Imidazol-4-one-5-propionic acid

Imidazol-4-one-5-propionic acid is an intermediate in the metabolism of histidine. It is a colorless compound that is sensitive to light in air. The compound features an imidazolone ring.[1] It arises via the action of urocanase on urocanic acid. Hydrolysis of the heterocycle to the glutamic acid derivative is catalyzed by imidazolonepropionate hydrolase.

Imidazol-4-one-5-propionic acid

Names
IUPAC name 3-(5-Oxo-1,4-dihydroimidazol-4-yl)propanoic acid
Identifiers
CAS Number	17340-16-8^Y
3D model (JSmol)	Interactive image
ChemSpider	125^N
MeSH	Imidazol-4-one-5-propionic+acid
PubChem CID	128
CompTox Dashboard (EPA)	DTXSID40938378
InChI InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)^N Key: HEXMLHKQVUFYME-UHFFFAOYSA-N^N InChI=1/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11) Key: HEXMLHKQVUFYME-UHFFFAOYAX
SMILES O=C1N\C=N/C1CCC(=O)O
Properties
Chemical formula	C6H8N2O3
Molar mass	156.139
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

See also

• Formiminoglutamic acid
• Urocanate
• Urocanate hydratase

References

1. Hassall, H.; Greenberg, D. M. (1971). "Preparation and properties of 4(5)-imidazolone-5(4)-propionic acid". Methods Enzymol. 17(Pt. B): 89–91. doi:10.1016/0076-6879(71)17014-0.