Oxaloacetate (BioCAD00000015666)

blood cellular cytoplasm cerebrospinal fluid (csf) urine liver

Metabolite Card

Formula: C4H4O5 (132.0059)
SMILES: OC(=O)CC(=O)C(O)=O

Synonyms [en]

oxalacetic acid; oxaloacetate; 2-Oxobutanedioic acid; oxaloacetic acid; 2-Oxosuccinic acid; keto-oxaloacetate

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Oxaloacetate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000015666). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Oxalacetic acid, also known as oxaloacetic acid, keto-oxaloacetate or 2-oxobutanedioate, 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 metabolic intermediate in many processes that occur in animals and plants. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle. Oxalacetic acid exists in all living species, ranging from bacteria to plants to humans. Within humans, oxalacetic acid participates in a number of enzymatic reactions. In particular, oxalacetic acid is an intermediate of the citric acid cycle, where it reacts with acetyl-CoA to form citrate, catalyzed by citrate synthase. It is also involved in gluconeogenesis and the urea cycle. In gluconeogenesis oxaloacetate is decarboxylated and phosphorylated by phosphoenolpyruvate carboxykinase and becomes 2-phosphoenolpyruvate using guanosine triphosphate (GTP) as phosphate source. In the urea cycle, malate is acted on by malate dehydrogenase to become oxaloacetate, producing a molecule of NADH. After that, oxaloacetate can be recycled to aspartate, as this recycling maintains the flow of nitrogen into the cell. In mice, injections of oxalacetic acid have been shown to promote brain mitochondrial biogenesis, activate the insulin signaling pathway, reduce neuroinflammation and activate hippocampal neurogenesis (PMID: 25027327). Oxalacetic acid has also been reported to reduce hyperglycemia in type II diabetes and to extend longevity in C. elegans (PMID: 25027327). Outside of the human body, oxalacetic acid has been detected, but not quantified in, several different foods, such as Persian limes, lemon balms, wild rice, canola, and peanuts. This could make oxalacetic acid a potential biomarker for the consumption of these foods.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 328-42-7
  • PubChem: 970
  • ChEBI: ChEBI:16452
  • ChEBI: ChEBI:30744
  • HMDB: HMDB0000223
  • HMDB: HMDB00223
  • LipidMaps: LMFA01170061
  • LipidMaps: LMFA01170120
  • KEGG: C00036
  • BioCyc: OXALACETIC_ACID
  • NCBI MeSH: Oxaloacetic Acid
  • Wikipedia: Oxaloacetic_acid
  • DrugBank: DB16921
  • RefMet: RM0134987
  • MoNA: BAF_UVA_POS001107
  • MoNA: CCMSLIB00000578311
  • MoNA: FiehnHILIC001420
  • MoNA: FiehnHILIC002903
  • MoNA: FiehnLib000603
  • MoNA: HMDB0000223_c_ms_1110
  • MoNA: HMDB0000223_c_ms_1159
  • MoNA: HMDB0000223_c_ms_1336
  • MoNA: HMDB0000223_ms_ms_367
  • MoNA: HMDB0000223_ms_ms_368
  • MoNA: HMDB0000223_ms_ms_369
  • MoNA: PS048801
  • MoNA: PS048802
  • Metlin: METLIN_123
  • Coconut NaturalProduct: CNP0390338.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00217 1.1.1.38 oxaloacetate carboxy-lyase (pyruvate-forming)
KEGG:R00338 3.7.1.1 oxaloacetate acetylhydrolase
KEGG:R00339 4.2.1.32 (R,R)-tartrate hydro-lyase (oxaloacetate-forming)
KEGG:R00340 4.2.1.81 (S,S)-tartrate hydro-lyase (oxaloacetate-forming)
KEGG:R00341 4.1.1.49 ATP:oxaloacetate carboxy-lyase (transphosphorylating;phosphoenolpyruvate-forming)
KEGG:R00342 1.1.1.37 (S)-malate:NAD+ oxidoreductase
KEGG:R00343 1.1.1.82 (S)-malate:NADP+ oxidoreductase
KEGG:R00344 6.4.1.1 pyruvate:carbon-dioxide ligase (ADP-forming)
KEGG:R00345 4.1.1.31 phosphate:oxaloacetate carboxy-lyase (adding phosphate;phosphoenolpyruvate-forming)
KEGG:R00346 4.1.1.38 diphosphate:oxaloacetate carboxy-lyase (transphosphorylating;phosphoenolpyruvate-forming);
KEGG:R00347 4.3.1.20 erythro-3-hydroxy-Ls-aspartate ammonia-lyase (oxaloacetate-forming)
KEGG:R00348 3.5.1.3 2-oxosuccinamate amidohydrolase
KEGG:R00350 4.1.3.17 4-carboxy-4-hydroxy-2-oxoadipate oxaloacetate-lyase (pyruvate-forming)
KEGG:R00351 2.3.3.1 acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)
KEGG:R00352 2.3.3.8 acetyl-CoA:oxaloacetate C-acetyltransferase [(pro-S)-carboxymethyl-forming, ADP-phosphorylating]
KEGG:R00353 2.1.3.1 malonyl-CoA:pyruvate carboxytransferase
KEGG:R00354 4.1.3.34 (3S)-citryl-CoA oxaloacetate-lyase (acetyl-CoA-forming)
KEGG:R00355 2.6.1.1 L-aspartate:2-oxoglutarate aminotransferase
KEGG:R00357 1.4.3.2 L-aspartic acid:oxygen oxidoreductase (deaminating)
KEGG:R00359 1.4.3.1 D-aspartate:oxygen oxidoreductase (deaminating)
View More
Organism Source

Taxonomy Source

  1. Citrullus lanatus [ncbi taxid: 3654]
  2. Delonix regia [ncbi taxid: 72433]
  3. Escherichia coli [ncbi taxid: 562]
  4. Euonymus alatus [ncbi taxid: 4307]
  5. FOOD SAKE [ncbi taxid: ]
  6. Homo sapiens [ncbi taxid: 9606]
  7. Hordeum vulgare [ncbi taxid: 4513]
  8. Saccharomyces cerevisiae [ncbi taxid: 4932]
  9. Thermotoga maritima [ncbi taxid: 2336]

Pathway Synthetic

pathway id name
BioCyc:CALBI_PWY3B3-100 TCA cycle, aerobic respiration
BioCyc:CALBI_GLUCONEO-PWY gluconeogenesis
BioCyc:CALBI_ASPARAGINE-DEG1-PWY asparagine degradation
BioCyc:CALBI_ASPBIO-PWY aspartate biosynthesis
BioCyc:CALBI_MALATE-ASPARTATE-SHUTTLE-PWY aspartate degradation
BioCyc:CALBI_GLUTAMINEFUM-PWY glutamine degradation
BioCyc:CALBI_GLYOXYLATE-BYPASS glyoxylate cycle
BioCyc:CALBI_ASPARAGINE-BIOSYNTHESIS asparagine biosynthesis
WikiPathways:WP3583 Central carbon metabolism
PathBank:SMP0000802 TCA Cycle
PathBank:SMP0000809 Aspartate Metabolism
PathBank:SMP0000811 L-Glutamate Metabolism
PathBank:SMP0000833 Asparagine Biosynthesis
PathBank:SMP0000837 Threonine Biosynthesis
PathBank:SMP0000839 Gluconeogenesis from L-Malic Acid
PathBank:SMP0000957 Propanoate Metabolism
PathBank:SMP0000983 Secondary Metabolites: Glyoxylate Cycle
PathBank:SMP0001018 TCA cycle (ubiquinol-2)
PathBank:SMP0001019 TCA cycle (ubiquinol-3)
PathBank:SMP0001020 TCA cycle (ubiquinol-4)
View All Pathways