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Imidazol-4-one-5-propionic acid

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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 theirstandard 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 ofhistidine. It is a colorless compound that is sensitive to light in air. The compound features animidazolone ring.^[1]

Occurrence

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It arises via the action ofurocanase onurocanic acid. Hydrolysis of theheterocycle 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 totype II diabetes.^[2]

Imidazole propionate has been causally implicated in atherosclerosis and Parkinson’s disease, primarily by triggering inflammation.Streptococcus mutans, known for its role indental caries, has been identified as a contributor to elevated ImP levels through the urdA gene, which is involved in the conversion of urocanate to ImP.^[3]^[4]

References

[edit]

^Hassall, H.; Greenberg, D. M. (1971). "The preparation and properties of 4(5)-imidazolone-5(4)-propionic acid".Metabolism of Amino Acids and Amines Part B. Methods Enzymol. Vol. 17(Pt. B). pp. 89–91.doi:10.1016/0076-6879(71)17014-0.ISBN 978-0-12-181877-7.
^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.
^Park, H.; Cheon, J.; Kim, H.; et al. (2025)."Gut microbial production of imidazole propionate drives Parkinson's pathologies".Nature Communications.16: 8216.doi:10.1038/s41467-025-63473-4.PMC 12413466.
^Mastrangelo, A.; Robles-Vera, I.; Mañanes, D.; et al. (2025)."Imidazole propionate is a driver and therapeutic target in atherosclerosis".Nature.645:254–261.doi:10.1038/s41586-025-09263-w.

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