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Record Information
Version4.0
Creation Date2006-08-13 23:30:18 UTC
Update Date2017-09-27 08:24:28 UTC
HMDB IDHMDB0004667
Secondary Accession Numbers
  • HMDB04667
  • HMDB06939
Metabolite Identification
Common Name13S-hydroxyoctadecadienoic acid
Description13-hydroxyoctadecadienoic acid (13-HODE) is synthesized in the body from linoleic acid. 13-HODE prevents cell adhesion to endothelial cells and can inhibit cancer metastasis. 13-HODE synthesis is enhanced by cyclic AMP. Gamma-linolenic acid, a desaturated metabolite of linoleic acid, causes substantial stimulation of 13-HODE synthesis. A fall in gamma-linolenic acid synthesis with age may be related to the age-related fall in 13-HODE formation. (PMID 9561154 ) 13-HODE is considered an intermediate in Linoleic acid metabolism(KEGG ID C14762). It is generated from 13(S)-HPODE via the enzyme lipoxygenase [EC:1.13.11.12].
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
13S-HydroxyoctadecadienoateGenerator
(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
13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomerMeSH
13-Hydroxy-9,11-octadecadienoic acidMeSH
13-Hydroxy-9,11-octadecadienoic acid, (e,e)-isomerMeSH
13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomerMeSH
13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomerMeSH
13-Hydroxy-9,11-octadecadienoic acid, (R)-(e,Z)-isomerMeSH
13-HODDMeSH
13-LOXMeSH
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 Number5204-88-6
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 KeyHNICUWMFWZBIFP-IRQZEAMPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Industrial application:

Biological role:

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 Solubility0.003 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.03 m³·mol⁻¹ChemAxon
Polarizability37.26 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-6960000000-8cc8c4da0c87c3d65f03View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fbi-9342100000-19627880cd07ec05cb84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-bed7738fb8e72e8df932View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h7j-4490000000-e9f46847d2cc004e1b77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9520000000-57ec0699995e3751af99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-3ff43b79ccb7acee5d87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1190000000-59a7f430444bdc36b530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-2687cbf01f8a4a08925fView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0106 +/- 0.00128 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.230 +/- 0.038 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0473 +/- 0.00053 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0582 +/- 0.028 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0139 +/- 0.0048 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
UrineDetected and Quantified353.60 +/- 117.12 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2162.16 +/- 112.61 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.310 +/- 0.064 uMAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected and Quantified467.0 +/- 67.0 umol/mmol creatinineAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Autosomal dominant polycystic kidney disease
  1. Wang D, Strandgaard S, Borresen ML, Luo Z, Connors SG, Yan Q, Wilcox CS: Asymmetric dimethylarginine and lipid peroxidation products in early autosomal dominant polycystic kidney disease. Am J Kidney Dis. 2008 Feb;51(2):184-91. doi: 10.1053/j.ajkd.2007.09.020. [PubMed:18215696 ]
Associated OMIM IDs
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023395
KNApSAcK IDNot Available
Chemspider ID4947055
KEGG Compound IDC14762
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6443013
PDB ID243
ChEBI ID34154
References
Synthesis ReferenceBanks, A.; Keay, J. N.; Smith, J. G. M. Structure of conjugated methyl linoleate hydroperoxide. Nature (London, United Kingdom) (1957), 179 1078.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Horrobin DF, Ziboh VA: The importance of linoleic acid metabolites in cancer metastasis and in the synthesis and actions of 13-HODE. Adv Exp Med Biol. 1997;433:291-4. [PubMed:9561154 ]