General Information of MET (ID: META00791)
Name Indole
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-Azaindene; 1-Benzazole; 2,3-Benzopyrrole; Benzo[b]pyrrole; Indol; Indole; Ketole
Source Endogenous;Escherichia Coli Metabolite;Food;Carcinogenic Potency;Agricultural Chemicals;Cosmetic;Food additives;TCM Ingredients;Microbial
Structure Type   Indoles  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Indoles and derivatives
Indoles
PubChem CID
798
HMDB ID
HMDB0000738
Formula
C8H7N
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00463
DrugBank ID
DB04532
ChEBI ID
16881
FooDB ID
FDB012008
ChemSpider ID
776
METLIN ID
286
Physicochemical Properties Molecular Weight 117.15 Topological Polar Surface Area 15.8
XlogP 2.1 Complexity 101
Heavy Atom Count 9 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count N.A.
Function
Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine. Indole is a microbial metabolite and it can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, indole has a flowery smell and is a constituent of many flower scents (such as orange blossoms) and perfumes. As a volatile organic compound, indole has been identified as a fecal biomarker of Clostridium difficile infection. Natural jasmine oil, used in the perfume industry, contains around 2.5% of indole. Indole also occurs in coal tar. Indole has been found to be produced in a number of bacterial genera including Alcaligenes, Aspergillus, Escherichia, and Pseudomonas. Indole plays a role in bacterial biofilm formation, bacterial motility, bacterial virulence, plasmid stability, and antibiotic resistance. It also functions as an intercellular signalling molecule. Recently, it was determined that the bacterial membrane-bound histidine sensor kinase (HK) known as CpxA acts as a bacterial indole sensor to facilitate signalling. It has been found that decreased indole concentrations in the gut promote bacterial pathogenesis, while increased levels of indole in the gut decrease bacterial virulence gene expression. As a result, enteric pathogens sense a gradient of indole concentrations in the gut to migrate to different niches and successfully establish an infection.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of TP53
                      Induced Change Indole concentration: increase (Log2 FC=1.15)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of indole levels compared with control group.
References
1 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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