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 20:52:10 UTC |
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Update Date | 2022-03-07 02:54:39 UTC |
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HMDB ID | HMDB0035846 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Anguidol |
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Description | Anguidol, also known as scirpenetriol, 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. Anguidol is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC1=CC2OC3C(O)C(O)C(C)(C33CO3)C2(CO)CC1 InChI=1S/C15H22O5/c1-8-3-4-14(6-16)9(5-8)20-12-10(17)11(18)13(14,2)15(12)7-19-15/h5,9-12,16-18H,3-4,6-7H2,1-2H3 |
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Synonyms | Value | Source |
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12,13-Epoxy-trichothec-9-ene-3alpha,4beta,15-triol | HMDB | Anguidine deriv scirpentriol | HMDB | Scirpene-3,4,15-triol | HMDB | Scirpenetriol | HMDB | Scirpenol | HMDB | Scirpentriol | HMDB | T-2 Triol | MeSH | 3,4,15-Trihydroxy-8-(3-methylbutyryloxy)-1,2,3-epoxytrichothec--9-ene | MeSH |
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Chemical Formula | C15H22O5 |
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Average Molecular Weight | 282.3322 |
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Monoisotopic Molecular Weight | 282.146723814 |
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IUPAC Name | 2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-ene-10',11'-diol |
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Traditional Name | 2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-ene-10',11'-diol |
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CAS Registry Number | 2270-41-9 |
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SMILES | CC1=CC2OC3C(O)C(O)C(C)(C33CO3)C2(CO)CC1 |
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InChI Identifier | InChI=1S/C15H22O5/c1-8-3-4-14(6-16)9(5-8)20-12-10(17)11(18)13(14,2)15(12)7-19-15/h5,9-12,16-18H,3-4,6-7H2,1-2H3 |
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InChI Key | PXEBOIUZEXXBGH-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 | Not Available |
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Substituents | Not Available |
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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 | 189 - 191 °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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Anguidol,1TMS,isomer #1 | CC1=CC2OC3C(O[Si](C)(C)C)C(O)C(C)(C2(CO)CC1)C31CO1 | 2359.9 | Semi standard non polar | 33892256 | Anguidol,1TMS,isomer #2 | CC1=CC2OC3C(O)C(O[Si](C)(C)C)C(C)(C2(CO)CC1)C31CO1 | 2371.3 | Semi standard non polar | 33892256 | Anguidol,1TMS,isomer #3 | CC1=CC2OC3C(O)C(O)C(C)(C2(CO[Si](C)(C)C)CC1)C31CO1 | 2323.6 | Semi standard non polar | 33892256 | Anguidol,2TMS,isomer #1 | CC1=CC2OC3C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C2(CO)CC1)C31CO1 | 2365.7 | Semi standard non polar | 33892256 | Anguidol,2TMS,isomer #2 | CC1=CC2OC3C(O[Si](C)(C)C)C(O)C(C)(C2(CO[Si](C)(C)C)CC1)C31CO1 | 2329.3 | Semi standard non polar | 33892256 | Anguidol,2TMS,isomer #3 | CC1=CC2OC3C(O)C(O[Si](C)(C)C)C(C)(C2(CO[Si](C)(C)C)CC1)C31CO1 | 2331.4 | Semi standard non polar | 33892256 | Anguidol,3TMS,isomer #1 | CC1=CC2OC3C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C2(CO[Si](C)(C)C)CC1)C31CO1 | 2356.5 | Semi standard non polar | 33892256 | Anguidol,1TBDMS,isomer #1 | CC1=CC2OC3C(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C2(CO)CC1)C31CO1 | 2612.8 | Semi standard non polar | 33892256 | Anguidol,1TBDMS,isomer #2 | CC1=CC2OC3C(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C2(CO)CC1)C31CO1 | 2624.6 | Semi standard non polar | 33892256 | Anguidol,1TBDMS,isomer #3 | CC1=CC2OC3C(O)C(O)C(C)(C2(CO[Si](C)(C)C(C)(C)C)CC1)C31CO1 | 2578.5 | Semi standard non polar | 33892256 | Anguidol,2TBDMS,isomer #1 | CC1=CC2OC3C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C2(CO)CC1)C31CO1 | 2849.1 | Semi standard non polar | 33892256 | Anguidol,2TBDMS,isomer #2 | CC1=CC2OC3C(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C2(CO[Si](C)(C)C(C)(C)C)CC1)C31CO1 | 2809.3 | Semi standard non polar | 33892256 | Anguidol,2TBDMS,isomer #3 | CC1=CC2OC3C(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C2(CO[Si](C)(C)C(C)(C)C)CC1)C31CO1 | 2813.1 | Semi standard non polar | 33892256 | Anguidol,3TBDMS,isomer #1 | CC1=CC2OC3C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C2(CO[Si](C)(C)C(C)(C)C)CC1)C31CO1 | 3031.8 | Semi 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 - Anguidol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fk9-3980000000-70e0c82b919ac960d454 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Anguidol GC-MS (3 TMS) - 70eV, Positive | splash10-000t-7964800000-3fe4b14d05f42aabb777 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Anguidol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Anguidol 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 - Anguidol 10V, Positive-QTOF | splash10-0159-0090000000-464ef52cd83df1b85f0b | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 20V, Positive-QTOF | splash10-066s-1590000000-80f55d84841d3b245048 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 40V, Positive-QTOF | splash10-0gba-9640000000-31027155a4571b4c96c1 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 10V, Negative-QTOF | splash10-001i-0090000000-dafc5573bf4d9a60e7dd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 20V, Negative-QTOF | splash10-0gx0-0390000000-441c56c96bb039aec8cf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 40V, Negative-QTOF | splash10-0a4j-6900000000-783e38eac8480236c061 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 10V, Negative-QTOF | splash10-001i-0090000000-4206ab54dd729eeefe27 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 20V, Negative-QTOF | splash10-001i-0190000000-a703d689dc48fee95783 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 40V, Negative-QTOF | splash10-0uec-1390000000-eef9ee988a3cf07e6528 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 10V, Positive-QTOF | splash10-001i-0090000000-0d73455ff384d5026de7 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 20V, Positive-QTOF | splash10-00lr-0190000000-7cb1ce92533c3aa5266c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anguidol 40V, Positive-QTOF | splash10-0zgi-4090000000-4789e9a33c6444e84c05 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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