13(S)-Hydroperoxylinolenic acid (CHEM023722)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:15:09 UTC
Update Date2016-11-09 01:17:46 UTC
Accession NumberCHEM023722
Identification
Common Name13(S)-Hydroperoxylinolenic acid
ClassSmall Molecule
DescriptionA lipid hydroperoxide, obtained by the formal substitution of a hydrogen at position 9 of (9Z,11E,15Z)-octadeca-9,11,15-trienoic acid by a hydroperoxy group (the 13S-stereoisomer). Biochemically, it is an 18-C rearrangement and primary peroxidation product of alpha-linolenic acid, an intermediate in prostaglandin and leukotriene metabolism, and the substrate of the lyase enzyme hydroperoxide dehydratase.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(9Z,11E,15Z)-(13S)-13-Hydroperoxyoctadeca-9,11,15-trienoic acidChEBI
(9Z,11E,15Z)-(13S)-Hydroperoxyoctadeca-9,11,15-trienoateChEBI
13(S)-HPOTChEBI
13(S)-HpOTrEChEBI
13(S)-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoic acidChEBI
13(S)-Hydroperoxylinolenic acidChEBI
13-HPOTChEBI
13S-HpOTrEChEBI
13S-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoic acidChEBI
13S-Hydroperoxy-9Z,11E,15Z-octadecatrienoic acidChEBI
(9Z,11E,15Z)-(13S)-13-Hydroperoxyoctadeca-9,11,15-trienoateGenerator
(9Z,11E,15Z)-(13S)-Hydroperoxyoctadeca-9,11,15-trienoic acidGenerator
13(S)-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoateGenerator
13(S)-HydroperoxylinolenateGenerator
13S-Hydroperoxy-9(Z),11(e),15(Z)-octadecatrienoateGenerator
13S-Hydroperoxy-9Z,11E,15Z-octadecatrienoateGenerator
(9Z,11E,13S,15Z)-13-Hydroperoxyoctadeca-9,11,15-trienoateGenerator
13-Hydroperoxy-9,11,15-octadecatrienoic acidMeSH
Chemical FormulaC18H30O4
Average Molecular Mass310.428 g/mol
Monoisotopic Mass310.214 g/mol
CAS Registry Number67597-26-6
IUPAC Name(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid
Traditional Name13(S)-HpOTrE
SMILESCC\C=C/C[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O
InChI IdentifierInChI=1S/C18H30O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h3,7,9,11-12,15,17,21H,2,4-6,8,10,13-14,16H2,1H3,(H,19,20)/b9-7-,11-3-,15-12+/t17-/m0/s1
InChI KeyUYQGVDXDXBAABN-FQSPHKRJSA-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 Solubility0.0042 g/LALOGPS
logP5.46ALOGPS
logP5.28ChemAxon
logS-4.9ALOGPS
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 Count14ChemAxon
Refractivity92.5 m³·mol⁻¹ChemAxon
Polarizability36.78 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0295000000-7bceeb67ef82db3c2c75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-4981000000-0e947fcae49e860e5eacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldm-9620000000-93f1b98e9f06d2dd75b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1149000000-565fa404c042d0829423Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aos-3393000000-a59a598dde5117fbff42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9330000000-8f6b878a5bebf4db37d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0591000000-d0bc121c45f15c6aae68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-1950000000-9f7031f4e0f47c858c26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o3-9500000000-cb42787800e5a6ce9cd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-0096000000-b41fadcfdc13a28d6ea4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1190000000-f0708581583845bef578Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-9150000000-649b6a690207294ae2e8Spectrum
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 IDHMDB0301803
FooDB IDFDB001431
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-725
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4593698
ChEBI ID48905
PubChem Compound ID5497123
Kegg Compound IDC04785
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=7893744