Record Information |
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Version | 1.0 |
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Created at | 2020-12-09 01:32:12 UTC |
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Updated at | 2021-07-15 16:48:01 UTC |
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NP-MRD ID | NP0004020 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Verrucarin M |
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Provided By | NPAtlas |
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Description | (1'R,3'R,18'E,20'E)-27'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]Heptacosane]-4',12',18',20'-tetraene-11',17',22'-trione 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. Verrucarin M is found in Albifimbria verrucaria and Myrothecium. It was first documented in 2001 (PMID: 11827043). Based on a literature review very few articles have been published on (1'R,3'R,18'E,20'E)-27'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]Heptacosane]-4',12',18',20'-tetraene-11',17',22'-trione. |
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Structure | [H]O[C@]1([H])[C@@]2([H])O[C@]3([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]33C([H])([H])OC(=O)\C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])OC(=O)\C([H])=C(\[H])/C(/[H])=C([H])\C(=O)O[C@@]1([H])[C@@]3(C([H])([H])[H])[C@]21OC1([H])[H] InChI=1S/C27H32O9/c1-16-8-10-26-14-33-21(30)13-17(2)9-11-32-19(28)6-4-5-7-20(29)36-23-22(31)24(35-18(26)12-16)27(15-34-27)25(23,26)3/h4-7,12-13,18,22-24,31H,8-11,14-15H2,1-3H3/b6-4-,7-5-,17-13-/t18-,22+,23-,24-,25-,26-,27-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C27H32O9 |
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Average Mass | 500.5440 Da |
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Monoisotopic Mass | 500.20463 Da |
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IUPAC Name | (1'R,2R,3'R,8'R,12'Z,18'Z,20'Z,24'S,25'S,27'S)-27'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',12',18',20'-tetraene-11',17',22'-trione |
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Traditional Name | (1'R,2R,3'R,8'R,12'Z,18'Z,20'Z,24'S,25'S,27'S)-27'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',12',18',20'-tetraene-11',17',22'-trione |
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CAS Registry Number | Not Available |
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SMILES | CC1=C[C@H]2O[C@@H]3C(O)C4OC(=O)\C=C\C=C\C(=O)OCCC(C)=CC(=O)OCC2(CC1)C4(C)C31CO1 |
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InChI Identifier | InChI=1S/C27H32O9/c1-16-8-10-26-14-33-21(30)13-17(2)9-11-32-19(28)6-4-5-7-20(29)36-23-22(31)24(35-18(26)12-16)27(15-34-27)25(23,26)3/h4-7,12-13,18,22-24,31H,8-11,14-15H2,1-3H3/b6-4+,7-5+,17-13?/t18-,22?,23?,24-,25?,26?,27?/m1/s1 |
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InChI Key | SBDCDLYTQBGFRK-KUPGYVKFSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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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
- Tricarboxylic acid or derivatives
- Oxepane
- Oxane
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Cyclic alcohol
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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