Livestock Metabolome Database: Showing metabocard for N6,N6,N6-Trimethyl-L-lysine (LMDB00319)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:13 UTC

Update Date

2016-07-20 20:59:51 UTC

Lmdb

LMDB00319

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N6,N6,N6-Trimethyl-L-lysine

Description

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

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abc-9300000000-17fb5edf4cea1b4dcafd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-6900000000-f1602619e61c625d69c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-5900000000-932e6c169445b94455b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0019-5900000000-1a10f83950431edf55b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0900000000-da852a06c44090497022	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a5c-9000000000-259b17dcbcd89ac303fc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-5900000000-34a50370b70a804c255b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-0a0007f7f545c6797887	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0019-3900000000-853327bd0e39b33319f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0019-2900000000-7bc743d45af1a8804ef1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-9000000000-226e1500e9ae9494b4bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001r-5900000000-5182d0d6a3ab64a06c09	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-d5736c9d1d529490c9b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-628513f87fa53b8eb808	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-dff395556a2686da0f1d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001r-5900000000-b01e2dbf67baf33ef6e7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-053r-9000000000-9eb55f6f4d8669a538a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0536-9000000000-7dc3464380609c193782	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0900000000-0f467f0c771ad5024ac5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0900000000-6306038d328c591e1128	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01y7-2900000000-44354c8813190fe25a0e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08mi-9400000000-499e4dafbd41d754a57d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-3bc9f6f2c730e7f3785c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2900000000-9928cba63f73f9126887	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9100000000-da0cc13b89df68e4b27f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-29ace4cf19de37bcc077	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details