Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-16 03:42:19 UTC |
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Update Date | 2022-03-07 03:17:52 UTC |
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HMDB ID | HMDB0062302 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid |
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Description | 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid is an eicosanoid lipid molecule. It is classified as a member of the hydroxyeicosatetraenoic acids. Hydroxyeicosatetraenoic acids are eicosanoic acids with an attached hydroxyl group and four CC double bonds. 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic. |
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Structure | CCC(O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11- |
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Synonyms | Value | Source |
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(5Z,8Z,11Z,14Z)-18-Hydroxy-5,8,11,14-eicosatetraenoic acid | ChEBI | (5Z,8Z,11Z,14Z)-18-Hydroxyeicosa-5,8,11,14-tetraenoic acid | ChEBI | (5Z,8Z,11Z,14Z)-18-Hydroxyicosa-5,8,11,14-tetraenoic acid | ChEBI | (Z,Z,Z,Z)-18-Hydroxy-5,8,11,14-eicosatetraenoic acid | ChEBI | (Z,Z,Z,Z)-18-Hydroxy-5,8,11,14-icosatetraenoic acid | ChEBI | 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid | ChEBI | (5Z,8Z,11Z,14Z)-18-Hydroxy-5,8,11,14-eicosatetraenoate | Generator | (5Z,8Z,11Z,14Z)-18-Hydroxyeicosa-5,8,11,14-tetraenoate | Generator | (5Z,8Z,11Z,14Z)-18-Hydroxyicosa-5,8,11,14-tetraenoate | Generator | (Z,Z,Z,Z)-18-Hydroxy-5,8,11,14-eicosatetraenoate | Generator | (Z,Z,Z,Z)-18-Hydroxy-5,8,11,14-icosatetraenoate | Generator | 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate | Generator | 18-Hydroxy-5,8,11,14-eicosatetraenoic acid | HMDB | 18-Hydroxyeicosatetraenoic acid | HMDB | 18-Hydroxyarachidonic acid | HMDB | 18-HETE | HMDB |
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Chemical Formula | C20H32O3 |
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Average Molecular Weight | 320.473 |
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Monoisotopic Molecular Weight | 320.23514489 |
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IUPAC Name | (5Z,8Z,11Z,14Z)-18-hydroxyicosa-5,8,11,14-tetraenoic acid |
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Traditional Name | 18-hete |
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CAS Registry Number | 133268-58-3 |
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SMILES | CCC(O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11- |
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InChI Key | PPCHNRUZQWLEMF-XBOCNYGYSA-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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Not Available | Not Available |
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Physical Properties |
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State | Not Available |
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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 | 0.002 g/l | ALOGPS | LogP | 5.81 | ALOGPS |
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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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18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,1TMS,isomer #1 | CCC(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2712.9 | Semi standard non polar | 33892256 | 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,1TMS,isomer #2 | CCC(O)CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C | 2568.7 | Semi standard non polar | 33892256 | 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,2TMS,isomer #1 | CCC(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2605.0 | Semi standard non polar | 33892256 | 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,1TBDMS,isomer #1 | CCC(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2955.7 | Semi standard non polar | 33892256 | 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,1TBDMS,isomer #2 | CCC(O)CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 2818.2 | Semi standard non polar | 33892256 | 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid,2TBDMS,isomer #1 | CCC(CC/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 | 3086.0 | 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 - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f97-7291000000-33d0a3568a9892f04813 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid GC-MS (2 TMS) - 70eV, Positive | splash10-009i-9436500000-0c21440f1fd79ba11984 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic 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 - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 10V, Positive-QTOF | splash10-0udi-0059000000-a75bea5dd5332be1a84f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 20V, Positive-QTOF | splash10-0udr-1292000000-a91689bb888d83d363db | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 40V, Positive-QTOF | splash10-1000-8790000000-0eab084330a82cf88226 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 10V, Negative-QTOF | splash10-014i-0019000000-710912287685513d0e07 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 20V, Negative-QTOF | splash10-0uxr-1059000000-ad675311c547d18f97bb | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 40V, Negative-QTOF | splash10-0a4l-9030000000-a7c5a41adbeb99e30dbc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 10V, Negative-QTOF | splash10-014i-0009000000-777fdb814292c66079c9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 20V, Negative-QTOF | splash10-0gb9-3059000000-c59628baf2569d14b3c3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 40V, Negative-QTOF | splash10-0a4l-9020000000-d11651945eb0a6c4f27d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 10V, Positive-QTOF | splash10-0uk9-1339000000-0392a1ab82d4e70b35db | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 20V, Positive-QTOF | splash10-0fri-4953000000-34622f97ba9d1fd54e9b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid 40V, Positive-QTOF | splash10-015c-9600000000-7cde68db4ec7173c6177 | 2021-09-24 | Wishart Lab | View Spectrum |
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General References | - 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 ]
- Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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