Record Information |
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Version | 2.0 |
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Created at | 2021-06-20 21:20:57 UTC |
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Updated at | 2021-06-30 00:11:42 UTC |
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NP-MRD ID | NP0038744 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | spicochalasin A |
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Provided By | JEOL Database |
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Description | (1S,2R,3R,6S,7R,8S,11R,13R,14R,16R)-10,13-dihydroxy-1,5,6-trimethyl-8-(2-methylpropyl)-19-oxa-9-azapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁷,¹¹]Nonadeca-4,9-diene-12,15-dione belongs to the class of organic compounds known as aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group. spicochalasin A is found in Spicaria elegans. It was first documented in 2009 (Lin, Z., et al.). Based on a literature review very few articles have been published on (1S,2R,3R,6S,7R,8S,11R,13R,14R,16R)-10,13-dihydroxy-1,5,6-trimethyl-8-(2-methylpropyl)-19-oxa-9-azapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁷,¹¹]Nonadeca-4,9-diene-12,15-dione. |
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Structure | [H]O[C@@]1([H])C(=O)[C@@]23C(=O)N([H])[C@@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@]2([H])[C@@]([H])(C(=C([H])[C@]3([H])[C@]2([H])[C@@]1([H])C(=O)[C@]1([H])O[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H])C([H])([H])[H])C([H])([H])[H] InChI=1S/C24H33NO5/c1-10(2)8-14-17-12(4)11(3)9-13-18-16(19(26)15-6-7-23(18,5)30-15)20(27)21(28)24(13,17)22(29)25-14/h9-10,12-18,20,27H,6-8H2,1-5H3,(H,25,29)/t12-,13-,14+,15-,16+,17+,18-,20-,23+,24+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C24H33NO5 |
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Average Mass | 415.5300 Da |
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Monoisotopic Mass | 415.23587 Da |
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IUPAC Name | (1S,2R,3R,6S,7R,8S,11S,13R,14R,16R)-13-hydroxy-1,5,6-trimethyl-8-(2-methylpropyl)-19-oxa-9-azapentacyclo[14.2.1.0^{2,14}.0^{3,11}.0^{7,11}]nonadec-4-ene-10,12,15-trione |
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Traditional Name | (1S,2R,3R,6S,7R,8S,11S,13R,14R,16R)-13-hydroxy-1,5,6-trimethyl-8-(2-methylpropyl)-19-oxa-9-azapentacyclo[14.2.1.0^{2,14}.0^{3,11}.0^{7,11}]nonadec-4-ene-10,12,15-trione |
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CAS Registry Number | Not Available |
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SMILES | [H]O[C@@]1([H])C(=O)[C@@]23C(=O)N([H])[C@@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@]2([H])[C@@]([H])(C(=C([H])[C@]3([H])[C@]2([H])[C@@]1([H])C(=O)[C@]1([H])O[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H])C([H])([H])[H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C24H33NO5/c1-10(2)8-14-17-12(4)11(3)9-13-18-16(19(26)15-6-7-23(18,5)30-15)20(27)21(28)24(13,17)22(29)25-14/h9-10,12-18,20,27H,6-8H2,1-5H3,(H,25,29)/t12-,13-,14+,15-,16+,17+,18-,20-,23+,24+/m1/s1 |
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InChI Key | AUNPAALTSVXOPF-LOXSIOOTSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 600 MHz, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, NULL, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Species Name | Source | Reference |
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Mariannaea elegans | JEOL database | - Lin, Z., et al, EurJ. Org. Chem. 2009, 3045
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Cytochalasans |
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Sub Class | Aspochalasins |
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Direct Parent | Aspochalasins |
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Alternative Parents | |
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Substituents | - Aspochalasin skeleton
- Naphthopyran
- Azaspirodecane
- Naphthalene
- Isoindolone
- Isoindoline
- Isoindole or derivatives
- Oxane
- Pyran
- Pyrrolidone
- 2-pyrrolidone
- Pyrrolidine
- Cyclic alcohol
- Tetrahydrofuran
- Carboxamide group
- Lactam
- Secondary alcohol
- Secondary carboxylic acid amide
- Ketone
- Carboxylic acid derivative
- Dialkyl ether
- Ether
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Organic oxide
- Organopnictogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- Organonitrogen 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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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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