(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate (CHEM041753)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:41:08 UTC
Update Date2016-11-09 01:22:32 UTC
Accession NumberCHEM041753
Identification
Common Name(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoateChEBI
(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acidChEBI
13S-Hydroperoxy-9Z,11E-octadecadienoic acidChEBI
13(S)-HPODEKegg
13S-Hydroperoxy-9Z,11E-octadecadienoateGenerator
13-L-HydroperoxylinoleateGenerator
(9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoic acidHMDB
(9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoateHMDB
(13S,9Z,11E)-13-Hydroperoxy-9,11-octadecadienoateHMDB
(13S,9Z,11E)-13-Hydroperoxy-9,11-octadecadienoic acidHMDB
13(S)-Hydroperoxy-9Z,11E-octadecadienoateHMDB
13(S)-Hydroperoxy-9Z,11E-octadecadienoic acidHMDB
13(S)-Hydroperoxylinoleic acidHMDB
13-HPODHMDB
13-HpodeHMDB
13-L-Hydroperoxy-9-cis,11-trans-octadecadienoateHMDB
13-L-Hydroperoxy-9-cis,11-trans-octadecadienoic acidHMDB
13-L-Hydroperoxy-cis-9,trans-11-octadecadienoateHMDB
13-L-Hydroperoxy-cis-9,trans-11-octadecadienoic acidHMDB
HpodeHMDB
Linoleic acid 13(S)-hydroperoxideHMDB
13-Hydroperoxy-9,11-octadecadienoic acidHMDB
13-Hydroperoxy-9,11-octadecadienoic acid, (Z,e)-isomerHMDB
Chemical FormulaC18H32O4
Average Molecular Mass312.444 g/mol
Monoisotopic Mass312.230 g/mol
CAS Registry NumberNot Available
IUPAC Name(9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoic acid
Traditional Name13-HpODE
SMILESCCCCC[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O
InChI IdentifierInChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7-,15-12+/t17-/m0/s1
InChI KeyJDSRHVWSAMTSSN-IRQZEAMPSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP5.76ALOGPS
logP5.64ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
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
Polarizability37.14 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lv-5930000000-8cce9b35b53a054c4f06Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00v0-9833000000-b058eeece5c0d35efc4dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0192000000-8901325cb7e062b9df46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr2-4690000000-a7a0479469a6409a29c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g4-9520000000-94dc42e5d4d562d9e058Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0049000000-f858b43abe2e420068f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01oy-2292000000-43fbe3658909492d215dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9340000000-9de0efa9f8357ac365c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0029000000-6109e2991a8f70f9b092Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1291000000-7a8262a60fa6aac089acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01vt-9180000000-ecc5c55edc141deff801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0491000000-14168164306c962c44e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tj-2960000000-0d34e09e6afa84c664c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9300000000-e52ec41d50c5aa80e190Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003871
FooDB IDFDB030136
Phenol Explorer IDNot Available
KNApSAcK IDC00000394
BiGG IDNot Available
BioCyc ID13-HYDROPEROXYOCTADECA-911-DIENOATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444304
ChEBI ID15655
PubChem Compound ID5280720
Kegg Compound IDC04717
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Baba, N.; Yoneda, K.; Iwasa, J.; Tahara, S. Asymmetric synthesis of diacylglycerophosphocholine hydroperoxide VIa, lipoxygenase-catalyzed hydroperoxidation of linoleic acid and lipase-catalyzed enantioselective stearoylation of 2-O-benzoyl-1,3-propanediol. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1992), 31B(12), 824-7.
2. Kuhn H: Biosynthesis, metabolization and biological importance of the primary 15-lipoxygenase metabolites 15-hydro(pero)XY-5Z,8Z,11Z,13E-eicosatetraenoic acid and 13-hydro(pero)XY-9Z,11E-octadecadienoic acid. Prog Lipid Res. 1996 Sep;35(3):203-26.