Imidazol-4-one-5-propionic acid

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

Chemical compound

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]

References

^ 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.
^ Koh, Ara; Molinaro, Antonio; Ståhlman, Marcus; Khan, Muhammad Tanweer; Schmidt, Caroline; Mannerås-Holm, Louise; Wu, Hao; Carreras, Alba; Jeong, Heeyoon; Olofsson, Louise E.; Bergh, Per-Olof; Gerdes, Victor; Hartstra, Annick; De Brauw, Maurits; Perkins, Rosie; Nieuwdorp, Max; Bergström, Göran; Bäckhed, Fredrik (2018). "Microbially Produced Imidazole Propionate Impairs Insulin Signaling through mTORC1". Cell. 175 (4): 947–961.e17. doi:10.1016/j.cell.2018.09.055. PMID 30401435. S2CID 53229780.

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→
citrate

glycine→ serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA