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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:04 UTC
Update Date2017-10-23 19:06:00 UTC
HMDB IDHMDB0012151
Secondary Accession Numbers
  • HMDB12151
Metabolite Identification
Common Name2-Keto-6-aminocaproate
Description2-Keto-6-aminocaproate is an intermediate in lysine degradation and can be formed from L-lysine. L-Lysine is an essential amino-acid that is a necessary building block for all protein in the body. L-Lysine plays a major role in calcium absorption; building muscle protein; recovering from surgery or sports injuries; and the body's production of hormones, enzymes, and antibodies. L-Lysine can be converted to 2-keto-6-aminocaproate via the enzyme L-lysine alpha-oxidase. 2-Keto-6-aminocaproate can spontaneously decarboxylate to 5-aminovalerate in the presence of the reaction product, hydrogen peroxide. It can also be spontaneously converted in solution to its cyclic form delta-piperideine-2-carboxylate. This has been demonstrated in vitro in the presence of catalase, which splits hydrogen peroxide.
Structure
Thumb
Synonyms
ValueSource
2-oxo-6-AminocaproateChEBI
6-amino-2-OxohexanoateChEBI
2-oxo-6-Aminocaproic acidGenerator
2-keto-6-Aminocaproic acidGenerator
6-amino-2-Oxohexanoic acidGenerator
2-keto-6-amino-CaproateHMDB
2-keto-6-amino-Caproic acidHMDB
2-oxo-6-AminohexanoateHMDB
2-oxo-6-Aminohexanoic acidHMDB
alpha-keto-epsilon-AminocaproateHMDB
alpha-keto-epsilon-Aminocaproic acidHMDB
alpha-keto-epsilon-AminohexanoateHMDB
alpha-keto-epsilon-Aminohexanoic acidHMDB
alpha-KetolysineHMDB
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Name6-amino-2-oxohexanoic acid
Traditional Name6-amino-2-oxohexanoic acid
CAS Registry NumberNot Available
SMILES
NCCCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c7-4-2-1-3-5(8)6(9)10/h1-4,7H2,(H,9,10)
InChI KeyGWENQMVPLJAMAE-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
  • Amino acid
  • Amino acid or derivatives
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Primary amine
  • 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 Solubility17.1 g/LALOGPS
logP-2.3ALOGPS
logP-2.2ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)10.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.4 m³·mol⁻¹ChemAxon
Polarizability14.62 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, Positivesplash10-001l-9100000000-72e8fece7209f3479d83View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9100000000-d7815fff47f4701aa6bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0900000000-2e07e1b290d6ac0922a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u0-7900000000-36d3c2eaaad6e51164f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-3a14a26fbeb218e4867aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-6672acf922f761c7db06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufv-5900000000-0eab9451d3d5c3835bd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f10b35b4dc759c1cab39View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDFDB028808
KNApSAcK IDNot Available
Chemspider ID388981
KEGG Compound IDC03239
BioCyc ID2-KETO-6-AMINO-CAPROATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439954
PDB IDNot Available
ChEBI ID17534
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available