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 21:13:17 UTC |
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Update Date | 2022-03-07 02:54:48 UTC |
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HMDB ID | HMDB0036158 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Deacetylneosolaniol |
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Description | 4-Deacetylneosolaniol, also known as 4-DANS, 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. Based on a literature review a significant number of articles have been published on 4-Deacetylneosolaniol. |
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Structure | CC(=O)OCC12CC(O)C(C)=CC1OC1C(O)C(O)C2(C)C11CO1 InChI=1S/C17H24O7/c1-8-4-11-16(5-10(8)19,6-22-9(2)18)15(3)13(21)12(20)14(24-11)17(15)7-23-17/h4,10-14,19-21H,5-7H2,1-3H3 |
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Synonyms | Value | Source |
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4-DANS | MeSH | 4-Desacetylneosolaniol | HMDB | TMR 1 | HMDB | {4',10',11'-trihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-yl}methyl acetic acid | Generator |
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Chemical Formula | C17H24O7 |
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Average Molecular Weight | 340.3683 |
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Monoisotopic Molecular Weight | 340.152203122 |
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IUPAC Name | 4',10',11'-trihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate |
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Traditional Name | 4',10',11'-trihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate |
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CAS Registry Number | 74833-39-9 |
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SMILES | CC(=O)OCC12CC(O)C(C)=CC1OC1C(O)C(O)C2(C)C11CO1 |
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InChI Identifier | InChI=1S/C17H24O7/c1-8-4-11-16(5-10(8)19,6-22-9(2)18)15(3)13(21)12(20)14(24-11)17(15)7-23-17/h4,10-14,19-21H,5-7H2,1-3H3 |
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InChI Key | FCLYQYOJLQDQNA-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
- Oxepane
- Oxane
- Cyclic alcohol
- Carboxylic acid ester
- Secondary alcohol
- Oxacycle
- Carboxylic acid derivative
- Organoheterocyclic compound
- Dialkyl ether
- Oxirane
- Ether
- Monocarboxylic acid or derivatives
- Polyol
- Alcohol
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- 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 | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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4-Deacetylneosolaniol,1TMS,isomer #1 | CC(=O)OCC12CC(O[Si](C)(C)C)C(C)=CC1OC1C(O)C(O)C2(C)C12CO2 | 2575.4 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,1TMS,isomer #2 | CC(=O)OCC12CC(O)C(C)=CC1OC1C(O[Si](C)(C)C)C(O)C2(C)C12CO2 | 2592.7 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,1TMS,isomer #3 | CC(=O)OCC12CC(O)C(C)=CC1OC1C(O)C(O[Si](C)(C)C)C2(C)C12CO2 | 2598.4 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,2TMS,isomer #1 | CC(=O)OCC12CC(O[Si](C)(C)C)C(C)=CC1OC1C(O[Si](C)(C)C)C(O)C2(C)C12CO2 | 2577.6 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,2TMS,isomer #2 | CC(=O)OCC12CC(O[Si](C)(C)C)C(C)=CC1OC1C(O)C(O[Si](C)(C)C)C2(C)C12CO2 | 2581.5 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,2TMS,isomer #3 | CC(=O)OCC12CC(O)C(C)=CC1OC1C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2(C)C12CO2 | 2600.9 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,3TMS,isomer #1 | CC(=O)OCC12CC(O[Si](C)(C)C)C(C)=CC1OC1C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2(C)C12CO2 | 2579.4 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,1TBDMS,isomer #1 | CC(=O)OCC12CC(O[Si](C)(C)C(C)(C)C)C(C)=CC1OC1C(O)C(O)C2(C)C12CO2 | 2805.8 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,1TBDMS,isomer #2 | CC(=O)OCC12CC(O)C(C)=CC1OC1C(O[Si](C)(C)C(C)(C)C)C(O)C2(C)C12CO2 | 2842.9 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,1TBDMS,isomer #3 | CC(=O)OCC12CC(O)C(C)=CC1OC1C(O)C(O[Si](C)(C)C(C)(C)C)C2(C)C12CO2 | 2844.3 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,2TBDMS,isomer #1 | CC(=O)OCC12CC(O[Si](C)(C)C(C)(C)C)C(C)=CC1OC1C(O[Si](C)(C)C(C)(C)C)C(O)C2(C)C12CO2 | 3027.1 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,2TBDMS,isomer #2 | CC(=O)OCC12CC(O[Si](C)(C)C(C)(C)C)C(C)=CC1OC1C(O)C(O[Si](C)(C)C(C)(C)C)C2(C)C12CO2 | 3019.5 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,2TBDMS,isomer #3 | CC(=O)OCC12CC(O)C(C)=CC1OC1C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2(C)C12CO2 | 3081.9 | Semi standard non polar | 33892256 | 4-Deacetylneosolaniol,3TBDMS,isomer #1 | CC(=O)OCC12CC(O[Si](C)(C)C(C)(C)C)C(C)=CC1OC1C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2(C)C12CO2 | 3259.1 | 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 - 4-Deacetylneosolaniol GC-MS (Non-derivatized) - 70eV, Positive | splash10-077l-6569000000-185d55bedc1a77170562 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Deacetylneosolaniol GC-MS (3 TMS) - 70eV, Positive | splash10-0006-7039880000-f42a21f055952805b91e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Deacetylneosolaniol 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 - 4-Deacetylneosolaniol 10V, Positive-QTOF | splash10-00dl-0049000000-50fcb8d1187d535d4bcd | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 20V, Positive-QTOF | splash10-06z9-0695000000-e17ff9e833c53f5b9db4 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 40V, Positive-QTOF | splash10-03dl-3691000000-424bc6c42699986895f2 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 10V, Negative-QTOF | splash10-000i-3019000000-9c84b0899ddb4da3e163 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 20V, Negative-QTOF | splash10-0a4u-9437000000-3154bb9b3b2a21aa0543 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 40V, Negative-QTOF | splash10-1001-8900000000-251fbcbc9b20dc97da68 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 10V, Positive-QTOF | splash10-001i-0091000000-0368a95ffbb6634e8f16 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 20V, Positive-QTOF | splash10-03e9-0091000000-937bd05ec2ffc96e68de | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 40V, Positive-QTOF | splash10-00xu-1595000000-755b0fedc7c5c84e8097 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 10V, Negative-QTOF | splash10-002b-1092000000-7e274b54bf3a7c214425 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 20V, Negative-QTOF | splash10-0a6s-7090000000-3b67d733900eca76a798 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Deacetylneosolaniol 40V, Negative-QTOF | splash10-0a4l-7913000000-8f78e34dfc2f37be1f74 | 2021-09-23 | 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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