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Showing metabocard for N6,N6,N6-Trimethyl-L-lysine (HMDB0001325)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:36 UTC
HMDB IDHMDB0001325
Secondary Accession Numbers
  • HMDB01325
Metabolite Identification
Common NameN6,N6,N6-Trimethyl-L-lysine
DescriptionN6,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
Data?1676999736
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001325 (N6,N6,N6-Trimethyl-L-lysine)


  Mrv0541 02231219032D          

 13 12  0  0  1  0            999 V2000
   -2.1032    0.1897    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.3896   -0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8205   -0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032    1.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -0.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758    0.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379   -0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516    0.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4689   -0.2241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1826    0.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4689   -1.0482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826    1.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964   -0.2241    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  1  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
M  CHG  2   1   1  13  -1
M  END
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3D MOL for HMDB0001325 (N6,N6,N6-Trimethyl-L-lysine)

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
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3D SDF for HMDB0001325 (N6,N6,N6-Trimethyl-L-lysine)


  Mrv0541 02231219032D          

 13 12  0  0  1  0            999 V2000
   -2.1032    0.1897    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.3896   -0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8205   -0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032    1.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -0.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758    0.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379   -0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516    0.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4689   -0.2241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1826    0.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4689   -1.0482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826    1.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964   -0.2241    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  1  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
M  CHG  2   1   1  13  -1
M  END
> <DATABASE_ID>
HMDB0001325

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C9H20N2O2

> <MOLECULAR_WEIGHT>
188.2673

> <EXACT_MASS>
188.152477894

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.554315786682526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-6-(trimethylazaniumyl)hexanoate

> <ALOGPS_LOGP>
-3.18

> <JCHEM_LOGP>
-6.198754912366285

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.407558396399148

> <JCHEM_PKA_STRONGEST_BASIC>
9.526420173475088

> <JCHEM_POLAR_SURFACE_AREA>
66.15

> <JCHEM_REFRACTIVITY>
74.62950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
n-trimethyllysine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001325 (N6,N6,N6-Trimethyl-L-lysine)

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
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PDB for HMDB0001325 (N6,N6,N6-Trimethyl-L-lysine)

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
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3D PDB for HMDB0001325 (N6,N6,N6-Trimethyl-L-lysine)

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
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SMILES for HMDB0001325 (N6,N6,N6-Trimethyl-L-lysine)

C[N+](C)(C)CCCC[C@H](N)C([O-])=O
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INCHI for HMDB0001325 (N6,N6,N6-Trimethyl-L-lysine)

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
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(S)-2-Amino-6-(trimethylammonio)hexanoateHMDB
(S)-2-Amino-6-(trimethylammonio)hexanoic acidHMDB
delta-TrimethyllysineHMDB
epsilon-N-Trimethyl-L-lysineHMDB
epsilon-Trimethyl-L-lysineHMDB
N(6),N(6),N(6)-Trimethyl-L-lysineHMDB
S)-5-Amino-5-carboxy-N,N,N-trimethyl-1-pentanaminiumHMDB
TrimethyllysineHMDB
6-N-L-Trimethyl-L-lysineHMDB
epsilon-N-Trimethyl-lysineHMDB
TRIMETHYLLLYSINEHMDB
Trimethyllysine hydroxide, inner salt, (S)-isomerHMDB
Trimethyllysine, (+-)-isomerHMDB
Trimethyllysine hydroxide,inner salt, (+-)-isomerHMDB
Trimethyllysine chloride, (S)-isomerHMDB
(2S)-2-Amino-6-(trimethylazaniumyl)hexanoic acidHMDB
Chemical FormulaC9H20N2O2
Average Molecular Weight188.2673
Monoisotopic Molecular Weight188.152477894
IUPAC Name(2S)-2-amino-6-(trimethylazaniumyl)hexanoate
Traditional Namen-trimethyllysine
CAS Registry Number19253-88-4
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 KeyMXNRLFUSFKVQSK-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos141.95830932474
[M+H]+Not Available141.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00000496
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP-3.2ALOGPS
logP-6.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.15 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity74.63 m³·mol⁻¹ChemAxon
Polarizability21.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+142.82132859911
AllCCS[M-H]-151.06632859911
DeepCCS[M+H]+138.19330932474
DeepCCS[M-H]-135.56830932474
DeepCCS[M-2H]-171.75530932474
DeepCCS[M+Na]+147.25530932474
AllCCS[M+H]+142.832859911
AllCCS[M+H-H2O]+139.332859911
AllCCS[M+NH4]+146.132859911
AllCCS[M+Na]+147.132859911
AllCCS[M-H]-151.132859911
AllCCS[M+Na-2H]-152.332859911
AllCCS[M+HCOO]-153.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 1.22 minutes32390414
Predicted by Siyang on May 30, 20229.2589 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20227.36 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid420.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid392.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid231.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid98.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid168.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid60.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid252.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid264.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)961.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid676.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid40.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid852.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid170.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid189.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate933.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA638.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water196.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N6,N6,N6-Trimethyl-L-lysineC[N+](C)(C)CCCC[C@H](N)C([O-])=O1936.8Standard polar33892256
N6,N6,N6-Trimethyl-L-lysineC[N+](C)(C)CCCC[C@H](N)C([O-])=O1258.5Standard non polar33892256
N6,N6,N6-Trimethyl-L-lysineC[N+](C)(C)CCCC[C@H](N)C([O-])=O1499.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N6,N6,N6-Trimethyl-L-lysine,1TMS,isomer #1C[N+](C)(C)CCCC[C@H](N[Si](C)(C)C)C(=O)[O-]1509.2Semi standard non polar33892256
N6,N6,N6-Trimethyl-L-lysine,1TMS,isomer #1C[N+](C)(C)CCCC[C@H](N[Si](C)(C)C)C(=O)[O-]1574.0Standard non polar33892256
N6,N6,N6-Trimethyl-L-lysine,1TMS,isomer #1C[N+](C)(C)CCCC[C@H](N[Si](C)(C)C)C(=O)[O-]1897.7Standard polar33892256
N6,N6,N6-Trimethyl-L-lysine,2TMS,isomer #1C[N+](C)(C)CCCC[C@@H](C(=O)[O-])N([Si](C)(C)C)[Si](C)(C)C1715.8Semi standard non polar33892256
N6,N6,N6-Trimethyl-L-lysine,2TMS,isomer #1C[N+](C)(C)CCCC[C@@H](C(=O)[O-])N([Si](C)(C)C)[Si](C)(C)C1717.9Standard non polar33892256
N6,N6,N6-Trimethyl-L-lysine,2TMS,isomer #1C[N+](C)(C)CCCC[C@@H](C(=O)[O-])N([Si](C)(C)C)[Si](C)(C)C1818.4Standard polar33892256
N6,N6,N6-Trimethyl-L-lysine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCC[N+](C)(C)C)C(=O)[O-]1721.4Semi standard non polar33892256
N6,N6,N6-Trimethyl-L-lysine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCC[N+](C)(C)C)C(=O)[O-]1791.0Standard non polar33892256
N6,N6,N6-Trimethyl-L-lysine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCC[N+](C)(C)C)C(=O)[O-]1997.7Standard polar33892256
N6,N6,N6-Trimethyl-L-lysine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([C@@H](CCCC[N+](C)(C)C)C(=O)[O-])[Si](C)(C)C(C)(C)C2144.0Semi standard non polar33892256
N6,N6,N6-Trimethyl-L-lysine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([C@@H](CCCC[N+](C)(C)C)C(=O)[O-])[Si](C)(C)C(C)(C)C2130.0Standard non polar33892256
N6,N6,N6-Trimethyl-L-lysine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([C@@H](CCCC[N+](C)(C)C)C(=O)[O-])[Si](C)(C)C(C)(C)C1956.6Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Placenta
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.5 +/- 2.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified5.3 (3.8-10.4) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022556
KNApSAcK IDNot Available
Chemspider ID389120
KEGG Compound IDC03793
BioCyc IDN6N6N6-TRIMETHYL-L-LYSINE
BiGG ID42542
Wikipedia LinkNot Available
METLIN ID6161
PubChem Compound440120
PDB IDNot Available
ChEBI ID17311
Food Biomarker OntologyNot Available
VMH IDTMLYS
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChen F M; Benoiton N L A synthesis of N6,N6,N6-trimethyl-L-lysine dioxalate in gram amounts. Biochemistry and cell biology = Biochimie et biologie cellulaire (1986), 64(3), 182-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:10491993 ]
  2. 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. [PubMed:454517 ]
  3. 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. [PubMed:2106342 ]
  4. 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. [PubMed:3093513 ]
  5. 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. [PubMed:3111294 ]
  6. 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. [PubMed:3136187 ]
  7. 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 ]

Enzymes

Enzyme Details
1. Signal peptidase complex subunit 1
General function:
Involved in peptidase activity
Specific function:
Component of the microsomal signal peptidase complex which removes signal peptides from nascent proteins as they are translocated into the lumen of the endoplasmic reticulum
Gene Name:
SPCS1
Uniprot ID:
Q9Y6A9
Molecular weight:
11804.7
Enzyme Details
2. Trimethyllysine dioxygenase, mitochondrial
General function:
Involved in oxidation reduction
Specific function:
Converts trimethyllysine (TML) into hydroxytrimethyllysine (HTML).
Gene Name:
TMLHE
Uniprot ID:
Q9NVH6
Molecular weight:
44048.895
Reactions
N6,N6,N6-Trimethyl-L-lysine + Oxoglutaric acid + Oxygen → 3-hydroxy-N(6),N(6),N(6)-trimethyl-L-lysine + Succinic acid + CO(2)details
N6,N6,N6-Trimethyl-L-lysine + Oxoglutaric acid + Oxygen → 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine + Succinic acid + Carbon dioxidedetails