Details of Metabolite

General Information of MET (ID: META00842)
Name Tryptophol
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1H-Indole-3-ethanol; 1H-Indolyl-3-ethanol; 2-(1H-indol-3-yl)Ethanol; 2-(3-Indolyl)ethanol; 2-(3-Indolylethanol; 2-(indol-3-yl)Ethanol; 3-(2-Hydroxyethyl)indole; 3-(b-Hydroxyethyl)indole; 3-(beta-Hydroxyethyl)indole; 3-Indoleethanol; 3-Indolylethanol; DL-Tryptophanol; IEA; Indole ethanol; Indole-3-ethanol; Indoleethanol; Tryptophanol; Tryptophol; b-(3-Indole)ethanol; beta-(3-Indole)ethanol; beta-indol-3-Ylethanol
Source Endogenous;Yeast Metabolite;Food;TCM Ingredients;Microbial
Structure Type   Indoles  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Indoles and derivatives
Indoles
PubChem CID
10685
HMDB ID
HMDB0003447
Formula
C10H11NO
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
C00955
ChEBI ID
17890
FooDB ID
FDB010973
ChemSpider ID
10235
METLIN ID
6932
Physicochemical Properties Molecular Weight 161.2 Topological Polar Surface Area 36
XlogP 1.8 Complexity 149
Heavy Atom Count 12 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 1
Function
Tryptophol, also known as indole-3-ethanol, is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine. Tryptophol production was negatively associated with interferon-gamma production (IFN) which suggests that tryptophol has anti-inflammatory properties. Tryptophol has also been identified as the hypnotic agent in trypanosomal sleeping sickness, and because it is formed in vivo after ethanol or disulfiram treatment, it is also associated with the study of alcoholism.
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 Tryptophol concentration: decrease (Log2 FC=0.64)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of tryptophol 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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