MiMeDB: Showing metabocard for N6,N6,N6-Trimethyl-L-lysine (MMDBc0000387)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:39 UTC

Update Date

2024-04-30 19:32:04 UTC

Metabolite ID

MMDBc0000387

Metabolite Identification

Common Name

N6,N6,N6-Trimethyl-L-lysine

Description

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0001325
     RDKit          3D
N6,N6,N6-Trimethyl-L-lysine
 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.5233    0.4175   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3226    0.0839    0.2509 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5991    0.5537    1.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -1.3436    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2257    0.7577   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898   -0.0352   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1026    0.8287   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999    0.3914   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2524    0.1236    0.2811 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6500   -0.1920   -0.0791 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149   -1.1145    0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -1.2390    2.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352   -2.0826    0.4601 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.2833   -0.3695   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    1.4008   -0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2253    0.6023   -1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    1.6629    1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149    0.1789    1.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9020    0.1217    2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904   -1.8417   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518   -1.6092    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730   -1.7432    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241    1.7400    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3890    0.8670   -1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3154   -0.1716    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0028   -0.9792   -0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476    0.9735   -1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0240    1.9061   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110   -0.5363   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1281    1.1685   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    0.9914    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331   -0.7677   -0.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1057   -0.7443    0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
M  CHG  2   2   1  13  -1
M  END

HMDB0001325
     RDKit          3D
N6,N6,N6-Trimethyl-L-lysine
 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.5233    0.4175   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3226    0.0839    0.2509 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5991    0.5537    1.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -1.3436    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2257    0.7577   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898   -0.0352   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1026    0.8287   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999    0.3914   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2524    0.1236    0.2811 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6500   -0.1920   -0.0791 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149   -1.1145    0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -1.2390    2.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352   -2.0826    0.4601 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.2833   -0.3695   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    1.4008   -0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2253    0.6023   -1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    1.6629    1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149    0.1789    1.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9020    0.1217    2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904   -1.8417   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518   -1.6092    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730   -1.7432    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241    1.7400    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3890    0.8670   -1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3154   -0.1716    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0028   -0.9792   -0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476    0.9735   -1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0240    1.9061   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110   -0.5363   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1281    1.1685   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    0.9914    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331   -0.7677   -0.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1057   -0.7443    0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
M  CHG  2   2   1  13  -1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      -3.926   0.354   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      -2.594  -0.418   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.265  -0.418   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.926   1.892   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.527  -1.139   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.261   0.354   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.071  -0.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.403   0.354   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.742  -0.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.074   0.354   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.742  -1.957   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       4.074   1.892   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.407  -0.418   0.000  0.00  0.00           O-1
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   12   13                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0001325
HETATM    1  C1  UNL     1      -3.523   0.418  -0.517  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.323   0.084   0.251  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -2.599   0.554   1.617  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.195  -1.344   0.327  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.226   0.758  -0.343  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.090  -0.035  -0.227  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.103   0.829  -0.899  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.500   0.391  -0.997  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.252   0.124   0.281  1.00  0.00           C  
HETATM   10  N2  UNL     1       4.650  -0.192  -0.079  1.00  0.00           N  
HETATM   11  C9  UNL     1       2.815  -1.115   0.991  1.00  0.00           C  
HETATM   12  O1  UNL     1       3.233  -1.239   2.188  1.00  0.00           O  
HETATM   13  O2  UNL     1       2.035  -2.083   0.460  1.00  0.00           O1-
HETATM   14  H1  UNL     1      -4.283  -0.370  -0.419  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.897   1.401  -0.153  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.225   0.602  -1.587  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.656   1.663   1.643  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.615   0.179   1.867  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.902   0.122   2.339  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.990  -1.842  -0.622  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.452  -1.609   1.097  1.00  0.00           H  
HETATM   22  H9  UNL     1      -3.173  -1.743   0.695  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.024   1.740   0.080  1.00  0.00           H  
HETATM   24  H11 UNL     1      -1.389   0.867  -1.438  1.00  0.00           H  
HETATM   25  H12 UNL     1       0.315  -0.172   0.848  1.00  0.00           H  
HETATM   26  H13 UNL     1       0.003  -0.979  -0.792  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.748   0.974  -1.982  1.00  0.00           H  
HETATM   28  H15 UNL     1       1.024   1.906  -0.522  1.00  0.00           H  
HETATM   29  H16 UNL     1       2.611  -0.536  -1.630  1.00  0.00           H  
HETATM   30  H17 UNL     1       3.128   1.168  -1.541  1.00  0.00           H  
HETATM   31  H18 UNL     1       3.227   0.991   0.927  1.00  0.00           H  
HETATM   32  H19 UNL     1       4.633  -0.768  -0.949  1.00  0.00           H  
HETATM   33  H20 UNL     1       5.106  -0.744   0.679  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4    5
CONECT    3   17   18   19
CONECT    4   20   21   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   10   11   31
CONECT   10   32   33
CONECT   11   12   12   13
END

HMDB0001325
     RDKit          3D
N6,N6,N6-Trimethyl-L-lysine
 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.5233    0.4175   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3226    0.0839    0.2509 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5991    0.5537    1.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -1.3436    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2257    0.7577   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898   -0.0352   -0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1026    0.8287   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999    0.3914   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2524    0.1236    0.2811 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6500   -0.1920   -0.0791 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149   -1.1145    0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -1.2390    2.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352   -2.0826    0.4601 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.2833   -0.3695   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    1.4008   -0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2253    0.6023   -1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    1.6629    1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149    0.1789    1.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9020    0.1217    2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904   -1.8417   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518   -1.6092    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730   -1.7432    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241    1.7400    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3890    0.8670   -1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3154   -0.1716    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0028   -0.9792   -0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476    0.9735   -1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0240    1.9061   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110   -0.5363   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1281    1.1685   -1.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    0.9914    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331   -0.7677   -0.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1057   -0.7443    0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
M  CHG  2   2   1  13  -1
M  END

Synonyms

Value	Source
(S)-2-Amino-6-(trimethylammonio)hexanoate	HMDB
(S)-2-Amino-6-(trimethylammonio)hexanoic acid	HMDB
delta-Trimethyllysine	HMDB
epsilon-N-Trimethyl-L-lysine	HMDB
epsilon-Trimethyl-L-lysine	HMDB
N(6),N(6),N(6)-Trimethyl-L-lysine	HMDB
S)-5-Amino-5-carboxy-N,N,N-trimethyl-1-pentanaminium	HMDB
Trimethyllysine	HMDB
6-N-L-Trimethyl-L-lysine	HMDB
epsilon-N-Trimethyl-lysine	HMDB
TRIMETHYLLLYSINE	HMDB
Trimethyllysine hydroxide, inner salt, (S)-isomer	HMDB
Trimethyllysine, (+-)-isomer	HMDB
Trimethyllysine hydroxide,inner salt, (+-)-isomer	HMDB
Trimethyllysine chloride, (S)-isomer	HMDB
(2S)-2-Amino-6-(trimethylazaniumyl)hexanoic acid	HMDB

Molecular Formula

C₉H₂₀N₂O₂

Average Mass

188.2673

Monoisotopic Mass

188.152477894

IUPAC Name

(2S)-2-amino-6-(trimethylazaniumyl)hexanoate

Traditional Name

n-trimethyllysine

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)CCCC[C@H](N)C([O-])=O

InChI Identifier

InChI=1S/C9H20N2O2/c1-11(2,3)7-5-4-6-8(10)9(12)13/h8H,4-7,10H2,1-3H3/t8-/m0/s1

InChI Key

MXNRLFUSFKVQSK-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Fatty acyl
Fatty acid
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid salt
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Organic zwitterion
Organic salt
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-6.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.41	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	74.63 m³·mol⁻¹	ChemAxon
Polarizability	21.55 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abc-9300000000-17fb5edf4cea1b4dcafd	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-6900000000-f1602619e61c625d69c6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-5900000000-932e6c169445b94455b5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0019-5900000000-1a10f83950431edf55b5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0900000000-da852a06c44090497022	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a5c-9000000000-259b17dcbcd89ac303fc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-5900000000-34a50370b70a804c255b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-0a0007f7f545c6797887	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0019-3900000000-853327bd0e39b33319f1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0019-2900000000-7bc743d45af1a8804ef1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-9000000000-226e1500e9ae9494b4bc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001r-5900000000-5182d0d6a3ab64a06c09	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-d5736c9d1d529490c9b1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-628513f87fa53b8eb808	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-dff395556a2686da0f1d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001r-5900000000-b01e2dbf67baf33ef6e7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-053r-9000000000-9eb55f6f4d8669a538a1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0536-9000000000-7dc3464380609c193782	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0900000000-0f467f0c771ad5024ac5	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0900000000-6306038d328c591e1128	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01y7-2900000000-44354c8813190fe25a0e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08mi-9400000000-499e4dafbd41d754a57d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-3bc9f6f2c730e7f3785c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2900000000-9928cba63f73f9126887	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9100000000-da0cc13b89df68e4b27f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-29ace4cf19de37bcc077	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Testis
Urine

Tissue Locations

Placenta
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193752	Signal peptidase complex subunit 1	Enzyme	Q9Y6A9	Homo sapiens
MMDBp0193925	Trimethyllysine dioxygenase, mitochondrial	Unknown	Q9NVH6	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0002259	Oxoglutaric acid	3-Hydroxy-N6,N6,N6-trimethyl-L-lysine	Trimethyllysine hydroxylase, epsilon	VMH	11431483 11802770 627563
MMDBr0002260	N6,N6,N6-Trimethyl-L-lysine	N6,N6,N6-Trimethyl-L-lysine	Not Available	VMH	30371894
MMDBr0006076	N6,N6,N6-Trimethyl-L-lysine	N6,N6,N6-Trimethyl-L-lysine	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	14	Human stool; Human feces; Human mucosa; Human ; Human sputum; Human subgingival plaque; Human saliva; Human urine; Human vaginal fluid; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	2	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	5.3		3.8	10.4	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	5472370
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.5	2.0			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001325

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022556

KNApSAcK ID

Not Available

Chemspider ID

389120

KEGG Compound ID

C03793

BioCyc ID

N6N6N6-TRIMETHYL-L-LYSINE

BiGG ID

42542

Wikipedia Link

Not Available

METLIN ID

6161

PubChem Compound

440120

PDB ID

Not Available

ChEBI ID

17311

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Inoue R, Miyake M, Kanazawa A, Sato M, Kakimoto Y: Decrease of 3-methylhistidine and increase of NG,NG-dimethylarginine in the urine of patients with muscular dystrophy. Metabolism. 1979 Aug;28(8):801-4. doi: 10.1016/0026-0495(79)90205-1. [PubMed:454517 ]
Mizobuchi M, Miyake M, Sano A, Kakimoto Y: High concentration of free trimethyllysine in red blood cells. Biochim Biophys Acta. 1990 Feb 26;1033(2):119-23. doi: 10.1016/0304-4165(90)90001-d. [PubMed:2106342 ]
Minkler PE, Erdos EA, Ingalls ST, Griffin RL, Hoppel CL: Improved high-performance liquid chromatographic method for the determination of 6-N,N,N-trimethyllysine in plasma and urine: biomedical application of chromatographic figures of merit and amine mobile phase modifiers. J Chromatogr. 1986 Aug 2;380(2):285-99. doi: 10.1016/s0378-4347(00)83657-9. [PubMed:3093513 ]
Lehman LJ, Olson AL, Rebouche CJ: Measurement of epsilon-N-trimethyllysine in human blood plasma and urine. Anal Biochem. 1987 Apr;162(1):137-42. doi: 10.1016/0003-2697(87)90018-2. [PubMed:3111294 ]
Park KS, Lee HW, Hong SY, Shin S, Kim S, Paik WK: Determination of methylated amino acids in human serum by high-performance liquid chromatography. J Chromatogr. 1988 May 25;440:225-30. doi: 10.1016/s0021-9673(00)94526-6. [PubMed:3136187 ]
Terada N, Inoue F, Okochi M, Nakajima H, Kizaki Z, Kinugasa A, Sawada T: Measurement of carnitine precursors, epsilon-trimethyllysine and gamma-butyrobetaine in human serum by tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Aug 6;731(1):89-95. doi: 10.1016/s0378-4347(99)00112-7. [PubMed:10491993 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for N6,N6,N6-Trimethyl-L-lysine (MMDBc0000387)

MOL for #<Metabolite:0x000055e070cbd8c8>

3D MOL for #<Metabolite:0x000055e070cbd8c8>

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Structure for #<Metabolite:0x000055e070cbd8c8>

3D Structure for #<Metabolite:0x000055e070cbd8c8>