Details of Metabolite

General Information of MET (ID: META01263)
Name N-Acetyltryptophan
Synonyms   Click to Show/Hide Synonyms of This Metabolite
N-Acetyl-L-tryptophan; 1218-34-4; Ac-Trp-OH; acetyltryptophan; Acetyl-L-tryptophan; L-Tryptophan, N-acetyl-; Acetyl-L-trp; AC-Try; (S)-N-Acetyltryptophan; L-ACETYLTRYPTOPHAN; UNII-U9264T8OAE; (S)-2-Acetamido-3-(1H-indol-3-yl)propanoic acid; (2S)-2-acetamido-3-(1H-indol-3-yl)propanoic acid; TRYPTOPHAN, N-ACETYL-, L-; NSC 90726; CHEMBL54170; U9264T8OAE; CHEBI:74640; MFCD00065976
Source Aromatic heteropolycyclic compounds
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
700653
HMDB ID
HMDB0013713
Formula
C13H14N2O3
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=700653"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
74640
Physicochemical Properties Molecular Weight 246.26 Topological Polar Surface Area 82.2
XlogP 1.1 Complexity 332
Heavy Atom Count 18 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Function
N-Acetyltryptophan, also known as acetyl-L-Trp or NAT, belongs to the class of organic compounds known as N-acyl-L-alpha-amino acids. These are N-acylated alpha-amino acids that have the L-configuration of the alpha-carbon atom. N-Acetyltryptophan has been used as a protein stabilizer. It prevents protein molecules from oxidative degradation by scavenging oxygen dissolved in protein solutions. N-Acetyltryptophan 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.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            R2R3-MYB (AN2) 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 Overexpression of AN2
                      Induced Change N-Acetyltryptophan concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of N-acetyltryptophan levels compared with control group.
References
1 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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