Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-05-22 14:17:29 UTC |
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Update Date | 2022-03-07 02:49:11 UTC |
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HMDB ID | HMDB0001965 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Troxilin B3 |
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Description | Troxilin B3 is the enzymatically formed derivative of Hepoxilin B3. Normal human epidermis incubated with exogenous AA produces 12-oxo-eicosatetraenoic acid (12-oxo-ETE), hepoxilin A3 (HxA3), and hepoxilin B3 (HxB3) through the 12- Lipoxygenase (LO) pathway. 12-LO is the major arachidonic acid (AA) oxygenation pathway in epidermal cells with total product formation generally exceeding cyclooxygenase activity. Platelet-type 12-LO has been found to be the predominant isoenzyme expressed in human and murine skin epidermis. Increased levels of nonesterified hepoxilins and trioxilins occur in the psoriatic scales. Normal human epidermis synthesized only one of the two possible 10-hydroxy epimers of HxB3 whose formation is probably catalyzed by 12-LO. Hepoxilins exert action on plasma permeability on skin, and induce a specific-receptor-dependent Ca2+ mobilization from endogenous sources and the release of AA and diacylglycerols. (PMID: 11851887 ). |
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Structure | CCCCC\C=C/C[C@@H](O)[C@H](O)C(O)\C=C/C\C=C/CCCC(O)=O InChI=1S/C20H34O5/c1-2-3-4-5-8-11-14-17(21)20(25)18(22)15-12-9-6-7-10-13-16-19(23)24/h6-8,11-12,15,17-18,20-22,25H,2-5,9-10,13-14,16H2,1H3,(H,23,24)/b7-6-,11-8-,15-12-/t17-,18?,20+/m1/s1 |
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Synonyms | Value | Source |
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(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoic acid | ChEBI | (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acid | ChEBI | 10,11S,12R-TriOH all-cis-5,8,14-20:3 | ChEBI | 10,11S,12R-TriOH all-cis-5,8,14-C20:3 | ChEBI | (5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoic acid | Kegg | (5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acid | Kegg | (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoate | Generator | (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoate | Generator | (5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoate | Generator | (5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoate | Generator | (5Z,8Z,11S,12R,14Z)-10,11,12-Trihydroxyicosa-5,8,14-trienoate | HMDB | (5Z,8Z,11S,12R,14Z)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acid | HMDB | (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoicacid | HMDB | 10,11S,12R-Trihydroxy-5Z,8Z,14Z-eicosatrienoate | HMDB | 10,11S,12R-Trihydroxy-5Z,8Z,14Z-eicosatrienoic acid | HMDB | TRXB(3) | HMDB | Trioxilin b3 | HMDB | Troxilin b3 | ChEBI |
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Chemical Formula | C20H34O5 |
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Average Molecular Weight | 354.481 |
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Monoisotopic Molecular Weight | 354.240624198 |
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IUPAC Name | (5Z,8Z,11S,12R,14Z)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid |
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Traditional Name | trioxilin B3 |
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CAS Registry Number | Not Available |
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SMILES | CCCCC\C=C/C[C@@H](O)[C@H](O)C(O)\C=C/C\C=C/CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H34O5/c1-2-3-4-5-8-11-14-17(21)20(25)18(22)15-12-9-6-7-10-13-16-19(23)24/h6-8,11-12,15,17-18,20-22,25H,2-5,9-10,13-14,16H2,1H3,(H,23,24)/b7-6-,11-8-,15-12-/t17-,18?,20+/m1/s1 |
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InChI Key | GOHNIXDAQODZKP-OZPSOFALSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds. |
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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 | Hydroxyeicosatrienoic acids |
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Alternative Parents | |
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Substituents | - Hydroxyeicosatrienoic acid
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Polyol
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic 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 | |
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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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Troxilin B3,1TMS,isomer #1 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O | 2847.2 | Semi standard non polar | 33892256 | Troxilin B3,1TMS,isomer #2 | CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O | 2873.8 | Semi standard non polar | 33892256 | Troxilin B3,1TMS,isomer #3 | CCCCC/C=C\C[C@@H](O)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2884.1 | Semi standard non polar | 33892256 | Troxilin B3,1TMS,isomer #4 | CCCCC/C=C\C[C@@H](O)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2887.0 | Semi standard non polar | 33892256 | Troxilin B3,2TMS,isomer #1 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O | 2822.9 | Semi standard non polar | 33892256 | Troxilin B3,2TMS,isomer #2 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2859.9 | Semi standard non polar | 33892256 | Troxilin B3,2TMS,isomer #3 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2820.7 | Semi standard non polar | 33892256 | Troxilin B3,2TMS,isomer #4 | CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2874.1 | Semi standard non polar | 33892256 | Troxilin B3,2TMS,isomer #5 | CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2834.3 | Semi standard non polar | 33892256 | Troxilin B3,2TMS,isomer #6 | CCCCC/C=C\C[C@@H](O)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2842.5 | Semi standard non polar | 33892256 | Troxilin B3,3TMS,isomer #1 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2829.4 | Semi standard non polar | 33892256 | Troxilin B3,3TMS,isomer #2 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2758.7 | Semi standard non polar | 33892256 | Troxilin B3,3TMS,isomer #3 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2809.2 | Semi standard non polar | 33892256 | Troxilin B3,3TMS,isomer #4 | CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2812.6 | Semi standard non polar | 33892256 | Troxilin B3,4TMS,isomer #1 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2808.6 | Semi standard non polar | 33892256 | Troxilin B3,1TBDMS,isomer #1 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O | 3118.7 | Semi standard non polar | 33892256 | Troxilin B3,1TBDMS,isomer #2 | CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O | 3142.9 | Semi standard non polar | 33892256 | Troxilin B3,1TBDMS,isomer #3 | CCCCC/C=C\C[C@@H](O)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3124.6 | Semi standard non polar | 33892256 | Troxilin B3,1TBDMS,isomer #4 | CCCCC/C=C\C[C@@H](O)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3160.3 | Semi standard non polar | 33892256 | Troxilin B3,2TBDMS,isomer #1 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O | 3321.6 | Semi standard non polar | 33892256 | Troxilin B3,2TBDMS,isomer #2 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3326.2 | Semi standard non polar | 33892256 | Troxilin B3,2TBDMS,isomer #3 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3329.3 | Semi standard non polar | 33892256 | Troxilin B3,2TBDMS,isomer #4 | CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3323.4 | Semi standard non polar | 33892256 | Troxilin B3,2TBDMS,isomer #5 | CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3335.5 | Semi standard non polar | 33892256 | Troxilin B3,2TBDMS,isomer #6 | CCCCC/C=C\C[C@@H](O)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3322.9 | Semi standard non polar | 33892256 | Troxilin B3,3TBDMS,isomer #1 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3525.0 | Semi standard non polar | 33892256 | Troxilin B3,3TBDMS,isomer #2 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3519.0 | Semi standard non polar | 33892256 | Troxilin B3,3TBDMS,isomer #3 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3549.4 | Semi standard non polar | 33892256 | Troxilin B3,3TBDMS,isomer #4 | CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3522.5 | Semi standard non polar | 33892256 | Troxilin B3,4TBDMS,isomer #1 | CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3715.7 | Semi standard non polar | 33892256 |
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