Oxaluric acid

Oxaluric acid
	Skeletal formula of oxaluric acid
Names
	Preferred IUPAC name 2-(carbamoylamino)-2-oxoacetic acid
Identifiers
CAS Number	585-05-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16582;
ChEMBL	ChEMBL899896;
ChemSpider	443;
KEGG	C00802;
PubChem CID	456;
CompTox Dashboard (EPA)	DTXSID00207214 ;
	InChI InChI=1S/C3H4N2O4/c4-3(9)5-1(6)2(7)8/h(H,7,8)(H3,4,5,6,9) Key: UWBHMRBRLOJJAA-UHFFFAOYSA-N;
	SMILES C(=O)(C(=O)O)NC(=O)N;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Oxaluric acid is an organic compound with the formula C₃H₄N₂O₄. It is a 2-oxo monocarboxylic acid that is amino(oxo)acetic acid with a nitrogen atom substituted by a carbamoylamino group. It is a urea.^[1]

Occurrence

Oxaluric acid appears naturally in Escherichia coli as a metabolite, and has been reported in Apis cerana, Euglena gracilis, and Trypanosoma brucei. It is also found in the cocoa bean.^[1]

Production and synthesis

Oxaluric acid is made in Escherichia coli in the allantoin degradation metabolic pathway, where (S)-ureidoglycolic acid and NADP react to make hydrogen, NADPH, and oxaluric acid.^[2] The chemical is also produced through the spontaneous degradation of parabanic acid in the yeast species Saccharomyces cerevisiae.^[3]

Uses

Oxaluric acid is also used in allantoin degradation, where it and phosphate react to make carbamoyl phosphate and oxamate.^[2]

References

1 2 "Oxaluric acid". PubChem. National Center for Biotechnology Information. Retrieved May 6, 2026.
1 2 "Allantoin Degradation (Anaerobic)". May 18, 2022. Retrieved May 6, 2026.
↑ Sumrada R, Cooper TG (1974). "Oxaluric Acid: a Non-Metabolizable Inducer of the Allantoin Degradative Enzymes in Saccharomyces cerevisiae". Journal of Bacteriology. 117 (3): 1240–1247. doi:10.1128/jb.117.3.1240-1247.1974. ISSN 0021-9193. PMC 246607. PMID 4591950.

[PubChem-1] 1 2 "Oxaluric acid". PubChem. National Center for Biotechnology Information. Retrieved May 6, 2026.

[Allantoin-2] 1 2 "Allantoin Degradation (Anaerobic)". May 18, 2022. Retrieved May 6, 2026.

[3] Sumrada R, Cooper TG (1974). "Oxaluric Acid: a Non-Metabolizable Inducer of the Allantoin Degradative Enzymes in Saccharomyces cerevisiae". Journal of Bacteriology. 117 (3): 1240–1247. doi:10.1128/jb.117.3.1240-1247.1974. ISSN 0021-9193. PMC 246607. PMID 4591950.

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