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Contents

   



(Top)
  


1 Occurrence  




2 See also  




3 References  













Imidazol-4-one-5-propionic acid






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From Wikipedia, the free encyclopedia
  

Imidazol-4-one-5-propionic acid
Names
IUPAC name

3-(5-Oxo-1,4-dihydroimidazol-4-yl)propanoic acid

Identifiers

CAS Number

3D model (JSmol)
ChemSpider
MeSH Imidazol-4-one-5-propionic+acid

PubChem CID

CompTox Dashboard (EPA)

  • 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

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 checkY☒N ?)

Infobox references

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[edit]

It arises via the action of urocanaseonurocanic 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]

See also[edit]

References[edit]

  1. ^ Hassall, H.; Greenberg, D. M. (1971). Preparation and properties of 4(5)-imidazolone-5(4)-propionic acid. 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.


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    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Imidazol-4-one-5-propionic_acid&oldid=1230294500"
    Categories: 
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     ●Imidazolines
     ●Lactams
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