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 Date2014-04-16 20:46:29 UTC
Update Date2016-02-11 08:25:59 UTC
HMDB IDHMDB61708
Secondary Accession NumbersNone
Metabolite Identification
Common Name13-HODE
Description13-Hydroxyoctadecadienoic acid (13-HODE) is the major lipoxygenation product derived from linoleic acid. It has been shown to be involved in cell proliferation and differentiation in a number of systems. 13-HODE is found to be produced by prostate tumors and cell lines and researchers believe there is a link between linoleic acid metabolism and the development or progression of prostate cancer. (PMID: 9367845 )
Structure
Thumb
Synonyms
ValueSource
(13S)-Hydroxyoctadecadienoic acidChEBI
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acidChEBI
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acidChEBI
(13S)-HydroxyoctadecadienoateGenerator
(9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoateGenerator
(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoateGenerator
(9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoateGenerator
13(S) HODEHMDB
13-HODEHMDB
13-HydroxyoctadecadienoateHMDB
13-Hydroxyoctadecadienoic acidHMDB
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid
Traditional Name13-hydroxyoctadecadienoic acid
CAS Registry NumberNot Available
SMILES
CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1
InChI KeyInChIKey=HNICUWMFWZBIFP-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
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.003 mg/mLALOGPS
logP5.88ALOGPS
logP5.19ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.03 m3·mol-1ChemAxon
Polarizability37.26 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB61708
Metagene LinkHMDB61708
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Spindler SA, Sarkar FH, Sakr WA, Blackburn ML, Bull AW, LaGattuta M, Reddy RG: Production of 13-hydroxyoctadecadienoic acid (13-HODE) by prostate tumors and cell lines. Biochem Biophys Res Commun. 1997 Oct 29;239(3):775-81. [9367845 ]