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 00:20:18 UTC |
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Update Date | 2022-03-07 02:49:21 UTC |
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HMDB ID | HMDB0004682 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 11(R)-HETE |
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Description | 11(R)-HETE is produced from arachidonic acid by both COX-1 and COX-2 (cyclooxygenases). Using a model of intestinal epithelial cells that express the COX-2 permanently, 11(R)-HETE is produced upon stimulation. However, 11(R)-HETE is not detected in intact cells. Endothelial cells release several factors which influence vascular tone, leukocyte function and platelet aggregation; 11(R)-HETE is one of these factors. (PMID: 15964853 , 8555273 ). |
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Structure | CCCCC\C=C/C=C\[C@H](O)C\C=C/C\C=C\CCCC(O)=O InChI=1S/C20H32O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b9-6+,10-7-,14-11-,16-13-/t19-/m0/s1 |
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Synonyms | Value | Source |
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11R-Hydroxy-5E,8Z,12Z,14Z-eicosatetraenoate | HMDB | 11-HETE | HMDB | 11-Hydroxy-5,8,12,14-eicosatetraenoic acid | HMDB | 11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (R)-(e,Z,Z,Z)-isomer | HMDB | 11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomer | HMDB | 11-Hydroxy-5,8,12,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer | HMDB | 11-Hydroxy-arachidonic acid | HMDB | 11-Hydroxyeicosatetraenoate | HMDB | 11-Hydroxyeicosatetraenoic acid | HMDB | 11R-Hydroxy-5E,8Z,12Z,14Z-eicosatetraenoic acid | HMDB |
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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 | (5E,8Z,11R,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid |
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Traditional Name | (5E,8Z,11R,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid |
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CAS Registry Number | 73347-43-0 |
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SMILES | CCCCC\C=C/C=C\[C@H](O)C\C=C/C\C=C\CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H32O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b9-6+,10-7-,14-11-,16-13-/t19-/m0/s1 |
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InChI Key | GCZRCCHPLVMMJE-RSPKXIRXSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four 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 | Hydroxyeicosatetraenoic acids |
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Alternative Parents | |
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Substituents | - Hydroxyeicosatetraenoic acid
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- 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 | 4.056 | 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(R)-HETE,1TMS,isomer #1 | CCCCC/C=C\C=C/[C@@H](C/C=C\C/C=C/CCCC(=O)O)O[Si](C)(C)C | 2737.7 | Semi standard non polar | 33892256 | 11(R)-HETE,1TMS,isomer #2 | CCCCC/C=C\C=C/[C@H](O)C/C=C\C/C=C/CCCC(=O)O[Si](C)(C)C | 2633.6 | Semi standard non polar | 33892256 | 11(R)-HETE,2TMS,isomer #1 | CCCCC/C=C\C=C/[C@@H](C/C=C\C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2707.9 | Semi standard non polar | 33892256 | 11(R)-HETE,1TBDMS,isomer #1 | CCCCC/C=C\C=C/[C@@H](C/C=C\C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2979.1 | Semi standard non polar | 33892256 | 11(R)-HETE,1TBDMS,isomer #2 | CCCCC/C=C\C=C/[C@H](O)C/C=C\C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C | 2872.8 | Semi standard non polar | 33892256 | 11(R)-HETE,2TBDMS,isomer #1 | CCCCC/C=C\C=C/[C@@H](C/C=C\C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3191.5 | 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(R)-HETE GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udm-7963000000-7e505779bd4cf8c106b6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 11(R)-HETE GC-MS (2 TMS) - 70eV, Positive | splash10-004i-9124200000-72c62505c0bcc5ae92f8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 11(R)-HETE 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(R)-HETE 10V, Positive-QTOF | splash10-0udi-0149000000-aaebfb498059d4b967d7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 20V, Positive-QTOF | splash10-0pi0-4984000000-0636fbf2aeaf64246034 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 40V, Positive-QTOF | splash10-052f-9640000000-ab33f1b4bf6e7e265a69 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 10V, Negative-QTOF | splash10-014i-0019000000-af55d77ea16ec753f131 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 20V, Negative-QTOF | splash10-0uxr-1249000000-0674eb2063fd2da82890 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 40V, Negative-QTOF | splash10-0a4l-9820000000-f4a00ee31348f64040b2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 10V, Negative-QTOF | splash10-014i-0009000000-49b5e5d0235eaaa77907 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 20V, Negative-QTOF | splash10-0uxr-0239000000-8c5726cdda1443135e59 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 40V, Negative-QTOF | splash10-052e-6490000000-105233c675229d88affa | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 10V, Positive-QTOF | splash10-0udi-1439000000-b6967c53e413d28d9785 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 20V, Positive-QTOF | splash10-0frj-3922000000-f74837099563f2e9a341 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 11(R)-HETE 40V, Positive-QTOF | splash10-014l-9210000000-aa08bbfe3cf858c45f43 | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
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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 | 0.000425 +/- 0.0000095 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.00102 +/- 0.00125 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.000401 +/- 0.00036 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.000727 +/- 0.00006 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.000125 +/- 0.000077 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 | FDB023402 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4472406 |
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KEGG Compound ID | C14780 |
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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 | 5312981 |
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PDB ID | Not Available |
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ChEBI ID | 34126 |
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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 | - Lee SH, Williams MV, Dubois RN, Blair IA: Cyclooxygenase-2-mediated DNA damage. J Biol Chem. 2005 Aug 5;280(31):28337-46. Epub 2005 Jun 17. [PubMed:15964853 ]
- Rosolowsky M, Campbell WB: Synthesis of hydroxyeicosatetraenoic (HETEs) and epoxyeicosatrienoic acids (EETs) by cultured bovine coronary artery endothelial cells. Biochim Biophys Acta. 1996 Jan 19;1299(2):267-77. [PubMed:8555273 ]
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