Record Information
Version1.0
Creation Date2016-09-30 22:26:59 UTC
Update Date2020-06-04 19:53:36 UTC
MCDB ID BMDB0000223
Secondary Accession Numbers
  • BMDB00223
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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oxalacetic acid exists in all living species, ranging from bacteria to humans.
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility134 mg/mLNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00dr-4900000000-9d943d40beaca3c602a12014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-007a-9210000000-020f60717e2ea79d1ccd2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-000b-9540000000-a53f674cc98960834f882014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-001a-8940000000-40b790e06141d71809382014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-007a-9210000000-020f60717e2ea79d1ccd2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000b-9540000000-a53f674cc98960834f882017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001a-8940000000-40b790e06141d71809382017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-4930000000-7e995327b0b9c1af09142017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9100000000-6718417e7196063f95442016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-9520000000-5a082ec8843f6fbc3b152017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-0be675f3aa3e973393b72012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000f-9000000000-4fba97fcd7b0f2215f752012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-9b1f4171aee6283a3cbd2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-7c598fd9c78acb94dacd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-014i-4900000000-e7803730ae7986a1b9fb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-014r-5900000000-8e478338a7c0e65e62ba2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-014r-7900000000-f681763317e1ae86e6912020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-00kr-9600000000-aa8adf9a96041dddbbdd2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-000i-9200000000-e62c47ca2bc4929001782020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-000i-9000000000-5485ddd84a64ea0ca0b92020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-000i-9000000000-79521cb04a2b23e39c1e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-000m-9000000000-601c8d2ec63f8b01a61e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-000e-9000000000-13d369c58d8930958d922020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0005-9000000000-df8387ef907fb71342eb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0005-9000000000-908644b5d7041346f5822020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0005-9000000000-ecca787a800164d0296f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0005-9000000000-180a7c51b1f93cb8fff22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0005-9000000000-709c49f609f5a711a2882020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0005-9000000000-aa103ab9beb03bd6eb222020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3900000000-6f4e965a3f513bf8db132015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9600000000-8ae7abf60057088e14db2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-9100000000-5724c215c46a4f5681402015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-8900000000-829898d0849b1fbf1c282015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9100000000-5a5ff8fb7cb52eebf0c82015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-657d1384d478ddc33b6d2015-04-25View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f371299a07d43c23ff1d2015-03-01View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Sodium phosphate (pH 7.4) in 90% H2O /10% D2O, experimental)Not Available2019-09-11View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 800 MHz, experimental)Not Available2019-09-11View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified7 - 24 uM details
HMDB IDHMDB0000223
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031075
KNApSAcK IDC00001197
Chemspider ID945
KEGG Compound IDC00036
BioCyc IDOXALACETIC_ACID
BiGG ID33604
Wikipedia LinkOxaloacetic_acid
METLIN ID123
PubChem Compound970
PDB IDNot Available
ChEBI ID30744
References
Synthesis ReferenceHeidelberger, Charles; Hurlbert, Robert B. The synthesis of oxalacetic acid-I-C14 and orotic acid-6-C14. Journal of the American Chemical Society (1950), 72 4704-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  2. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]