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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:16:06 UTC
Update Date2023-02-21 17:29:49 UTC
HMDB IDHMDB0060287
Secondary Accession Numbers
  • HMDB60287
Metabolite Identification
Common Name4-Hydroperoxy-2-nonenal
Description4-Hydroperoxy-2-nonenal belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, 4-hydroperoxy-2-nonenal is considered to be a fatty aldehyde lipid molecule. 4-Hydroperoxy-2-nonenal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1677000589
Synonyms
ValueSource
4-Hydroxyperoxy-trans-2-nonenalHMDB
Chemical FormulaC9H16O3
Average Molecular Weight172.2215
Monoisotopic Molecular Weight172.109944378
IUPAC Name(2E)-4-hydroperoxynon-2-enal
Traditional Name(2E)-4-hydroperoxynon-2-enal
CAS Registry NumberNot Available
SMILES
CCCCCC(OO)\C=C\C=O
InChI Identifier
InChI=1S/C9H16O3/c1-2-3-4-6-9(12-11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+
InChI KeyTVNYLRYVAZWBEH-FNORWQNLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentMedium-chain aldehydes
Alternative Parents
Substituents
  • Medium-chain aldehyde
  • Allylic hydroperoxide
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Hydroperoxide
  • Alkyl hydroperoxide
  • Peroxol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.18 g/LALOGPS
logP1.91ALOGPS
logP2.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity47.91 m³·mol⁻¹ChemAxon
Polarizability19.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.55931661259
DarkChem[M-H]-141.07931661259
DeepCCS[M+H]+141.23430932474
DeepCCS[M-H]-138.01930932474
DeepCCS[M-2H]-175.61330932474
DeepCCS[M+Na]+150.71930932474
AllCCS[M+H]+142.732859911
AllCCS[M+H-H2O]+138.832859911
AllCCS[M+NH4]+146.432859911
AllCCS[M+Na]+147.532859911
AllCCS[M-H]-141.632859911
AllCCS[M+Na-2H]-143.232859911
AllCCS[M+HCOO]-145.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroperoxy-2-nonenalCCCCCC(OO)\C=C\C=O2431.4Standard polar33892256
4-Hydroperoxy-2-nonenalCCCCCC(OO)\C=C\C=O1310.9Standard non polar33892256
4-Hydroperoxy-2-nonenalCCCCCC(OO)\C=C\C=O1381.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroperoxy-2-nonenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-6900000000-c9402f289b5f4bad794b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroperoxy-2-nonenal 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 - 4-Hydroperoxy-2-nonenal 10V, Positive-QTOFsplash10-00di-0900000000-5a43df684b29e2f408ef2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 20V, Positive-QTOFsplash10-0ab9-9700000000-29995493f38834cf5ef22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 40V, Positive-QTOFsplash10-0a4l-9000000000-62b7d7120cfa223d614f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 10V, Negative-QTOFsplash10-00di-1900000000-bdc2ca77ce700e7c97a62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 20V, Negative-QTOFsplash10-00di-3900000000-2e68a262c61bbd1340192017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 40V, Negative-QTOFsplash10-0006-9200000000-bd6fe6d216c0f47210f72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 10V, Positive-QTOFsplash10-05fu-9300000000-f69c1cfbffe3ccd2fc2f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 20V, Positive-QTOFsplash10-0a4i-9000000000-2d20026b54da8a35bddb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 40V, Positive-QTOFsplash10-0a4u-9000000000-9826012832cebf72b6972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 10V, Negative-QTOFsplash10-00fr-1900000000-03fb0e183eba59f939cc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 20V, Negative-QTOFsplash10-05n3-3900000000-387e37aaabf071c724f32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroperoxy-2-nonenal 40V, Negative-QTOFsplash10-07c7-9100000000-a203720b38bc6bde126a2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6435432
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 References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]