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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:33 UTC

Update Date

2023-02-21 17:16:05 UTC

HMDB ID

HMDB0002038

Secondary Accession Numbers

HMDB02038

Metabolite Identification

Common Name

N(6)-Methyllysine

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0002038
HETATM    1  C1  UNL     1       4.044  -0.724   0.555  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.581   0.294  -0.344  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.217   0.109  -0.771  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.212   0.299   0.322  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.160   0.075  -0.285  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.264   0.247   0.730  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.575  -0.003  -0.030  1.00  0.00           C  
HETATM    8  N2  UNL     1      -2.651   0.984  -1.105  1.00  0.00           N  
HETATM    9  C7  UNL     1      -3.733   0.150   0.888  1.00  0.00           C  
HETATM   10  O1  UNL     1      -4.560   1.063   0.654  1.00  0.00           O  
HETATM   11  O2  UNL     1      -3.847  -0.731   1.969  1.00  0.00           O  
HETATM   12  H1  UNL     1       5.084  -1.027   0.268  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.416  -1.641   0.529  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.096  -0.275   1.578  1.00  0.00           H  
HETATM   15  H4  UNL     1       4.177   0.275  -1.210  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.003   0.857  -1.574  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.046  -0.888  -1.223  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.288   1.357   0.661  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.394  -0.355   1.184  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.263  -0.966  -0.673  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.341   0.742  -1.143  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.168  -0.469   1.566  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.269   1.275   1.139  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.503  -1.014  -0.480  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.356   0.593  -2.026  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.599   1.423  -1.129  1.00  0.00           H  
HETATM   27  H16 UNL     1      -4.269  -1.649   1.792  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8    9   24
CONECT    8   25   26
CONECT    9   10   10   11
CONECT   11   27
END

View in JSmol View Stereo Labels

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 )

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

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	134.207	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000048
[M+H]+	Not Available	132.489	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000048

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.576	31661259
DarkChem	[M-H]-	135.299	31661259
DeepCCS	[M+H]+	133.91	30932474
DeepCCS	[M-H]-	130.177	30932474
DeepCCS	[M-2H]-	167.651	30932474
DeepCCS	[M+Na]+	142.961	30932474
AllCCS	[M+H]+	137.8	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	141.4	32859911
AllCCS	[M+Na]+	142.5	32859911
AllCCS	[M-H]-	135.8	32859911
AllCCS	[M+Na-2H]-	137.7	32859911
AllCCS	[M+HCOO]-	139.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.11 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0216 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.71 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	435.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	389.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	257.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	52.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	286.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	236.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	958.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	567.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	39.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	582.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	174.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	1054.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	676.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	373.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N(6)-Methyllysine	CNCCCC[C@H](N)C(O)=O	2265.5	Standard polar	33892256
N(6)-Methyllysine	CNCCCC[C@H](N)C(O)=O	1512.1	Standard non polar	33892256
N(6)-Methyllysine	CNCCCC[C@H](N)C(O)=O	1546.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N(6)-Methyllysine,1TMS,isomer #1	CNCCCC[C@H](N)C(=O)O[Si](C)(C)C	1472.8	Semi standard non polar	33892256
N(6)-Methyllysine,1TMS,isomer #2	CNCCCC[C@H](N[Si](C)(C)C)C(=O)O	1600.8	Semi standard non polar	33892256
N(6)-Methyllysine,1TMS,isomer #3	CN(CCCC[C@H](N)C(=O)O)[Si](C)(C)C	1688.8	Semi standard non polar	33892256
N(6)-Methyllysine,2TMS,isomer #1	CNCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1594.5	Semi standard non polar	33892256
N(6)-Methyllysine,2TMS,isomer #1	CNCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1701.7	Standard non polar	33892256
N(6)-Methyllysine,2TMS,isomer #1	CNCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1903.6	Standard polar	33892256
N(6)-Methyllysine,2TMS,isomer #2	CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1673.7	Semi standard non polar	33892256
N(6)-Methyllysine,2TMS,isomer #2	CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1716.2	Standard non polar	33892256
N(6)-Methyllysine,2TMS,isomer #2	CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2296.3	Standard polar	33892256
N(6)-Methyllysine,2TMS,isomer #3	CN(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1772.7	Semi standard non polar	33892256
N(6)-Methyllysine,2TMS,isomer #3	CN(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1712.4	Standard non polar	33892256
N(6)-Methyllysine,2TMS,isomer #3	CN(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2166.1	Standard polar	33892256
N(6)-Methyllysine,2TMS,isomer #4	CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1734.7	Semi standard non polar	33892256
N(6)-Methyllysine,2TMS,isomer #4	CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1722.2	Standard non polar	33892256
N(6)-Methyllysine,2TMS,isomer #4	CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2081.1	Standard polar	33892256
N(6)-Methyllysine,3TMS,isomer #1	CN(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1782.5	Semi standard non polar	33892256
N(6)-Methyllysine,3TMS,isomer #1	CN(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1801.0	Standard non polar	33892256
N(6)-Methyllysine,3TMS,isomer #1	CN(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1871.6	Standard polar	33892256
N(6)-Methyllysine,3TMS,isomer #2	CNCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1769.0	Semi standard non polar	33892256
N(6)-Methyllysine,3TMS,isomer #2	CNCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1811.8	Standard non polar	33892256
N(6)-Methyllysine,3TMS,isomer #2	CNCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1808.2	Standard polar	33892256
N(6)-Methyllysine,3TMS,isomer #3	CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1933.9	Semi standard non polar	33892256
N(6)-Methyllysine,3TMS,isomer #3	CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1840.4	Standard non polar	33892256
N(6)-Methyllysine,3TMS,isomer #3	CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2010.2	Standard polar	33892256
N(6)-Methyllysine,4TMS,isomer #1	CN(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1989.8	Semi standard non polar	33892256
N(6)-Methyllysine,4TMS,isomer #1	CN(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1920.3	Standard non polar	33892256
N(6)-Methyllysine,4TMS,isomer #1	CN(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1817.6	Standard polar	33892256
N(6)-Methyllysine,1TBDMS,isomer #1	CNCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1717.9	Semi standard non polar	33892256
N(6)-Methyllysine,1TBDMS,isomer #2	CNCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1832.3	Semi standard non polar	33892256
N(6)-Methyllysine,1TBDMS,isomer #3	CN(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	1914.2	Semi standard non polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #1	CNCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2047.9	Semi standard non polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #1	CNCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2101.6	Standard non polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #1	CNCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2102.2	Standard polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #2	CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2129.8	Semi standard non polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #2	CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2144.7	Standard non polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #2	CN(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2394.4	Standard polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #3	CN(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2246.3	Semi standard non polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #3	CN(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2152.2	Standard non polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #3	CN(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2300.7	Standard polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #4	CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2188.1	Semi standard non polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #4	CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2134.1	Standard non polar	33892256
N(6)-Methyllysine,2TBDMS,isomer #4	CNCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2201.8	Standard polar	33892256
N(6)-Methyllysine,3TBDMS,isomer #1	CN(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2456.5	Semi standard non polar	33892256
N(6)-Methyllysine,3TBDMS,isomer #1	CN(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2405.8	Standard non polar	33892256
N(6)-Methyllysine,3TBDMS,isomer #1	CN(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2237.1	Standard polar	33892256
N(6)-Methyllysine,3TBDMS,isomer #2	CNCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2450.9	Semi standard non polar	33892256
N(6)-Methyllysine,3TBDMS,isomer #2	CNCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2390.6	Standard non polar	33892256
N(6)-Methyllysine,3TBDMS,isomer #2	CNCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2160.1	Standard polar	33892256
N(6)-Methyllysine,3TBDMS,isomer #3	CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2578.0	Semi standard non polar	33892256
N(6)-Methyllysine,3TBDMS,isomer #3	CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2446.9	Standard non polar	33892256
N(6)-Methyllysine,3TBDMS,isomer #3	CN(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2306.3	Standard polar	33892256
N(6)-Methyllysine,4TBDMS,isomer #1	CN(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2841.3	Semi standard non polar	33892256
N(6)-Methyllysine,4TBDMS,isomer #1	CN(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2669.5	Standard non polar	33892256
N(6)-Methyllysine,4TBDMS,isomer #1	CN(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2277.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-Methyllysine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9200000000-ffd641fb87aeadd70b06	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-Methyllysine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9400000000-4cf1396c874f63f9def4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-Methyllysine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 30V, Positive-QTOF	splash10-001i-9000000000-720709019d470b5b26a9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 40V, Positive-QTOF	splash10-0a59-9000000000-2c5717b9db79491c54e7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 20V, Positive-QTOF	splash10-001i-9000000000-829bc985a42f10a8b03f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 10V, Positive-QTOF	splash10-001i-9600000000-4da6280bf8bb3a92eee4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 10V, Positive-QTOF	splash10-001i-9600000000-da13e67645fe6a97f162	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 30V, Positive-QTOF	splash10-001i-9000000000-bc7c06f67943fd6a6d53	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 10V, Positive-QTOF	splash10-014i-9100000000-69c3801dd92e711a2454	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 0V, Positive-QTOF	splash10-03di-0900000000-08b6e77529dea2292e23	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 30V, Positive-QTOF	splash10-0a4i-9000000000-633b5054da131f317103	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N(6)-Methyllysine 0V, Positive-QTOF	splash10-03di-1900000000-156784647dbf4c823eb9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 10V, Positive-QTOF	splash10-02u0-2900000000-962be595f0e859b8d985	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 20V, Positive-QTOF	splash10-0159-9700000000-2144bace5bb9c5b6025a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 40V, Positive-QTOF	splash10-05gl-9000000000-06030ce76181ed4a1d0c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 10V, Negative-QTOF	splash10-0a4i-1900000000-589d432fd4c47a5744e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 20V, Negative-QTOF	splash10-0a4i-3900000000-d7f6c3fd68783dbd7ddf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 40V, Negative-QTOF	splash10-00e9-9100000000-19d8207948713cbc50ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 10V, Positive-QTOF	splash10-015a-9800000000-ca61b8d321495f277583	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 20V, Positive-QTOF	splash10-001i-9100000000-28e6fa8744c27ae8b631	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 40V, Positive-QTOF	splash10-05fu-9000000000-c41527c31d1720fd59a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 10V, Negative-QTOF	splash10-0a4i-0900000000-36337815605e095a6505	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 20V, Negative-QTOF	splash10-0a4i-0900000000-e9f680371b982c2c0bcf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N(6)-Methyllysine 40V, Negative-QTOF	splash10-0006-9000000000-2377be5dcacaac56991f	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	7.0 +/- 6.0 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.2 +/- 1.1 uM	Adult (>18 years old)	Both	Normal	8491808	details
Urine	Detected and Quantified	0.90 (0.22-1.58) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	5472370	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]

Showing metabocard for N(6)-Methyllysine (HMDB0002038)

MOL for HMDB0002038 (N(6)-Methyllysine)

3D MOL for HMDB0002038 (N(6)-Methyllysine)

3D SDF for HMDB0002038 (N(6)-Methyllysine)

3D-SDF for HMDB0002038 (N(6)-Methyllysine)

PDB for HMDB0002038 (N(6)-Methyllysine)

3D PDB for HMDB0002038 (N(6)-Methyllysine)

SMILES for HMDB0002038 (N(6)-Methyllysine)

INCHI for HMDB0002038 (N(6)-Methyllysine)

Structure for HMDB0002038 (N(6)-Methyllysine)

3D Structure for HMDB0002038 (N(6)-Methyllysine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra