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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.

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.

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.

References

References

  1. (1971). "Metabolism of Amino Acids and Amines Part B".
  2. (2018). "Microbially Produced Imidazole Propionate Impairs Insulin Signaling through mTORC1". Cell.
  3. (2025). "Gut microbial production of imidazole propionate drives Parkinson’s pathologies". Nature Communications.
  4. (2025). "Imidazole propionate is a driver and therapeutic target in atherosclerosis". Nature.
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carboxylic-acids imidazolines lactams
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