Structure via PubChem · Public domain (PubChem)
oxaloacetic acid
Sign in to saveAlso known as OAA, 2-oxosuccinic acid, ketosuccinic acid, 3-carboxy-3-oxopropanoic acid, Oxaloethanoic acid, alpha-Ketosuccinic acid, a-Ketosuccinic acid, 2-Ketosuccinic acid
chemical compound
Chemical data
- Formula
- C4H4O5
- Molecular weight
- 132.07 g/mol
- IUPAC name
- 2-oxobutanedioic acid
- SMILES
- C(C(=O)C(=O)O)C(=O)O
- InChIKey
- KHPXUQMNIQBQEV-UHFFFAOYSA-N
- XLogP
- -0.6
- Polar surface area
- 91.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- breast carcinoma in situ, Myasthenia gravis, Alzheimer disease, amyotrophic lateral sclerosis
via ChEMBL · EBI
Research
1,360 papers- Oxaloacetic acid induces muscle energy substrate depletion and fatigue by JNK-mediated mitochondrial uncoupling.FASEB journal : official publication of the Federation of American Societies for Experimental Biology · 2024
- Oxaloacetic acid mediates ADP-dependent inhibition of mitochondrial complex II-driven respiration.The Journal of biological chemistry · 2018
- The use of differential scanning fluorimetry to detect ligand interactions that promote protein stability.Nature protocols · 2007
- Oxaloacetate Treatment For Mental And Physical Fatigue In Myalgic Encephalomyelitis/Chronic Fatigue Syndrome (ME/CFS) and Long-COVID fatigue patients: a non-randomized controlled clinical trial.Journal of translational medicine · 2022
- Itaconic acid derivatives: structure, function, biosynthesis, and perspectives.Applied microbiology and biotechnology · 2020
via PubMed
Wikidata facts
- Subclass of
- dicarboxylic acid
- Has part
- carbon
- Mass
- 132.005873
Show 9 more facts
- found in taxon
- Arabidopsis thaliana
- chemical formula
- C₄H₄O₅
- canonical SMILES
- C(C(=O)C(=O)O)C(=O)O
- Commons category
- Oxaloacetic acid
- standard enthalpy of formation
- -943.21
- combustion enthalpy
- -1205.58
- safety classification and labelling
- Regulation (EC) No. 1272/2008
- described by source
- Brockhaus and Efron Encyclopedic Dictionary
- subject has role
- primary metabolite
Sources (5)
via Wikidata · CC0
~7 min read
Encyclopedic overview
Oxaloacetic acid (also known as oxalacetic acid or OAA) is a crystalline organic compound with the chemical formula HO2CC(O)CH2CO2H. Oxaloacetic acid, in the form of its conjugate base oxaloacetate, is a metabolic intermediate in many processes that occur in animals. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle.
Properties
Excerpted from Wikipedia’s “oxaloacetic acid” article, available under the CC BY-SA 4.0 licence.