Record Information |
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Version | 1.0 |
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Created at | 2022-04-29 00:06:58 UTC |
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Updated at | 2022-04-29 00:06:58 UTC |
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NP-MRD ID | NP0079037 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-Eupachinilide J |
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Description | (3AR,4R,8R,9R,11aS)-8,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-4-(acetyloxy)-2-methylbut-2-enoate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. (+)-Eupachinilide J is found in Eupatorium chinense. It was first documented in 2022 (PMID: 35490355). Based on a literature review a significant number of articles have been published on (3aR,4R,8R,9R,11aS)-8,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-4-(acetyloxy)-2-methylbut-2-enoate (PMID: 35490354) (PMID: 35490353) (PMID: 35490352) (PMID: 35490351). |
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Structure | CC(=O)OC\C=C(\C)C(=O)O[C@@H]1C\C(C)=C/[C@@H](O)[C@H](O)\C(C)=C\[C@@H]2OC(=O)C(=C)[C@H]12 InChI=1S/C22H28O8/c1-11-8-16(24)20(25)13(3)10-18-19(14(4)22(27)30-18)17(9-11)29-21(26)12(2)6-7-28-15(5)23/h6,8,10,16-20,24-25H,4,7,9H2,1-3,5H3/b11-8-,12-6-,13-10+/t16-,17-,18+,19-,20-/m1/s1 |
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Synonyms | Value | Source |
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(3AR,4R,8R,9R,11as)-8,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl (2Z)-4-(acetyloxy)-2-methylbut-2-enoic acid | Generator |
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Chemical Formula | C22H28O8 |
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Average Mass | 420.4580 Da |
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Monoisotopic Mass | 420.17842 Da |
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IUPAC Name | (3aR,4R,8R,9R,11aS)-8,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-4-(acetyloxy)-2-methylbut-2-enoate |
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Traditional Name | (3aR,4R,8R,9R,11aS)-8,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-4-(acetyloxy)-2-methylbut-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)OC\C=C(\C)C(=O)O[C@@H]1C\C(C)=C/[C@@H](O)[C@H](O)\C(C)=C\[C@@H]2OC(=O)C(=C)[C@H]12 |
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InChI Identifier | InChI=1S/C22H28O8/c1-11-8-16(24)20(25)13(3)10-18-19(14(4)22(27)30-18)17(9-11)29-21(26)12(2)6-7-28-15(5)23/h6,8,10,16-20,24-25H,4,7,9H2,1-3,5H3/b11-8-,12-6-,13-10+/t16-,17-,18+,19-,20-/m1/s1 |
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InChI Key | RTTZVQOUFITRBN-YLQRBJMZSA-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 germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. |
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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 | Germacranolides and derivatives |
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Alternative Parents | |
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Substituents | - Germacranolide
- Sesquiterpenoid
- Germacrane sesquiterpenoid
- Tricarboxylic acid or derivatives
- Fatty acid ester
- Fatty acyl
- Gamma butyrolactone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- 1,2-diol
- Oxacycle
- Organoheterocyclic compound
- 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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