Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:54:58 UTC |
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Updated at | 2021-11-26 17:46:22 UTC |
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NP-MRD ID | NP0044185 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 2-Deacetyl-4-O-tigloylchamissonolide |
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Description | CHEMBL453279 belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. 2-Deacetyl-4-O-tigloylchamissonolide is found in Arnica angustifolia and Gaillardia pulchella. It was first documented in 1995 (Schmidt, et al.). Based on a literature review very few articles have been published on CHEMBL453279. |
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Structure | C\C=C(/C)C(=O)O[C@@H]1C[C@H](O)[C@H]2[C@H](C)C[C@H]3OC(=O)C(=C)[C@H]3[C@H](O)[C@]12C InChI=1S/C20H28O6/c1-6-9(2)18(23)26-14-8-12(21)16-10(3)7-13-15(11(4)19(24)25-13)17(22)20(14,16)5/h6,10,12-17,21-22H,4,7-8H2,1-3,5H3/b9-6+/t10-,12+,13-,14-,15-,16-,17+,20-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C20H28O6 |
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Average Mass | 364.4380 Da |
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Monoisotopic Mass | 364.18859 Da |
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IUPAC Name | (3aS,4S,4aR,5R,7S,7aS,8R,9aR)-4,7-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-5-yl (2E)-2-methylbut-2-enoate |
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Traditional Name | (3aS,4S,4aR,5R,7S,7aS,8R,9aR)-4,7-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3aH-azuleno[6,5-b]furan-5-yl (2E)-2-methylbut-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | C\C=C(/C)C(=O)O[C@@H]1C[C@H](O)[C@H]2[C@H](C)C[C@H]3OC(=O)C(=C)[C@H]3[C@H](O)[C@]12C |
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InChI Identifier | InChI=1S/C20H28O6/c1-6-9(2)18(23)26-14-8-12(21)16-10(3)7-13-15(11(4)19(24)25-13)17(22)20(14,16)5/h6,10,12-17,21-22H,4,7-8H2,1-3,5H3/b9-6+/t10-,12+,13-,14-,15-,16-,17+,20-/m1/s1 |
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InChI Key | WUMRXBPDXGXSJC-JYJHRMTHSA-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, 50 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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 | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. |
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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 | Terpene lactones |
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Direct Parent | Sesquiterpene lactones |
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Alternative Parents | |
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Substituents | - Helenalin-skeleton
- Ambrosanolide
- Pseudoguaiane sesquiterpenoid
- Sesquiterpenoid
- Fatty acid ester
- Dicarboxylic acid or derivatives
- Gamma butyrolactone
- Fatty acyl
- Cyclic alcohol
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Lactone
- Carboxylic acid ester
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organic oxygen compound
- Carbonyl group
- 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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