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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-02-23 10:34:24 UTC
Update Date2021-10-13 04:36:08 UTC
HMDB IDHMDB0001864
Secondary Accession Numbers
  • HMDB01864
Metabolite Identification
Common Name2-Ketohexanoic acid
Description2-Ketohexanoic acid, also known as alpha-ketocaproic acid or 2-oxohexanoate, 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. 2-Ketohexanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-ketohexanoic acid a potential biomarker for the consumption of these foods. 2-Ketohexanoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 2-Ketohexanoic acid.
Structure
Data?1582752213
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-KetocaproateMeSH
alpha-Ketocaproic acid, sodium saltMeSH
2-Ketocaproic acidHMDB
2-oxo-HexanoateHMDB
2-oxo-Hexanoic acidHMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point198.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility145000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.350 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.0731661259
DarkChem[M-H]-125.34731661259
AllCCS[M+H]+131.26432859911
AllCCS[M-H]-128.43632859911
DeepCCS[M+H]+132.04530932474
DeepCCS[M-H]-129.2830932474
DeepCCS[M-2H]-165.74330932474
DeepCCS[M+Na]+140.53130932474
AllCCS[M+H]+131.332859911
AllCCS[M+H-H2O]+127.132859911
AllCCS[M+NH4]+135.232859911
AllCCS[M+Na]+136.332859911
AllCCS[M-H]-128.432859911
AllCCS[M+Na-2H]-131.132859911
AllCCS[M+HCOO]-134.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Ketohexanoic acidCCCCC(=O)C(O)=O1894.2Standard polar33892256
2-Ketohexanoic acidCCCCC(=O)C(O)=O1382.6Standard non polar33892256
2-Ketohexanoic acidCCCCC(=O)C(O)=O1046.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Ketohexanoic acid,1TMS,isomer #1CCCCC(=O)C(=O)O[Si](C)(C)C1169.3Semi standard non polar33892256
2-Ketohexanoic acid,1TMS,isomer #2CCCC=C(O[Si](C)(C)C)C(=O)O1273.3Semi standard non polar33892256
2-Ketohexanoic acid,2TMS,isomer #1CCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1331.0Semi standard non polar33892256
2-Ketohexanoic acid,2TMS,isomer #1CCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1277.7Standard non polar33892256
2-Ketohexanoic acid,2TMS,isomer #1CCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1337.9Standard polar33892256
2-Ketohexanoic acid,1TBDMS,isomer #1CCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C1392.6Semi standard non polar33892256
2-Ketohexanoic acid,1TBDMS,isomer #2CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O1513.1Semi standard non polar33892256
2-Ketohexanoic acid,2TBDMS,isomer #1CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1773.3Semi standard non polar33892256
2-Ketohexanoic acid,2TBDMS,isomer #1CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1663.6Standard non polar33892256
2-Ketohexanoic acid,2TBDMS,isomer #1CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1668.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Ketohexanoic acid GC-EI-TOF (Non-derivatized)splash10-000j-8920000000-9e106a172aeaca6001ea2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Ketohexanoic acid GC-EI-TOF (Non-derivatized)splash10-000j-8920000000-9e106a172aeaca6001ea2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ketohexanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-e0cebba0b69620390c092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ketohexanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-007a-9300000000-87b7d0f0e16ba9e212cb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ketohexanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Ketohexanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-01p9-9500000000-5145cab306a85b6e9d7f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Ketohexanoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-9000000000-4cd8f41133a4d23b1d4c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Ketohexanoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-01qj-9100000000-caf6abf28104b7765cef2012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 10V, Positive-QTOFsplash10-01qi-4900000000-702612249f0615c78f6b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 20V, Positive-QTOFsplash10-0btm-9300000000-d02ff05157ccb2f8d4162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-dfcf44ed2c628b6b914a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 10V, Negative-QTOFsplash10-004i-3900000000-d751dca8c7b118a0dea92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 20V, Negative-QTOFsplash10-01s9-9500000000-c04f00087e8e89956b262017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-4a26ce3589a801c4bcef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 10V, Positive-QTOFsplash10-052u-9000000000-a1430045d6ae5d2e494c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 20V, Positive-QTOFsplash10-0a4l-9000000000-d6e0a51fd3a4a90d9ceb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-ed2b82d47ad4721d3a012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 10V, Negative-QTOFsplash10-004i-0900000000-8be0a8820bd022f7267b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 20V, Negative-QTOFsplash10-001i-9000000000-761b5c64b393cb442dcc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 40V, Negative-QTOFsplash10-066u-9000000000-1763f75b095d5d429e5b2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1620931
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 ]