Showing metabocard for N-Alpha-ccetyllysine (BMDB0000446)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:52 UTC
Update Date2020-04-21 18:14:07 UTC
BMDB IDBMDB0000446
Secondary Accession Numbers
  • BMDB00446
Metabolite Identification
Common NameN-Alpha-ccetyllysine
DescriptionAcetyllysine 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. Acetyllysine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Acetyllysine exists in all eukaryotes, ranging from yeast to humans.
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 Weight188.227
Monoisotopic Molecular Weight188.116092383
IUPAC Name(2S)-6-amino-2-acetamidohexanoic acid
Traditional Namenα-acetyllysine
CAS Registry Number1946-82-3
SMILES
CC(=O)N[C@@H](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)/t7-/m0/s1
InChI KeyVEYYWZRYIYDQJM-ZETCQYMHSA-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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003i-1900000000-1bb977fd5835c87c7d01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9200000000-08d9b5954a220181ea5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-9404d66c59d266164c23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-052b-9600000000-64d02b65a9438fd24af1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-2900000000-4e4307890c5505c5aebaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3d476e678ca9d6df5ea4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-28b149c70053eaa89aa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-0900000000-b154acfb571fb75b00f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-003r-2900000000-b607df4d59ad27d4f5c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-003r-2900000000-bde2837d508c6909ec12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0900000000-0c503af7c1fbf54b2c2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9700000000-cecd553985bf6c4d7160View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-f705bda3174a35c518f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-637ed07817e215db5233View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-92bf1c9bbc3af7b68c0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-57df45c6e237a09f2c4bView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 15.08 MHz, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000446
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112380
KNApSAcK IDC00052355
Chemspider ID83869
KEGG Compound IDC12989
BioCyc IDN-ACETYL-L-LYSINE
BiGG IDNot Available
Wikipedia LinkAcetyllysine
METLIN ID5435
PubChem Compound92907
PDB IDNot Available
ChEBI ID35704
References
Synthesis ReferenceAkagi, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]