Showing metabocard for 13-L-Hydroperoxylinoleic acid (BMDB0003871)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:24 UTC
Update Date2020-04-22 15:12:51 UTC
BMDB IDBMDB0003871
Secondary Accession Numbers
  • BMDB03871
Metabolite Identification
Common Name13-L-Hydroperoxylinoleic acid
Description13-L-Hydroperoxylinoleic acid, also known as 13(S)-hpode or linoleic acid 13(S)-hydroperoxide, 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. 13-L-Hydroperoxylinoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
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 Weight312.4443
Monoisotopic Molecular Weight312.230059512
IUPAC Name(9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoic acid
Traditional Name13-HpODE
CAS Registry Number33964-75-9
SMILES
CCCCC[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lv-5930000000-8cce9b35b53a054c4f06View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00v0-9833000000-b058eeece5c0d35efc4dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0192000000-8901325cb7e062b9df46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr2-4690000000-a7a0479469a6409a29c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g4-9520000000-94dc42e5d4d562d9e058View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0049000000-f858b43abe2e420068f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01oy-2292000000-43fbe3658909492d215dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9340000000-9de0efa9f8357ac365c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0029000000-6109e2991a8f70f9b092View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1291000000-7a8262a60fa6aac089acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01vt-9180000000-ecc5c55edc141deff801View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0491000000-14168164306c962c44e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tj-2960000000-0d34e09e6afa84c664c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9300000000-e52ec41d50c5aa80e190View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003871
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030136
KNApSAcK IDC00000394
Chemspider ID4444304
KEGG Compound IDC04717
BioCyc ID13-HYDROPEROXYOCTADECA-911-DIENOATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280720
PDB IDNot Available
ChEBI ID15655
References
Synthesis ReferenceBaba, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available