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Record Information
Version3.6
Creation Date2006-05-22 14:17:33 UTC
Update Date2016-02-11 01:05:14 UTC
HMDB IDHMDB02038
Secondary Accession NumbersNone
Metabolite Identification
Common NameN(6)-Methyllysine
DescriptionN(6)-Methyllysine is a naturally occurring amino acid found in human biofluids. N-monomethyl-lysine is generated by metabolic transmethylation of endogenous lysine. Lysine methylation displays the highest degree of complexity among known covalent histone modifications, with each site of methylation regulating the association of different effector molecules. The versatility of lysine methylation marks is perhaps best exemplified by modifications implicated in transcriptional regulation as well as being required for double-strand break repair in several organisms. Identification of the numerous biological functions encoded by histone lysine methylation is a major area of research interest, as these mechanisms are intimately associated with cellular senescence, genomic instability, and leukemogenesis. While multiple sites of lysine methylation have been linked with gene activation, each modification is distributed to unique positions across the active gene. (PMID: 17030614 , 1122639 , 15756599 , 3111294 ).
Structure
Thumb
Synonyms
ValueSource
(S)-2-amino-6-Methylaminohexanoic acidChEBI
epsilon-MethyllysineChEBI
Epsilon-N-MethyllysineChEBI
MeLysChEBI
N(6)-MethyllysineChEBI
N(zeta)-MethyllysineChEBI
N-Epsilon-MethyllysineChEBI
N-Methyl-L-lysineChEBI
N6-Methyl-L-lysineChEBI
N(epsilon)-Methyl-L-lysineChEBI
(S)-2-amino-6-MethylaminohexanoateGenerator
(2S)-2-amino-6-(methylamino)HexanoateGenerator
N(Z)-MethyllysineGenerator
N(ζ)-methyllysineGenerator
N(6)-Methyl-L-lysineHMDB
N-Methyl-lysineHMDB
Chemical FormulaC7H16N2O2
Average Molecular Weight160.2141
Monoisotopic Molecular Weight160.121177766
IUPAC Name(2S)-2-amino-6-(methylamino)hexanoic acid
Traditional NameN-methyl-L-lysine
CAS Registry Number1188-07-4
SMILES
CNCCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C7H16N2O2/c1-9-5-3-2-4-6(8)7(10)11/h6,9H,2-5,8H2,1H3,(H,10,11)/t6-/m0/s1
InChI KeyInChIKey=PQNASZJZHFPQLE-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility51.5 mg/mLALOGPS
logP-2.4ALOGPS
logP-2.9ChemAxon
logS-0.49ALOGPS
pKa (Strongest Acidic)2.8ChemAxon
pKa (Strongest Basic)10.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.35 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.58 m3·mol-1ChemAxon
Polarizability18.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.0 +/- 6.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified1.2 +/- 1.1 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.90 (0.22-1.58) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022812
KNApSAcK IDNot Available
Chemspider ID144469
KEGG Compound IDC02728
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02038
Metagene LinkHMDB02038
METLIN IDNot Available
PubChem Compound164795
PDB IDMLZ
ChEBI ID17604
References
Synthesis ReferenceBenoiton, Leo. Amino acids and peptides. II. Synthesis of e-N-methyl-L-lysine and related compounds. Canadian Journal of Chemistry (1964), 42(9), 2043-7.
Material Safety Data Sheet (MSDS)Not Available
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. [3111294 ]
  2. Vakoc CR, Sachdeva MM, Wang H, Blobel GA: Profile of histone lysine methylation across transcribed mammalian chromatin. Mol Cell Biol. 2006 Dec;26(24):9185-95. Epub 2006 Oct 9. [17030614 ]
  3. Lower R, Lange HW, Hempel K: Diagnostic meaning of the urinary output of Nepsilon-methylated lysines. Investigation of healthy individuals and patients with malignant diseases, myopathies or renal failure. Clin Chim Acta. 1975 Jan 20;58(2):155-64. [1122639 ]
  4. Kalasz H, Klebovich I, Balogh-Nemes K, Szilagyi A, Tihanyi M, Szarvas T, Lengyel J: Detection of N-monomethyl-lysine generated by metabolic transmethylation. Anal Bioanal Chem. 2005 Jun;382(3):760-4. Epub 2005 Mar 9. [15756599 ]