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Human Metabolome Database Version 2.5

 

Showing metabocard for Hepoxilin B3 (HMDB04690)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-14 01:33:07
Update Date 2009-05-05 21:00:01
Accession Number HMDB04690
Secondary Accession Numbers Not Available
Common Name Hepoxilin B3
Description Hepoxilin 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)
Synonyms
  1. 10-hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid
  2. (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoicacid
  3. (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acid
  4. (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoicacid
  5. (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acid
  6. (5Z,8Z)-10-hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
  7. 10-hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoate
  8. (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoate
  9. (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoate
  10. (5Z,8Z)-10-hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoate
Chemical IUPAC Name (5Z,8Z)-10-hydroxy-10-[(2S,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoic acid
Chemical Formula C20H32O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Fatty acids
Class
  • Eicosanoids
Sub Class
  • Hepoxilins
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • dialkyl ether
  • carboxylic acid
  • alkene
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 336.466
Monoisotopic Molecular Weight 336.230072
Isomeric SMILES CCCCCC=C/C[C@@H]1O[C@@H]1C(O)C=C/CC=C/CCCC(O)=O
Canonical SMILES CCCCCC=CCC1OC1C(O)C=CCC=CCCCC(O)=O
KEGG Compound ID C14810 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04690 Link Image
Metagene Link HMDB04690 Link Image
METLIN ID 7071 Link Image
PubChem Compound 5283209 Link Image
PubChem Substance 17395808 Link Image
ChEBI ID 34784 Link Image
CAS Registry Number Not Available
InChI Identifier InChI=1/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-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 9.24e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.2 [Predicted by PubChem via XLOGP]; 5.11 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane, mitochondria
Biofluid Location Not Available
Tissue Location
Tissue References
Epidermis —
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways 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 Link Image]
  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 Link Image]