Milk Composition Database: Showing metabocard for N-Alpha-ccetyllysine (BMDB0000446)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:30:52 UTC

Update Date

2020-04-21 18:14:07 UTC

MCDB ID

BMDB0000446

Secondary Accession Numbers

BMDB00446

Metabolite Identification

Common Name

N-Alpha-ccetyllysine

Description

Acetyllysine belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Acetyllysine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Acetyllysine exists in all eukaryotes, ranging from yeast to humans.

Structure

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

Synonyms

Value	Source
(2S)-2-(Acetylamino)-6-aminohexanoic acid	ChEBI
N(alpha)-Acetyllysine	ChEBI
N-Acetyl-L-lysine	ChEBI
N2-Acetyl-L-lysine	ChEBI
N(alpha)-Acetyl-L-lysine	ChEBI
(2S)-2-(Acetylamino)-6-aminohexanoate	Generator
N(a)-Acetyllysine	Generator
N(Α)-acetyllysine	Generator
N(a)-Acetyl-L-lysine	Generator
N(Α)-acetyl-L-lysine	Generator
N-a-Acetyl-L-lysine	Generator
N-Α-acetyl-L-lysine	Generator
6-Amino-L-2-acetamidohexanoic acid	HMDB
N2-Acetyllysine	HMDB
Nα-acetyl-L-lysine	HMDB
Nα-acetyllysine	HMDB
Nalpha-acetyl-L-lysine	HMDB
Nalpha-acetyllysine	HMDB
N-a-Acetyllysine	HMDB
N-Α-acetyllysine	HMDB
6-Amino-L-2-acetamidohexanoate	HMDB
N-Acetyl poly-L-lysine	HMDB
N-Acetyl polylysine	HMDB
Acetyllysine	HMDB
6-Amino-2-[(1-hydroxyethylidene)amino]hexanoate	HMDB
N(2)-Acetyllysine	HMDB
N(alpha)-Acetyllysine, (DL)-isomer	HMDB
N-alpha-Acetyllysine	HMDB
N-alpha-Acetyl-L-lysine	ChEBI

Chemical Formula

C₈H₁₆N₂O₃

Average Molecular Weight

188.227

Monoisotopic Molecular Weight

188.116092383

IUPAC Name

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

Traditional Name

nα-acetyllysine

CAS Registry Number

1946-82-3

SMILES

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

InChI Identifier

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

InChI Key

VEYYWZRYIYDQJM-ZETCQYMHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Fatty acyl
Fatty acid
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Organooxygen compound
Organonitrogen compound
Primary amine
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetyl-L-lysine (CHEBI:35704 )

Physical Properties

State

Solid

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	-2.5	ALOGPS
logP	-3.2	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	10.21	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	19.96 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
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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	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)	splash10-003i-1900000000-1bb977fd5835c87c7d01	2019-03-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9200000000-08d9b5954a220181ea5f	2019-03-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-9404d66c59d266164c23	2019-03-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-052b-9600000000-64d02b65a9438fd24af1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-2900000000-4e4307890c5505c5aeba	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-3d476e678ca9d6df5ea4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-28b149c70053eaa89aa0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-0900000000-b154acfb571fb75b00f5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-003r-2900000000-b607df4d59ad27d4f5c3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-003r-2900000000-bde2837d508c6909ec12	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-0900000000-0c503af7c1fbf54b2c2c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9700000000-cecd553985bf6c4d7160	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-9000000000-f705bda3174a35c518f8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-637ed07817e215db5233	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1900000000-92bf1c9bbc3af7b68c0c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-57df45c6e237a09f2c4b	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2019-03-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.08 MHz, D₂O, experimental)	Not Available	2019-03-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2019-03-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28306241	details
Detected but not Quantified	Not Applicable		PMID: 29291809	details

External Links

HMDB ID

HMDB0000446

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Acetyllysine

METLIN ID

5435

PubChem Compound

92907

PDB ID

Not Available

ChEBI ID

35704

References

Synthesis Reference

Akagi, Aru; Soejima, Yasuhiro; Izumiya, Nobuo. Facile syntheses of e-acyl-L-lysines and abnormal optical rotations of a-acyl-L-lysines. Kyushu Sangyo Daigaku Kogakubu Kenkyu Hokoku (1992), 29 119-24.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
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 N-Alpha-ccetyllysine (BMDB0000446)

Structure for BMDB0000446 (N-Alpha-ccetyllysine)