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)	DTXSID10864771 DTXSID40938378, DTXSID10864771
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

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]

Occurrence

It arises via the action of urocanase on urocanic acid. Hydrolysis of the heterocycle to the glutamic acid derivative is catalyzed by imidazolonepropionate hydrolase.

Microbial production of imidazol-4-one-5-propionic acid in the human gut has been shown to affect insulin signaling, which is relevant to type II diabetes.^[2]