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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-02-23 10:34:24 UTC
Update Date2019-07-23 05:45:08 UTC
HMDB IDHMDB0001864
Secondary Accession Numbers
  • HMDB01864
Metabolite Identification
Common Name2-Ketohexanoic acid
Description2-Ketohexanoic acid is a potent insulin secretagogue. (PMID 7045091 ). 2-Ketohexanoic acid directly inhibits the ATP-sensitive K+ channel (KATP channel) in pancreatic beta-cells (stimulated in isolated mouse islets), but it is unknown whether direct KATP channel inhibition contributes to insulin release by 2-ketohexanoic acid and related alpha-keto acid anions, which are generally believed to act via beta-cell metabolism. (PMID 16014804 ).
Structure
Data?1563860708
Synonyms
ValueSource
2-Keto-N-caproic acidChEBI
2-oxo 6:0ChEBI
2-oxo C6:0ChEBI
2-OxohexanoateChEBI
alpha-Ketocaproic acidChEBI
alpha-Ketohexanoic acidChEBI
2-Keto-N-caproateGenerator
2-Oxohexanoic acidGenerator
a-KetocaproateGenerator
a-Ketocaproic acidGenerator
alpha-KetocaproateGenerator
Α-ketocaproateGenerator
Α-ketocaproic acidGenerator
a-KetohexanoateGenerator
a-Ketohexanoic acidGenerator
alpha-KetohexanoateGenerator
Α-ketohexanoateGenerator
Α-ketohexanoic acidGenerator
2-KetohexanoateGenerator
2-KetocaproateHMDB
2-Ketocaproic acidHMDB
2-oxo-HexanoateHMDB
2-oxo-Hexanoic acidHMDB
alpha-Ketocaproic acid, sodium saltHMDB
2-Ketohexanoic acidChEBI
Chemical FormulaC6H10O3
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
IUPAC Name2-oxohexanoic acid
Traditional Name2-oxohexanoic acid
CAS Registry Number2492-75-3
SMILES
CCCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-2-3-4-5(7)6(8)9/h2-4H2,1H3,(H,8,9)
InChI KeyXNIHZNNZJHYHLC-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

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 Solubility8.02 g/LALOGPS
logP0.94ALOGPS
logP1.66ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.82 m³·mol⁻¹ChemAxon
Polarizability13.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-8920000000-9e106a172aeaca6001eaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-8920000000-9e106a172aeaca6001eaJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-e0cebba0b69620390c09JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007a-9300000000-87b7d0f0e16ba9e212cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01p9-9500000000-5145cab306a85b6e9d7fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-4cd8f41133a4d23b1d4cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01qj-9100000000-caf6abf28104b7765cefJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qi-4900000000-702612249f0615c78f6bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btm-9300000000-d02ff05157ccb2f8d416JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-dfcf44ed2c628b6b914aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-d751dca8c7b118a0dea9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01s9-9500000000-c04f00087e8e89956b26JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4a26ce3589a801c4bcefJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022718
KNApSAcK IDNot Available
Chemspider ID140384
KEGG Compound IDC00902
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4144
PubChem Compound159664
PDB IDNot Available
ChEBI ID17308
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceIgarashi, Minoru; Midorikawa, Hiroshi. Synthesis of a-oxo acids from diethyl alkylidenemalonates. Journal of Organic Chemistry (1964), 29(7), 2080-2.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nakahara T, Ishida J, Yamaguchi M, Nakamura M: Determination of alpha-keto acids including phenylpyruvic acid in human plasma by high-performance liquid chromatography with chemiluminescence detection. Anal Biochem. 1990 Nov 1;190(2):309-13. [PubMed:2291475 ]
  2. Shroads AL, Henderson GN, Cheung J, James MO, Stacpoole PW: Unified gas chromatographic-mass spectrometric method for quantitating tyrosine metabolites in urine and plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Sep 5;808(2):153-61. [PubMed:15261808 ]
  3. Lenzen S, Formanek H, Panten U: Signal function of metabolism of neutral amino acids and 2-keto acids for initiation of insulin secretion. J Biol Chem. 1982 Jun 25;257(12):6631-3. [PubMed:7045091 ]
  4. Heissig H, Urban KA, Hastedt K, Zunkler BJ, Panten U: Mechanism of the insulin-releasing action of alpha-ketoisocaproate and related alpha-keto acid anions. Mol Pharmacol. 2005 Oct;68(4):1097-105. Epub 2005 Jul 13. [PubMed:16014804 ]