Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2019-11-26 02:54:51 UTC
Primary IDFDB000476
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN6-Acetyl-L-lysine
DescriptionIsolated 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 Number692-04-6
Structure
Thumb
Synonyms
SynonymSource
(2S)-6-(acetylamino)-2-AminohexanoateGenerator
(2S)-6-(acetylamino)-2-aminohexanoic acidbiospider
E-acetyl-l-lysinebiospider
E-n-acetyl-l-lysinebiospider
E-n-acetyllysinebiospider
Epsilon-acetyl-l-lysinebiospider
Epsilon-n-acetyl-l-lysinebiospider
Epsilon-n-acetyllysinebiospider
L-e-n-acetyllysinebiospider
L-epsilon-n-acetyllysinebiospider
N-e-acetyl-l-lysinebiospider
N-e-acetyllysinebiospider
N-epsilon-acetyl-l-lysinebiospider
N-epsilon-acetyllysinebiospider
N(6)-Acetyl-L-lysinebiospider
N(6)-ACETYLLYSINEbiospider
N(epsilon)-acetyl-l-lysinebiospider
N(Z)-Acetyl-L-lysineGenerator
N(Z)-AcetyllysineGenerator
N(zeta)-acetyl-l-lysinebiospider
N(zeta)-acetyllysinebiospider
N(ζ)-acetyl-L-lysineGenerator
N(ζ)-acetyllysineGenerator
N6-Acetyl-L-lysinebiospider
N6-Acetyllysinebiospider
Ne-acetyl-l-lysinebiospider
Ne-acetyllysinebiospider
Nepsilon-acetyl-l-lysinebiospider
Omega-n-acetyl-l-lysinebiospider
W-n-acetyl-l-lysinebiospider
Predicted Properties
PropertyValueSource
Water Solubility17.5 g/LALOGPS
logP-2.6ALOGPS
logP-3.2ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)2.43ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability20.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H16N2O3
IUPAC name2-amino-6-acetamidohexanoic acid
InChI IdentifierInChI=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 KeyDTERQYGMUDWYAZ-UHFFFAOYSA-N
Isomeric SMILESCC(=O)NCCCCC(N)C(O)=O
Average Molecular Weight188.2242
Monoisotopic Molecular Weight188.116092388
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 51.05%; H 8.57%; N 14.88%; O 25.50%DFC
Melting Point250
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +4 (c, 5 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID83801
ChEMBL IDCHEMBL1230958
KEGG Compound IDC02727
Pubchem Compound ID92832
Pubchem Substance IDNot Available
ChEBI ID17752
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00206
CRC / DFC (Dictionary of Food Compounds) IDBCS45-Z:BCS57-E
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDALY
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference