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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:03 UTC
Update Date2017-12-07 02:35:58 UTC
HMDB IDHMDB0012150
Secondary Accession Numbers
  • HMDB12150
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 KeyNGCXIFFZXAZRAF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassKeto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Amino fatty acid
  • Alpha-keto acid
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Acetamide
  • Carboxamide group
  • Ketone
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity44.85 m³·mol⁻¹ChemAxon
Polarizability18.88 ųChemAxon
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-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-d77cc429a6b80831b2e4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9120000000-24931882682cc9ca4557View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00g4-0900000000-6d348a4fb73306ffc1ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ba-4900000000-59ff96e4bdcba1a928c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9100000000-ceec5d761829d1e1d9b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-1900000000-4b2f9cf7c679af8556dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-3900000000-ccfc2e6d68e971b0dde3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-6d27ffe991d97f72e3f8View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
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