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Showing Compound Oxalacetic acid (FDB001479)

Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2020-09-17 15:38:29 UTC
Primary IDFDB001479
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number328-42-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
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
3-carboxy-3-oxopropanoic acidbiospider
A-ketosuccinatebiospider
A-ketosuccinic acidbiospider
Alpha-ketosuccinatebiospider
Alpha-ketosuccinic acidbiospider
Butanedioic acid, 2-oxo-biospider
Butanedioic acid, oxo-biospider
Butanedioic acid, oxo- (9CI)biospider
keto-SuccinateGenerator
Oxalacetic aceticbiospider
Oxalacetic acid (8CI)biospider
Oxalacetic acid hybri-max(TM)biospider
Oxalacetic acid,cis formbiospider
Oxalacetic_acidbiospider
Oxaloacetic acidsbiospider
Predicted Properties
PropertyValueSource
Water Solubility57.1 g/LALOGPS
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
Chemical FormulaC4H4O5
IUPAC name2-oxobutanedioic acid
InChI IdentifierInChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
InChI KeyKHPXUQMNIQBQEV-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC(=O)C(O)=O
Average Molecular Weight132.0716
Monoisotopic Molecular Weight132.005873238
Classification
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point161 oC
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)splash10-0006-9000000000-f371299a07d43c23ff1d2015-03-01View Spectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-4900000000-9d943d40beaca3c602a1Spectrum
GC-MSOxalacetic acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-007a-9210000000-020f60717e2ea79d1ccdSpectrum
GC-MSOxalacetic acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-000b-9540000000-a53f674cc98960834f88Spectrum
GC-MSOxalacetic acid, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-001a-8940000000-40b790e06141d7180938Spectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-007a-9210000000-020f60717e2ea79d1ccdSpectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-000b-9540000000-a53f674cc98960834f88Spectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-001a-8940000000-40b790e06141d7180938Spectrum
GC-MSOxalacetic acid, non-derivatized, GC-MS Spectrumsplash10-0002-4930000000-7e995327b0b9c1af0914Spectrum
Predicted GC-MSOxalacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-9100000000-6718417e7196063f9544Spectrum
Predicted GC-MSOxalacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ds-9520000000-5a082ec8843f6fbc3b15Spectrum
Predicted GC-MSOxalacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxalacetic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-0be675f3aa3e973393b72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000f-9000000000-4fba97fcd7b0f2215f752012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-9b1f4171aee6283a3cbd2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-7c598fd9c78acb94dacd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-014i-4900000000-e7803730ae7986a1b9fb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-014r-5900000000-8e478338a7c0e65e62ba2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-014r-7900000000-f681763317e1ae86e6912020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-00kr-9600000000-aa8adf9a96041dddbbdd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-000i-9200000000-e62c47ca2bc4929001782020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-000i-9000000000-5485ddd84a64ea0ca0b92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-000i-9000000000-79521cb04a2b23e39c1e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-000m-9000000000-601c8d2ec63f8b01a61e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-000e-9000000000-13d369c58d8930958d922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0005-9000000000-df8387ef907fb71342eb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0005-9000000000-908644b5d7041346f5822020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0005-9000000000-ecca787a800164d0296f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0005-9000000000-180a7c51b1f93cb8fff22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0005-9000000000-709c49f609f5a711a2882020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0005-9000000000-aa103ab9beb03bd6eb222020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3900000000-6f4e965a3f513bf8db132015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9600000000-8ae7abf60057088e14db2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-9100000000-5724c215c46a4f5681402015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-8900000000-829898d0849b1fbf1c282015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9100000000-5a5ff8fb7cb52eebf0c82015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-657d1384d478ddc33b6d2015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Sodium phosphate (pH 7.4) in 90% H2O /10% D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 800 MHz, experimental)Spectrum
ChemSpider ID945
ChEMBL IDCHEMBL1794791
KEGG Compound IDC00036
Pubchem Compound ID970
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00223
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDOXALOACETIC-ACID|OXALACETIC-ACID
BIGG ID33604
KNApSAcK IDC00001197
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOxaloacetic_acid
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
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
ATP-citrate synthaseACLYP53396
Citrate synthase, mitochondrialCSO75390
Putative aspartate aminotransferase, cytoplasmic 2GOT1L1Q8NHS2
Pathways
NameSMPDB LinkKEGG Link
Alanine MetabolismSMP00055 map00250
Aspartate MetabolismSMP00067 map00250
Citric Acid CycleSMP00057 map00020
GluconeogenesisSMP00128 map00010
Malate-Aspartate ShuttleSMP00129 Not Available
Pyruvate MetabolismSMP00060 map00620
Transfer of Acetyl Groups into MitochondriaSMP00466 Not Available
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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.