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Record Information
Version3.6
Creation Date2006-08-13 23:51:34 UTC
Update Date2016-02-11 01:06:46 UTC
HMDB IDHMDB04669
Secondary Accession NumbersNone
Metabolite Identification
Common Name9-OxoODE
Description9-OxoODE results from oxidation of the allylic hydroxyl of either 9(S)- or 9(R)-HODE. Rabbit reticulocyte plasma and mitochondrial membranes contain both 9- and 13-oxoODEs, representing about 2% of the total linoleate residues in the membranes. Most of these oxidized linoleate residues are esterified to membrane lipids.
Structure
Thumb
Synonyms
ValueSource
9-keto-10E,12Z-Octadecadienoic acidChEBI
9-KODEChEBI
9-oxo-10E,12Z-Octadecadienoic acidChEBI
9-OxoODEChEBI
9-keto-10E,12Z-OctadecadienoateGenerator
(10E,12Z)-9-Oxooctadeca-10,12-dienoateGenerator
9-oxo-10E,12Z-OctadecadienoateGenerator
9-oxo-ODEHMDB
Chemical FormulaC18H30O3
Average Molecular Weight294.429
Monoisotopic Molecular Weight294.219494826
IUPAC Name(10E,12Z)-9-oxooctadeca-10,12-dienoic acid
Traditional Name9-OxoODE
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C=C/C(=O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+
InChI KeyInChIKey=LUZSWWYKKLTDHU-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
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • 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
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 Solubility0.0013 mg/mLALOGPS
logP5.62ALOGPS
logP5.6ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.61ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity89.14 m3·mol-1ChemAxon
Polarizability35.92 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
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00241 +/- 0.00029 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00241 +/- 0.00029 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0053 +/- 0.0027 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00063 +/- 0.00011 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
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 IDFDB023397
KNApSAcK IDNot Available
Chemspider ID8014803
KEGG Compound IDC14766
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04669
Metagene LinkHMDB04669
METLIN IDNot Available
PubChem Compound9839084
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available