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Showing Compound N6,N6,N6-Trimethyl-L-lysine (FDB022556)

Record Information
Version1.0
Creation date2011-09-21 00:15:49 UTC
Update date2015-07-21 06:57:15 UTC
Primary IDFDB022556
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number19253-88-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted 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
Chemical FormulaC9H20N2O2
IUPAC name(2S)-2-amino-6-(trimethylazaniumyl)hexanoate
InChI IdentifierInChI=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
Isomeric SMILESC[N+](C)(C)CCCC[C@H](N)C([O-])=O
Average Molecular Weight188.2673
Monoisotopic Molecular Weight188.152477894
Classification
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
Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN6,N6,N6-Trimethyl-L-lysine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0abc-9300000000-17fb5edf4cea1b4dcafdSpectrum
Predicted GC-MSN6,N6,N6-Trimethyl-L-lysine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-6900000000-f1602619e61c625d69c62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-5900000000-932e6c169445b94455b52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-5900000000-1a10f83950431edf55b52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0900000000-da852a06c440904970222021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9000000000-259b17dcbcd89ac303fc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-5900000000-34a50370b70a804c255b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-0a0007f7f545c67978872021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-3900000000-853327bd0e39b33319f12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-2900000000-7bc743d45af1a8804ef12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-9000000000-226e1500e9ae9494b4bc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001r-5900000000-5182d0d6a3ab64a06c092021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-d5736c9d1d529490c9b12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-628513f87fa53b8eb8082021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-dff395556a2686da0f1d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001r-5900000000-b01e2dbf67baf33ef6e72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-9eb55f6f4d8669a538a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0536-9000000000-7dc3464380609c1937822021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0900000000-0f467f0c771ad5024ac52021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0900000000-6306038d328c591e11282017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01y7-2900000000-44354c8813190fe25a0e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mi-9400000000-499e4dafbd41d754a57d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3bc9f6f2c730e7f3785c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-9928cba63f73f91268872017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9100000000-da0cc13b89df68e4b27f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-29ace4cf19de37bcc0772021-09-22View Spectrum
NMRNot Available
ChemSpider ID389120
ChEMBL IDNot Available
KEGG Compound IDC03793
Pubchem Compound ID440120
Pubchem Substance IDNot Available
ChEBI ID17311
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01325
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID42542
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference