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Record Information
Creation Date2006-08-14 00:33:07 UTC
Update Date2017-03-02 21:27:36 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameHepoxilin B3
DescriptionHepoxilin B3 is a normal human epidermis eicosanoid. Hepoxilin B3 is dramatically elevated in psoriatic lesions. The primary biological action of the hepoxilins appears to relate to their ability to release calcium from intracellular stores through a receptor-mediated action. The receptor is intracellular, and appears to be G-protein coupled. The conversion of hepoxilin into its omega-hydroxy catabolite has recently been demonstrated through the action of an omega-hydroxylase. This enzyme is different from that which oxidizes leukotriene B4, as the former activity is lost when the cell is disrupted, while leukotriene B4-catabolic activity is recovered in both the intact and disrupted cell. Additionally, hepoxilin catabolism is inhibited by CCCP, a mitochondrial uncoupler, while leukotriene catabolism is unaffected. As hepoxilins cause the translocation of calcium from intracellular stores in the endoplasmic reticulum to the mitochondria, it is speculated that hepoxilin omega-oxidation takes place in the mitochondria, and the omega-oxidation product facilitates accumulation of the elevated cytosolic calcium by the mitochondria. (PMID 10692117 , 11851887 , 10086189 ).
(5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acidKegg
(5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acidKegg
(5Z,8Z)-10-Hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acidHMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acidHMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acidHMDB
10-Hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acidHMDB
10-Hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acidMeSH
erythro-Hepoxilin b3MeSH
Hepoxilin bMeSH
threo-Hepoxilin b3MeSH
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z)-10-hydroxy-10-[(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid
Traditional Nameepheta
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHepoxilins
Alternative Parents
  • Hepoxilin
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
StatusExpected but not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Mitochondria
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0092 mg/mLALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.57 m3·mol-1ChemAxon
Polarizability39.72 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Location
  • Epidermis
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023407
KNApSAcK IDNot Available
Chemspider ID4446330
KEGG Compound IDC14810
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04690
Metagene LinkHMDB04690
PubChem Compound5283209
PDB IDNot Available
ChEBI ID34784
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Anton R, Vila L: Stereoselective biosynthesis of hepoxilin B3 in human epidermis. J Invest Dermatol. 2000 Mar;114(3):554-9. [PubMed:10692117 ]
  2. Anton R, Camacho M, Puig L, Vila L: Hepoxilin B3 and its enzymatically formed derivative trioxilin B3 are incorporated into phospholipids in psoriatic lesions. J Invest Dermatol. 2002 Jan;118(1):139-46. [PubMed:11851887 ]
  3. Pace-Asciak CR, Reynaud D, Demin P, Nigam S: The hepoxilins. A review. Adv Exp Med Biol. 1999;447:123-32. [PubMed:10086189 ]