Details of Metabolite (Meta)

General Information of Metabolite (ID: MT053)
  Meta Name
Indole-3-acetate
  Unify Name
Indoleacetic acid
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
(indol-3-yl)Acetate;(indol-3-yl)Acetic acid;2-(indol-3-yl)Ethanoic acid;3-Indolylessigsaeure;Heteroauxin;IAA;IES;Indoleacetate;2-(indol-3-yl)Ethanoate;(1H-indol-3-yl)-Acetate;(1H-indol-3-yl)-Acetic acid;1H-indol-3-Ylacetate;1H-indol-3-Ylacetic acid;1H-Indole-3-acetate;1H-Indole-3-acetic acid;2-(1H-indol-3-yl)Acetate;2-(1H-indol-3-yl)Acetic acid;2-(3-Indolyl)acetate;2-(3-Indolyl)acetic acid;3-(Carboxymethyl)indole;3-IAA;3-Indole-acetic acid;3-Indoleacetate;3-Indoleacetic acid;3-Indolylacetate;3-Indolylacetic acid;alpha-indol-3-yl-Acetic acid;b-Indoleacetate;b-Indoleacetic acid;b-Indolylacetate;b-Indolylacetic acid;beta-Indole-3-acetic acid;beta-Indoleacetate;beta-Indoleacetic acid;beta-Indolylacetate;beta-Indolylacetic acid;indol-3-Ylacetate;indol-3-Ylacetic acid;Indole-3-acetate;Indole-3-acetic acid;Indolyl-3-acetate;Indolyl-3-acetic acid;Indolylacetate;Indolylacetic acid;Kyselina 3-indolyloctova;Rhizopin;Rhizopon a;Skatole carboxylate;Skatole carboxylic acid;Indoleacetic acid, calcium salt;Indoleacetic acid, monopotassium salt;Indoleacetic acid, monosodium salt;IES CPD;Indole acetic acid;Indoleacetic acid, alpha-(14)C-labeled;
  Molecule Type
Tryptophan metabolites
  Formula
C10H8NO2
  Inchi Key
SEOVTRFCIGRIMH-UHFFFAOYSA-M
  Description    Click to Show/Hide the Detailed Description of This Metabolite
Human Metabolome Database (HMDB): Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. IAA frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with phenylketonuria ((PMID: 13610897). Using material extracted from human urine, it was discovered by Kogl in 1933 that Indoleacetic acid is also an important plant hormone (PMID: 13610897). Specifically IAA is a member of the group of phytohormones called auxins. IAA is generally considered to be the most important native auxin. Plant cells synthesize IAA from tryptophan. (wikipedia) IAA and some derivatives can be oxidised by horseradish peroxidase (HRP) to cytotoxic species. IAA is only toxic after oxidative decarboxylation; the effect of IAA/HRP is thought to be due in part to the formation of methylene-oxindole, which may conjugate with DNA bases and protein thiols. IAA/HRP could be used as the basis for targeted cancer, a potential new role for plant auxins in cancer therapy. (PMID: 11163327).
  External Links   HMDB ID   HMDB0000197
  VMH ID   ind3ac
  KEGG ID   C00954
  Metlin ID   5211

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 [1], [2]
         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 [3], [4]
         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 [3]
         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 [7], [8]
         Description
Lactobacillus sp. is a bacteria of gram-positive, aerotolerant anaerobics or microaerophilic, rod-shaped, non-spore-forming bacteria.

References
1 Evidence that asthma is a developmental origin disease influenced by maternal diet and bacterial metabolites. Nat Commun. 2015 Jun 23;6:7320. doi: 10.1038/ncomms8320.
2 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.
3 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.
4 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.
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 Acetate functions as an epigenetic metabolite to promote lipid synthesis under hypoxia. Nat Commun. 2016 Jun 30;7:11960. doi: 10.1038/ncomms11960.
8 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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