Record Information |
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Version | 2.0 |
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Created at | 2022-09-05 21:12:03 UTC |
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Updated at | 2022-09-05 21:12:04 UTC |
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NP-MRD ID | NP0220009 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione |
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Description | Chaetoglobosin K, also known as penochalasin K, belongs to the class of organic compounds known as chaetoglobosins. These are cytochalasans with a structure in which the hydrogenated isoindole bears an (indol-3-yl)methyl group. (1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione is found in Stenocarpella macrospora. (1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione was first documented in 2013 (PMID: 23695013). Based on a literature review a small amount of articles have been published on Chaetoglobosin K (PMID: 24504633) (PMID: 30542835) (PMID: 25304379) (PMID: 25404879). |
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Structure | CC[C@H]1[C@H]2[C@@H](NC(=O)[C@@]22[C@@H](\C=C/C[C@H](C)\C=C(C)/[C@@H](O)C(=O)\C=C/C2=O)[C@@H]2O[C@]12C)[C@H](C)C1=CNC2=CC=CC=C12 InChI=1S/C34H40N2O5/c1-6-23-28-29(20(4)22-17-35-25-13-8-7-11-21(22)25)36-32(40)34(28)24(31-33(23,5)41-31)12-9-10-18(2)16-19(3)30(39)26(37)14-15-27(34)38/h7-9,11-18,20,23-24,28-31,35,39H,6,10H2,1-5H3,(H,36,40)/b12-9-,15-14-,19-16-/t18-,20+,23-,24-,28-,29-,30+,31-,33+,34+/m0/s1 |
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Synonyms | Value | Source |
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Chaetoglobosin a | MeSH | Chaetoglobosin b | MeSH | Chaetoglobosin C | MeSH | Chaetoglobosin D | MeSH | Chaetoglobosin e | MeSH | Chaetoglobosin F | MeSH | Chaetoglobosin Q | MeSH | Chaetoglobosin R | MeSH | Chaetoglobosin T | MeSH | Chaetoglobosin u | MeSH | Chaetoglobosin V | MeSH | Chaetoglobosin W | MeSH | Chaetoglobosin y | MeSH | Chaetoglobosins | MeSH | Penochalasin K | MeSH |
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Chemical Formula | C34H40N2O5 |
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Average Mass | 556.7030 Da |
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Monoisotopic Mass | 556.29372 Da |
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IUPAC Name | (1R,3E,6R,7E,9S,11E,13R,14S,16R,17S,18R,19S)-17-ethyl-6-hydroxy-19-[(1R)-1-(1H-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-3,7,11-triene-2,5,21-trione |
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Traditional Name | (1R,3E,6R,7E,9S,11E,13R,14S,16R,17S,18R,19S)-17-ethyl-6-hydroxy-19-[(1R)-1-(1H-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-3,7,11-triene-2,5,21-trione |
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CAS Registry Number | Not Available |
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SMILES | CC[C@H]1[C@H]2[C@@H](NC(=O)[C@@]22[C@@H](\C=C/C[C@H](C)\C=C(C)/[C@@H](O)C(=O)\C=C/C2=O)[C@@H]2O[C@]12C)[C@H](C)C1=CNC2=CC=CC=C12 |
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InChI Identifier | InChI=1S/C34H40N2O5/c1-6-23-28-29(20(4)22-17-35-25-13-8-7-11-21(22)25)36-32(40)34(28)24(31-33(23,5)41-31)12-9-10-18(2)16-19(3)30(39)26(37)14-15-27(34)38/h7-9,11-18,20,23-24,28-31,35,39H,6,10H2,1-5H3,(H,36,40)/b12-9-,15-14-,19-16-/t18-,20+,23-,24-,28-,29-,30+,31-,33+,34+/m0/s1 |
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InChI Key | RSYKJHLWNMXRKZ-RYYZKKQRSA-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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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as chaetoglobosins. These are cytochalasans with a structure in which the hydrogenated isoindole bears an (indol-3-yl)methyl 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 | Chaetoglobosins |
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Direct Parent | Chaetoglobosins |
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Alternative Parents | |
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Substituents | - Chaetoglobosin skeleton
- Macrolactam
- Isoindolone
- 3-alkylindole
- Indole
- Indole or derivatives
- Isoindoline
- Isoindole or derivatives
- Oxepane
- Benzenoid
- Substituted pyrrole
- 2-pyrrolidone
- Pyrrolidone
- Heteroaromatic compound
- Pyrrole
- Pyrrolidine
- Cyclic ketone
- Carboxamide group
- Ketone
- Lactam
- Secondary carboxylic acid amide
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Azacycle
- Carboxylic acid derivative
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Alcohol
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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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