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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:15 UTC
Update Date2021-09-14 15:46:39 UTC
HMDB IDHMDB0010219
Secondary Accession Numbers
  • HMDB10219
Metabolite Identification
Common Name8,15-DiHETE
Description8,15-DiHETE is a double oxidation product of arachadonic acid. It is generated through the action of 15-lipoxygenase (PMID: 8334154 ). 8,15-DiHETE is also known as eosinophil chemotactic factor of anaphylaxis (ECF-A). In particular it is able to selectively attract eosinophils and neutrophils from mixed leukocyte populations.Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
Structure
Thumb
Synonyms
ValueSource
8,15-Dihydroxy-5,9,11,13-eicosatetraenoateHMDB
8,15-Dihydroxy-5,9,11,13-eicosatetraenoic acidHMDB
8,15-Leukotriene b(4)HMDB
8,15-Leukotriene b4HMDB
8,15-LTB4HMDB
8,15-Leukotriene b4, (R-(r*,s*-(e,e,e,Z)))-isomerHMDB
8,15-Leukotriene b4, (S-(r*,s*-(e,e,Z,Z)))-isomerHMDB
8,15-Leukotriene b4, (S-(r*,r*-(e,e,e,Z)))-isomerHMDB
8,15-Leukotriene b4, (S-(r*,r*-(e,e,Z,Z)))-isomerHMDB
8,15-Leukotriene b4, (S-(r*,s*-(e,e,e,Z)))-isomerHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,9E,11Z,13E)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid
Traditional Name8,15-DiHETE
CAS Registry Number77667-08-4
SMILES
CCCCCC(O)\C=C\C=C/C=C/C(O)C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-8-13-18(21)14-9-4-5-10-15-19(22)16-11-6-7-12-17-20(23)24/h4-6,9-11,14-15,18-19,21-22H,2-3,7-8,12-13,16-17H2,1H3,(H,23,24)/b5-4-,11-6-,14-9+,15-10+
InChI KeyNNPWRKSGORGTIM-RCDCWWQHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • 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 DescriptorsNot Available
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
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027372
KNApSAcK IDNot Available
Chemspider ID35031963
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480358
PDB IDNot Available
ChEBI ID88456
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. Kuhn H, Barnett J, Grunberger D, Baecker P, Chow J, Nguyen B, Bursztyn-Pettegrew H, Chan H, Sigal E: Overexpression, purification and characterization of human recombinant 15-lipoxygenase. Biochim Biophys Acta. 1993 Jul 21;1169(1):80-9. [PubMed:8334154 ]