You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-08-13 06:22:37 UTC
Update Date2016-02-11 01:06:27 UTC
HMDB IDHMDB03871
Secondary Accession NumbersNone
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 15-1ipoxygenase 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
Thumb
Synonyms
ValueSource
(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoateChEBI
(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acidChEBI
(9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoic acidChEBI
13S-Hydroperoxy-9Z,11E-octadecadienoic acidChEBI
(9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoateGenerator
13S-Hydroperoxy-9Z,11E-octadecadienoateGenerator
(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
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 KeyInChIKey=JDSRHVWSAMTSSN-IRQZEAMPSA-N
Chemical Taxonomy
DescriptionThis compound 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
ClassLineolic acids and derivatives
Sub ClassNot Available
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Hydroperoxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Hydroperoxide
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0033 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.38 m3·mol-1ChemAxon
Polarizability37.15 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023240
KNApSAcK IDNot Available
Chemspider ID4444304
KEGG Compound IDC04717
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03871
Metagene LinkHMDB03871
METLIN IDNot Available
PubChem Compound5280720
PDB ID13S
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)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. [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