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(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate (FDB030133)

Record Information
Version1.0
Creation date2015-05-07 18:40:44 UTC
Update date2019-11-26 03:21:36 UTC
Primary IDFDB030133
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate
Description(9s,10e,12z,15z)-9-hydroperoxy-10,12,15-octadecadienoate, also known as 9(S)-hpod or 9-hydroperoxy-11,12-octadecadienoic acid, belongs to lineolic acids and derivatives class of compounds. Those 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. Thus, (9s,10e,12z,15z)-9-hydroperoxy-10,12,15-octadecadienoate is considered to be an octadecanoid lipid molecule (9s,10e,12z,15z)-9-hydroperoxy-10,12,15-octadecadienoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (9s,10e,12z,15z)-9-hydroperoxy-10,12,15-octadecadienoate can be found in a number of food items such as burdock, oat, parsnip, and cocoa bean, which makes (9s,10e,12z,15z)-9-hydroperoxy-10,12,15-octadecadienoate a potential biomarker for the consumption of these food products.
CAS Number29774-12-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0037 g/LALOGPS
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
Chemical FormulaC18H32O4
IUPAC name(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid
InChI IdentifierInChI=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
Isomeric SMILES[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCCCCC(O)=O)OO
Average Molecular Weight312.45
Monoisotopic Molecular Weight312.23005951
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00mo-9450000000-9f9ce00144bf1470f46eSpectrum
Predicted GC-MS(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01di-9533000000-12686f18ef669f139867Spectrum
Predicted GC-MS(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0192000000-4f03d2f2bc968d55402e2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066s-5590000000-fbcb5ed3adc3871bd0fa2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9320000000-3472d061677ef7793c532017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0149000000-4a41775c40edba3c555e2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-1693000000-822907c2888d3b6c86e72017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9730000000-1e8118a529f287df673d2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0059000000-401bcd66b7485f93725e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-0294000000-545cafa8f501f8c695462021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0553-5970000000-a710051ee52e3fa925c52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-1392000000-aea7db3f968af10d17252021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00c0-5940000000-1c5206d809c856cefc972021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9300000000-065159558ba433dab8cd2021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference