ChemFOnt: Showing chemical card for N6,N6,N6-Trimethyl-L-lysine (CFc000001022)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:34 UTC

Chemfont ID

CFc000001022

Molecule Identification

Common Name

N6,N6,N6-Trimethyl-L-lysine

Definition

N6,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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2-Amino-6-(trimethylammonio)hexanoate	HMDB
(S)-2-Amino-6-(trimethylammonio)hexanoic acid	HMDB
delta-Trimethyllysine	HMDB
epsilon-N-Trimethyl-L-lysine	HMDB
epsilon-Trimethyl-L-lysine	HMDB
N(6),N(6),N(6)-Trimethyl-L-lysine	HMDB
S)-5-Amino-5-carboxy-N,N,N-trimethyl-1-pentanaminium	HMDB
Trimethyllysine	HMDB
6-N-L-Trimethyl-L-lysine	HMDB
epsilon-N-Trimethyl-lysine	HMDB
TRIMETHYLLLYSINE	HMDB
Trimethyllysine hydroxide, inner salt, (S)-isomer	HMDB
Trimethyllysine, (+-)-isomer	HMDB
Trimethyllysine hydroxide,inner salt, (+-)-isomer	HMDB
Trimethyllysine chloride, (S)-isomer	HMDB
(2S)-2-Amino-6-(trimethylazaniumyl)hexanoic acid	HMDB

Chemical Formula

C₉H₂₀N₂O₂

Average Molecular Weight

188.2673

Monoisotopic Molecular Weight

188.152477894

IUPAC Name

(2S)-2-amino-6-(trimethylazaniumyl)hexanoate

Traditional Name

n-trimethyllysine

CAS Registry Number

19253-88-4

SMILES

C[N+](C)(C)CCCC[C@H](N)C([O-])=O

InChI Identifier

InChI=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 Key

MXNRLFUSFKVQSK-QMMMGPOBSA-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 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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0001325)
Cerebrospinal fluid (HMDB: HMDB0001325)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 5472370)
Feces (PMID: 27015276)

Cellular substructure

Cytoplasm (HMDB: HMDB0001325)

Organelle

Endoplasmic reticulum (HMDB: HMDB0001325)

Source

Exogenous

Exogenous (HMDB: HMDB0001325)

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: HMDB0001325)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Carnitine Synthesis (HMDB: HMDB0001325)
Carnitine Synthesis (PathBank: SMP0087187)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-6.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.41	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	74.63 m³·mol⁻¹	ChemAxon
Polarizability	21.55 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

HMDB0001325

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022556

KNApSAcK ID

Not Available

Chemspider ID

389120

KEGG Compound ID

C03793

BioCyc ID

N6N6N6-TRIMETHYL-L-LYSINE

BiGG ID

42542

Wikipedia Link

Not Available

METLIN ID

6161

PubChem Compound

440120

PDB ID

Not Available

ChEBI ID

17311

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Chen F M; Benoiton N L A synthesis of N6,N6,N6-trimethyl-L-lysine dioxalate in gram amounts. Biochemistry and cell biology = Biochimie et biologie cellulaire (1986), 64(3), 182-3.

Showing chemical card for N6,N6,N6-Trimethyl-L-lysine (CFc000001022)

MOL for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)

3D MOL for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)

3D SDF for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)

3D-SDF for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)

PDB for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)

3D PDB for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)

SMILES for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)

INCHI for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)

Structure for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)

3D Structure for CFc000001022 (N6,N6,N6-Trimethyl-L-lysine)