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Record Information
Version3.6
Creation Date2009-04-06 16:20:03 UTC
Update Date2016-02-11 01:23:41 UTC
HMDB IDHMDB12150
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Keto-6-acetamidocaproate
Description2-Keto-6-acetamidocaproate is an intermediate in lysine degradation. It can be generated from N6-acetyl-L-lysine. N-acetyl-lysine is an acetylated amino acid. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins. Acetylation of specific lysine residues in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. N6-acetyl-L-lysine can be converted to 2-Keto-6-acetamidocaproate via the enzyme N6-acetyllysine aminotransferase and then 2-keto-6-acetamidocaproate can be reduced enzymatically to 5-acetamidovalerate.
Structure
Thumb
Synonyms
ValueSource
2-keto-6-Acetamidocaproic acidChEBI
2-keto-6-Acetamidohexanoic acidChEBI
2-oxo-6-Acetamidocaproic acidChEBI
2-keto-6-AcetamidohexanoateGenerator
2-oxo-6-AcetamidocaproateGenerator
6-acetamido-2-OxohexanoateHMDB
6-acetamido-2-Oxohexanoic acidHMDB
Chemical FormulaC8H13NO4
Average Molecular Weight187.1931
Monoisotopic Molecular Weight187.084457909
IUPAC Name6-acetamido-2-oxohexanoic acid
Traditional Name6-acetamido-2-oxohexanoic acid
CAS Registry NumberNot Available
SMILES
CC(=O)NCCCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C8H13NO4/c1-6(10)9-5-3-2-4-7(11)8(12)13/h2-5H2,1H3,(H,9,10)(H,12,13)
InChI KeyInChIKey=NGCXIFFZXAZRAF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Amino fatty acid
  • Fatty acyl
  • Alpha-keto acid
  • Acetamide
  • Alpha-hydroxy ketone
  • Secondary carboxylic acid amide
  • Ketone
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.75 mg/mLALOGPS
logP-0.1ALOGPS
logP-0.069ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.36ChemAxon
pKa (Strongest Basic)-0.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity44.85 m3·mol-1ChemAxon
Polarizability18.88 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
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 IDFDB028807
KNApSAcK IDNot Available
Chemspider ID168403
KEGG Compound IDC05548
BioCyc ID2-KETO-6-ACETAMIDOCAPROATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12150
Metagene LinkHMDB12150
METLIN IDNot Available
PubChem Compound194080
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available