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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-14 00:33:07 UTC
Update Date2017-12-07 01:54:02 UTC
HMDB IDHMDB0004690
Secondary Accession Numbers
  • HMDB04690
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 ).
Structure
Thumb
Synonyms
ValueSource
(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,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoateGenerator
(5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoateGenerator
(5Z,8Z)-10-Hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoateHMDB
(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-trienoateHMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acidHMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoicacidHMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoateHMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acidHMDB
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoicacidHMDB
10-Hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoateHMDB
10-Hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acidHMDB
10-Hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acidMeSH
EPHETAMeSH
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
SMILES
CCCCC\C=C/C[C@@H]1O[C@@H]1C(O)\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18-20(24-18)17(21)14-11-8-6-7-10-13-16-19(22)23/h6-7,9,11-12,14,17-18,20-21H,2-5,8,10,13,15-16H2,1H3,(H,22,23)/b7-6-,12-9-,14-11-/t17?,18-,20+/m0/s1
InChI KeyDWNBPRRXEVJMPO-YZTVQBIISA-N
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
Substituents
  • 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
Ontology
Disposition

Biological Location:

  Subcellular:

  Tissue and substructures:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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 Solubility0.0092 g/LALOGPS
logP5.11ALOGPS
logP4.73ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.57 m³·mol⁻¹ChemAxon
Polarizability39.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-1900000000-7e176d0aeaf4c4f1ee84View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-7509200000-646f9e780523dd7060e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0419000000-8de60f1d7da49d39d629View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0100-2901000000-2b574e8af2bff160c04aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-171ed87708ea6a95def5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0319000000-57e762a656ee448ceae4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0902000000-c21e19e865d525b26795View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-683be61d26516deb4500View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Location
  • Epidermis
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
METLIN ID7071
PubChem Compound5283209
PDB IDNot Available
ChEBI ID34784
References
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 ]