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
3D model (JSmol)
ChemSpider
MeSHImidazol-4-one-5-propionic+acid
  • 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
  • O=C1N\C=N/C1CCC(=O)O
Properties
C6H8N2O3
Molar mass156.139
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

Imidazole propionate has been causally implicated in atherosclerosis and Parkinson’s disease, primarily by triggering inflammation. Streptococcus mutans, known for its role in dental 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]

See also

References

  1. ^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.
  2. ^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.
  3. ^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.
  4. ^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.
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