General Information of Metabolite (ID: MT052)
  Meta Name
Indole-3-aldehyde
  Unify Name
Indole-3-carboxaldehyde
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
Indole-3-carbaldehyde;1H-Indole-3-carbaldehyde;1H-Indole-3-carboxaldehde;3-Formylindole;3-Indolealdehyde;3-Indolecarbaldehyde;3-Indolecarboxaldehyde;3-Indolemethanal;b-Indolylaldehyde;beta-Indolylaldehyde;indol-3-Carbaldehyd;indol-3-Carbaldehyde;indol-3-Carboxaldehyde;Indole-3-aldehyde;INDOLE-3-carboxyaldehyde;1H-Indole-3-carboxaldehyde;I3cho;Indole-3-carboxaldehyde;beta-Indolylaldehyde;1H-Indol-3-yl carboxaldehyde;1H-Indole-3-aldehyde;1H-Indole-3-methanal;3-Formyl-1H-indole;3-Indolylformaldehyde;I3A;Indole-3-carboxylaldehyde;Indole-3-formaldehyde
  Molecule Type
Tryptophan metabolites
  Formula
C9H7NO
  Inchi Key
OLNJUISKUQQNIM-UHFFFAOYSA-N
  Description    Click to Show/Hide the Detailed Description of This Metabolite
Indole-3-carboxaldehyde (IAld or I3A), also known as 3-formylindole or 3-indolealdehyde, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. I3A is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells. It stimulates the production of interleukin-22 which facilitates mucosal reactivity (PMID: 27102537 ). I3A is a microbially derived tryptophan metabolite produced by Clostridium and Lactobacillus (PMID: 30120222 , 27102537). I3A has also been found in the urine of patients with untreated phenylketonuria (PMID: 5073866 ). Outside of the human body, I3A has been detected, but not quantified in, several different foods, such as beans, Brussels sprouts, cucumbers, cereals and cereal products, and white cabbages. This could make I3A a potential biomarker for the consumption of these foods.
  External Links   HMDB ID   HMDB0029737
  KEGG ID   C08493

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
DNA Methylation DNMT EM Info . . . [1], [2]

The microbes that produce this metabolite
      Escherichia coli
         Detailed Information MIC Info click to show the detail information of this Microbiota [3], [4]
         Description
Escherichia coli, also known as E. coli, is a gram-negative, facultative anaerobic, rod-shaped, coliform bacteria of the genus Escherichia.
      Bifidobacterium
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Bifidobacteria is a genus of gram-positive, nonmotile, often branched anaerobic bacteria. They are ubiquitous inhabitants of the gastrointestinal tract, vagina and mouth of mammals, including humans.
      Eubacterium hallii
         Detailed Information MIC Info click to show the detail information of this Microbiota [5], [6]
         Description
Anaerobutyricum hallii is an anaerobic bacteria that lives inside the human digestive system.
      Clostridium sporogenes
         Detailed Information MIC Info click to show the detail information of this Microbiota [1]
         Description
Clostridium sporogenes is a species of gram-positive bacteria that belongs to the genus Clostridium.
      Lactobacillus spp.
         Detailed Information MIC Info click to show the detail information of this Microbiota [3], [7]
         Description
Lactobacillus sp. is a bacteria of gram-positive, aerotolerant anaerobics or microaerophilic, rod-shaped, non-spore-forming bacteria.

References
1 Gut Microbiota as Important Mediator Between Diet and DNA Methylation and Histone Modifications in the Host. Nutrients. 2020 Feb 25;12(3):597. doi: 10.3390/nu12030597.
2 Arachidonic and oleic acid exert distinct effects on the DNA methylome. Epigenetics. 2016 May 3;11(5):321-34. doi: 10.1080/15592294.2016.1161873. Epub 2016 Apr 18.
3 Acetate functions as an epigenetic metabolite to promote lipid synthesis under hypoxia. Nat Commun. 2016 Jun 30;7:11960. doi: 10.1038/ncomms11960.
4 Fermentation Products of Commensal Bacteria Alter Enterocyte Lipid Metabolism Cell Host Microbe. 2020 Mar 11;27(3):358-375.e7. doi: 10.1016/j.chom.2020.01.028. Epub 2020 Feb 25.
5 Dietary metabolites derived from gut microbiota: critical modulators of epigenetic changes in mammals. Nutr Rev. 2017 May 1;75(5):374-389. doi: 10.1093/nutrit/nux001.
6 Mucin Cross-Feeding of Infant Bifidobacteria and Eubacterium hallii Microb Ecol. 2018 Jan;75(1):228-238. doi: 10.1007/s00248-017-1037-4. Epub 2017 Jul 18.
7 Antifungal Activity of Lactobacillus pentosusOCK 0979 in the Presence of Polyols and Galactosyl-Polyols Probiotics Antimicrob Proteins. 2018 Jun;10(2):186-200. doi: 10.1007/s12602-017-9344-0.

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