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Details

Stereochemistry ACHIRAL
Molecular Formula C4H4O5
Molecular Weight 132.0717
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXALOACETIC ACID

SMILES

OC(=O)CC(=O)C(O)=O

InChI

InChIKey=KHPXUQMNIQBQEV-UHFFFAOYSA-N
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)

HIDE SMILES / InChI

Molecular Formula C4H4O5
Molecular Weight 132.0717
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Oxaloacetate (OAA), a salt of oxaloacetic acid, is a metabolic intermediate in many processes, e.g., urea cycle, gluconeogenesis, etc. that occur in animals. Experiments on animal have revealed that OAA was able to protect hepatocytes from hypoxia and liver ischemia/reperfusion injury. OAA also possesses a neuroprotective effect against ischemic injury, which strengthens the likelihood of its future applicability as a novel neuroprotective agent for the treatment of ischemic stroke patients. In addition, experiments on adipose stromal cells have shown that OAA directly protected cerebellar granule neurons from apoptosis induced by serum and potassium deprivation.

Approval Year

PubMed

PubMed

TitleDatePubMed
Protein 4.1N is required for translocation of inositol 1,4,5-trisphosphate receptor type 1 to the basolateral membrane domain in polarized Madin-Darby canine kidney cells.
2003-02-07
Aluminum detoxification in Pseudomonas fluorescens is mediated by oxalate and phosphatidylethanolamine.
2003-01-02
Glial-neuronal interactions following kainate injection in rats.
2003-01
Malate:quinone oxidoreductase is essential for growth on ethanol or acetate in Pseudomonas aeruginosa.
2002-12
Glucose metabolites inhibit protein phosphatases and directly promote insulin exocytosis in pancreatic beta-cells.
2002-12
Demonstration of pyruvate recycling in primary cultures of neocortical astrocytes but not in neurons.
2002-11
Growth of Bacillus subtilis on citrate and isocitrate is supported by the Mg2+-citrate transporter CitM.
2002-11
Lysine 213 and histidine 233 participate in Mn(II) binding and catalysis in Saccharomyces cerevisiae phosphoenolpyruvate carboxykinase.
2002-10-22
beta-Cell adaptation to insulin resistance. Increased pyruvate carboxylase and malate-pyruvate shuttle activity in islets of nondiabetic Zucker fatty rats.
2002-10-18
Tartrate dehydrogenase catalyzes the stepwise oxidative decarboxylation of D-malate with both NAD and thio-NAD.
2002-10-08
The effect of active site mutations in the oxaloacetate decarboxylase and pyruvate kinase-like activities of Anaerobiospirillum succiniciproducens phosphoenolpyruvate carboxykinase.
2002-10
Ligand interactions and protein conformational changes of phosphopyridoxyl-labeled Escherichia coli phosphoenolpyruvate carboxykinase determined by fluorescence spectroscopy.
2002-10
Free fatty acid-induced hepatic insulin resistance: a potential role for protein kinase C-delta.
2002-10
Comparative characterization of Aedes 3-hydroxykynurenine transaminase/alanine glyoxylate transaminase and Drosophila serine pyruvate aminotransferase.
2002-09-11
Mutants of 4-oxalocrotonate tautomerase catalyze the decarboxylation of oxaloacetate through an imine mechanism.
2002-09-02
The succinate mechanism of insulin release.
2002-09
Gene-expression profile comparisons distinguish seven organs of maize.
2002-08-29
Response of regional brain glutamate transaminases of rat to aluminum in protein malnutrition.
2002-08-28
Evaluation by site-directed mutagenesis of active site amino acid residues of Anaerobiospirillum succiniciproducens phosphoenolpyruvate carboxykinase.
2002-08
Differences between mouse and rat pancreatic islets: succinate responsiveness, malic enzyme, and anaplerosis.
2002-08
Molecular cloning and domain structure of chicken pyruvate carboxylase.
2002-07-12
Identification of a novel transporter for dicarboxylates and tricarboxylates in plant mitochondria. Bacterial expression, reconstitution, functional characterization, and tissue distribution.
2002-07-05
Characterization of bacterial homocitrate synthase involved in lysine biosynthesis.
2002-07-03
[Uterine metabolic activity].
2002-07
Identifying and characterizing plastidic 2-oxoglutarate/malate and dicarboxylate transporters in Arabidopsis thaliana.
2002-07
Hepatic gluconeogenic capacity from various precursors in young versus old rats.
2002-07
Setting the stage for new catalytic functions in designed proteins--exploring the imine pathway in the efficient decarboxylation of oxaloacetate by an Arg-Lys site in a four-helix bundle protein scaffold.
2002-06-03
A novel Mammalian homologue of a bacterial citrate-metabolizing enzyme.
2002-06
2-Amino-3-carboxy-1,4-naphthoquinone affects the end-product profile of bifidobacteria through the mediated oxidation of NAD(P)H.
2002-06
Role of conserved residues within helices IV and VIII of the oxaloacetate decarboxylase beta subunit in the energy coupling mechanism of the Na+ pump.
2002-06
Aspartate aminotransferase isotope exchange reactions: implications for glutamate/glutamine shuttle hypothesis.
2002-06
Urea-induced unfolding studies of free- and ligand-bound tetrameric ATP-dependent Saccharomyces cerevisiae phosphoenolpyruvate carboxykinase. Influence of quaternary structure on protein conformational stability.
2002-06
Suppression of ammonia-induced swelling by aspartate but not by ornithine in primary cultures of rat astrocytes.
2002-05-22
RIO: analyzing proteomes by automated phylogenomics using resampled inference of orthologs.
2002-05-16
The novel protein phosphatase PphA from Synechocystis PCC 6803 controls dephosphorylation of the signalling protein PII.
2002-05
Atomistic simulations of competition between substrates binding to an enzyme.
2002-05
Probing the specificity of a trypanosomal aromatic alpha-hydroxy acid dehydrogenase by site-directed mutagenesis.
2002-04-26
Inhibition of gluconeogenesis by vanadium and metformin in kidney-cortex tubules isolated from control and diabetic rabbits.
2002-04-01
Metabolic network analysis of an adipoyl-7-ADCA-producing strain of Penicillium chrysogenum: elucidation of adipate degradation.
2002-04
Characterization of isocitrate dehydrogenase from the green sulfur bacterium Chlorobium limicola. A carbon dioxide-fixing enzyme in the reductive tricarboxylic acid cycle.
2002-04
Insulin increases NADH/NAD+ redox state, which stimulates guanylate cyclase in vascular smooth muscle.
2002-03
The level of pyruvate-formate lyase controls the shift from homolactic to mixed-acid product formation in Lactococcus lactis.
2002-03
2-Oxoglutarate increases the binding affinity of the NtcA (nitrogen control) transcription factor for the Synechococcus glnA promoter.
2002-02-13
Metabolic compartmentation in cortical synaptosomes: influence of glucose and preferential incorporation of endogenous glutamate into GABA.
2002-02
13C-NMR analysis of glucose metabolism during citric acid production by Aspergillus niger.
2002-02
Evolution of the enzymes of the citric acid cycle and the glyoxylate cycle of higher plants. A case study of endosymbiotic gene transfer.
2002-02
Hepatic gluconeogenesis and Krebs cycle fluxes in a CCl4 model of acute liver failure.
2002-02
A comparative study on diurnal changes in metabolite levels in the leaves of three crassulacean acid metabolism (CAM) species, Ananas comosus, Kalanchoë daigremontiana and K. pinnata.
2002-02
Subunit gamma of the oxaloacetate decarboxylase Na(+) pump: interaction with other subunits/domains of the complex and binding site for the Zn(2+) metal ion.
2002-01-29
Activity of enzymes involved in energy production in the small intestine during suckling-weaning transition of pigs.
2002
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:53:22 GMT 2025
Edited
by admin
on Mon Mar 31 18:53:22 GMT 2025
Record UNII
2F399MM81J
Record Status FAILED
Record Version
  • Download
Name Type Language
OXALOACETIC ACID
Systematic Name English
OXOSUCCINIC ACID
INCI  
INCI  
Preferred Name English
2-OXOBUTANEDIOIC ACID
Systematic Name English
KETOSUCCINIC ACID
Systematic Name English
Oxalacetic acid [WHO-DD]
Common Name English
OXALOACETATE
Systematic Name English
OXALACETIC ACID
MI   WHO-DD  
Systematic Name English
OXALACETIC ACID TRANS-(Z)-ENOL FORM [MI]
Common Name English
NSC-77688
Code English
OAA
Common Name English
ANHYDROUS ENOL-OXALOACETATE
Common Name English
OXALACETIC ACID [MI]
Common Name English
BIOEPG
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 370412
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
DSLD 4402 (Number of products:3)
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
FDA ORPHAN DRUG 488015
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
Code System Code Type Description
DRUG BANK
DB02637
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
CAS
6153-53-3
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
ALTERNATIVE
CHEBI
30744
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
RXCUI
1661330
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
SMS_ID
100000125942
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
FDA UNII
2F399MM81J
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
CAS
1115-67-9
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
ALTERNATIVE
CAS
7619-04-7
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
ALTERNATIVE
RXCUI
1661329
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
ALTERNATIVE RxNorm
CHEBI
16452
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
NCI_THESAURUS
C168687
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
PUBCHEM
970
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID8021646
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-329-8
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
CAS
328-42-7
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
MERCK INDEX
m8278
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
OXALOACETIC ACID
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
EVMPD
SUB32802
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
NSC
77688
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY