Record Information
Version1.0
Creation date2011-09-21 00:18:25 UTC
Update date2015-10-09 22:31:07 UTC
Primary IDFDB022718
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number2492-75-3
Structure
Thumb
Synonyms
SynonymSource
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-KetocaproateMeSH
alpha-Ketocaproic acid, sodium saltMeSH
2-Ketocaproic acidHMDB
2-oxo-HexanoateHMDB
2-oxo-Hexanoic acidHMDB
2-Ketohexanoic acidChEBI
2-keto-n-caproatehmdb
2-keto-n-caproic acidhmdb
2-ketocaproic acidhmdb
2-oxo-hexanoatehmdb
2-oxo-hexanoic acidhmdb
α-ketocaproateGenerator
α-ketocaproic acidGenerator
α-ketohexanoateGenerator
α-ketohexanoic acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H10O3
IUPAC name2-oxohexanoic acid
InChI IdentifierInChI=1S/C6H10O3/c1-2-3-4-5(7)6(8)9/h2-4H2,1H3,(H,8,9)
InChI KeyXNIHZNNZJHYHLC-UHFFFAOYSA-N
Isomeric SMILESCCCCC(=O)C(O)=O
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2-Ketohexanoic acid, non-derivatized, GC-MS Spectrumsplash10-000j-8920000000-9e106a172aeaca6001eaSpectrum
GC-MS2-Ketohexanoic acid, non-derivatized, GC-MS Spectrumsplash10-000j-8920000000-9e106a172aeaca6001eaSpectrum
Predicted GC-MS2-Ketohexanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-9000000000-e0cebba0b69620390c09Spectrum
Predicted GC-MS2-Ketohexanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007a-9300000000-87b7d0f0e16ba9e212cbSpectrum
Predicted GC-MS2-Ketohexanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01p9-9500000000-5145cab306a85b6e9d7fSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-4cd8f41133a4d23b1d4cSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01qj-9100000000-caf6abf28104b7765cefSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qi-4900000000-702612249f0615c78f6bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btm-9300000000-d02ff05157ccb2f8d416Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-dfcf44ed2c628b6b914aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-d751dca8c7b118a0dea9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01s9-9500000000-c04f00087e8e89956b26Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4a26ce3589a801c4bcefSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052u-9000000000-a1430045d6ae5d2e494cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-d6e0a51fd3a4a90d9cebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-ed2b82d47ad4721d3a01Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8be0a8820bd022f7267bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-761b5c64b393cb442dccSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-9000000000-1763f75b095d5d429e5bSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID140384
ChEMBL IDCHEMBL3247426
KEGG Compound IDC00902
Pubchem Compound ID159664
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01864
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference