Legend: 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 |
|
||||||||||||||||||
| 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 | |||||||||||||||||||
| Chemical Taxonomy |
|
||||||||||||||||||
| 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 ![]() |
||||||||||||||||||
| BioCyc ID | Not Available | ||||||||||||||||||
| BiGG ID | Not Available | ||||||||||||||||||
| Wikipedia Link | Not Available | ||||||||||||||||||
| NuGOwiki Link | HMDB04690 ![]() |
||||||||||||||||||
| Metagene Link | HMDB04690 ![]() |
||||||||||||||||||
| METLIN ID | 7071 ![]() |
||||||||||||||||||
| PubChem Compound | 5283209 ![]() |
||||||||||||||||||
| PubChem Substance | 17395808 ![]() |
||||||||||||||||||
| ChEBI ID | 34784 ![]() |
||||||||||||||||||
| 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 ![]() |
||||||||||||||||||
| SDF File | Show ![]() |
||||||||||||||||||
| PDB File | Show ![]() |
||||||||||||||||||
| 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 Show Peaklist |
||||||||||||||||||
| Mass Spectrum | Not Available | ||||||||||||||||||
| Simplified TOCSY Spectrum | Not Available | ||||||||||||||||||
| BMRB Spectrum | Not Available | ||||||||||||||||||
| Cellular Location |
|
||||||||||||||||||
| Biofluid Location | Not Available | ||||||||||||||||||
| Tissue Location |
|
||||||||||||||||||
| Concentrations (Normal) | Not Available | ||||||||||||||||||
| Concentrations (Abnormal) | Not Available | ||||||||||||||||||
| Associated Disorders | Not Available | ||||||||||||||||||
| OMIM ID | Not Available | ||||||||||||||||||
| Pathways | Not Available | ||||||||||||||||||
| General References |
|