Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2020-09-17 15:38:26 UTC
Primary IDFDB003361
Secondary Accession Numbers
  • FDB030357
  • FDB007242
Chemical Information
FooDB Name2-Oxopentanedioic acid
DescriptionOxoglutaric acid, also known as oxoglutarate or alpha-ketoglutarate, 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. Oxoglutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Oxoglutaric acid exists in all living species, ranging from bacteria to humans. Within humans, oxoglutaric acid participates in a number of enzymatic reactions. In particular, oxoglutaric acid can be biosynthesized from isocitric acid; which is mediated by the enzyme isocitrate dehydrogenase. In addition, oxoglutaric acid can be converted into succinyl-CoA; which is mediated by the enzyme oxoglutarate dehydrogenase complex. In humans, oxoglutaric acid is involved in the oncogenic action of fumarate. Oxoglutaric acid is an odorless tasting compound. Outside of the human body, Oxoglutaric acid is found, on average, in the highest concentration within star fruits and milk (cow). Oxoglutaric acid has also been detected, but not quantified in, several different foods, such as common chokecherries, red beetroots, adzuki beans, buffalo currants, and grapefruit/pummelo hybrids. This could make oxoglutaric acid a potential biomarker for the consumption of these foods. Oxoglutaric acid is a potentially toxic compound. An oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2.
CAS Number328-50-7
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-OxoglutarateHMDB
Oxogluric acidHMDB
2 Oxoglutaric acidHMDB
Ketoglutaric acidHMDB
alpha Ketoglutaric acidHMDB
2 Ketoglutaric acidHMDB
alpha KetoglutarateHMDB
alpha OxoglutarateHMDB
2 KetoglutarateHMDB
2 OxoglutarateHMDB
alpha-Oxoglutaric acidHMDB
alpha-Oxopentanedioic acidHMDB
alpha-Keto-glutaric acidHMDB
Α-oxoglutaric acidHMDB
Α-oxopentanedioic acidHMDB
Α-keto-glutaric acidHMDB
α-ketoglutaric acidbiospider
α-oxoglutaric acidbiospider
2-Oxo-1,5-dipentanedioic acidbiospider
2-Oxo-1,5-pentanedioatebiospider
2-Oxo-1,5-pentanedioic acidbiospider
2-Oxo-Glutaric Acidbiospider
2-oxopentanedionatebiospider
2-oxopentanedionic acidbiospider
2-Oxyglutaric Acidbiospider
305-72-6 (di-hydrochloride salt)biospider
997-43-3 (mono-potassium salt)biospider
AKGbiospider
Alpha ketoglutaratebiospider
Alpha-keto-glutaric acidbiospider
Alpha-ketoglutaratebiospider
Alpha-ketoglutaric acid alphabiospider
Alpha-oxoglutaratebiospider
Alpha-oxopentanedioic acidbiospider
Alphaketoglutaric acidbiospider
Bis(L-arginin)-2-oxoglutaratbiospider
FEMA 3891db_source
Glutaric acid, &alphabiospider
Glutaric acid, 2-oxo-biospider
Glutaric acid, 2-oxo- (8CI)biospider
Glutaric acid, alpha ketobiospider
ketobiospider
Ketoglutaratebiospider
Oxoglutaric acidbiospider
Pentanedioic acid, 2-oxo-biospider
Pentanedioic acid, 2-oxo- (9CI)biospider
α-ketoglutarateGenerator
α-ketoglutaric acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 41.11%; H 4.14%; O 54.76%DFC
Melting PointMp 115°DFC
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0fba-9200000000-4e367c66e94c51eb1a1bSpectrum
GC-MS2-Oxopentanedioic acid, 2 TMS, GC-MS Spectrumsplash10-000b-3910000000-4097b7eb52c2910a4277Spectrum
GC-MS2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-3277227b9c4da4baa1f7Spectrum
GC-MS2-Oxopentanedioic acid, 2 TMS; 1 MEOX, GC-MS Spectrumsplash10-00di-9300000000-974bce546caa4fbe6b0fSpectrum
GC-MS2-Oxopentanedioic acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-000i-9710000000-d0aea11e947b042571f9Spectrum
GC-MS2-Oxopentanedioic acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-052s-4920000000-bf7ed92c68fd4c8dbb6bSpectrum
GC-MS2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrumsplash10-000b-3910000000-4097b7eb52c2910a4277Spectrum
GC-MS2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-3277227b9c4da4baa1f7Spectrum
GC-MS2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9300000000-974bce546caa4fbe6b0fSpectrum
GC-MS2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9710000000-d0aea11e947b042571f9Spectrum
GC-MS2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrumsplash10-052s-4920000000-bf7ed92c68fd4c8dbb6bSpectrum
GC-MS2-Oxopentanedioic acid, non-derivatized, GC-MS Spectrumsplash10-000b-2900000000-e514f7afea2490bbe9edSpectrum
Predicted GC-MS2-Oxopentanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kfx-9200000000-0ee77a39e9862659f8a7Spectrum
Predicted GC-MS2-Oxopentanedioic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9730000000-5e17bd8cfd944963c79fSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-6900000000-7fc343a243ce5d2a4f39Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9200000000-1a7af9946604baa8b3d2Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4l-9800000000-30495b2afdd3526854e7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0925200000-af33449c9638276466c2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-6e43f767847790112b65Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4cacc41705b7b385e91eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-1367eeeb6ad64c67a0aaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000t-0915051100-91cda631ee54800322b8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-4f842c3673925d29c402Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-5e751351656f6eb62de3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-7729faa24733fbad77b7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-c3c62f83bff99f44f7abSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0zfr-6900000000-b6d8379db3e3f1480b14Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-4fde39bb93cde5a27f23Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00i0-9000000000-4343832f3a55842423a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a65Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a65Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9t-8900000000-b2d3fa8d7ab01a220d9aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9100000000-554bfbd6839bc376cba0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0cSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID50
ChEMBL IDCHEMBL1686
KEGG Compound IDC00026
Pubchem Compound ID51
Pubchem Substance IDNot Available
ChEBI ID16810
Phenol-Explorer IDNot Available
DrugBank IDDB02926
HMDB IDHMDB00208
CRC / DFC (Dictionary of Food Compounds) IDCWH02-C:CWH02-C
EAFUS ID2852
Dr. Duke IDALPHA-KETO-GLUTARIC-ACID
BIGG ID33565
KNApSAcK IDC00000769
HET IDAKG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1048551
SuperScent IDNot Available
Wikipedia IDOxoglutarate
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
Enzymes
NameGene NameUniProt ID
Tyrosine aminotransferaseTATP17735
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
Aminoadipate-semialdehyde synthaseAASSA4D0W4
Branched-chain-amino-acid aminotransferase, cytosolicBCAT1P54687
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT2O15382
Lysine-specific demethylase 2AKDM2AQ9Y2K7
Lysine-specific demethylase 2BKDM2BQ8NHM5
Alanine--glyoxylate aminotransferase 2, mitochondrialAGXT2Q9BYV1
Kynurenine--oxoglutarate transaminase 3CCBL2Q6YP21
Ornithine aminotransferase, mitochondrialOATP04181
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Alanine aminotransferase 1GPTP24298
Alanine aminotransferase 2GPT2Q8TD30
Prolyl 4-hydroxylase subunit alpha-2P4HA2O15460
Prolyl 4-hydroxylase subunit alpha-1P4HA1P13674
Prolyl 4-hydroxylase subunit alpha-3P4HA3Q7Z4N8
Egl nine homolog 1EGLN1Q9GZT9
Egl nine homolog 2EGLN2Q96KS0
Egl nine homolog 3EGLN3Q9H6Z9
Transmembrane prolyl 4-hydroxylaseP4HTMQ9NXG6
Phosphoserine aminotransferasePSAT1Q9Y617
Putative aspartate aminotransferase, cytoplasmic 2GOT1L1Q8NHS2
2-oxoglutarate dehydrogenase, mitochondrialOGDHQ02218
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialAADATQ8N5Z0
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Mitochondrial 2-oxoglutarate/malate carrier proteinSLC25A11Q02978
Probable 2-oxoglutarate dehydrogenase E1 component DHKTD1, mitochondrialDHTKD1Q96HY7
Pathways
NameSMPDB LinkKEGG Link
Alanine MetabolismSMP00055 map00250
Ammonia RecyclingSMP00009 map00910
Carnitine SynthesisSMP00465 Not Available
Citric Acid CycleSMP00057 map00020
GluconeogenesisSMP00128 map00010
Glucose-Alanine CycleSMP00127 Not Available
Glutamate MetabolismSMP00072 map00250
Glycine and Serine MetabolismSMP00004 map00260
Malate-Aspartate ShuttleSMP00129 Not Available
Phytanic Acid Peroxisomal OxidationSMP00450 Not Available
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.