Details of Metabolite

General Information of MET (ID: META00409)
Name N6,N6,N6-Trimethyl-L-lysine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S)-2-Amino-6-(trimethylazaniumyl)hexanoic acid; (S)-2-Amino-6-(trimethylammonio)hexanoate; (S)-2-Amino-6-(trimethylammonio)hexanoic acid; 6-N-L-Trimethyl-L-lysine; N(6),N(6),N(6)-Trimethyl-L-lysine; S)-5-Amino-5-carboxy-N,N,N-trimethyl-1-pentanaminium; TRIMETHYLLLYSINE; Trimethyllysine; Trimethyllysine chloride, (S)-isomer; Trimethyllysine hydroxide, inner salt, (S)-isomer; Trimethyllysine hydroxide,inner salt, (+-)-isomer; Trimethyllysine, (+-)-isomer; delta-Trimethyllysine; epsilon-N-Trimethyl-L-lysine; epsilon-N-Trimethyl-lysine; epsilon-Trimethyl-L-lysine
Source Endogenous;Food
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
440120
HMDB ID
HMDB0001325
Formula
C9H20N2O2
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=440120"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C03793
ChEBI ID
17311
FooDB ID
FDB022556
ChemSpider ID
389120
METLIN ID
6161
Physicochemical Properties Molecular Weight 188.27 Topological Polar Surface Area 66.2
XlogP -1.6 Complexity 158
Heavy Atom Count 13 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Function
N6,N6,N6-Trimethyl-L-lysine is a methylated derivative of the amino acid lysine. It is a component of histone proteins, a precursor of carnitine and a coenzyme of fatty acid oxidation. N6,N6,N6-Trimethyl-L-lysine residues are found in a number of proteins and are generated by the action of S-adenosyl-L-methionine on exposed lysine residues. When trimethyllysine is released from cognate proteins via proteolysis, it serves as a precursor for carnitine biosynthesis. Mitochondrial 6-N-trimethyllysine dioxygenase converts 6-N-trimethyllysine to 3-hydroxy-6-N-trimethyllysine as the first step for carnitine biosynthesis. Because the subsequent carnitine biosynthesis enzymes are cytosolic, 3-hydroxy-6-N-trimethyllysine must be transported out of the mitochondria by a putative mitochondrial 6-N-trimethyllysine/3-hydroxy-6-N-trimethyllysine transporter system. Plasma -N-trimethyllysine concentrations are significantly lower in systemic carnitine deficiency patients compared to normal individuals, but no significant difference in urinary -N-trimethyllysine excretion is seen between the two groups.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) 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 Mutation (-265T >C(rs5082)) of APOA2
                      Induced Change N6,N6,N6-Trimethyl-L-lysine concentration: decrease (FC = 0.81)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the decrease of N6,N6,N6-Trimethyl-L-lysine levels compared with control group.
      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 [2]
                      Introduced Variation Knockout of TP53
                      Induced Change N6,N6,N6-Trimethyl-L-lysine concentration: decrease (Log2 FC=0.83)
                      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 N6,N6,N6-Trimethyl-L-lysine levels compared with control group.
References
1 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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