saltHMDB
alpha-OxoglutarateHMDB
Oxogluric acidHMDB
2 Oxoglutaric acidHMDB
Calcium alpha ketoglutarateHMDB
Ketoglutaric acidHMDB
alpha Ketoglutaric acidHMDB
alpha Ketoglutaric acid, potassium saltHMDB
2 Ketoglutaric acidHMDB
alpha KetoglutarateHMDB
alpha Ketoglutaric acid, diammonium saltHMDB
alpha Ketoglutaric acid, dipotassium saltHMDB
alpha Ketoglutaric acid, sodium saltHMDB
alpha OxoglutarateHMDB
2 KetoglutarateHMDB
alpha Ketoglutaric acid, disodium saltHMDB
alpha Ketoglutaric acid, monosodium saltHMDB
alpha-Ketoglutarate, calciumHMDB
2 OxoglutarateHMDB
Ketoglutaric acidsHMDB
OxoglutaratesHMDB
alpha Ketoglutaric acid, monopotassium saltHMDB
Predicted Properties
PropertyValueSource
Water Solubility53.1 g/LALOGPS
logP-0.6ALOGPS
logP-0.11ChemAxon
logS-0.44ALOGPS
pKa (Strongest Acidic)2.66ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.88 m³·mol⁻¹ChemAxon
Polarizability12.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H6O5
IUPAC name2-oxopentanedioic acid
InChI IdentifierInChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
InChI KeyKPGXRSRHYNQIFN-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCC(=O)C(O)=O
Average Molecular Weight146.0981
Monoisotopic Molecular Weight146.021523302
Classification
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
  • Short-chain keto acid
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-000b-3910000000-4097b7eb52c2910a4277View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-1910000000-3277227b9c4da4baa1f7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)splash10-00di-9300000000-974bce546caa4fbe6b0fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-000i-9710000000-d0aea11e947b042571f9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-052s-4920000000-bf7ed92c68fd4c8dbb6bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000b-3910000000-4097b7eb52c2910a4277View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1910000000-3277227b9c4da4baa1f7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9300000000-974bce546caa4fbe6b0fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9710000000-d0aea11e947b042571f9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-052s-4920000000-bf7ed92c68fd4c8dbb6bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000b-2900000000-e514f7afea2490bbe9edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kfx-9200000000-0ee77a39e9862659f8a7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9730000000-5e17bd8cfd944963c79fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-6900000000-7fc343a243ce5d2a4f39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9200000000-1a7af9946604baa8b3d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4l-9800000000-30495b2afdd3526854e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0925200000-af33449c9638276466c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-6e43f767847790112b65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4cacc41705b7b385e91eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-1367eeeb6ad64c67a0aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000t-0915051100-91cda631ee54800322b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-4f842c3673925d29c402View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-5e751351656f6eb62de3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-7729faa24733fbad77b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-c3c62f83bff99f44f7abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0zfr-6900000000-b6d8379db3e3f1480b14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-4fde39bb93cde5a27f23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00i0-9000000000-4343832f3a55842423a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9t-8900000000-b2d3fa8d7ab01a220d9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9100000000-554bfbd6839bc376cba0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0fba-9200000000-4e367c66e94c51eb1a1bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference