Showing metabocard for N6,N6,N6-Trimethyl-L-lysine (BMDB0001325)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:10 UTC
Update Date2020-05-21 16:28:30 UTC
BMDB IDBMDB0001325
Secondary Accession Numbers
  • BMDB01325
Metabolite Identification
Common NameN6,N6,N6-Trimethyl-L-lysine
DescriptionN6,N6,N6-Trimethyl-L-lysine, also known as epsilon-N-trimethyl-L-lysine or n6,n6,n6-trimethyl-l-lysine, 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. N6,N6,N6-Trimethyl-L-lysine is possibly soluble (in water) and 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. N6,N6,N6-Trimethyl-L-lysine participates in a number of enzymatic reactions, within cattle. In particular, N6,N6,N6-Trimethyl-L-lysine and S-adenosylhomocysteine can be biosynthesized from L-lysine and S-adenosylmethionine; which is catalyzed 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; which is mediated by the enzyme n6,n6,n6-trimethyl-l-lysine dioxygenase, mitochondrial. In cattle, N6,N6,N6-trimethyl-L-lysine is involved in the metabolic pathway called carnitine synthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
Physical Properties
StateSolid
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abc-9300000000-17fb5edf4cea1b4dcafdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-6900000000-f1602619e61c625d69c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-5900000000-932e6c169445b94455b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-5900000000-1a10f83950431edf55b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0900000000-da852a06c44090497022View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9000000000-259b17dcbcd89ac303fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-5900000000-34a50370b70a804c255bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-0a0007f7f545c6797887View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-3900000000-853327bd0e39b33319f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-2900000000-7bc743d45af1a8804ef1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-9000000000-226e1500e9ae9494b4bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001r-5900000000-5182d0d6a3ab64a06c09View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-d5736c9d1d529490c9b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-628513f87fa53b8eb808View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-dff395556a2686da0f1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001r-5900000000-b01e2dbf67baf33ef6e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-9eb55f6f4d8669a538a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0536-9000000000-7dc3464380609c193782View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0900000000-0f467f0c771ad5024ac5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0900000000-6306038d328c591e1128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01y7-2900000000-44354c8813190fe25a0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mi-9400000000-499e4dafbd41d754a57dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3bc9f6f2c730e7f3785cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-9928cba63f73f9126887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9100000000-da0cc13b89df68e4b27fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-29ace4cf19de37bcc077View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
Biospecimen Locations
  • Placenta
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001325
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
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Trimethyllysine dioxygenase, mitochondrial
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Converts trimethyllysine (TML) into hydroxytrimethyllysine (HTML).
Gene Name:
TMLHE
Uniprot ID:
Q0VC74
Molecular weight:
49837.0
Reactions
N6,N6,N6-Trimethyl-L-lysine + Oxoglutaric acid + Oxygen → 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine + Succinic acid + Carbon dioxidedetails
Enzyme Details
2. Histone-lysine N-methyltransferase SETD7
General function:
Not Available
Specific function:
Histone methyltransferase that specifically monomethylates 'Lys-4' of histone H3. H3 'Lys-4' methylation represents a specific tag for epigenetic transcriptional activation. Plays a central role in the transcriptional activation of genes.
Gene Name:
SETD7
Uniprot ID:
F1MUT0
Molecular weight:
40648.0
Reactions
S-Adenosylmethionine + L-Lysine → S-Adenosylhomocysteine + N6,N6,N6-Trimethyl-L-lysinedetails