You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-09-22 21:06:17 UTC
HMDB IDHMDB00446
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Alpha-acetyllysine
DescriptionN-Alpha-acetyllysine is a N-acetylated amino acid. It is a normal constituent of human urine with concentrations in normal samples too small to allow its routine detection; however, it has been found at increased levels in the urine of a patient with aminoacylase I deficiency. (PMID 16274666 ).
Structure
Thumb
Synonyms
ValueSource
6-amino-L-2-AcetamidohexanoateHMDB
6-amino-L-2-Acetamidohexanoic acidHMDB
AcetyllysineHMDB
N-a-Acetyl-L-lysineHMDB
N-a-AcetyllysineHMDB
N-Acetyl poly-L-lysineHMDB
N-Acetyl-L-lysineHMDB
N-alpha-Acetyl-L-lysineHMDB
N2-Acetyl-L-lysineHMDB
N2-AcetyllysineHMDB
Chemical FormulaC8H16N2O3
Average Molecular Weight188.2242
Monoisotopic Molecular Weight188.116092388
IUPAC Name6-amino-2-acetamidohexanoic acid
Traditional Name6-amino-2-acetamidohexanoic acid
CAS Registry Number1946-82-3
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 KeyInChIKey=VEYYWZRYIYDQJM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point256 - 258 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity47.25 m3·mol-1ChemAxon
Polarizability19.84 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022051
KNApSAcK IDNot Available
Chemspider ID167134
KEGG Compound IDC12989
BioCyc IDN-ACETYL-L-LYSINE
BiGG IDNot Available
Wikipedia LinkAcetyllysine
NuGOwiki LinkHMDB00446
Metagene LinkHMDB00446
METLIN ID5435
PubChem Compound192590
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)Download (PDF)
General References
  1. 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. [16274666 ]