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Human Metabolome Database Version 3.5

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Showing metabocard for 8,15-DiHETE (HMDB10219)

Record Information
Version 3.5
Creation Date 2008-09-15 03:55:15 -0600
Update Date 2013-02-08 17:24:16 -0700
HMDB ID HMDB10219
Secondary Accession Numbers None
Metabolite Identification
Common Name 8,15-DiHETE
Description 8,15-DiHETE is a double oxidation product of arachadonic acid. It is generated through the action of 15-lipoxygenase (PMID: 8334154 Link_out). 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 signaling pathways.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 8,15-Dihydroxy-5,9,11,13-eicosatetraenoate
  2. 8,15-Dihydroxy-5,9,11,13-eicosatetraenoic acid
  3. 8,15-Leukotriene B(4)
  4. 8,15-Leukotriene B4
Chemical Formula C20H32O4
Average Molecular Weight 336.4657
Monoisotopic Molecular Weight 336.230059512
IUPAC Name (5Z,9E,11Z,13E)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid
Traditional IUPAC Name (5Z,9E,11Z,13E)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid
CAS Registry Number 77667-08-4
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 Key NNPWRKSGORGTIM-RCDCWWQHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Hydroxyeicosatetraenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroxy Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct Parent Hydroxyeicosatetraenoic Acids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Signaling
Application
  • Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.017 g/L ALOGPS
LogP 5.37 ALOGPS
LogP 4.13 ChemAxon
LogS -4.31 ALOGPS
pKa (strongest acidic) 4.68 ChemAxon
pKa (strongest basic) -1.3 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 77.76 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 102.98 ChemAxon
Polarizability 39.95 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
<0.1 uM Adult (>18 years old) Not Specified Normal HM Replicate Plasma (n=3)
Blood Detected and Quantified
Article_icon
<0.1 uM Adult (>18 years old) Not Specified Normal Pennington Plasma (n=70)
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027372
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB10219 Link_out
Metagene Link HMDB10219 Link_out
METLIN ID Not Available
PubChem Compound 53480358 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available