Imidazole propionate

Imidazole propionate
Clinical data
Other namesImP; 5-Imidazolepropionic acid; Imidazolylpropionic acid
Drug classImidazoline I1 receptor activator
ATC code
  • None
Identifiers
  • 3-(1H-imidazol-5-yl)propanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.769
Chemical and physical data
FormulaC6H8N2O2
Molar mass140.142 g·mol−1
3D model (JSmol)
  • C1=C(NC=N1)CCC(=O)O
  • InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)
  • Key:ZCKYOWGFRHAZIQ-UHFFFAOYSA-N

Imidazole propionate (ImP), also known as 5-imidazolepropionic acid, is a bacterial metabolite of histidine and a neurotoxin.[1][2][3] It is produced by Streptococcus mutans and its enzyme urocanate reductase (UrdA) in the gut.[1] S. mutans, as well as ImP production and circulating levels, have been found to be elevated in people with Parkinson's disease.[1] In addition, administration of ImP, or colonization with ImP-producing bacteria, causes dopaminergic neurotoxicity and Parkinson's disease-like symptoms in rodents.[1] Based on these findings, UrdA-expressing and ImP-producing bacteria may be involved in the etiology of Parkinson's disease in humans.[1] ImP has also been implicated in the pathophysiology of other diseases such as atherosclerosis,[4][5][6] diabetes,[7] and Alzheimer's disease,[8] among others.[9][2][10] ImP activates the imidazoline I1 receptor and this appears to be involved in some of its toxic effects.[6][11] Relatedly, imidazoline I1 receptor antagonists have been proposed for possible therapeutic purposes.[6][11]

See also

References

  1. ^ a b c d e Park H, Cheon J, Kim H, Kim J, Kim J, Shin JY, et al. (September 2025). "Gut microbial production of imidazole propionate drives Parkinson's pathologies". Nat Commun. 16 (1) 8216. Bibcode:2025NatCo..16.8216P. doi:10.1038/s41467-025-63473-4. PMC 12413466. PMID 40913049.
  2. ^ a b Zhang Y, Wei S, Zhang H, Jo Y, Kang JS, Ha KT, et al. (May 2024). "Gut microbiota-generated metabolites: missing puzzles to hosts' health, diseases, and aging". BMB Rep. 57 (5): 207–215. doi:10.5483/BMBRep.2024-0022. PMC 11139682. PMID 38627947.
  3. ^ Warmbrunn MV, Attaye I, Horak A, Banerjee R, Massey WJ, Varadharajan V, et al. (November 2024). "Kinetics of imidazole propionate from orally delivered histidine in mice and humans". npj Biofilms Microbiomes. 10 (1) 118. doi:10.1038/s41522-024-00592-8. PMC 11535228. PMID 39496629.
  4. ^ Puca P, Coppola G, Parello S, Capobianco I, Colantuono S, Scaldaferri F, et al. (September 2025). "Atherosclerotic cardiovascular disease and inflammatory bowel disease: epidemiology, pathogenesis and risk assessment". Best Pract Res Clin Gastroenterol. 78 102056. doi:10.1016/j.bpg.2025.102056. PMID 41350098.
  5. ^ He JH, Wang H, Qiu E, Qi Q, Wang Z (December 2025). "Gut Microbiota and Atherosclerosis: Integrative Multi-Omics and Mechanistic Insights". Curr Atheroscler Rep. 28 (1) 1. doi:10.1007/s11883-025-01371-2. PMC 12715051. PMID 41410816.
  6. ^ a b c Mastrangelo A, Robles-Vera I, Mañanes D, Galán M, Femenía-Muiña M, Redondo-Urzainqui A, et al. (September 2025). "Imidazole propionate is a driver and therapeutic target in atherosclerosis". Nature. 645 (8079): 254–261. Bibcode:2025Natur.645..254M. doi:10.1038/s41586-025-09263-w. PMC 12408353. PMID 40670786.
  7. ^ Xu Q, Wang W, Li Y, Liu Y, Liu Y (2024). "Imidazole propionate in type 2 diabetes mellitus and cardiovascular diseases: a mini review". Front Immunol. 15 1454210. doi:10.3389/fimmu.2024.1454210. PMC 11390552. PMID 39267755.
  8. ^ Vemuganti V, Kang JW, Zhang Q, Aquino-Martinez R, Harding S, Harpt JL, et al. (June 2025). "Gut bacterial metabolite imidazole propionate potentiates Alzheimer's disease pathology". bioRxiv 10.1101/2025.06.08.657719.
  9. ^ Zeng Y, Wu Q, Guo M, Teng F, Jiang C, Chen J, et al. (2025). "Gut microbiota-derived imidazole propionate: an emerging target for the prevention and treatment of cardiometabolic diseases". Front Endocrinol (Lausanne). 16 1409119. doi:10.3389/fendo.2025.1409119. PMC 11872695. PMID 40034229.
  10. ^ Raju SC, Molinaro A, Awoyemi A, Jørgensen SF, Braadland PR, Nendl A, et al. (February 2024). "Microbial-derived imidazole propionate links the heart failure-associated microbiome alterations to disease severity". Genome Med. 16 (1) 27. doi:10.1186/s13073-024-01296-6. PMC 10854170. PMID 38331891.
  11. ^ a b Wang W, Semo D, Godfrey R (October 2025). "Gut-derived imidazole propionate promotes atherosclerosis through myeloid imidazoline-1 receptor signaling: new biomarker and therapeutic target". Signal Transduct Target Ther. 10 (1) 353. doi:10.1038/s41392-025-02440-3. PMC 12554895. PMID 41139705.
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