Common NameOxaloacetate
DescriptionOxalacetic 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.
Structure
Molecular FormulaC4H4O5
Average Mass132.07160
Monoisotopic Mass132.00587
IUPAC Name2-oxobutanedioic acid
Traditional NameOxaloacetic acid
CAS Registry Number328-42-7
SMILESO=C([O-])CC(=O)C(=O)[O-]
InChI IdentifierInChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
InChI KeyKHPXUQMNIQBQEV-UHFFFAOYSA-N
CHEBI IDCHEBI:16452
HMDB IDHMDB0000223
Pathways
NameSMPDB/PathBank
Alanine, aspartate and glutamate metabolism
Pyruvate metabolism
Tyrosine metabolism
Arginine and proline metabolism
Citrullinemia Type I
Carbamoyl Phosphate Synthetase Deficiency
Argininosuccinic Aciduria
Citric Acid Cycle
Urea Cycle
Aspartate Metabolism
Glutamate Metabolism
Gluconeogenesis
Malate-Aspartate Shuttle
2-Hydroxyglutric Aciduria (D And L Form)
Alkaptonuria
Canavan Disease
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)
Hawkinsinuria
Hypoacetylaspartia
Leigh Syndrome
Ornithine Transcarbamylase Deficiency (OTC Deficiency)
Prolidase Deficiency (PD)
Prolinemia Type II
Pyruvate Dehydrogenase Complex Deficiency
Tyrosinemia Type I
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Lactic Acidemia
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Hyperinsulinism-Hyperammonemia Syndrome
Pyruvate Carboxylase Deficiency
Primary Hyperoxaluria Type I
Argininemia
Hyperprolinemia Type II
Hyperprolinemia Type I
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)
Ornithine Aminotransferase Deficiency (OAT Deficiency)
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease
Homocarnosinosis
Disulfiram Action Pathway
Transfer of Acetyl Groups into Mitochondria
Tyrosinemia, transient, of the newborn
Dopamine beta-hydroxylase deficiency
Creatine deficiency, guanidinoacetate methyltransferase deficiency
Hyperornithinemia with gyrate atrophy (HOGA)
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]
L-arginine:glycine amidinotransferase deficiency
Monoamine oxidase-a deficiency (MAO-A)
Congenital lactic acidosis
Fumarase deficiency
Mitochondrial complex II deficiency
2-ketoglutarate dehydrogenase complex deficiency
Pyruvate dehydrogenase deficiency (E3)
Pyruvate dehydrogenase deficiency (E2)
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)
Fructose-1,6-diphosphatase deficiency
Triosephosphate isomerase
Succinic semialdehyde dehydrogenase deficiency
Glycogenosis, Type IB
Glycogenosis, Type IC
Glycogenosis, Type IA. Von gierke disease
Warburg Effect
The oncogenic action of 2-hydroxyglutarate
The Oncogenic Action of Succinate
The Oncogenic Action of Fumarate
Glutaminolysis and Cancer
The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria
StateSolid
Water Solubility5.71e+01 g/l
logP-0.68
logS-0.36
pKa (Strongest Acidic)2.41
pKa (Strongest Basic)-9.87
Hydrogen Acceptor Count5
Hydrogen Donor Count2
Polar Surface Area91.67 Ų
Rotatable Bond Count3
Physiological Charge-2
Formal Charge0
Refractivity24.33 m³·mol⁻¹
Polarizability10.06

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