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Record Information
Version3.6
Creation Date2008-09-11 00:41:42 UTC
Update Date2016-02-11 01:08:08 UTC
HMDB IDHMDB06940
Secondary Accession NumbersNone
Metabolite Identification
Common Name9(S)-HPODE
Description9(S)-HPODE is an intermediate in Linoleic acid metabolism(KEGG ID C14827). It is the second to last step in the synthesis of 9-oxoODE, and is converted from linoleate via the enzyme arachidonate 5-lipoxygenase [EC:1.13.11.34]. It is then converted to 9(S)-HODE.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H32O4
Average Molecular Weight312.4443
Monoisotopic Molecular Weight312.230059512
IUPAC Name(10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid
Traditional Name9(S)-hpode
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C=C/C(CCCCCCCC(O)=O)OO
InChI Identifier
InChI=1S/C18H32O4/c1-2-3-4-5-6-8-11-14-17(22-21)15-12-9-7-10-13-16-18(19)20/h6,8,11,14,17,21H,2-5,7,9-10,12-13,15-16H2,1H3,(H,19,20)/b8-6-,14-11+
InChI KeyInChIKey=JGUNZIWGNMQSBM-ZJHFMPGASA-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 DescriptorsNot Available
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
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 Solubility0.0037 mg/mLALOGPS
logP5.74ALOGPS
logP5.64ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
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
Polarizability37.49 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
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00514 +/- 0.0038 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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID4944227
KEGG Compound IDC14827
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06940
Metagene LinkHMDB06940
METLIN IDNot Available
PubChem Compound6439847
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595
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