Showing Compound N6-Acetyl-L-lysine (FDB000476)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:35 UTC

Update date

2019-11-26 02:54:51 UTC

Primary ID

FDB000476

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N6-Acetyl-L-lysine

Description

Isolated from sugarbeet (Beta vulgaris) N-acetyl-lysine is an acetylated amino acid. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins. Acetylation of specific lysine residues in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. By modifying chromatin proteins and transcription-related factors, these acetylases are believed to regulate the transcription of many genes. The best-characterized mechanism is acetylation, catalyzed by histone acetyltransferase (HAT) enzymes. HATs function enzymatically by transferring an acetyl group from acetyl-coenzyme A (acetyl-CoA) to the -amino group of certain lysine side chains within a histone's basic N-terminal tail region. Within a histone octamer, these regions extend out from the associated globular domains, and in the context of a nucleosome, they are believed to bind the DNA through charge interactions (positively charged histone tails associated with negatively charged DNA) or mediate interactions between nucleosomes. Lysine acetylation, which neutralizes part of a tail region's positive charge, is postulated to weaken histone-DNA or nucleosome-nucleosome interactions and/or signal a conformational change, thereby destabilizing nucleosome structure or arrangement and giving other nuclear factors, such as the transcription complex, more access to a genetic locus. In agreement with this is the fact that acetylated chromatin has long been associated with states of transcriptional activation. Specific recognition of N-acetyl-lysine is a conserved function of all bromodomains found in different proteins, recognized as an emerging intracellular signaling mechanism that plays critical roles in regulating gene transcription, cell-cycle progression, apoptosis, DNA repair, and cytoskeletal organization. (PMID 9169194, 10827952, 17340003, 16247734, 9478947, 10839822).

CAS Number

692-04-6

Structure

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

Synonyms

Synonym	Source
(2S)-6-(acetylamino)-2-Aminohexanoate	Generator
(2S)-6-(acetylamino)-2-aminohexanoic acid	biospider
E-acetyl-l-lysine	biospider
E-n-acetyl-l-lysine	biospider
E-n-acetyllysine	biospider
Epsilon-acetyl-l-lysine	biospider
Epsilon-n-acetyl-l-lysine	biospider
Epsilon-n-acetyllysine	biospider
L-e-n-acetyllysine	biospider
L-epsilon-n-acetyllysine	biospider
N-e-acetyl-l-lysine	biospider
N-e-acetyllysine	biospider
N-epsilon-acetyl-l-lysine	biospider
N-epsilon-acetyllysine	biospider
N(6)-Acetyl-L-lysine	biospider
N(6)-ACETYLLYSINE	biospider
N(epsilon)-acetyl-l-lysine	biospider
N(Z)-Acetyl-L-lysine	Generator
N(Z)-Acetyllysine	Generator
N(zeta)-acetyl-l-lysine	biospider
N(zeta)-acetyllysine	biospider
N(ζ)-acetyl-L-lysine	Generator
N(ζ)-acetyllysine	Generator
N6-Acetyl-L-lysine	biospider
N6-Acetyllysine	biospider
Ne-acetyl-l-lysine	biospider
Ne-acetyllysine	biospider
Nepsilon-acetyl-l-lysine	biospider
Omega-n-acetyl-l-lysine	biospider
W-n-acetyl-l-lysine	biospider

Predicted Properties

Property	Value	Source
Water Solubility	17.5 g/L	ALOGPS
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	20.14 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

Chemical Formula

C8H16N2O3

IUPAC name

2-amino-6-acetamidohexanoic acid

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)

InChI Key

DTERQYGMUDWYAZ-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)NCCCCC(N)C(O)=O

Average Molecular Weight

188.2242

Monoisotopic Molecular Weight

188.116092388

Classification

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Fatty acid
Fatty acyl
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organopnictogen compound
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic oxygen compound
Organic oxide
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 51.05%; H 8.57%; N 14.88%; O 25.50%	DFC
Melting Point	250
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D +4 (c, 5 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available