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 22:48:37 UTC |
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Update Date | 2022-03-07 02:55:23 UTC |
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HMDB ID | HMDB0037559 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cadabicilone |
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Description | Cadabicilone belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a small amount of articles have been published on Cadabicilone. |
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Structure | CC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O InChI=1S/C15H22O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h8-10,12-13H,4-7H2,1-3H3 |
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Synonyms | Not Available |
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Chemical Formula | C15H22O3 |
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Average Molecular Weight | 250.3334 |
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Monoisotopic Molecular Weight | 250.15689457 |
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IUPAC Name | 3,5a,9-trimethyl-dodecahydronaphtho[1,2-b]furan-2,8-dione |
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Traditional Name | 3,5a,9-trimethyl-octahydro-3H-naphtho[1,2-b]furan-2,8-dione |
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CAS Registry Number | 14804-47-8 |
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SMILES | CC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O |
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InChI Identifier | InChI=1S/C15H22O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h8-10,12-13H,4-7H2,1-3H3 |
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InChI Key | BXRGGUXPWTWACZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene lactones |
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Direct Parent | Eudesmanolides, secoeudesmanolides, and derivatives |
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Alternative Parents | |
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Substituents | - Eudesmanolide
- Sesquiterpenoid
- Naphthofuran
- Gamma butyrolactone
- Tetrahydrofuran
- Cyclic ketone
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 118 - 120 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 902.3 mg/L @ 25 °C (est) | The Good Scents Company Information System | 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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Cadabicilone,1TMS,isomer #1 | CC1=C(O[Si](C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C12 | 2170.5 | Semi standard non polar | 33892256 | Cadabicilone,1TMS,isomer #1 | CC1=C(O[Si](C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C12 | 2066.2 | Standard non polar | 33892256 | Cadabicilone,1TMS,isomer #2 | CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C)C(C)C21 | 2162.9 | Semi standard non polar | 33892256 | Cadabicilone,1TMS,isomer #2 | CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C)C(C)C21 | 2022.5 | Standard non polar | 33892256 | Cadabicilone,1TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C12 | 2385.5 | Semi standard non polar | 33892256 | Cadabicilone,1TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C12 | 2327.3 | Standard non polar | 33892256 | Cadabicilone,1TBDMS,isomer #2 | CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)C21 | 2392.0 | Semi standard non polar | 33892256 | Cadabicilone,1TBDMS,isomer #2 | CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)C21 | 2236.9 | 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 - Cadabicilone GC-MS (Non-derivatized) - 70eV, Positive | splash10-009f-2960000000-0f725431c374e162b182 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cadabicilone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cadabicilone 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 - Cadabicilone 10V, Positive-QTOF | splash10-0udi-0390000000-ef79242d3d8ed92df432 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 20V, Positive-QTOF | splash10-0udi-0960000000-0e31a2abe3fc23ef704a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 40V, Positive-QTOF | splash10-014l-9300000000-18f7baac75a5bf82d828 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 10V, Negative-QTOF | splash10-0002-0090000000-9b15449c1771ca1ca357 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 20V, Negative-QTOF | splash10-052b-0190000000-db53a1d787fa4bc45630 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 40V, Negative-QTOF | splash10-0udi-7930000000-365fbba38169a90c6914 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 10V, Positive-QTOF | splash10-001i-0290000000-754dd18a87ade78d631c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 20V, Positive-QTOF | splash10-0ka9-0970000000-7c888b536a8ea7e866ac | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 40V, Positive-QTOF | splash10-056r-1900000000-0548aa46854407ab988f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 10V, Negative-QTOF | splash10-0002-0090000000-09b8c5776dceef2c388e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 20V, Negative-QTOF | splash10-0002-0190000000-181a6ad7f7eb4f01b276 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cadabicilone 40V, Negative-QTOF | splash10-000b-1930000000-511b9486ec0e22ae8c73 | 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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