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 20:56:40 UTC |
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Update Date | 2022-03-07 02:54:41 UTC |
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HMDB ID | HMDB0035898 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Robustocin |
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Description | Robustocin 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. Based on a literature review a small amount of articles have been published on Robustocin. |
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Structure | CCCCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(CCCCCCCC2=CC(C)OC2=O)O1 InChI=1S/C35H62O5/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-31(36)32-25-26-34(40-32)33-24-23-30(39-33)21-18-15-13-14-17-20-29-27-28(2)38-35(29)37/h27-28,30-34,36H,3-26H2,1-2H3 |
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Synonyms | Not Available |
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Chemical Formula | C35H62O5 |
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Average Molecular Weight | 562.8638 |
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Monoisotopic Molecular Weight | 562.459725094 |
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IUPAC Name | 3-(7-{5-[5-(1-hydroxypentadecyl)oxolan-2-yl]oxolan-2-yl}heptyl)-5-methyl-2,5-dihydrofuran-2-one |
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Traditional Name | 3-(7-{5-[5-(1-hydroxypentadecyl)oxolan-2-yl]oxolan-2-yl}heptyl)-5-methyl-5H-furan-2-one |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(CCCCCCCC2=CC(C)OC2=O)O1 |
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InChI Identifier | InChI=1S/C35H62O5/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-31(36)32-25-26-34(40-32)33-24-23-30(39-33)21-18-15-13-14-17-20-29-27-28(2)38-35(29)37/h27-28,30-34,36H,3-26H2,1-2H3 |
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InChI Key | XINHKDZHJWEKBB-UHFFFAOYSA-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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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 | 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 IndicesUnderivatizedDerivatized |
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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 - Robustocin GC-MS (Non-derivatized) - 70eV, Positive | splash10-02td-0398210000-cfae1241ebd7e59ecd0f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Robustocin GC-MS (1 TMS) - 70eV, Positive | splash10-00kr-9148724000-f1c1932595b0d4a40a8c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Robustocin GC-MS ("Robustocin,1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-14 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Robustocin GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | 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 - Robustocin 10V, Positive-QTOF | splash10-03di-0031190000-ba7d4d863888e9a9b16b | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 20V, Positive-QTOF | splash10-0002-1922450000-91dbd9b3b3ac094d044a | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 40V, Positive-QTOF | splash10-0005-5940300000-a940361cd874660e104e | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 10V, Negative-QTOF | splash10-03di-0000090000-abb45654760e92937a2c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 20V, Negative-QTOF | splash10-03xv-1154090000-5e65c225ee9d0db9e08d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 40V, Negative-QTOF | splash10-0303-1393110000-98a6cc895a27bdbcfbda | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 10V, Positive-QTOF | splash10-03dj-1000190000-ce76a3d15526ba3991b4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 20V, Positive-QTOF | splash10-02vs-1000090000-cb59bffdc11d9249f1be | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 40V, Positive-QTOF | splash10-0006-9100000000-1fae6481dfc1ef92fa4a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 10V, Negative-QTOF | splash10-03di-0011090000-501468b6bd5c0e0d253d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 20V, Negative-QTOF | splash10-03xr-2042090000-12628a4b9e77a68e0082 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Robustocin 40V, Negative-QTOF | splash10-05n0-5298020000-b8b29db12fed7ca11500 | 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 ]
- (). 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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