Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:46 UTC |
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Update Date | 2022-03-07 02:49:14 UTC |
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HMDB ID | HMDB0002283 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 14R,15S-EpETrE |
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Description | 14R,15S-EpETrE is the dominant extracellular metabolite of epoxygenase products of arachidonic acid released from human luteinised granulosa cells. Epoxyeicosatrienoic acids (EpETrEs) have been reported recently having vasodilatory effects and a role of P-450-dependent arachidonic acid monooxygenase metabolites is suggested in vasoregulation. The physiological role of this compound has not been totally established, although in other tissues EpETrEs are mainly involved in hormone production and in the vascular and renal systems. Some studies have implicated epoxygenase metabolites of arachidonic acid in the control of steroidogenesis in luteinised granulosa cells. (PMID: 12749593 , 12361727 , 1650001 ). |
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Structure | CCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-/t18-,19+/m0/s1 |
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Synonyms | Value | Source |
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(14R,15S)-EpETrE | ChEBI | (14R,15S)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid | ChEBI | (14R,15S)-Epoxy-(5Z,8Z,11Z)-icosatrienoic acid | ChEBI | 14(S),15(R)-EET | ChEBI | 14R,15S-Epoxy-5Z,8Z,11Z-eicosatrienoic acid | ChEBI | (14R,15S)-Epoxy-(5Z,8Z,11Z)-eicosatrienoate | Generator | (14R,15S)-Epoxy-(5Z,8Z,11Z)-icosatrienoate | Generator | 14R,15S-Epoxy-5Z,8Z,11Z-eicosatrienoate | Generator | 14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoate | HMDB | 14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid | HMDB | 14,15-EET | HMDB | 14,15-Epoxy-5,8,11-eicosatrienoic acid | HMDB | 14,15-Epoxy-5,8,11-eicosatrienoic acid, (2alpha(5Z,8Z,11Z),3alpha)-isomer | HMDB | 14,15-Epoxyeicosatrienoic acid | HMDB | 14,15-Oxido-5,8,11-eicosatrienoic acid | HMDB | 14R,15S-EpETrE | ChEBI |
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Chemical Formula | C20H32O3 |
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Average Molecular Weight | 320.4663 |
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Monoisotopic Molecular Weight | 320.23514489 |
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IUPAC Name | (5Z,8Z,11Z)-13-[(2R,3S)-3-pentyloxiran-2-yl]trideca-5,8,11-trienoic acid |
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Traditional Name | 14R,15S-EpETrE |
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CAS Registry Number | 98103-48-1 |
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SMILES | CCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-/t18-,19+/m0/s1 |
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InChI Key | JBSCUHKPLGKXKH-LLZJRKGESA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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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 | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain fatty acid
- Epoxy fatty acid
- Heterocyclic fatty acid
- Unsaturated fatty acid
- Carboxylic acid derivative
- Carboxylic acid
- Dialkyl ether
- Oxirane
- Ether
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Oxacycle
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Organic oxygen 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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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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 - 14R,15S-EpETrE GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4j-7390000000-0a6ea9221818f7ca6b61 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 14R,15S-EpETrE GC-MS (1 TMS) - 70eV, Positive | splash10-00bj-9152000000-75e265bfced30aca2f55 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 14R,15S-EpETrE 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 - 14R,15S-EpETrE 10V, Positive-QTOF | splash10-0udi-1139000000-d1b1217f1a0ab449ee76 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Positive-QTOF | splash10-0f80-9562000000-3a641d61ec600d27001a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Positive-QTOF | splash10-0f77-9610000000-4d2f2f7c7445ce34caa9 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 10V, Negative-QTOF | splash10-014i-1029000000-03d83d003242098cb3c2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Negative-QTOF | splash10-0gb9-4159000000-4a32a74e26b6a8978859 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Negative-QTOF | splash10-052f-9120000000-efc218792d62c8df73a5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 10V, Negative-QTOF | splash10-014i-0009000000-fa339ab07ef5a66d93e2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Negative-QTOF | splash10-0gb9-2149000000-f932d9bc138901e04dad | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Negative-QTOF | splash10-052f-9140000000-91f3f678f570fc1a1ff6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 10V, Positive-QTOF | splash10-0uki-2259000000-adfdaf1e87da0a4fbf5f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Positive-QTOF | splash10-0udr-9375000000-fdf50048f25a924a6bb2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Positive-QTOF | splash10-00mo-9200000000-f15fc52cfe999f85655e | 2021-09-24 | Wishart Lab | View Spectrum |
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