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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:10 UTC
Update Date2023-02-21 17:20:17 UTC
HMDB IDHMDB0031295
Secondary Accession Numbers
  • HMDB31295
Metabolite Identification
Common NameEthyl pentyl ketone
DescriptionEthyl pentyl ketone, also known as 3-oxooctane or EAK, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, ethyl pentyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group. Ethyl pentyl ketone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Ethyl pentyl ketone has been detected, but not quantified, in cardamoms and lemons. This could make ethyl pentyl ketone a potential biomarker for the consumption of these foods. Ethyl pentyl ketone, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1677000017
Synonyms
ValueSource
3-OxooctaneChEBI
Amyl ethyl ketoneChEBI
EAKChEBI
Ethyl amyl ketoneChEBI
Ethyl N-amyl ketoneChEBI
Ethyl N-pentyl ketoneChEBI
N-Amyl ethyl ketoneChEBI
Octan-3-oneChEBI
3-OctanonHMDB
3-OctanoneHMDB
Ethyl N-amylketoneHMDB
FEMA 2803HMDB
N-Octanone-3HMDB
Ethyl pentyl ketoneChEBI
Chemical FormulaC8H16O
Average Molecular Weight128.212
Monoisotopic Molecular Weight128.120115134
IUPAC Nameoctan-3-one
Traditional Name3-octanone
CAS Registry Number106-68-3
SMILES
CCCCCC(=O)CC
InChI Identifier
InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3
InChI KeyRHLVCLIPMVJYKS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-23.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point167.00 to 170.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.6 mg/mL at 20 °CNot Available
LogP2.506 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.48 g/LALOGPS
logP2.61ALOGPS
logP2.84ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.25 m³·mol⁻¹ChemAxon
Polarizability16.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.15331661259
DarkChem[M-H]-127.08731661259
DeepCCS[M+H]+134.37230932474
DeepCCS[M-H]-131.56730932474
DeepCCS[M-2H]-168.27630932474
DeepCCS[M+Na]+143.10930932474
AllCCS[M+H]+133.332859911
AllCCS[M+H-H2O]+129.132859911
AllCCS[M+NH4]+137.232859911
AllCCS[M+Na]+138.332859911
AllCCS[M-H]-135.932859911
AllCCS[M+Na-2H]-138.632859911
AllCCS[M+HCOO]-141.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl pentyl ketoneCCCCCC(=O)CC1251.2Standard polar33892256
Ethyl pentyl ketoneCCCCCC(=O)CC954.5Standard non polar33892256
Ethyl pentyl ketoneCCCCCC(=O)CC972.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethyl pentyl ketone,1TMS,isomer #1CC=C(CCCCC)O[Si](C)(C)C1158.9Semi standard non polar33892256
Ethyl pentyl ketone,1TMS,isomer #1CC=C(CCCCC)O[Si](C)(C)C1152.1Standard non polar33892256
Ethyl pentyl ketone,1TMS,isomer #2CCCCC=C(CC)O[Si](C)(C)C1167.3Semi standard non polar33892256
Ethyl pentyl ketone,1TMS,isomer #2CCCCC=C(CC)O[Si](C)(C)C1151.5Standard non polar33892256
Ethyl pentyl ketone,1TBDMS,isomer #1CC=C(CCCCC)O[Si](C)(C)C(C)(C)C1376.2Semi standard non polar33892256
Ethyl pentyl ketone,1TBDMS,isomer #1CC=C(CCCCC)O[Si](C)(C)C(C)(C)C1344.2Standard non polar33892256
Ethyl pentyl ketone,1TBDMS,isomer #2CCCCC=C(CC)O[Si](C)(C)C(C)(C)C1379.0Semi standard non polar33892256
Ethyl pentyl ketone,1TBDMS,isomer #2CCCCC=C(CC)O[Si](C)(C)C(C)(C)C1341.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized)splash10-05bf-9000000000-781901ca764a5f8411042017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized)splash10-05bf-9000000000-c5ad6888f5d8235bbcbd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized)splash10-05bf-9000000000-781901ca764a5f8411042018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized)splash10-05bf-9000000000-c5ad6888f5d8235bbcbd2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl pentyl ketone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-c2c048174c4c8d3d82282016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl pentyl ketone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-05i3-9000000000-91e0504d51c6adb6a6dc2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Positive-QTOFsplash10-004i-1900000000-ffaa377d52d739ba9f442015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Positive-QTOFsplash10-0a6r-9400000000-f7381b3ecccb7b1c99362015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Positive-QTOFsplash10-0a4l-9000000000-7f234320bd480d9871b62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Negative-QTOFsplash10-004i-1900000000-e4a3fd9e0a2d4bb131552015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Negative-QTOFsplash10-004i-7900000000-5ba281eb40ef59122e532015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Negative-QTOFsplash10-0avi-9100000000-0ccdc24b3e039027a03a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Negative-QTOFsplash10-004i-0900000000-e8448bc978ba2df6edde2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Negative-QTOFsplash10-056r-9300000000-2bbefe45e3391c2f9e162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Negative-QTOFsplash10-0a4i-9000000000-07772b5c8be44e02f68e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Positive-QTOFsplash10-05tf-9000000000-7376e27c0ccc450d2e872021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Positive-QTOFsplash10-052f-9000000000-9a9cbad9068425131f562021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Positive-QTOFsplash10-052f-9000000000-390b61087232d1c443692021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005050
KNApSAcK IDC00034765
Chemspider ID215929
KEGG Compound IDC17145
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Octanone
METLIN IDNot Available
PubChem Compound246728
PDB IDNot Available
ChEBI ID80946
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004231
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .