N(6)-Methyllysine (CHEM021851)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:59 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021851
Identification
Common NameN(6)-Methyllysine
ClassSmall Molecule
DescriptionAn L-lysine derivative that is L-lysine in which one of the hydrogens attached to N(6) is substituted by a methyl group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-2-Amino-6-methylaminohexanoic acidChEBI
epsilon-MethyllysineChEBI
Epsilon-N-MethyllysineChEBI
MeLysChEBI
N(zeta)-MethyllysineChEBI
N-Epsilon-MethyllysineChEBI
N-Methyl-L-lysineChEBI
N6-Methyl-L-lysineChEBI
N(epsilon)-Methyl-L-lysineChEBI
(S)-2-Amino-6-methylaminohexanoateGenerator
N(Z)-MethyllysineGenerator
N(Ζ)-methyllysineGenerator
(2S)-2-amino-6-(methylamino)HexanoateHMDB
(2S)-2-amino-6-(methylamino)Hexanoic acidHMDB
N(6)-Methyl-L-lysineHMDB
N-Methyl-lysineHMDB
epsilon-N-Methyllysine hydrochloride, (L-lys)-isomerMeSH, HMDB
epsilon-N-Methyllysine, (DL-lys)-isomerMeSH, HMDB
N(epsilon)-Monomethyl-lysineMeSH, HMDB
N(6)-MethyllysineChEBI
Chemical FormulaC7H16N2O2
Average Molecular Mass160.214 g/mol
Monoisotopic Mass160.121 g/mol
CAS Registry Number1188-07-4
IUPAC Name(2S)-2-amino-6-(methylamino)hexanoic acid
Traditional NameN-methyl-L-lysine
SMILESCNCCCC[C@H](N)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility51.5 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.58 m³·mol⁻¹ChemAxon
Polarizability18.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9200000000-ffd641fb87aeadd70b06Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9400000000-4cf1396c874f63f9def4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-9000000000-720709019d470b5b26a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9000000000-2c5717b9db79491c54e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-829bc985a42f10a8b03fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9600000000-4da6280bf8bb3a92eee4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9600000000-da13e67645fe6a97f162Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-9000000000-bc7c06f67943fd6a6d53Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-9100000000-69c3801dd92e711a2454Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-03di-0900000000-08b6e77529dea2292e23Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-9000000000-633b5054da131f317103Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-03di-1900000000-156784647dbf4c823eb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02u0-2900000000-962be595f0e859b8d985Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-9700000000-2144bace5bb9c5b6025aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gl-9000000000-06030ce76181ed4a1d0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-589d432fd4c47a5744e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3900000000-d7f6c3fd68783dbd7ddfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9100000000-19d8207948713cbc50eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015a-9800000000-ca61b8d321495f277583Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-28e6fa8744c27ae8b631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-c41527c31d1720fd59a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-36337815605e095a6505Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-e9f680371b982c2c0bcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-2377be5dcacaac56991fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01714
HMDB IDHMDB0002038
FooDB IDFDB022812
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID144469
ChEBI ID17604
PubChem Compound ID164795
Kegg Compound IDC02728
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14032673
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1730244
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17636967
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19772323
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20711534
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=413481
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=426794
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=518920
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=5222990
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=5332039
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=5347964
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=5356590
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=5368259
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=5846984
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=6770375
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=6790681
17. Benoiton, 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.
18. 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.
19. 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.
20. 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.
21. 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.