epsilon-Acetyl-L-lysine
Basic information
- CAS
692-04-6- Standard SMILES
CC(=O)NCCCC[C@H](N)C(=O)O- InChIKey
DTERQYGMUDWYAZ-ZETCQYMHSA-N- Molecular formula
- C8H16N2O3
- Average molar mass
- 188.22 g/mol
- Monoisotopic mass
- 188.11609238
Overview
N(6)-acetyl-L-lysine is an N6-acyl-L-lysine where the N6-acyl group is specified as acetyl. It has a role as a human metabolite. It is a N(6)-acyl-L-lysine and an acetyl-L-lysine. It is a tautomer of a N(6)-acetyl-L-lysine zwitterion.
Names & identifiers
- Preferred name
- epsilon-Acetyl-L-lysine
- IUPAC
- (2S)-6-acetamido-2-aminohexanoic acid
- English name
- N-epsilon-Acetyl-L-lysine
- Molecular formula
- C8H16N2O3
- Molecular weight
- 188.22
Names & synonyms
692-04-6N6-Acetyl-L-lysineN-Epsilon-acetyllysineOmega-acetyllsineN(6)-acetyllsine(2S)-2-amino-6-acetamidohexanoic acidepsilon-Acetyl-L-lysine470AD5VY1XDTXSID90862371RefChem:921071DTXCID401527695N-epsilon-Acetyl-L-lysine
Show more names
lys(ac)N-EPSILON-ACETYL-L-LYSNSC 102777LYSINE(AC)-OHH-L-LYS(AC)-OHNε-Ac-L-Lys-OHNε-Acetyllysine
H-Lys(Ac)-OHNepsilon-Acetyl-L-lysinen6-acetyllysine(S)-6-Acetamido-2-aminohexanoic acidNe-AcetyllysineN(6)-Acetyl-L-lysineN(6)-ACETYLLYSINEMFCD00002639
Database identifiers
- CAS
692-04-6- PubChem CID
- 92832
- DTXSID
DTXSID90862371- ChEMBL
CHEMBL1230958- ChEBI
CHEBI:17752- UNII
- 470AD5VY1X
- EC Number
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 92.4 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 182
Experimental & physicochemical properties
Melting Point250 °C
Physical DescriptionSolid
Collision Cross Section142.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 250 °C · 250 °C (dec.)(lit.)
- Boiling point
- 323.23 °C · 323.23°C (rough estimate)
- Density
- 1.1793 · 1.1793 (rough estimate)
- refractive index
- 1.45 · 1.4500 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Aqueous Base (Slightly), Water (Slightly)
- form
- Powder
- pka
- 2.53 · 2.53±0.24(Predicted)
- color
- White
- Water Solubility
- 80 % · Soluble in water (miscible), and 80% acetic acid (50 mg/ml).
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- hs_code
- 29241900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P280-P261
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
Applications
DescriptionAcetyllysine (or acetylated lysine) is an acetyl-derivative of the amino acid lysine. There are multiple forms of acetyllysine - this article refers to N-ε-acetyl-L-lysine. The other form is N-α-acetyl-Llysine. In proteins, the acetylation of lysine residues is an important mechanism of epigenetics. It functions by regulating the binding of histones to DNA in nucleosomes and thereby controlling the expression of genes on that DNA. Non-histone proteins are acetylated as well. Unlike the functionally similar methyllysine, acetyllysine does not carry a positive charge on its side chain. Histone acetyltransferases (HATs) catalyze the addition of acetyl groups from acetyl-CoA onto certain lysine residues of histones and non-histone proteins. Histone deacetylases (HDACs) catalyze the removal of acetyl groups from acetylated lysines. Acetyllysine can be synthesized from lysine by the selective acetylation of the terminal amine group.
UsesN-Epsilon-acetyl-l-lysine is used in the metabolomics study on the combined effect of cocaine and ethanol via liquid chromatography-mass spectrometry metabolomics approach.
Additional notes
DefinitionChEBI: An N6-acyl-L-lysine where the N6-acyl group is specified as acetyl.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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