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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 23:30:18 UTC
Update Date2019-10-16 15:20:44 UTC
HMDB IDHMDB0004667
Secondary Accession Numbers
  • HMDB0006939
  • HMDB0061708
  • HMDB0112194
  • HMDB04667
  • HMDB06939
  • HMDB61708
Metabolite Identification
Common Name13-HODE
Description13-Hydroxyoctadecadienoic acid (13-HODE) (CAS: 18104-45-5), also known as 13(S)-hydroxy-9Z,11E-octadecadienoic acid or 13(S)-HODE, is the major lipoxygenation product 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. It is generated from 13(S)-HPODE via the enzyme lipoxygenase (EC 1.13.11.12). 13-HODE 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 tumours and cell lines and researchers believe that there is a link between linoleic acid metabolism and the development or progression of prostate cancer (PMID: 9367845 ).
Structure
Data?1571239244
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
13S-HydroxyoctadecadienoateHMDB
13-Hydroxy-9,11-octadecadienoic acidHMDB
13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomerHMDB
13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomerHMDB
13-Hydroxyoctadecadienoic acidHMDB
13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomerHMDB
13(S) HODEHMDB
13-HydroxyoctadecadienoateHMDB
(+)-Coriolic acidHMDB
(13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acidHMDB
(9Z,11E)-13-Hydroxy-9,11-octadecadienoic acidHMDB
(9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acidHMDB
(9Z,11E,13S)-13-Hydroxyoctadecadienoic acidHMDB
(S)-Coriolic acidHMDB
(±)-coriolic acidHMDB
13-Hydroxy-9(Z),11(e)-octadecadienoic acidHMDB
13-Hydroxy-9,11-cis,trans-octadecadienoic acidHMDB
13-Hydroxy-9-cis-11-trans-octadecadienoic acidHMDB
13-Hydroxy-cis-9-trans-11-octadecadienoic acidHMDB
13-Hydroxylinoleic acidHMDB
13-Hydroxyoctadeca-9,11-dienoic acidHMDB
13S-HODEHMDB
13S-Hydroxy-9Z,11E-octadecadienoic acidHMDB
L-13-Hydroxy-cis-9,trans-11-octadecadienoic acidHMDB
alpha-Artemisolic acidHMDB
Α-artemisolic acidHMDB
13-HODEHMDB, MeSH
(9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoateGenerator
(9Z,11E)-13-HODEHMDB
(9Z,11E)-13-hydroxyoctadecadienoic acidHMDB
FA(18:2(9Z,11E,13-OH))HMDB
FA(18:2(9Z,11E,13S-OH))HMDB
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 Number29623-28-7
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
Description 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
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-6960000000-8cc8c4da0c87c3d65f03JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fbi-9342100000-19627880cd07ec05cb84JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-bed7738fb8e72e8df932JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h7j-4490000000-e9f46847d2cc004e1b77JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9520000000-57ec0699995e3751af99JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-3ff43b79ccb7acee5d87JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1190000000-59a7f430444bdc36b530JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-2687cbf01f8a4a08925fJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.310 +/- 0.064 uMAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
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 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
  • 601313 (Autosomal dominant polycystic kidney disease)
  • 114500 (Colorectal cancer)
DrugBank IDDB06926
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023395
KNApSAcK IDC00000403
Chemspider ID4947055
KEGG Compound IDC14762
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link13-Hydroxyoctadecadienoic acid
METLIN IDNot Available
PubChem Compound6443013
PDB IDNot Available
ChEBI ID34154
Food Biomarker OntologyNot Available
VMH IDM00336
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 ]
  2. 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. [PubMed:9367845 ]
  3. Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. [PubMed:25303528 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.