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 17:33:52 UTC |
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Update Date | 2022-03-07 02:52:22 UTC |
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HMDB ID | HMDB0029969 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Squamostanal A |
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Description | Squamostanal A 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 Squamostanal A. |
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Structure | CC1OC(=O)C(CCCCCCCCCCCCC=O)=C1 InChI=1S/C18H30O3/c1-16-15-17(18(20)21-16)13-11-9-7-5-3-2-4-6-8-10-12-14-19/h14-16H,2-13H2,1H3 |
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Synonyms | Not Available |
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Chemical Formula | C18H30O3 |
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Average Molecular Weight | 294.429 |
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Monoisotopic Molecular Weight | 294.219494826 |
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IUPAC Name | 13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecanal |
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Traditional Name | 13-(5-methyl-2-oxo-5H-furan-3-yl)tridecanal |
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CAS Registry Number | 156764-90-8 |
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SMILES | CC1OC(=O)C(CCCCCCCCCCCCC=O)=C1 |
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InChI Identifier | InChI=1S/C18H30O3/c1-16-15-17(18(20)21-16)13-11-9-7-5-3-2-4-6-8-10-12-14-19/h14-16H,2-13H2,1H3 |
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InChI Key | CWCAGZXBGYHWNE-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
- 2-furanone
- Alpha-hydrogen aldehyde
- Dihydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Lactone
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Aldehyde
- Organooxygen compound
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- 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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 66 - 68 °C | 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 - Squamostanal A GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ukc-3490000000-7b1ff54f858aadbde4b3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Squamostanal A 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 - Squamostanal A 10V, Positive-QTOF | splash10-0002-0090000000-d4ba155bce276c94202a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 20V, Positive-QTOF | splash10-0006-9570000000-c2d943e2d84d0422cb59 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 40V, Positive-QTOF | splash10-0fr6-7930000000-00efa5845f6074e39d76 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 10V, Negative-QTOF | splash10-0006-0090000000-728d4f1b4fb067f52fb4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 20V, Negative-QTOF | splash10-0007-2090000000-74b8c5488052f72e63fa | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 40V, Negative-QTOF | splash10-0006-9030000000-c937dc895cdf6ba2d727 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 10V, Positive-QTOF | splash10-0002-1390000000-1fae30d70610a199c197 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 20V, Positive-QTOF | splash10-0002-6590000000-ac52a0b936f35402e4e5 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 40V, Positive-QTOF | splash10-0537-9300000000-b93947502ce8ca261758 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 10V, Negative-QTOF | splash10-0006-0090000000-55e62f9f2f7dcc1fe39a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 20V, Negative-QTOF | splash10-0005-0090000000-69fb163913a9f7be08af | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Squamostanal A 40V, Negative-QTOF | splash10-05tb-3390000000-d020349e68b4ea57ec08 | 2021-09-25 | 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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