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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2023-02-21 17:16:05 UTC
HMDB IDHMDB0002038
Secondary Accession Numbers
  • HMDB02038
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
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 KeyPQNASZJZHFPQLE-LURJTMIESA-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 acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Carbonyl group
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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]-Not Available134.207http://allccs.zhulab.cn/database/detail?ID=AllCCS00000048
[M+H]+Not Available132.489http://allccs.zhulab.cn/database/detail?ID=AllCCS00000048
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB01714
Phenol Explorer Compound IDNot Available
FooDB IDFDB022812
KNApSAcK IDNot Available
Chemspider ID144469
KEGG Compound IDC02728
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound164795
PDB IDNot Available
ChEBI ID17604
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:15756599 ]