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 Date2017-03-16 03:41:31 UTC
Update Date2021-09-14 14:57:31 UTC
HMDB IDHMDB0062281
Secondary Accession Numbers
  • HMDB62281
Metabolite Identification
Common Name11-HpODE
Description(11S)-11-hydroperoxylinoleic acid 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 (11S)-11-hydroperoxylinoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866290
Synonyms
ValueSource
(9Z,12Z)-(11S)-11-Hydroperoxyoctadeca-9,12-dienoateChEBI
(9Z,12Z)-(11S)-11-Hydroperoxyoctadeca-9,12-dienoic acidChEBI
(11S)-11-HydroperoxylinoleateGenerator
(9Z,11S,12Z)-11-Hydroperoxyoctadeca-9,12-dienoic acidChEBI, HMDB
(9Z,11S,12Z)-11-Hydroperoxyoctadeca-9,12-dienoateGenerator, HMDB
Chemical FormulaC18H32O4
Average Molecular Weight312.45
Monoisotopic Molecular Weight312.23005951
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
InChI=1S/C18H32O4/c1-2-3-4-8-11-14-17(22-21)15-12-9-6-5-7-10-13-16-18(19)20/h11-12,14-15,17,21H,2-10,13,16H2,1H3,(H,19,20)/b14-11-,15-12-/t17-/m0/s1
InChI KeyPLWDMWAXENHPLY-PDBSFCERSA-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

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0031 g/lALOGPS
LogP5.70ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.82831661259
DarkChem[M-H]-180.27231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11-HpODE[H]\C(CCCCC)=C(/[H])[C@]([H])(OO)C(\[H])=C(\[H])CCCCCCCC(O)=O3631.6Standard polar33892256
11-HpODE[H]\C(CCCCC)=C(/[H])[C@]([H])(OO)C(\[H])=C(\[H])CCCCCCCC(O)=O2355.5Standard non polar33892256
11-HpODE[H]\C(CCCCC)=C(/[H])[C@]([H])(OO)C(\[H])=C(\[H])CCCCCCCC(O)=O2423.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11-HpODE,1TMS,isomer #1CCCCC/C=C\[C@@H](/C=C\CCCCCCCC(=O)O[Si](C)(C)C)OO2485.7Semi standard non polar33892256
11-HpODE,1TBDMS,isomer #1CCCCC/C=C\[C@@H](/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OO2723.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11-HpODE GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9750000000-0218bff293abff2362c82017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-HpODE GC-MS (1 TMS) - 70eV, Positivesplash10-009i-9543000000-3e6d4d53f4c1cb7f61c32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-HpODE 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 - 11-HpODE 10V, Positive-QTOFsplash10-0002-0192000000-9d868daca44a20cb72452017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 20V, Positive-QTOFsplash10-0frt-7591000000-1ebb147af324754835f82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 40V, Positive-QTOFsplash10-052g-9420000000-93814a28b5aa786d007e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 10V, Negative-QTOFsplash10-03di-0049000000-feb6ca9a55b6aadce2472017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 20V, Negative-QTOFsplash10-01oy-2393000000-3e2c018aebc95d6958b82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 40V, Negative-QTOFsplash10-0a4m-9530000000-c29f39797afd88dce7442017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 10V, Positive-QTOFsplash10-03fr-1492000000-b3aad53e9d0c9cbd671b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 20V, Positive-QTOFsplash10-01ta-4940000000-b9b5e7d58c93a32acb012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 40V, Positive-QTOFsplash10-05al-9600000000-1ee2f7ec09e8655335ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 10V, Negative-QTOFsplash10-03di-0029000000-2cef4dfdbf17a93b9ec62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 20V, Negative-QTOFsplash10-01tc-1192000000-7fedbab0e18c8bcb322d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-HpODE 40V, Negative-QTOFsplash10-0096-2890000000-124d0762ff6e005a887d2021-09-24Wishart LabView Spectrum
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07338
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281026
PDB IDNot Available
ChEBI ID15657
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. 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.