Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-23 04:42:27 UTC |
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Update Date | 2022-03-07 03:17:57 UTC |
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HMDB ID | HMDB0062619 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid |
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Description | (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid, also known as Hepoxilin a3 or 8-EH-2, is classified as a member of the Hepoxilins. Hepoxilins are eicosanoids containing an oxirane group attached to the fatty acyl chain. (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid is considered to be practically insoluble (in water) and acidic |
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Structure | [H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC InChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/b9-7-,10-6-,16-15+/t17?,18?,19-/m0/s1 |
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Synonyms | Value | Source |
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(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoate | Kegg | (5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic acid | Generator | Hepoxilin a | MeSH | 8-EH-2 | MeSH | Hexophilin a3 | MeSH | 8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid | MeSH | HXA3 CPD | MeSH | Hepoxilin a3 | KEGG |
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Chemical Formula | C20H32O4 |
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Average Molecular Weight | 336.472 |
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Monoisotopic Molecular Weight | 336.23005951 |
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IUPAC Name | (5Z,9E)-8-hydroxy-10-[(2S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid |
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Traditional Name | (5Z,9E)-8-hydroxy-10-[(2S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC |
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InChI Identifier | InChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/b9-7-,10-6-,16-15+/t17?,18?,19-/m0/s1 |
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InChI Key | SGTUOBURCVMACZ-NSIHWEAISA-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 | Not Available |
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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 | Not Available |
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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 | 0.0094 g/l | ALOGPS | LogP | 5.57 | ALOGPS |
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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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid | [H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC | 4187.0 | Standard polar | 33892256 | (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid | [H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC | 2485.7 | Standard non polar | 33892256 | (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid | [H]\C(CCCC(O)=O)=C(/[H])CC([H])(O)C(\[H])=C(/[H])[C@]1([H])OC1([H])C\C([H])=C(\[H])CCCCC | 2620.7 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TMS,isomer #1 | CCCCC/C=C\CC1O[C@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C | 2637.7 | Semi standard non polar | 33892256 | (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TMS,isomer #2 | CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2738.1 | Semi standard non polar | 33892256 | (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,2TMS,isomer #1 | CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2689.9 | Semi standard non polar | 33892256 | (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TBDMS,isomer #1 | CCCCC/C=C\CC1O[C@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 2898.3 | Semi standard non polar | 33892256 | (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,1TBDMS,isomer #2 | CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2981.7 | Semi standard non polar | 33892256 | (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid,2TBDMS,isomer #1 | CCCCC/C=C\CC1O[C@H]1/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3168.3 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0403-4973000000-68b05a5879abdd2702ca | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (2 TMS) - 70eV, Positive | splash10-00fs-9504200000-b478b5ac38b9ea248120 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Positive-QTOF | splash10-014i-0119000000-f183a896d40b122d34a6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Positive-QTOF | splash10-0100-3923000000-55a8fa7b860b76630757 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Positive-QTOF | splash10-05tf-9320000000-806f2e69b92eec98be14 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Negative-QTOF | splash10-000i-0029000000-babbe7e5cbfec6729e52 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Negative-QTOF | splash10-014r-1849000000-46fca9cc7712fb3e7876 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Negative-QTOF | splash10-0a4l-9510000000-19c94ffaa2521c24fe09 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Negative-QTOF | splash10-000i-0009000000-4284d12526c896900597 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Negative-QTOF | splash10-000i-0697000000-b6393912f77c76528f02 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Negative-QTOF | splash10-0035-2961000000-b6e6a2b7949fd45ad206 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 10V, Positive-QTOF | splash10-014r-2229000000-797f9fb3ace53b814b60 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 20V, Positive-QTOF | splash10-0kxr-7986000000-202c1560017bfda5161a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid 40V, Positive-QTOF | splash10-00pi-9300000000-94a32c143312056553eb | 2021-09-22 | Wishart Lab | View Spectrum |
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