Structure Database (LMSD)
Common Name
Oxalacetic acid
Systematic Name
2-oxo-butanedioic acid
Synonyms
3D model of Oxalacetic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Oxaloacetic acid is an α-keto acid and a key component of cellular metabolism in its conjugate base form, oxaloacetate.1,2,3 Oxaloacetate reacts with acetyl-coenzyme A (acetyl-CoA) and water to form citrate in the first step of the citric acid cycle and is regenerated by oxidation of L-malate in the final step.2 It is an intermediate in gluconeogenesis that is formed in mitochondria via carboxylation of pyruvate and subsequently decarboxylated and phosphorylated to form phosphoenolpyruvate.3 It can be converted to aspartate via addition of an amino group from glutamate.1 Oxaloacetate (30 μmol/min per 100 g for 30 minutes, i.v.) reduces blood glutamate levels, severity of neurological dysfunction, and brain edema in a rat model of closed head injury.4
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
KHPXUQMNIQBQEV-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
SMILES (Click to copy)
C(=O)(O)C(=O)CC(O)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
9
Rings
0
Aromatic Rings
0
Rotatable Bonds
3
Van der Waals Molecular Volume
113.79
Topological Polar Surface Area
91.67
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
5
logP
-0.89
Molar Refractivity
24.90
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Created at
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Updated at
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