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 20:44:19 UTC |
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Update Date | 2022-03-07 02:54:36 UTC |
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HMDB ID | HMDB0035724 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 15-Deacetylcalonectrin |
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Description | Crotocin belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. Crotocin is an extremely weak basic (essentially neutral) compound (based on its pKa). Crotocin is a potentially toxic compound. |
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Structure | CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21CO InChI=1S/C17H24O5/c1-10-4-5-16(8-18)13(6-10)22-14-12(21-11(2)19)7-15(16,3)17(14)9-20-17/h6,12-14,18H,4-5,7-9H2,1-3H3 |
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Synonyms | Value | Source |
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15-Decalonectrin | HMDB | 15-Desacetylcalonectrin | HMDB | 15-O-Deacetylcalonectrin | HMDB | 2'-(Hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetic acid | Generator |
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Chemical Formula | C17H24O5 |
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Average Molecular Weight | 308.3695 |
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Monoisotopic Molecular Weight | 308.162373878 |
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IUPAC Name | 2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetate |
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Traditional Name | 2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetate |
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CAS Registry Number | 38818-66-5 |
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SMILES | CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21CO |
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InChI Identifier | InChI=1S/C17H24O5/c1-10-4-5-16(8-18)13(6-10)22-14-12(21-11(2)19)7-15(16,3)17(14)9-20-17/h6,12-14,18H,4-5,7-9H2,1-3H3 |
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InChI Key | DFPPNUOWRKIOKO-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. |
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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 | Sesquiterpenoids |
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Direct Parent | Trichothecenes |
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Alternative Parents | |
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Substituents | - Trichothecene skeleton
- Fatty acid ester
- Oxepane
- Oxane
- Fatty acyl
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Carboxylic acid derivative
- Dialkyl ether
- Oxirane
- Ether
- Monocarboxylic acid or derivatives
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- 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 | |
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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 | 184 - 186 °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 - 15-Deacetylcalonectrin GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-2790000000-58d5fe44c3d8451e2006 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 15-Deacetylcalonectrin GC-MS (1 TMS) - 70eV, Positive | splash10-000w-7974000000-b9f5a14f4ecaa9aa5353 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 15-Deacetylcalonectrin 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 - 15-Deacetylcalonectrin 10V, Positive-QTOF | splash10-0a4m-0093000000-1a76e07ae046fa9a9b0f | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 20V, Positive-QTOF | splash10-0007-1490000000-17c4d54e369c052c1cd9 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 40V, Positive-QTOF | splash10-0g02-9560000000-35060a99d57781469262 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 10V, Negative-QTOF | splash10-0a4i-3198000000-3fcf809901b942d3b454 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 20V, Negative-QTOF | splash10-0ap1-2291000000-25170e54a6b6bfb982d3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 40V, Negative-QTOF | splash10-0a4l-4900000000-a44bc6833c08dedf141f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 10V, Negative-QTOF | splash10-0aor-0079000000-60809020eca26b8c9a62 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 20V, Negative-QTOF | splash10-0a4i-9072000000-a130cf130eca5de8ca88 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 40V, Negative-QTOF | splash10-0a4i-9151000000-849c4f3bf5f58763e733 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 10V, Positive-QTOF | splash10-0a4i-0049000000-051e4a84519c33b4e7dc | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 20V, Positive-QTOF | splash10-052g-0091000000-c1387d5eff85992eb943 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 15-Deacetylcalonectrin 40V, Positive-QTOF | splash10-05mo-9140000000-6caa09c91f3ee2ceaaf7 | 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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