Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2009-07-25 00:02:28 UTC |
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Update Date | 2022-09-22 17:44:00 UTC |
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HMDB ID | HMDB0012535 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 12S-HHT |
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Description | 12(S)-HHTrE is an unusual product of the cyclooxygenase (COX) pathway and one of the primary arachidonic acid metabolites of the human platelet.1 It is biosynthesized by thromboxane (TX) synthesis from prostaglandin H2 (PGH2) concurrently with TXA2. The biological role of 12(S)-HHTrE is uncertain. It is avidly oxidized to 12-oxoHTrE by porcine 15-hydroxy PGDH. |
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Structure | CCCCC[C@H](O)\C=C\C=C\C\C=C/CCCC(O)=O InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1 |
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Synonyms | Value | Source |
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12-HHTrE | ChEBI | 12S-Hydroxy-5Z,8E,10E-heptadecatrienoic acid | ChEBI | (12S,5Z,8E,10E)-12-Hydroxy-5,8,10-heptadecatrienoic acid | Kegg | 12S-Hydroxy-5Z,8E,10E-heptadecatrienoate | Generator | (12S,5Z,8E,10E)-12-Hydroxy-5,8,10-heptadecatrienoate | Generator | 12-L-Hydroxy-5,8,10-heptadecatrienoic acid | MeSH | 12-Hydroxy-5,8,10-heptadecatrienoic acid | MeSH | 12-HHT | MeSH | 12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-(e,Z,Z)-isomer | MeSH | 12-Hydroxy-5,8,10-heptadecatrienoic acid, (e,Z,Z)-isomer | MeSH | 12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-(Z,e,e)-isomer | MeSH | 12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-isomer | MeSH | Hydroxyheptadecatrienoic acid | MeSH | 12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoate | HMDB | 12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acid | HMDB | 12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acid anion | HMDB | 12-Hydroxyheptadecatrienoate | HMDB | 12-Hydroxyheptadecatrienoic acid | HMDB | HHT | HMDB | Hydroxyheptadecatrienate | HMDB | Hydroxyheptadecatrienoate | HMDB | Hydroxyheptadecatrienoic acid anion | HMDB | 12S-HHT | ChEBI |
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Chemical Formula | C17H28O3 |
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Average Molecular Weight | 280.4024 |
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Monoisotopic Molecular Weight | 280.203844762 |
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IUPAC Name | (5Z,8E,10E,12S)-12-hydroxyheptadeca-5,8,10-trienoic acid |
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Traditional Name | 12-HHTrE |
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CAS Registry Number | 54397-84-1 |
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SMILES | CCCCC[C@H](O)\C=C\C=C\C\C=C/CCCC(O)=O |
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InChI Identifier | InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1 |
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InChI Key | KUKJHGXXZWHSBG-WBGSEQOASA-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
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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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12S-HHT,1TMS,isomer #1 | CCCCC[C@@H](/C=C/C=C/C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2426.0 | Semi standard non polar | 33892256 | 12S-HHT,1TMS,isomer #2 | CCCCC[C@H](O)/C=C/C=C/C/C=C\CCCC(=O)O[Si](C)(C)C | 2347.2 | Semi standard non polar | 33892256 | 12S-HHT,2TMS,isomer #1 | CCCCC[C@@H](/C=C/C=C/C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2422.8 | Semi standard non polar | 33892256 | 12S-HHT,1TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C=C/C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2673.6 | Semi standard non polar | 33892256 | 12S-HHT,1TBDMS,isomer #2 | CCCCC[C@H](O)/C=C/C=C/C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 2587.3 | Semi standard non polar | 33892256 | 12S-HHT,2TBDMS,isomer #1 | CCCCC[C@@H](/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 | 2906.7 | 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 - 12S-HHT GC-MS (Non-derivatized) - 70eV, Positive | splash10-0596-7940000000-88adc904734528989f76 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 12S-HHT GC-MS (2 TMS) - 70eV, Positive | splash10-009i-9223100000-1505e4bf1a2b098cc662 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 12S-HHT 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 - 12S-HHT 10V, Positive-QTOF | splash10-03di-0090000000-025c6c4f9cc74b291b50 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 20V, Positive-QTOF | splash10-044s-4490000000-e7b3a17b02d9bf372212 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 40V, Positive-QTOF | splash10-05tf-9510000000-a08ec733ca2fb7d71708 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 10V, Negative-QTOF | splash10-004i-0090000000-0cc456c0c372dc9dcfc6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 20V, Negative-QTOF | splash10-03fr-1090000000-a3df181a56e24018b9e5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 40V, Negative-QTOF | splash10-0a4l-9320000000-f4709ec871502770402e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 10V, Negative-QTOF | splash10-01t9-0090000000-901f14c9bb947096b214 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 20V, Negative-QTOF | splash10-03fr-0490000000-4d3abc99004a8aa63c02 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 40V, Negative-QTOF | splash10-052f-9410000000-8529271056414c39c9f7 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 10V, Positive-QTOF | splash10-03di-0590000000-800b65d657b078360d45 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 20V, Positive-QTOF | splash10-01wb-3920000000-6040d9c2d707a1656b95 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 12S-HHT 40V, Positive-QTOF | splash10-066v-9400000000-281fc4c65ccd705a48a1 | 2021-09-25 | Wishart Lab | View Spectrum |
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