Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:19:54 UTC
Update Date2021-09-14 15:46:46 UTC
HMDB IDHMDB0013105
Secondary Accession Numbers
  • HMDB13105
Metabolite Identification
Common Nametrans-4,5-epoxy-2(E)-decenal
DescriptionPolyunsaturated fatty acids such as arachidonate and linoeate, while essential to health maintenance, are subject to random peroxidation by ambient oxygen, resulting in fragmented and reactive decomposition products. One prominent autoxidation product of either trilinolein or arachidonic acid is trans-4,5-epoxy-2(E)-decenal. This aldehyde is responsible for a pungent metallic flavor of decomposed lipids, with a detection threshold of 1.5 pg/l in air.1 trans-4,5-epoxy-2(E)-Decenal also reacts with nucleophiles (lysine amino groups) on proteins, leading to loss of cell function and viability.2 This reactive aldehyde is therefore a useful tool in elucidating the effects of peroxidative damage in experimental models.
Structure
Data?1582753089
Synonyms
ValueSource
4,5-EDEHMDB
4,5-Epoxy-2(e)-decenalHMDB
4,5-Epoxy-2-decenalHMDB
Chemical FormulaC10H16O2
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
IUPAC Name(2E)-3-(3-pentyloxiran-2-yl)prop-2-enal
Traditional Name(2E)-3-(3-pentyloxiran-2-yl)prop-2-enal
CAS Registry Number134454-31-2
SMILES
CCCCCC1OC1\C=C\C=O
InChI Identifier
InChI=1S/C10H16O2/c1-2-3-4-6-9-10(12-9)7-5-8-11/h5,7-10H,2-4,6H2,1H3/b7-5+
InChI KeyHIOMEXREAUSUBP-FNORWQNLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnals
Alternative Parents
Substituents
  • Enal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxide
  • Hydrocarbon derivative
  • Aldehyde
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP10(2.75) g/LALOGPS
logP10(2.28) g/LChemAxon
logS10(-3) g/LALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity49.01 m³·mol⁻¹ChemAxon
Polarizability19.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.68231661259
DarkChem[M-H]-138.85631661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - trans-4,5-epoxy-2(E)-decenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-9100000000-edfc10da5e5b4c3e41ef2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-4,5-epoxy-2(E)-decenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-4,5-epoxy-2(E)-decenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 10V, Positive-QTOFsplash10-014i-2900000000-c80bd42d8bb1ccbe7bf52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 20V, Positive-QTOFsplash10-00m0-9200000000-51193039508e0a0926c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 40V, Positive-QTOFsplash10-052f-9000000000-0fb2d44d44658556af002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 10V, Negative-QTOFsplash10-014i-2900000000-66a800172aa2b8cc760b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 20V, Negative-QTOFsplash10-014i-4900000000-4387c048b539b31a88312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 40V, Negative-QTOFsplash10-0006-9000000000-57e5fbfbb07b8dd64dee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 10V, Positive-QTOFsplash10-0avl-9200000000-88b28388f33e703d52d72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 20V, Positive-QTOFsplash10-053f-9000000000-05feffc6b5294b36be522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 40V, Positive-QTOFsplash10-052o-9000000000-ccb1dfd717c58b7912f62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 10V, Negative-QTOFsplash10-016r-0900000000-c1ca78adff348fdd9eb12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 20V, Negative-QTOFsplash10-066r-8900000000-75f0f1ef34881748471a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-4,5-epoxy-2(E)-decenal 40V, Negative-QTOFsplash10-05mo-9000000000-3a283988ba5d7940ccb02021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013738
KNApSAcK IDC00053842
Chemspider ID4509321
KEGG Compound IDNot Available
BioCyc IDCPD-9824
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352429
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available