Milk Composition Database: Showing metabocard for N6-Acetyl-L-lysine (BMDB0000206)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:41 UTC

Update Date

2020-05-11 20:36:12 UTC

MCDB ID

BMDB0000206

Secondary Accession Numbers

BMDB00206

Metabolite Identification

Common Name

N6-Acetyl-L-lysine

Description

N6-Acetyl-L-lysine, also known as N(6)-acetyllysine or omega-acetyllsine, 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. N6-Acetyl-L-lysine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. N6-Acetyl-L-lysine exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(2S)-6-(Acetylamino)-2-aminohexanoic acid	ChEBI
N(6)-ACETYLLYSINE	ChEBI
N(zeta)-Acetyllysine	ChEBI
N-epsilon-Acetyl-L-lysine	ChEBI
N-Epsilon-Acetyllysine	ChEBI
N(epsilon)-Acetyl-L-lysine	ChEBI
N(zeta)-Acetyl-L-lysine	ChEBI
(2S)-6-(Acetylamino)-2-aminohexanoate	Generator
N(Z)-Acetyllysine	Generator
N(Ζ)-acetyllysine	Generator
N(Z)-Acetyl-L-lysine	Generator
N(Ζ)-acetyl-L-lysine	Generator
e-Acetyl-L-lysine	HMDB
e-N-Acetyl-L-lysine	HMDB
e-N-Acetyllysine	HMDB
epsilon-Acetyl-L-lysine	HMDB
epsilon-N-Acetyl-L-lysine	HMDB
epsilon-N-Acetyllysine	HMDB
L-e-N-Acetyllysine	HMDB
L-epsilon-N-Acetyllysine	HMDB
N-e-Acetyl-L-lysine	HMDB
N-e-Acetyllysine	HMDB
N6-Acetyllysine	HMDB
Ne-acetyl-L-lysine	HMDB
Ne-acetyllysine	HMDB
Omega-N-acetyl-L-lysine	HMDB
W-N-Acetyl-L-lysine	HMDB
N(6)-Acetyllsine	HMDB
Omega-acetyllsine	HMDB
(2S)-6-Acetamido-2-aminohexanoic acid	HMDB
6-Acetamido-2-aminohexanoic acid	HMDB
L-Ε-N-acetyllysine	HMDB
Nepsilon-acetyl-L-lysine	HMDB
Nepsilon-acetyllysine	HMDB
Nε-acetyl-L-lysine	HMDB
Nε-acetyllysine	HMDB
Ε-acetyl-L-lysine	HMDB
Ε-N-acetyl-L-lysine	HMDB
Ε-N-acetyllysine	HMDB
Ω-N-acetyl-L-lysine	HMDB
N6-Acetyl-L-lysine	ChEBI

Chemical Formula

C₈H₁₆N₂O₃

Average Molecular Weight

188.2242

Monoisotopic Molecular Weight

188.116092388

IUPAC Name

(2S)-2-amino-6-acetamidohexanoic acid

Traditional Name

N6-acetyllysine

CAS Registry Number

692-04-6

SMILES

CC(=O)NCCCC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C8H16N2O3/c1-6(11)10-5-3-2-4-7(9)8(12)13/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1

InChI Key

DTERQYGMUDWYAZ-ZETCQYMHSA-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
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Primary amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
Primary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N(6)-acyl-L-lysine (CHEBI:17752 )
acetyl-L-lysine (CHEBI:17752 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	250 °C	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	-2.6	ALOGPS
logP	-3.2	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	2.43	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	47.25 m³·mol⁻¹	ChemAxon
Polarizability	20.29 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0002-9610000000-6e30cfdb2a70cc49f983	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0002-9610000000-6e30cfdb2a70cc49f983	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-1900000000-e36d5532f4f0ed8ec34f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-9500000000-266c8b0fce84c71553b2	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9200000000-a186b34425c93ea31a66	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9110000000-255e47c2dfcdf6b61403	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004r-1900000000-4745f7cfa9eaaef208ad	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-635805826359aa05ec7c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-8857489c6ac957c71a5d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-39f91157038523017046	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000j-0900000000-183e1f50c20603f14c03	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-1900000000-da02d0f8bd73b5b96b46	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4j-9400000000-8531cdbb4e8108dbec95	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4l-9000000000-94d72f2c644db8c0b5cd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000i-0900000000-c6ff005564503774a853	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-004i-3900000000-dffc604f608a010e711e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9000000000-d6bc330de42890c4c091	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-8d68337bf7a8db380cd7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001i-9000000000-1400569a447d5f66c3a8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-39f91157038523017046	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000j-0900000000-183e1f50c20603f14c03	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-1900000000-da02d0f8bd73b5b96b46	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4j-9400000000-8531cdbb4e8108dbec95	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9000000000-94d72f2c644db8c0b5cd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-c6ff005564503774a853	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0077-0900000000-e0d9659d3d504e9c8d81	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ued-3900000000-ae84e0c568d22d7c62fb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-848f804e26f5a4edfcfb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-545e3c760ee61913f301	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05p2-3900000000-3a6e9f0c90d936bd6ae8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-33c2ede158e490bcc70f	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 26686724	details
Detected but not Quantified	Not Applicable		PMID: 29291809	details

External Links

HMDB ID

HMDB0000206

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000476

KNApSAcK ID

Not Available

Chemspider ID

83801

KEGG Compound ID

C02727

BioCyc ID

CPD-567

BiGG ID

Not Available

Wikipedia Link

Acetyllysine

METLIN ID

5216

PubChem Compound

92832

PDB ID

Not Available

ChEBI ID

17752

References

Synthesis Reference

Benoiton, Leo; Leclerc, Jean. An improved synthesis of e-N-acetyl-L-lysine and similar compounds. Canadian Journal of Chemistry (1965), 43(4), 991-3.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Showing metabocard for N6-Acetyl-L-lysine (BMDB0000206)

Structure for BMDB0000206 (N6-Acetyl-L-lysine)