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Record Information
Version1.0
Creation Date2016-07-13 19:42:25 UTC
Update Date2016-07-20 20:25:05 UTC
LmdbLMDB00103
Secondary Accession NumbersNone
Metabolite Identification
Common NameOxalacetic acid
DescriptionOxalacetic acid, also known as oxaloacetate or 2-oxosuccinate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Oxalacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Oxalacetic acid exists in all living species, ranging from bacteria to humans. Within humans, oxalacetic acid participates in a number of enzymatic reactions. In particular, oxalacetic acid can be biosynthesized from D-aspartic acid through the action of the enzyme D-aspartate oxidase. In addition, oxalacetic acid can be biosynthesized from D-aspartic acid through the action of the enzyme D-aspartate oxidase. In humans, oxalacetic acid is involved in the metabolic disorder called the canavan disease pathway. Outside of the human body, Oxalacetic acid has been detected, but not quantified in, several different foods, such as chinese mustards, lowbush blueberries, brassicas, maitakes, and kombus. This could make oxalacetic acid a potential biomarker for the consumption of these foods. An oxodicarboxylic acid that is succinic acid bearing a single oxo group.
Structure
Thumb
Synonyms
ValueSource
2-Oxobutanedioic acidChEBI
2-Oxosuccinic acidChEBI
3-Carboxy-3-oxopropanoic acidChEBI
Keto-succinic acidChEBI
Ketosuccinic acidChEBI
OAAChEBI
Oxobutanedioic acidChEBI
Oxosuccinic acidChEBI
Oxaloacetic acidKegg
Keto-oxaloacetateKegg
2-OxobutanedioateGenerator
2-OxosuccinateGenerator
3-Carboxy-3-oxopropanoateGenerator
Keto-succinateGenerator
KetosuccinateGenerator
OxobutanedioateGenerator
OxosuccinateGenerator
OxaloacetateGenerator
Keto-oxaloacetic acidGenerator
OxalacetateGenerator
2-KetosuccinateHMDB
2-Ketosuccinic acidHMDB
a-KetosuccinateHMDB
a-Ketosuccinic acidHMDB
alpha-KetosuccinateHMDB
alpha-Ketosuccinic acidHMDB
OxaloethanoateHMDB
Oxaloethanoic acidHMDB
Acid, oxaloaceticHMDB
Acid, oxalaceticHMDB
2 Ketosuccinic acidHMDB
2 oxo Butanedioic acidHMDB
2-oxo-Butanedioic acidHMDB
Chemical FormulaC4H4O5
Average Molecular Weight132.0716
Monoisotopic Molecular Weight132.005873238
IUPAC Name2-oxobutanedioic acid
Traditional Nameoxalacetate
CAS Registry Number328-42-7
SMILES
OC(=O)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
InChI KeyKHPXUQMNIQBQEV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.68ALOGPS
logP-0.042ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.33 m³·mol⁻¹ChemAxon
Polarizability10.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00dr-4900000000-9d943d40beaca3c602a1Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-007a-9210000000-020f60717e2ea79d1ccdSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-000b-9540000000-a53f674cc98960834f88Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-001a-8940000000-40b790e06141d7180938Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-007a-9210000000-020f60717e2ea79d1ccdSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000b-9540000000-a53f674cc98960834f88Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001a-8940000000-40b790e06141d7180938Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-4930000000-7e995327b0b9c1af0914Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9100000000-6718417e7196063f9544Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-9520000000-5a082ec8843f6fbc3b15Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-0be675f3aa3e973393b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000f-9000000000-4fba97fcd7b0f2215f75Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-9b1f4171aee6283a3cbdSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-7c598fd9c78acb94dacdSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-014i-4900000000-e7803730ae7986a1b9fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-014r-5900000000-8e478338a7c0e65e62baSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-014r-7900000000-f681763317e1ae86e691Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-00kr-9600000000-aa8adf9a96041dddbbddSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-000i-9200000000-e62c47ca2bc492900178Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-000i-9000000000-5485ddd84a64ea0ca0b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-000i-9000000000-79521cb04a2b23e39c1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-000m-9000000000-601c8d2ec63f8b01a61eSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-000e-9000000000-13d369c58d8930958d92Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0005-9000000000-df8387ef907fb71342ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0005-9000000000-908644b5d7041346f582Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0005-9000000000-ecca787a800164d0296fSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0005-9000000000-180a7c51b1f93cb8fff2Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0005-9000000000-709c49f609f5a711a288Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0005-9000000000-aa103ab9beb03bd6eb22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3900000000-6f4e965a3f513bf8db13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9600000000-8ae7abf60057088e14dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-9100000000-5724c215c46a4f568140Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-8900000000-829898d0849b1fbf1c28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9100000000-5a5ff8fb7cb52eebf0c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-657d1384d478ddc33b6dSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f371299a07d43c23ff1dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected and Quantified7-24 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0000223
FooDB IDFDB031075
Phenol Explorer IDNot Available
KNApSAcK IDC00001197
BiGG ID33604
BioCyc IDOXALACETIC_ACID
METLIN ID123
PDB IDNot Available
Wikipedia LinkOxaloacetic_acid
Chemspider ID945
ChEBI ID30744
PubChem Compound ID970
Kegg Compound IDC00036
YMDB IDYMDB00235
ECMDB IDECMDB00223
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available