ChemFOnt: Showing chemical card for N-alpha-Acetyl-L-lysine (CFc000000340)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:42 UTC

Chemfont ID

CFc000000340

Molecule Identification

Common Name

N-alpha-Acetyl-L-lysine

Definition

N-alpha-Acetyl-L-lysine also known as Nalpha-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. N-alpha-Acetyl-L-lysine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-alpha-Acetyl-L-lysine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-lysine. Unlike L-lysine, acetylated lysine derivatives such as N-alpha-Acetyl-L-lysine are zwitterionic compounds. These are molecules that contains an equal number of positively- and negatively-charged functional groups. N-alpha-Acetyl-L-lysine is found naturally in eukaryotes ranging from yeast to plants to humans. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT‚Äôs (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-alpha-Acetyl-L-lysine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free lysine can also occur. In particular, N-alpha-Acetyl-L-lysine can be biosynthesized from L-lysine and acetyl-CoA via the enzyme known as Lysine N-acetyltransferase. Individuals with hyperlysinaemia due to L-lysine alpha-ketoglutarate reductase deficiency will excrete high levels of N-alpha-Acetyl-L-lysine in their urine (PMID: 116084 ). L-lysine alpha-ketoglutarate reductase deficiency, if untreated, can lead to neurological and behavioral deficits (PMID: 116084 ). Many N-acetylamino acids are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-a-Acetyllysine	Generator
N-Α-acetyllysine	Generator
6-amino-L-2-Acetamidohexanoate	HMDB
6-amino-L-2-Acetamidohexanoic acid	HMDB
Acetyllysine	HMDB
N-a-Acetyl-L-lysine	HMDB
N-Acetyl poly-L-lysine	HMDB, MeSH
N-Acetyl-L-lysine	HMDB
N-alpha-Acetyl-L-lysine	HMDB
N2-Acetyl-L-lysine	HMDB
N2-Acetyllysine	HMDB
N-Acetyl polylysine	MeSH, HMDB
6-Amino-2-[(1-hydroxyethylidene)amino]hexanoate	Generator

Chemical Formula

C₈H₁₆N₂O₃

Average Molecular Weight

188.2242

Monoisotopic Molecular Weight

188.116092388

IUPAC Name

6-amino-2-acetamidohexanoic acid

Traditional Name

6-amino-2-acetamidohexanoic acid

CAS Registry Number

1946-82-3

SMILES

CC(O)=NC(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)

InChI Key

VEYYWZRYIYDQJM-UHFFFAOYSA-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
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Amine
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Feces (PMID: 26709303)
Urine (PMID: 32966057)

Cellular substructure

Cytoplasm (HMDB: HMDB0000446)

Source

Endogenous

Endogenous (HMDB: HMDB0000446)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Biological role

Waste product (PMID: 35448883)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.54 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.2	ChemAxon
logS	-1.9	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	19.84 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

External Links

HMDB ID

HMDB0000446

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022051

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

192590

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

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.

Showing chemical card for N-alpha-Acetyl-L-lysine (CFc000000340)

MOL for CFc000000340 (N-alpha-Acetyl-L-lysine)

3D MOL for CFc000000340 (N-alpha-Acetyl-L-lysine)

3D SDF for CFc000000340 (N-alpha-Acetyl-L-lysine)

3D-SDF for CFc000000340 (N-alpha-Acetyl-L-lysine)

PDB for CFc000000340 (N-alpha-Acetyl-L-lysine)

3D PDB for CFc000000340 (N-alpha-Acetyl-L-lysine)

SMILES for CFc000000340 (N-alpha-Acetyl-L-lysine)

INCHI for CFc000000340 (N-alpha-Acetyl-L-lysine)

Structure for CFc000000340 (N-alpha-Acetyl-L-lysine)

3D Structure for CFc000000340 (N-alpha-Acetyl-L-lysine)