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
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.
DBLinks
- CAS Registry Number: 328-42-7
- PubChem CID: 970
- ChEBI: 16452
- HMDB: HMDB0000223
- LipidMaps: LMFA01170120
- KEGG: C00036
- BioCyc: OXALACETIC_ACID
- NCBI MeSH: Oxaloacetic Acid
- Wikipedia: Oxaloacetic_acid
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
- WishartLab ClassyFire: [Short-chain keto acids and derivatives] Short-chain keto acids and derivatives
- RefMet: [TCA acids] TCA acids
- LipidMaps: [Dicarboxylic acids [FA0117]] Dicarboxylic acids [FA0117]
- ChEBI: [CHEBI:30744] oxaloacetic acid
- Coconut NaturalProduct: [Dicarboxylic acids] Dicarboxylic acids
| 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) |
Taxonomy Source
- Citrullus lanatus [ncbi taxid: 3654]
- Delonix regia [ncbi taxid: 72433]
- Escherichia coli [ncbi taxid: 562]
- Euonymus alatus [ncbi taxid: 4307]
- FOOD SAKE [ncbi taxid: ]
- Homo sapiens [ncbi taxid: 9606]
- Hordeum vulgare [ncbi taxid: 4513]
- Saccharomyces cerevisiae [ncbi taxid: 4932]
- 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) |