N-Alpha-acetyllysine (CHEM034867)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:17:20 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034867
Identification
Common NameN-Alpha-acetyllysine
ClassSmall Molecule
DescriptionAn acetyl-L-lysine where the acetyl group is located at the N(2)-posiiton.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2S)-2-(Acetylamino)-6-aminohexanoic acidChEBI
N(alpha)-AcetyllysineChEBI
N-Acetyl-L-lysineChEBI
N2-Acetyl-L-lysineChEBI
N(alpha)-Acetyl-L-lysineChEBI
(2S)-2-(Acetylamino)-6-aminohexanoateGenerator
N(a)-AcetyllysineGenerator
N(Α)-acetyllysineGenerator
N(a)-Acetyl-L-lysineGenerator
N(Α)-acetyl-L-lysineGenerator
N-a-Acetyl-L-lysineGenerator
N-Α-acetyl-L-lysineGenerator
6-Amino-L-2-acetamidohexanoic acidHMDB
N2-AcetyllysineHMDB
Nα-acetyl-L-lysineHMDB
Nα-acetyllysineHMDB
Nalpha-acetyl-L-lysineHMDB
Nalpha-acetyllysineHMDB
N-a-AcetyllysineHMDB
N-Α-acetyllysineHMDB
6-Amino-L-2-acetamidohexanoateHMDB
N-Acetyl poly-L-lysineHMDB
N-Acetyl polylysineHMDB
AcetyllysineHMDB
6-Amino-2-[(1-hydroxyethylidene)amino]hexanoateHMDB
N(2)-AcetyllysineHMDB
N(alpha)-Acetyllysine, (DL)-isomerHMDB
N-alpha-AcetyllysineHMDB
N-alpha-Acetyl-L-lysineChEBI
Chemical FormulaC8H16N2O3
Average Molecular Mass188.224 g/mol
Monoisotopic Mass188.116 g/mol
CAS Registry Number1946-82-3
IUPAC Name(2S)-6-amino-2-acetamidohexanoic acid
Traditional Namenα-acetyllysine
SMILESCC(=O)NC(CCCCN)C(O)=O
InChI IdentifierInChI=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 KeyVEYYWZRYIYDQJM-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP-2.5ALOGPS
logP-3.2ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability19.96 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003i-1900000000-1bb977fd5835c87c7d01Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9200000000-08d9b5954a220181ea5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-9404d66c59d266164c23Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-052b-9600000000-64d02b65a9438fd24af1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-2900000000-4e4307890c5505c5aebaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3d476e678ca9d6df5ea4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-28b149c70053eaa89aa0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-0900000000-b154acfb571fb75b00f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-003r-2900000000-b607df4d59ad27d4f5c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-003r-2900000000-bde2837d508c6909ec12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0900000000-0c503af7c1fbf54b2c2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9700000000-cecd553985bf6c4d7160Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-f705bda3174a35c518f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-637ed07817e215db5233Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-92bf1c9bbc3af7b68c0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-57df45c6e237a09f2c4bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000446
FooDB IDFDB112380
Phenol Explorer IDNot Available
KNApSAcK IDC00052355
BiGG IDNot Available
BioCyc IDN-ACETYL-L-LYSINE
METLIN ID5435
PDB IDNot Available
Wikipedia LinkAcetyllysine
Chemspider ID83869
ChEBI ID35704
PubChem Compound ID92907
Kegg Compound IDC12989
YMDB IDYMDB01633
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12212910
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15131313
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16274666
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26800898
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2897459
6. 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.
7. Van Coster RN, Gerlo EA, Giardina TG, Engelke UF, Smet JE, De Praeter CM, Meersschaut VA, De Meirleir LJ, Seneca SH, Devreese B, Leroy JG, Herga S, Perrier JP, Wevers RA, Lissens W: Aminoacylase I deficiency: a novel inborn error of metabolism. Biochem Biophys Res Commun. 2005 Dec 23;338(3):1322-6. Epub 2005 Nov 2.
8. Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18.
9. Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7.
10. Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z.
11. vd Heiden C, Brink M, de Bree PK, v Sprang FJ, Wadman SK, de Pater JM, van Biervliet JP: Familial hyperlysinaemia due to L-lysine alpha-ketoglutarate reductase deficiency: results of attempted treatment. J Inherit Metab Dis. 1978;1(3):89-94. doi: 10.1007/BF01805679.
12. Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015.
13. Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8.
14. Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20.