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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-14 02:00:43 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004706
Secondary Accession Numbers
  • HMDB04706
Metabolite Identification
Common Name8(R)-Hydroperoxylinoleic acid
Description8(R)-hydroperoxylinoleic acid (8(R)-EPODE) is an oxidized product of linoleic acid. Oxidized lipids such as 8(R)-HPODE can decrease cellular proteoglycan metabolism in endothelial monolayers and alter mRNA levels of major specific proteoglycans in a concentration-dependent manner. This may have implications in lipid-mediated disruption of endothelial barrier function and atherosclerosis. (PMID: 8645361 , 9507987 ).
Structure
Thumb
Synonyms
ValueSource
(8R)-8-Hydroperoxylinoleic acidChEBI
(9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoic acidChEBI
(8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoateKegg
(8R)-8-HydroperoxylinoleateGenerator
(9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoateGenerator
(8R,9Z,12Z)-8-Hydroperoxyoctadeca-9,12-dienoic acidGenerator
8(R)-HydroperoxylinoleateGenerator
(R-(Z,Z))-8-Hydroperoxy-9,12-octadecadienoateHMDB
(R-(Z,Z))-8-Hydroperoxy-9,12-octadecadienoic acidHMDB
8(R)-HPODEHMDB
8-HpodeHMDB
8-Hydroperoxylinoleic acidHMDB
8R-Hydroperoxy-9Z,12Z-octadecadienoateHMDB
8R-Hydroperoxy-9Z,12Z-octadecadienoic acidHMDB
Chemical FormulaC18H32O4
Average Molecular Weight312.4443
Monoisotopic Molecular Weight312.230059512
IUPAC Name(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoic acid
Traditional Name8-hpode
CAS Registry Number143343-95-7
SMILES
CCCCC\C=C/C\C=C/[C@@H](CCCCCCC(O)=O)OO
InChI Identifier
InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-11-14-17(22-21)15-12-9-10-13-16-18(19)20/h6-7,11,14,17,21H,2-5,8-10,12-13,15-16H2,1H3,(H,19,20)/b7-6-,14-11-/t17-/m0/s1
InChI KeyRGJSGXNKRWWCOQ-QMEIEYGNSA-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
  • Hydroperoxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Allylic hydroperoxide
  • Hydroperoxide
  • Carboxylic acid derivative
  • Alkyl hydroperoxide
  • Carboxylic acid
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112218
KNApSAcK IDNot Available
Chemspider ID4943210
KEGG Compound IDC14831
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438758
PDB IDNot Available
ChEBI ID34485
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ramasamy S, Lipke DW, Boissonneault GA, Guo H, Hennig B: Oxidized lipid-mediated alterations in proteoglycan metabolism in cultured pulmonary endothelial cells. Atherosclerosis. 1996 Feb;120(1-2):199-208. [PubMed:8645361 ]
  2. Ramasamy S, Parthasarathy S, Harrison DG: Regulation of endothelial nitric oxide synthase gene expression by oxidized linoleic acid. J Lipid Res. 1998 Feb;39(2):268-76. [PubMed:9507987 ]