Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-23 05:59:57 UTC |
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Update Date | 2022-03-07 03:17:59 UTC |
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HMDB ID | HMDB0062747 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 12(S)-HETrE |
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Description | 12(S)-HETrE, also known as 12S-hetre, 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. 12(S)-HETrE is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | [H]\C(CCCCC)=C(/[H])C[C@]([H])(O)C(\[H])=C(/[H])\C(\[H])=C(\[H])CCCCCCC(O)=O InChI=1S/C20H34O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h8,10-11,13-14,17,19,21H,2-7,9,12,15-16,18H2,1H3,(H,22,23)/b11-8-,13-10-,17-14+/t19-/m0/s1 |
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Synonyms | Value | Source |
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(12S)-Hydroxy-(8Z,10E,14Z)-eicosatrienoic acid | ChEBI | (12S)-Hydroxy-(8Z,10E,14Z)-icosatrienoic acid | ChEBI | 12S-HETrE | ChEBI | (12S)-Hydroxy-(8Z,10E,14Z)-eicosatrienoate | Generator | (12S)-Hydroxy-(8Z,10E,14Z)-icosatrienoate | Generator |
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Chemical Formula | C20H34O3 |
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Average Molecular Weight | 322.489 |
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Monoisotopic Molecular Weight | 322.250794955 |
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IUPAC Name | (8Z,10E,12S,14Z)-12-hydroxyicosa-8,10,14-trienoic acid |
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Traditional Name | (8Z,10E,12S,14Z)-12-hydroxyicosa-8,10,14-trienoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CCCCC)=C(/[H])C[C@]([H])(O)C(\[H])=C(/[H])\C(\[H])=C(\[H])CCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C20H34O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h8,10-11,13-14,17,19,21H,2-7,9,12,15-16,18H2,1H3,(H,22,23)/b11-8-,13-10-,17-14+/t19-/m0/s1 |
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InChI Key | YYIXZLMPKIFFGQ-ONNNWOQGSA-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
- 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 | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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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 | 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 | 0.0009 g/l | ALOGPS | LogP | 6.22 | 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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12(S)-HETrE,1TMS,isomer #1 | CCCCC/C=C\C[C@@H](/C=C/C=C\CCCCCCC(=O)O)O[Si](C)(C)C | 2735.4 | Semi standard non polar | 33892256 | 12(S)-HETrE,1TMS,isomer #2 | CCCCC/C=C\C[C@H](O)/C=C/C=C\CCCCCCC(=O)O[Si](C)(C)C | 2648.1 | Semi standard non polar | 33892256 | 12(S)-HETrE,2TMS,isomer #1 | CCCCC/C=C\C[C@@H](/C=C/C=C\CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2722.8 | Semi standard non polar | 33892256 | 12(S)-HETrE,1TBDMS,isomer #1 | CCCCC/C=C\C[C@@H](/C=C/C=C\CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2986.8 | Semi standard non polar | 33892256 | 12(S)-HETrE,1TBDMS,isomer #2 | CCCCC/C=C\C[C@H](O)/C=C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C | 2895.7 | Semi standard non polar | 33892256 | 12(S)-HETrE,2TBDMS,isomer #1 | CCCCC/C=C\C[C@@H](/C=C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3223.8 | 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 - 12(S)-HETrE GC-MS (Non-derivatized) - 70eV, Positive | splash10-0pxu-8793000000-9200b46247132b9ecf88 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 12(S)-HETrE GC-MS (2 TMS) - 70eV, Positive | splash10-004i-9323200000-25ccb92bb61a1bf0bf8d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 12(S)-HETrE GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 12(S)-HETrE 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 - 12(S)-HETrE 10V, Negative-QTOF | splash10-00di-0019000000-872177841a61153a7214 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 20V, Negative-QTOF | splash10-0uk9-1249000000-66e788c584658fc666ff | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 40V, Negative-QTOF | splash10-0a4l-9820000000-74587ae4724be9e672e5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 10V, Negative-QTOF | splash10-00di-0009000000-cc4c066d459035524935 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 20V, Negative-QTOF | splash10-0fk9-0319000000-b0b26def9838bdbce675 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 40V, Negative-QTOF | splash10-002f-7794000000-e5fb9a0ccb5d6f63e2c8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 10V, Positive-QTOF | splash10-0a4i-0149000000-64f28186a767ed014923 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 20V, Positive-QTOF | splash10-0a4r-4984000000-0643fa2f76504c2a75e4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 40V, Positive-QTOF | splash10-059f-9630000000-d24554929e112b30d986 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 10V, Positive-QTOF | splash10-0a4i-0439000000-da84ae91d991360530b3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 20V, Positive-QTOF | splash10-0a4i-4932000000-c62d2076d7a546336e03 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12(S)-HETrE 40V, Positive-QTOF | splash10-0a4i-9500000000-aae0257349c93a9cf506 | 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 ]
- Ikei KN, Yeung J, Apopa PL, Ceja J, Vesci J, Holman TR, Holinstat M: Investigations of human platelet-type 12-lipoxygenase: role of lipoxygenase products in platelet activation. J Lipid Res. 2012 Dec;53(12):2546-59. doi: 10.1194/jlr.M026385. Epub 2012 Sep 13. [PubMed:22984144 ]
- Powell WS, Hashefi M, Falck JR, Chauhan K, Rokach J, Wang SS, Mills E, MacLeod RJ: Effects of oxo and dihydro metabolites of 12-hydroxy-5,8,10,14-eicosatetraenoic acid on chemotaxis and cytosolic calcium levels in human neutrophils. J Leukoc Biol. 1995 Feb;57(2):257-63. [PubMed:7852839 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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