ChemFOnt: Showing chemical card for N(6)-Methyllysine (CFc000001366)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:59 UTC

Chemfont ID

CFc000001366

Molecule Identification

Common Name

N(6)-Methyllysine

Definition

N(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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2-Amino-6-methylaminohexanoic acid	ChEBI
epsilon-Methyllysine	ChEBI
Epsilon-N-Methyllysine	ChEBI
MeLys	ChEBI
N(zeta)-Methyllysine	ChEBI
N-Epsilon-Methyllysine	ChEBI
N-Methyl-L-lysine	ChEBI
N6-Methyl-L-lysine	ChEBI
N(epsilon)-Methyl-L-lysine	ChEBI
(S)-2-Amino-6-methylaminohexanoate	Generator
N(Z)-Methyllysine	Generator
N(Ζ)-methyllysine	Generator
(2S)-2-amino-6-(methylamino)Hexanoate	HMDB
(2S)-2-amino-6-(methylamino)Hexanoic acid	HMDB
N(6)-Methyl-L-lysine	HMDB
N-Methyl-lysine	HMDB
epsilon-N-Methyllysine hydrochloride, (L-lys)-isomer	MeSH, HMDB
epsilon-N-Methyllysine, (DL-lys)-isomer	MeSH, HMDB
N(epsilon)-Monomethyl-lysine	MeSH, HMDB
N(6)-Methyllysine	ChEBI

Chemical Formula

C₇H₁₆N₂O₂

Average Molecular Weight

160.2141

Monoisotopic Molecular Weight

160.121177766

IUPAC Name

(2S)-2-amino-6-(methylamino)hexanoic acid

Traditional Name

N-methyl-L-lysine

CAS Registry Number

1188-07-4

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 Key

PQNASZJZHFPQLE-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-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 Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:17604 )
L-lysine derivative (CHEBI:17604 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002038)
Cerebrospinal Fluid (CSF) (PMID: 8491808)
Cerebrospinal fluid (HMDB: HMDB0002038)

Excreta

Biofluid or Excreta

Urine (PMID: 5472370)

Source

Exogenous

Exogenous (HMDB: HMDB0002038)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002038)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002038)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	51.5 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.9	ChemAxon
logS	-0.49	ALOGPS
pKa (Strongest Acidic)	2.8	ChemAxon
pKa (Strongest Basic)	10.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	42.58 m³·mol⁻¹	ChemAxon
Polarizability	18.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002038

DrugBank ID

DB01714

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022812

KNApSAcK ID

Not Available

Chemspider ID

144469

KEGG Compound ID

C02728

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164795

PDB ID

Not Available

ChEBI ID

17604

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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.

Showing chemical card for N(6)-Methyllysine (CFc000001366)

MOL for CFc000001366 (N(6)-Methyllysine)

3D MOL for CFc000001366 (N(6)-Methyllysine)

3D SDF for CFc000001366 (N(6)-Methyllysine)

3D-SDF for CFc000001366 (N(6)-Methyllysine)

PDB for CFc000001366 (N(6)-Methyllysine)

3D PDB for CFc000001366 (N(6)-Methyllysine)

SMILES for CFc000001366 (N(6)-Methyllysine)

INCHI for CFc000001366 (N(6)-Methyllysine)

Structure for CFc000001366 (N(6)-Methyllysine)

3D Structure for CFc000001366 (N(6)-Methyllysine)