Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 21:24:37 UTC |
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Update Date | 2022-03-07 02:54:51 UTC |
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HMDB ID | HMDB0036288 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Campesteryl elaidate |
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Description | 6-Hydroxydesacetyluvaricin (incorr.) belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. 6-Hydroxydesacetyluvaricin (incorr.) is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CCCCCCCC\C=C/CCCCCCCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCC(C)C(C)C InChI=1S/C46H80O2/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-44(47)48-39-30-32-45(6)38(34-39)26-27-40-42-29-28-41(46(42,7)33-31-43(40)45)37(5)25-24-36(4)35(2)3/h15-16,26,35-37,39-43H,8-14,17-25,27-34H2,1-7H3/b16-15- |
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Synonyms | Value | Source |
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14-(5,6-Dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z)-octadec-9-enoic acid | Generator | Campesteryl elaidic acid | Generator |
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Chemical Formula | C46H80O2 |
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Average Molecular Weight | 665.1262 |
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Monoisotopic Molecular Weight | 664.615831804 |
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IUPAC Name | 14-(5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z)-octadec-9-enoate |
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Traditional Name | 14-(5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z)-octadec-9-enoate |
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CAS Registry Number | 64144-49-6 |
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SMILES | CCCCCCCC\C=C/CCCCCCCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCC(C)C(C)C |
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InChI Identifier | InChI=1S/C46H80O2/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-44(47)48-39-30-32-45(6)38(34-39)26-27-40-42-29-28-41(46(42,7)33-31-43(40)45)37(5)25-24-36(4)35(2)3/h15-16,26,35-37,39-43H,8-14,17-25,27-34H2,1-7H3/b16-15- |
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InChI Key | PBJGXWXGARTUCF-NXVVXOECSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. |
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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 alcohols |
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Direct Parent | Annonaceous acetogenins |
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Alternative Parents | |
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Substituents | - Annonaceae acetogenin skeleton
- Long chain fatty alcohol
- 2-furanone
- Dihydrofuran
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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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 | 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 IndicesUnderivatized |
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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 - Campesteryl elaidate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0674-7468059000-a90eb1c036914c149bff | 2017-09-01 | 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 - Campesteryl elaidate 10V, Positive-QTOF | splash10-014i-1162229000-1c3a6f143b7dd1fd2423 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 20V, Positive-QTOF | splash10-0fz0-7395221000-6d767f9732be76a6e3dc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 40V, Positive-QTOF | splash10-00ri-9385020000-d81e652d1d590f1ac07f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 10V, Negative-QTOF | splash10-03di-0024009000-9ffacbe32e972843e202 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 20V, Negative-QTOF | splash10-01ot-0059103000-0344196fda5c3ad60809 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 40V, Negative-QTOF | splash10-001m-3029000000-3ceb85285b76a9bf1682 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 10V, Negative-QTOF | splash10-03di-0020009000-c4a882d619f05b320fd7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 20V, Negative-QTOF | splash10-03di-0013009000-de3abdeea41c629d21d5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 40V, Negative-QTOF | splash10-06vj-7655669000-a5c46f7baa01d553634b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 10V, Positive-QTOF | splash10-015i-5059148000-8ad484feacfcf395c807 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 20V, Positive-QTOF | splash10-0a4u-9200000000-1cca4a379c2c448bbb30 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Campesteryl elaidate 40V, Positive-QTOF | splash10-0536-9100000000-a5c22c7b415c70e190bc | 2021-09-22 | 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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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