Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-14 00:33:07 UTC |
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Update Date | 2022-03-07 02:49:21 UTC |
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HMDB ID | HMDB0004690 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hepoxilin B3 |
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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 ). |
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Structure | CCCCC\C=C/C[C@@H]1O[C@@H]1C(O)\C=C/C\C=C/CCCC(O)=O 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 |
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Synonyms | Value | Source |
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(5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acid | Kegg | (5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acid | Kegg | (5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoate | Generator | (5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoate | Generator | 10-Hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acid | HMDB | EPHETA | HMDB | Hepoxilin b | HMDB | Threo-hepoxilin b3 | HMDB | Erythro-hepoxilin b3 | HMDB | (5Z,8Z)-10-Hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoate | HMDB | (5Z,8Z)-10-Hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid | HMDB | (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoate | HMDB | (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acid | HMDB | (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoicacid | HMDB | (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoate | HMDB | (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acid | HMDB | (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoicacid | HMDB | 10-Hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoate | HMDB | 10-Hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid | HMDB |
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Chemical Formula | C20H32O4 |
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Average Molecular Weight | 336.4657 |
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Monoisotopic Molecular Weight | 336.230059512 |
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IUPAC Name | (5Z,8Z)-10-hydroxy-10-[(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid |
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Traditional Name | epheta |
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CAS Registry Number | Not Available |
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SMILES | CCCCC\C=C/C[C@@H]1O[C@@H]1C(O)\C=C/C\C=C/CCCC(O)=O |
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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 |
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InChI Key | DWNBPRRXEVJMPO-YZTVQBIISA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Eicosanoids |
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Direct Parent | Hepoxilins |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Hepoxilin B3,1TMS,isomer #1 | CCCCC/C=C\C[C@@H]1O[C@@H]1C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2617.7 | Semi standard non polar | 33892256 | Hepoxilin B3,1TMS,isomer #2 | CCCCC/C=C\C[C@@H]1O[C@@H]1C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2580.3 | Semi standard non polar | 33892256 | Hepoxilin B3,2TMS,isomer #1 | CCCCC/C=C\C[C@@H]1O[C@@H]1C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2617.6 | Semi standard non polar | 33892256 | Hepoxilin B3,1TBDMS,isomer #1 | CCCCC/C=C\C[C@@H]1O[C@@H]1C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2833.9 | Semi standard non polar | 33892256 | Hepoxilin B3,1TBDMS,isomer #2 | CCCCC/C=C\C[C@@H]1O[C@@H]1C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 2831.2 | Semi standard non polar | 33892256 | Hepoxilin B3,2TBDMS,isomer #1 | CCCCC/C=C\C[C@@H]1O[C@@H]1C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3098.3 | Semi standard non polar | 33892256 |
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