Bovine Metabolome Database: Showing metabocard for N-Alpha-ccetyllysine (BMDB0000446)

Identification Taxonomy Physical properties Pathways 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

BMDB 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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Milk

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 28306241	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29291809	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000446

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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)

Not Available

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)