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{{chembox |
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| verifiedrevid = 338867771 |
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|ImageFile=Imidazol-4-one-5-propionic acid.png |
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| verifiedrevid = 436873535 |
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|ImageSize=200px |
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| ImageFile=Imidazol-4-one-5-propionic acid.png |
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|IUPACName=3-(5-Oxo-1,4-dihydroimidazol-4-yl)propanoic acid |
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|OtherNames= |
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| IUPACName=3-(5-Oxo-1,4-dihydroimidazol-4-yl)propanoic acid |
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|Section1= {{Chembox Identifiers |
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| CASNo=17340-16-8 |
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|Section1={{Chembox Identifiers |
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| PubChem=128 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| SMILES=C1=NC(C(=O)N1)CCC(=O)O |
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| CASNo=17340-16-8 |
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| MeSHName=Imidazol-4-one-5-propionic+acid |
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| PubChem=128 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 125 |
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| SMILES = O=C1N\C=N/C1CCC(=O)O |
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| 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) |
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| InChIKey = HEXMLHKQVUFYME-UHFFFAOYAX |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = HEXMLHKQVUFYME-UHFFFAOYSA-N |
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| MeSHName=Imidazol-4-one-5-propionic+acid |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>6</sub>H<sub>8</sub>N<sub>2</sub>O<sub>3</sub> |
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| Formula=C<sub>6</sub>H<sub>8</sub>N<sub>2</sub>O<sub>3</sub> |
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| MolarMass=156.139 |
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| MolarMass=156.139 |
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|Section3= {{Chembox Hazards |
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'''Imidazol-4-one-5-propionic acid''' is an intermediate in the metabolism of ]. It is a colorless compound that is sensitive to light in air. The compound features an ] ring.<ref>{{cite book|title=Preparation and properties of 4(5)-imidazolone-5(4)-propionic acid|author1=Hassall, H.|author2=Greenberg, D. M.|series=Methods Enzymol.|year=1971|volume=17(Pt. B)|pages=89–91|doi=10.1016/0076-6879(71)17014-0|isbn=978-0-12-181877-7 }}</ref> |
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'''Imidazol-4-one-5-propionic acid''' is an intermediate in the metabolism of ]. |
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==Occurrence== |
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It arises via the action of ] on ]. Hydrolysis of the ] to the glutamic acid derivative is catalyzed by imidazolonepropionate hydrolase. |
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Microbial production of imidazol-4-one-5-propionic acid in the human gut has been shown to affect insulin signaling, which is relevant to ].<ref>{{cite journal |doi=10.1016/j.cell.2018.09.055|title=Microbially Produced Imidazole Propionate Impairs Insulin Signaling through mTORC1|year=2018|last1=Koh|first1=Ara|last2=Molinaro|first2=Antonio|last3=Ståhlman|first3=Marcus|last4=Khan|first4=Muhammad Tanweer|last5=Schmidt|first5=Caroline|last6=Mannerås-Holm|first6=Louise|last7=Wu|first7=Hao|last8=Carreras|first8=Alba|last9=Jeong|first9=Heeyoon|last10=Olofsson|first10=Louise E.|last11=Bergh|first11=Per-Olof|last12=Gerdes|first12=Victor|last13=Hartstra|first13=Annick|last14=De Brauw|first14=Maurits|last15=Perkins|first15=Rosie|last16=Nieuwdorp|first16=Max|last17=Bergström|first17=Göran|last18=Bäckhed|first18=Fredrik|journal=Cell|volume=175|issue=4|pages=947–961.e17|pmid=30401435|s2cid=53229780|doi-access=free}}</ref> |
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==See also== |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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<references /> |
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{{Amino acid metabolism intermediates}} |
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{{Amino acid metabolism intermediates}} |
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{{heterocyclic-stub}} |
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{{heterocyclic-stub}} |
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