General Information of MET (ID: META00946)
Name Tryptamine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(3-Indolyl)ethylamine; 1H-Indole-3-ethanamine; 2-(1H-Indol-3-yl)ethan-1-amine; 2-(1H-indol-3-yl)ETHANAMINE; 2-(1H-indol-3-yl)Ethylamine; 2-(3-Indolyl)ethylamine; 2-indol-3-yl-Aethylamin; 2-indol-3-yl-Ethylamine; 3-(2-Aminoethyl)-1H-indole; 3-(2-Aminoethyl)indole; 3-Indoleethanamine; 3-Indoleethylamine; TrpN; Tryptamin; Tryptamine
Source Food;Drug;TCM Ingredients
Structure Type   Tryptamines and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Indoles and derivatives
Tryptamines and derivatives
PubChem CID
1150
HMDB ID
HMDB0000303
Formula
C10H12N2
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=1150"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00398
DrugBank ID
DB08653
ChEBI ID
16765
FooDB ID
FDB000917
ChemSpider ID
1118
Physicochemical Properties Molecular Weight 160.22 Topological Polar Surface Area 41.8
XlogP 1.6 Complexity 147
Heavy Atom Count 12 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 1
Function
Tryptamine, also known as TrpN, 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. Both Clostridium sp. and Ruminococcus sp. have been found to convert tryptophan into tryptamine. Tryptamine is a monoamine compound that is a common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, acerola, Japanese walnuts, custard apples, and green zucchinis. This could make tryptamine a potential biomarker for the consumption of these foods.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transferases (EC 2)
            Arylamine N-acetyltransferase 1 (NAT1) 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 NAT1
                      Induced Change Tryptamine concentration: decrease (FC = 0.5)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Breast cancer [ICD-11: 2C60]
                      Details It is reported that knockout of NAT1 leads to the decrease of tryptamine levels compared with control group.
References
1 CRISPR/Cas9 knockout of human arylamine N-acetyltransferase 1 in MDA-MB-231 breast cancer cells suggests a role in cellular metabolism. Sci Rep. 2020 Jun 17;10(1):9804.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.