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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:19:33 UTC
Update Date2022-03-07 03:17:54 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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0037 g/lALOGPS
LogP5.74ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.09731661259
DarkChem[M-H]-180.6431661259
DeepCCS[M+H]+187.71330932474
DeepCCS[M-H]-185.31830932474
DeepCCS[M-2H]-219.50230932474
DeepCCS[M+Na]+194.57130932474
AllCCS[M+H]+184.732859911
AllCCS[M+H-H2O]+181.832859911
AllCCS[M+NH4]+187.432859911
AllCCS[M+Na]+188.132859911
AllCCS[M-H]-182.732859911
AllCCS[M+Na-2H]-184.332859911
AllCCS[M+HCOO]-186.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCCCCC(O)=O)OO3707.1Standard polar33892256
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCCCCC(O)=O)OO2344.7Standard non polar33892256
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCCCCC(O)=O)OO2413.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid,1TMS,isomer #1CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OO2611.3Semi standard non polar33892256
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid,1TBDMS,isomer #1CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OO2845.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mo-9450000000-9f9ce00144bf1470f46e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-01di-9533000000-12686f18ef669f1398672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 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 - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 10V, Positive-QTOFsplash10-0002-0192000000-4f03d2f2bc968d55402e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 20V, Positive-QTOFsplash10-066s-5590000000-fbcb5ed3adc3871bd0fa2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 40V, Positive-QTOFsplash10-0536-9320000000-3472d061677ef7793c532017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 10V, Negative-QTOFsplash10-03di-0149000000-4a41775c40edba3c555e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 20V, Negative-QTOFsplash10-01ox-1693000000-822907c2888d3b6c86e72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 40V, Negative-QTOFsplash10-0abc-9730000000-1e8118a529f287df673d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 10V, Negative-QTOFsplash10-03di-0059000000-401bcd66b7485f93725e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 20V, Negative-QTOFsplash10-03fr-0294000000-545cafa8f501f8c695462021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 40V, Negative-QTOFsplash10-0553-5970000000-a710051ee52e3fa925c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 10V, Positive-QTOFsplash10-03fr-1392000000-aea7db3f968af10d17252021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 20V, Positive-QTOFsplash10-00c0-5940000000-1c5206d809c856cefc972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid 40V, Positive-QTOFsplash10-001i-9300000000-065159558ba433dab8cd2021-09-23Wishart 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 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 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.