Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2007-04-12 19:56:15 UTC |
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Update Date | 2022-03-07 02:49:29 UTC |
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HMDB ID | HMDB0005998 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 20-Hydroxyeicosatetraenoic acid |
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Description | 20-Hydroxyeicosatetraenoic acid (20-HETE) is a metabolite of arachidonic acid. Cytochrome P450 enzymes of the 4A and 4F families catalyze the omega-hydroxylation of arachidonic acid and produce 20-HETE. 20-HETE is a potent constrictor of renal, cerebral, and mesenteric arteries. The vasoconstrictor response to 20-HETE is associated with activation of protein kinase, Rho kinase, and the mitogen-activated protein (MAP) kinase pathway C. 20-HETE also increases intracellular Ca2+ by causing the depolarization of vascular smooth muscle membrane secondary to blocking the large-conductance Ca2+-activated K+-channels and by a direct effect on L-type Ca channels. Elevations in the production of 20-HETE mediate the myogenic response of skeletal, renal, and cerebral arteries to elevations in transmural pressure. There is an important interaction between nitric oxide (NO) and the formation of 20-HETE production. NO inhibits the formation of 20-HETE formation in renal and cerebral arteries. A fall in levels of 20-HETE contributes to the cyclic GMP-independent dilator effect of NO to activate the large-conductance Ca2+-activated K+-channels and to dilate the cerebral arteries (PMID: 16258232 ). |
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Structure | OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10- |
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Synonyms | Value | Source |
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(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoic acid | ChEBI | 20-Hydroxy arachidonic acid | ChEBI | 20-Hydroxyarachidonic acid | ChEBI | 20-Hydroxyicosatetraenoic acid | ChEBI | (5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoate | Generator | 20-Hydroxy arachidonate | Generator | 20-Hydroxyarachidonate | Generator | 20-Hydroxyicosatetraenoate | Generator | 20-Hydroxyeicosatetraenoate | Generator | (all-Z)-20-Hydroxy-5,8,11,14-eicosatetraenoate | HMDB | (all-Z)-20-Hydroxy-5,8,11,14-eicosatetraenoic acid | HMDB | 20-HETE | HMDB | 20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate | HMDB | 20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid | HMDB | 20-Hydroxy-5,8,11,14-eicosatetraenoate | HMDB | 20-Hydroxy-5,8,11,14-eicosatetraenoic acid | HMDB | 20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate | HMDB | 20-Hydroxy-5Z,8Z,11Z,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 | (5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid |
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Traditional Name | 20-hete |
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CAS Registry Number | 79551-86-3 |
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SMILES | OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10- |
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InChI Key | NNDIXBJHNLFJJP-DTLRTWKJSA-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
- Hydroxy fatty acid
- Unsaturated fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- 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 | |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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20-Hydroxyeicosatetraenoic acid,1TMS,isomer #1 | C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O | 2826.4 | Semi standard non polar | 33892256 | 20-Hydroxyeicosatetraenoic acid,1TMS,isomer #2 | C[Si](C)(C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO | 2608.4 | Semi standard non polar | 33892256 | 20-Hydroxyeicosatetraenoic acid,2TMS,isomer #1 | C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2694.4 | Semi standard non polar | 33892256 | 20-Hydroxyeicosatetraenoic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O | 3045.0 | Semi standard non polar | 33892256 | 20-Hydroxyeicosatetraenoic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO | 2863.7 | Semi standard non polar | 33892256 | 20-Hydroxyeicosatetraenoic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3184.2 | 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 - 20-Hydroxyeicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0007-3290000000-c19c2446fd09c9b5b114 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 20-Hydroxyeicosatetraenoic acid GC-MS (2 TMS) - 70eV, Positive | splash10-0g6s-8958400000-372a8a263c8ea8f0e5b0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 20-Hydroxyeicosatetraenoic 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 - 20-Hydroxyeicosatetraenoic acid 10V, Positive-QTOF | splash10-0uk9-0059000000-650b772489866747dfc1 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Positive-QTOF | splash10-0pdr-2293000000-4135e55c1f638956a165 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Positive-QTOF | splash10-0006-8890000000-7333663b79a20dc52435 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 10V, Negative-QTOF | splash10-014i-0039000000-b8b23d059895b0d51482 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Negative-QTOF | splash10-0gb9-2098000000-7fd830563f4a43d0b812 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Negative-QTOF | splash10-0a4l-9040000000-ac722c9b6528d7965c21 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 10V, Negative-QTOF | splash10-014i-0009000000-c55e430e69fa5c79a747 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Negative-QTOF | splash10-0gb9-1049000000-1b54cbfba7d53b2e17ab | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Negative-QTOF | splash10-006x-9151000000-9d68be1fa8ed76d657d4 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 10V, Positive-QTOF | splash10-0uk9-1229000000-2c09f1a1c932d016c5e4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Positive-QTOF | splash10-0fe1-5934000000-650155a4dedf606f2045 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Positive-QTOF | splash10-00lu-7900000000-c13624e44921230c2908 | 2021-09-24 | Wishart Lab | View Spectrum |
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Disease References | Hypertension |
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- Minuz P, Jiang H, Fava C, Turolo L, Tacconelli S, Ricci M, Patrignani P, Morganti A, Lechi A, McGiff JC: Altered release of cytochrome p450 metabolites of arachidonic acid in renovascular disease. Hypertension. 2008 May;51(5):1379-85. doi: 10.1161/HYPERTENSIONAHA.107.105395. Epub 2008 Mar 31. [PubMed:18378855 ]
| Cerebral vasospasm |
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- Poloyac SM, Reynolds RB, Yonas H, Kerr ME: Identification and quantification of the hydroxyeicosatetraenoic acids, 20-HETE and 12-HETE, in the cerebrospinal fluid after subarachnoid hemorrhage. J Neurosci Methods. 2005 Jun 15;144(2):257-63. Epub 2004 Dec 30. [PubMed:15910986 ]
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