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Showing NP-Card for N6,N6,N6-Trimethyl-L-lysine (NP0334685)

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Record Information
Version2.0
Created at2024-09-10 19:31:01 UTC
Updated at2024-09-10 19:31:01 UTC
NP-MRD IDNP0334685
Secondary Accession NumbersNone
Natural Product Identification
Common NameN6,N6,N6-Trimethyl-L-lysine
DescriptionN6,N6,N6-Trimethyl-L-lysine, also known as epsilon-N-trimethyl-L-lysine or delta-trimethyllysine, 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. Mitochondrial 6-N-N6,N6,N6-Trimethyl-L-lysine dioxygenase converts 6-N-N6,N6,N6-Trimethyl-L-lysine to 3-hydroxy-6-N-N6,N6,N6-Trimethyl-L-lysine as the first step for carnitine biosynthesis. It is a component of histone proteins, a precursor of carnitine and a coenzyme of fatty acid oxidation. N6,N6,N6-Trimethyl-L-lysine is a very strong basic compound (based on its pKa). N6,N6,N6-Trimethyl-L-lysine exists in all living organisms, ranging from bacteria to humans. Within humans, N6,N6,N6-trimethyl-L-lysine participates in a number of enzymatic reactions. In particular, N6,N6,N6-trimethyl-L-lysine and S-adenosylhomocysteine can be biosynthesized from L-lysine and S-adenosylmethionine; which is mediated by the enzyme histone-lysine N-methyltransferase SETD7. In addition, N6,N6,N6-trimethyl-L-lysine and oxoglutaric acid can be converted into 3-hydroxy-N6,N6,N6-trimethyl-L-lysine and succinic acid through its interaction with the enzyme trimethyllysine dioxygenase, mitochondrial. In humans, N6,N6,N6-trimethyl-L-lysine is involved in carnitine synthesis. N6,N6,N6-Trimethyl-L-lysine was first documented in 1979 (PMID: 454517). When N6,N6,N6-Trimethyl-L-lysine is released from cognate proteins via proteolysis, it serves as a precursor for carnitine biosynthesis (PMID: 3111294) (PMID: 2106342) (PMID: 3093513) (PMID: 3136187).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334685 (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 NP0334685 (N6,N6,N6-Trimethyl-L-lysine)

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3D SDF for NP0334685 (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>
NP0334685

> <DATABASE_NAME>
NP-MRD

> <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 NP0334685 (N6,N6,N6-Trimethyl-L-lysine)
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PDB for NP0334685 (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 NP0334685 (N6,N6,N6-Trimethyl-L-lysine)
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SMILES for NP0334685 (N6,N6,N6-Trimethyl-L-lysine)
C[N+](C)(C)CCCC[C@H](N)C([O-])=O
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INCHI for NP0334685 (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 JSmol
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 Mass188.2673 Da
Monoisotopic Mass188.15248 Da
IUPAC Name(2S)-2-amino-6-(trimethylazaniumyl)hexanoate
Traditional Namen-trimethyllysine
CAS Registry NumberNot 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 KeyMXNRLFUSFKVQSK-QMMMGPOBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0001325  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. 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  ] 
  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. doi: 10.1016/0026-0495(79)90205-1. [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. doi:  10.1016/0304-4165(90)90001-d. [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. doi: 10.1016/s0378-4347(00)83657-9. [PubMed:3093513  ] 
  5. 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  ]