Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-14 00:24:46 UTC |
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Update Date | 2022-03-07 02:49:21 UTC |
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HMDB ID | HMDB0004684 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 11,12,15-THETA |
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Description | 11,12,15-trihydroxyeicosatrienoic acid (11,12,15-THETA) is a metabolite of the 15-lipoxygenase (15-LO) pathway of arachidonic acid (AA). 11,12,15-THETA is an endothelium-derived relaxing factor. Acetylcholine stimulates AA release from membrane phospholipids of vascular endothelial cells (ECs). AA is released from phosphatidylcholine (PC) and phosphatidylethanolamine (PE) by phospholipase A2 (PLA2), or from phosphatidylinositol (PI) by phospholipase C (PLC) pathway. The diacylglycerol (DAG) lipase can convert DAG into 2-arachidonoylglycerol from which free AA can be released by monoacylglycerol (MAG) lipase or fatty acid amidohydrolase (FAAH). 11,12,15-THETA mediates the acetylcholine-induced vaso-relaxation, via activation of the K+ channels to hyperpolarize the smooth muscle membrane and induce relaxation. (PMID: 12907422 , 16024567 , 15388505 , 14622984 ). |
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Structure | CCCCC[C@H](O)\C=C\C(O)C(O)C\C=C/C\C=C/CCCC(O)=O InChI=1S/C20H34O5/c1-2-3-9-12-17(21)15-16-19(23)18(22)13-10-7-5-4-6-8-11-14-20(24)25/h4,6-7,10,15-19,21-23H,2-3,5,8-9,11-14H2,1H3,(H,24,25)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1 |
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Synonyms | Value | Source |
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11,12,15-Trihydroxyicosatrienoic acid | Kegg | (5Z,8Z,13E)-(15S)-11,12,15-Trihydroxyeicosa-5,8,12-trienoic acid | Kegg | (5Z,8Z,13E)-(15S)-11,12,15-Trihydroxyicosa-5,8,12-trienoic acid | Kegg | 11,12,15-Trihydroxyicosatrienoate | Generator | (5Z,8Z,13E)-(15S)-11,12,15-Trihydroxyeicosa-5,8,12-trienoate | Generator | (5Z,8Z,13E)-(15S)-11,12,15-Trihydroxyicosa-5,8,12-trienoate | Generator | 11,12,15-TriHETRE | HMDB | 11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoate | HMDB | 11,12,15S-Trihydroxy-5Z,8Z,13E-eicosatrienoic acid | HMDB |
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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,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid |
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Traditional Name | (5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCC[C@H](O)\C=C\C(O)C(O)C\C=C/C\C=C/CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H34O5/c1-2-3-9-12-17(21)15-16-19(23)18(22)13-10-7-5-4-6-8-11-14-20(24)25/h4,6-7,10,15-19,21-23H,2-3,5,8-9,11-14H2,1H3,(H,24,25)/b6-4-,10-7-,16-15+/t17-,18?,19?/m0/s1 |
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InChI Key | PRMWQIVYOYCJQC-YZSNCDGGSA-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 | |
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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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11,12,15-THETA,1TMS,isomer #1 | CCCCC[C@@H](/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 3020.5 | Semi standard non polar | 33892256 | 11,12,15-THETA,1TMS,isomer #2 | CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O | 2989.6 | Semi standard non polar | 33892256 | 11,12,15-THETA,1TMS,isomer #3 | CCCCC[C@H](O)/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2987.2 | Semi standard non polar | 33892256 | 11,12,15-THETA,1TMS,isomer #4 | CCCCC[C@H](O)/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2914.6 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TMS,isomer #1 | CCCCC[C@@H](/C=C/C(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2982.4 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TMS,isomer #2 | CCCCC[C@@H](/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 2994.7 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TMS,isomer #3 | CCCCC[C@@H](/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2928.0 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TMS,isomer #4 | CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2986.9 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TMS,isomer #5 | CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2916.7 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TMS,isomer #6 | CCCCC[C@H](O)/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2914.4 | Semi standard non polar | 33892256 | 11,12,15-THETA,3TMS,isomer #1 | CCCCC[C@@H](/C=C/C(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 2939.5 | Semi standard non polar | 33892256 | 11,12,15-THETA,3TMS,isomer #2 | CCCCC[C@@H](/C=C/C(O[Si](C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2876.3 | Semi standard non polar | 33892256 | 11,12,15-THETA,3TMS,isomer #3 | CCCCC[C@@H](/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 2886.0 | Semi standard non polar | 33892256 | 11,12,15-THETA,3TMS,isomer #4 | CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2895.1 | Semi standard non polar | 33892256 | 11,12,15-THETA,4TMS,isomer #1 | CCCCC[C@@H](/C=C/C(O[Si](C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 2852.6 | Semi standard non polar | 33892256 | 11,12,15-THETA,1TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3252.5 | Semi standard non polar | 33892256 | 11,12,15-THETA,1TBDMS,isomer #2 | CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O | 3241.9 | Semi standard non polar | 33892256 | 11,12,15-THETA,1TBDMS,isomer #3 | CCCCC[C@H](O)/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3235.6 | Semi standard non polar | 33892256 | 11,12,15-THETA,1TBDMS,isomer #4 | CCCCC[C@H](O)/C=C/C(O)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3171.6 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3437.8 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TBDMS,isomer #2 | CCCCC[C@@H](/C=C/C(O)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3444.3 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TBDMS,isomer #3 | CCCCC[C@@H](/C=C/C(O)C(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 | 3416.6 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TBDMS,isomer #4 | CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3432.1 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TBDMS,isomer #5 | CCCCC[C@H](O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(O)C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3399.6 | Semi standard non polar | 33892256 | 11,12,15-THETA,2TBDMS,isomer #6 | CCCCC[C@H](O)/C=C/C(O)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 | 3389.1 | Semi standard non polar | 33892256 | 11,12,15-THETA,3TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C(O[Si](C)(C)C(C)(C)C)C(C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3619.0 | Semi standard non polar | 33892256 | 11,12,15-THETA,3TBDMS,isomer #2 | CCCCC[C@@H](/C=C/C(O[Si](C)(C)C(C)(C)C)C(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 | 3609.9 | Semi standard non polar | 33892256 | 11,12,15-THETA,3TBDMS,isomer #3 | CCCCC[C@@H](/C=C/C(O)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)O[Si](C)(C)C(C)(C)C | 3627.6 | Semi standard non polar | 33892256 | 11,12,15-THETA,3TBDMS,isomer #4 | CCCCC[C@H](O)/C=C/C(O[Si](C)(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 | 3580.8 | Semi standard non polar | 33892256 | 11,12,15-THETA,4TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C(O[Si](C)(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)O[Si](C)(C)C(C)(C)C | 3768.2 | Semi standard non polar | 33892256 |
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Spectra |
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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 - 11,12,15-THETA GC-MS (Non-derivatized) - 70eV, Positive | splash10-000j-6923000000-729d8425f6b7961f12d6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 11,12,15-THETA GC-MS (4 TMS) - 70eV, Positive | splash10-004i-9114245000-a9570b215fa6eaa9ff8c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 11,12,15-THETA 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 - 11,12,15-THETA 10V, Positive-QTOF | splash10-00kr-0109000000-ab120d0eda68ea718566 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 20V, Positive-QTOF | splash10-066r-2914000000-0b5d4d8637219b27e389 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 40V, Positive-QTOF | splash10-0abc-9720000000-6f9ba40124a0e432ec2a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 10V, Negative-QTOF | splash10-0udi-0009000000-2fe2fc467f93d0346dcd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 20V, Negative-QTOF | splash10-0k9i-1926000000-cebc50fd199b4b5d0e57 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 40V, Negative-QTOF | splash10-0a4i-8910000000-87e98db32bedae5d986e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 10V, Positive-QTOF | splash10-00kr-0029000000-ebef111dafd7c78d37ac | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 20V, Positive-QTOF | splash10-014i-4569000000-4dc08f53204dfc55a344 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 40V, Positive-QTOF | splash10-0apl-9510000000-2862ca5a79b8eded3e16 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 10V, Negative-QTOF | splash10-0udi-0009000000-cbb73f896579bb3935fd | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 20V, Negative-QTOF | splash10-0f79-1649000000-07299e0617da708c9b9a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11,12,15-THETA 40V, Negative-QTOF | splash10-052b-9651000000-4bdcfd2275713a32e906 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | <0.0001 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | <0.0001 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023403 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 10128338 |
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KEGG Compound ID | C14782 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 11954043 |
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PDB ID | Not Available |
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ChEBI ID | 34128 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Campbell WB, Spitzbarth N, Gauthier KM, Pfister SL: 11,12,15-Trihydroxyeicosatrienoic acid mediates ACh-induced relaxations in rabbit aorta. Am J Physiol Heart Circ Physiol. 2003 Dec;285(6):H2648-56. Epub 2003 Aug 7. [PubMed:12907422 ]
- Tang X, Edwards EM, Holmes BB, Falck JR, Campbell WB: Role of phospholipase C and diacylglyceride lipase pathway in arachidonic acid release and acetylcholine-induced vascular relaxation in rabbit aorta. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H37-45. Epub 2005 Jul 15. [PubMed:16024567 ]
- Zhang DX, Gauthier KM, Chawengsub Y, Holmes BB, Campbell WB: Cyclooxygenase- and lipoxygenase-dependent relaxation to arachidonic acid in rabbit small mesenteric arteries. Am J Physiol Heart Circ Physiol. 2005 Jan;288(1):H302-9. Epub 2004 Sep 23. [PubMed:15388505 ]
- Pfister SL, Spitzbarth N, Zeldin DC, Lafite P, Mansuy D, Campbell WB: Rabbit aorta converts 15-HPETE to trihydroxyeicosatrienoic acids: potential role of cytochrome P450. Arch Biochem Biophys. 2003 Dec 1;420(1):142-52. [PubMed:14622984 ]
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