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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:19:33 UTC
Update Date2019-07-23 07:18:31 UTC
HMDB IDHMDB0062434
Secondary Accession Numbers
  • HMDB62434
Metabolite Identification
Common Name(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid
Description(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid, also known as 9(S)-HPOD or (9S,10E,12Z)-9-Hydroperoxy-10,12-octadecadienoate, is classified as a lineolic acid or a Lineolic acid derivative. Lineolic acids are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid is considered to be practically insoluble (in water) and acidic. (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid is an octadecanoid lipid molecule. (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid can be found throughout numerous foods such as Barley, Prunus (Cherry, Plum), Cherimoya, and Prairie turnips
Structure
Data?1563866311
Synonyms
ValueSource
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acidChEBI
(9S,10E,12Z)-9-Hydroperoxy-10,12-octadecadienoic acidChEBI
9(S)-HPODChEBI
(9S,10E,12Z)-9-Hydroperoxy-10,12-octadecadienoateKegg
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoateGenerator
(9S,10E,12Z,15Z)-9-Hydroperoxy-10,12,15-octadecadienoic acidGenerator
9-Hydroperoxy-11,12-octadecadienoic acidMeSH, HMDB
9-Hydroperoxy-11,12-octadecadienoic acid, (e,Z)-isomerMeSH, HMDB
9-Hydroperoxy-11,12-octadecadienoic acid, (Z,e)-isomerMeSH, HMDB
9-HPODEMeSH, HMDB
Chemical FormulaC18H32O4
Average Molecular Weight312.45
Monoisotopic Molecular Weight312.23005951
IUPAC Name(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid
Traditional Name9-HpODE
CAS Registry Number29774-12-7
SMILES
[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCCCCC(O)=O)OO
InChI Identifier
InChI=1S/C18H32O4/c1-2-3-4-5-6-8-11-14-17(22-21)15-12-9-7-10-13-16-18(19)20/h6,8,11,14,17,21H,2-5,7,9-10,12-13,15-16H2,1H3,(H,19,20)/b8-6-,14-11+/t17-/m1/s1
InChI KeyJGUNZIWGNMQSBM-UINYOVNOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Hydroperoxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Allylic hydroperoxide
  • Hydroperoxide
  • Carboxylic acid derivative
  • Alkyl hydroperoxide
  • Carboxylic acid
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0037 g/lALOGPS
LogP5.74ALOGPS
Predicted Properties
PropertyValueSource
logP5.74ALOGPS
logP5.64ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.38 m³·mol⁻¹ChemAxon
Polarizability38.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mo-9450000000-9f9ce00144bf1470f46eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01di-9533000000-12686f18ef669f139867Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0192000000-4f03d2f2bc968d55402eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066s-5590000000-fbcb5ed3adc3871bd0faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9320000000-3472d061677ef7793c53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0149000000-4a41775c40edba3c555eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-1693000000-822907c2888d3b6c86e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9730000000-1e8118a529f287df673dSpectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB030133
KNApSAcK IDC00000393
Chemspider IDNot Available
KEGG Compound IDC14827
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID34498
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.