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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 06:22:37 UTC
Update Date2021-09-14 15:46:58 UTC
HMDB IDHMDB0003871
Secondary Accession Numbers
  • HMDB03871
Metabolite Identification
Common Name13-L-Hydroperoxylinoleic acid
Description13-L-Hydroperoxylinoleic acid (13(S)-HPODE) is one of the primary products of the major polyunsaturated fatty acids (linoleic acid and arachidonic acid) from the 15-lipoxygenase pathway (EC 1.13.11.31). 13(S)-HPODE is a rather unstable metabolite and is rapidly metabolized to more stable secondary products such as diverse forms of hydroxy fatty acids (via reduction of the hydroperoxy group), alkoxy radicals (via homolytic cleavage of the peroxy group), forms of dihydro(pero)xy fatty acids (via lipoxygenase-catalysed double and triple oxygenation), or epoxy leukotrienes (via a hydrogen abstraction from a doubly allylic methylene group and a homolytic cleavage of the hydroperoxy group) (PMID: 9082450 ).
Structure
Data?1588268468
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP10(5.76) g/LALOGPS
logP10(5.64) g/LChemAxon
logS10(-5) g/LALOGPS
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
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]+183.66131661259
DarkChem[M-H]-185.08331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
13-L-Hydroperoxylinoleic acidCCCCC[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O3823.1Standard polar33892256
13-L-Hydroperoxylinoleic acidCCCCC[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O2336.1Standard non polar33892256
13-L-Hydroperoxylinoleic acidCCCCC[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O2502.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
13-L-Hydroperoxylinoleic acid,1TMS,isomer #1CCCCC[C@@H](/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)OO2610.1Semi standard non polar33892256
13-L-Hydroperoxylinoleic acid,1TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OO2843.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 13-L-Hydroperoxylinoleic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lv-5930000000-8cce9b35b53a054c4f062017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13-L-Hydroperoxylinoleic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00v0-9833000000-b058eeece5c0d35efc4d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13-L-Hydroperoxylinoleic 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 - 13-L-Hydroperoxylinoleic acid 10V, Positive-QTOFsplash10-0002-0192000000-8901325cb7e062b9df462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 20V, Positive-QTOFsplash10-0fr2-4690000000-a7a0479469a6409a29c62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 40V, Positive-QTOFsplash10-05g4-9520000000-94dc42e5d4d562d9e0582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 10V, Negative-QTOFsplash10-03di-0049000000-f858b43abe2e420068f42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 20V, Negative-QTOFsplash10-01oy-2292000000-43fbe3658909492d215d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 40V, Negative-QTOFsplash10-0a4l-9340000000-9de0efa9f8357ac365c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 10V, Negative-QTOFsplash10-03di-0029000000-6109e2991a8f70f9b0922021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 20V, Negative-QTOFsplash10-01t9-1291000000-7a8262a60fa6aac089ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 40V, Negative-QTOFsplash10-01vt-9180000000-ecc5c55edc141deff8012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 10V, Positive-QTOFsplash10-01t9-0491000000-14168164306c962c44e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 20V, Positive-QTOFsplash10-01tj-2960000000-0d34e09e6afa84c664c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-L-Hydroperoxylinoleic acid 40V, Positive-QTOFsplash10-0a5c-9300000000-e52ec41d50c5aa80e1902021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00601 +/- 0.0055 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDC04717
MarkerDB IDNot Available
Good Scents IDNot Available
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)Download (PDF)
General References
  1. 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. [PubMed:9082450 ]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Converts arachidonic acid exclusively to 15S-hydroperoxyeicosatetraenoic acid, while linoleic acid is less well metabolized.
Gene Name:
ALOX15B
Uniprot ID:
O15296
Molecular weight:
72522.25
General function:
Involved in metal ion binding
Specific function:
Converts arachidonic acid to 15S-hydroperoxyeicosatetraenoic acid. Also acts on C-12 of arachidonate as well as on linoleic acid.
Gene Name:
ALOX15
Uniprot ID:
P16050
Molecular weight:
74803.795
Reactions
Linoleic acid + Oxygen → 13-L-Hydroperoxylinoleic aciddetails