Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2010-05-17 15:47:38 UTC |
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Update Date | 2022-03-07 02:51:33 UTC |
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HMDB ID | HMDB0013620 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 19(20)-EpDPE |
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Description | 19(20)-EpDPE is a DHA epoxygenase metabolite, derived via epoxidation of the w-3 double bond of DHA. The EDHF (endothelium-derived hyperpolarizing factor) activity of 19(20)-EpDPE has not yet been determined. The epoxygenase metabolites of DHA have also been detected in a murine inflammation model (PMID: 12391014 ). EDHF is an unidentified mediator released from vascular endothelial cells in response to acetylcholine and bradykinin which is distinct from the NOS- (nitric oxide) and COX-derived (prostacyclin) vasodilators (PMID: 9504399 , 10519554 ). Cytochrome P450 (CYP450) metabolism of polyunsaturated fatty acids produces epoxides such as 14(15)-EpETrE which are prime candidates for the actual active mediator (PMID: 9401962 ). However, the CYP450 metabolites of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have been little studied relative to arachidonate epoxygenase metabolites. |
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Structure | CCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O InChI=1S/C22H32O3/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)/b4-3-,9-7-,10-8-,15-13-,16-14- |
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Synonyms | Value | Source |
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19(20)-Epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid | ChEBI | 19,20-EDP | ChEBI | 19,20-Epoxydocosapentaenoic acid | ChEBI | 19(20)-Epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoate | Generator | 19,20-Epoxydocosapentaenoate | Generator | 19(20)-EpDoPE | HMDB | Epox 22:6n3 | HMDB |
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Chemical Formula | C22H32O3 |
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Average Molecular Weight | 344.4877 |
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Monoisotopic Molecular Weight | 344.23514489 |
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IUPAC Name | (4Z,7Z,10Z,13Z,16Z)-18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid |
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Traditional Name | (4Z,7Z,10Z,13Z,16Z)-18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid |
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CAS Registry Number | Not Available |
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SMILES | CCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O |
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InChI Identifier | InChI=1S/C22H32O3/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)/b4-3-,9-7-,10-8-,15-13-,16-14- |
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InChI Key | OSXOPUBJJDUAOJ-MBYQGORISA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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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 | Lineolic acids and derivatives |
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Direct Parent | Lineolic acids and derivatives |
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Alternative Parents | |
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Substituents | - Octadecanoid
- Long-chain fatty acid
- Epoxy fatty acid
- Heterocyclic fatty acid
- Unsaturated fatty acid
- Fatty acid
- Monocarboxylic acid or derivatives
- Oxacycle
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- 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 | |
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Role | |
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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 - 19(20)-EpDPE GC-MS (Non-derivatized) - 70eV, Positive | splash10-00du-5491000000-06e9feded58033b38afb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 19(20)-EpDPE GC-MS (1 TMS) - 70eV, Positive | splash10-00g1-9244000000-98eaf576b716425a6e1d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 19(20)-EpDPE 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 - 19(20)-EpDPE 10V, Positive-QTOF | splash10-004j-1029000000-bf092b5708f301ca5c48 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 20V, Positive-QTOF | splash10-0a6u-4192000000-e7bc6fe81c4cf10494be | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 40V, Positive-QTOF | splash10-002f-9580000000-4d0b3bd18f872ae4698b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 10V, Negative-QTOF | splash10-0006-0019000000-66522a6a74b8576270e3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 20V, Negative-QTOF | splash10-002f-4059000000-a2411e92e43b689c02b4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 40V, Negative-QTOF | splash10-052f-9020000000-7466d099ee6fc10bdd74 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 10V, Negative-QTOF | splash10-0006-0019000000-6acea8536415463629f4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 20V, Negative-QTOF | splash10-002f-2039000000-6fd5d5db853015562c20 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 40V, Negative-QTOF | splash10-052f-9055000000-b5d027e9f2ef45a96e5c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 10V, Positive-QTOF | splash10-056s-2149000000-11f855435a160fefd89d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 20V, Positive-QTOF | splash10-0ara-4596000000-76c25ecbd1516e1574e8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19(20)-EpDPE 40V, Positive-QTOF | splash10-015c-6900000000-0a062778197c8cbc0d1c | 2021-09-22 | Wishart Lab | View Spectrum |
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General References | - Fisslthaler B, Popp R, Kiss L, Potente M, Harder DR, Fleming I, Busse R: Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature. 1999 Sep 30;401(6752):493-7. [PubMed:10519554 ]
- Serhan CN, Hong S, Gronert K, Colgan SP, Devchand PR, Mirick G, Moussignac RL: Resolvins: a family of bioactive products of omega-3 fatty acid transformation circuits initiated by aspirin treatment that counter proinflammation signals. J Exp Med. 2002 Oct 21;196(8):1025-37. [PubMed:12391014 ]
- Chataigneau T, Feletou M, Duhault J, Vanhoutte PM: Epoxyeicosatrienoic acids, potassium channel blockers and endothelium-dependent hyperpolarization in the guinea-pig carotid artery. Br J Pharmacol. 1998 Feb;123(3):574-80. [PubMed:9504399 ]
- Baron A, Frieden M, Beny JL: Epoxyeicosatrienoic acids activate a high-conductance, Ca(2+)-dependent K + channel on pig coronary artery endothelial cells. J Physiol. 1997 Nov 1;504 ( Pt 3):537-43. [PubMed:9401962 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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