| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-29 03:05:04 UTC |
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| Updated at | 2022-04-29 03:05:04 UTC |
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| NP-MRD ID | NP0082035 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (-)-Lobophytolide A |
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| Description | (3AR,15aR)-6,10,14-trimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-2-one belongs to the class of organic compounds known as cembranolides. These are diterpenoids with a structure based on a cembrane skeleton fused to a lactone ring (5- or 6-membered). (-)-Lobophytolide A is found in Lobophytum sp. Based on a literature review very few articles have been published on (3aR,15aR)-6,10,14-trimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-2-one. |
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| Structure | C\C1=C\CC\C(C)=C\C[C@H]2[C@@H](C\C(C)=C\CC1)OC(=O)C2=C InChI=1S/C20H28O2/c1-14-7-5-9-15(2)11-12-18-17(4)20(21)22-19(18)13-16(3)10-6-8-14/h7,10-11,18-19H,4-6,8-9,12-13H2,1-3H3/b14-7-,15-11+,16-10+/t18-,19-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C20H28O2 |
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| Average Mass | 300.4420 Da |
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| Monoisotopic Mass | 300.20893 Da |
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| IUPAC Name | (3aR,15aR)-6,10,14-trimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-2-one |
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| Traditional Name | (3aR,15aR)-6,10,14-trimethyl-3-methylidene-3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-2-one |
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| CAS Registry Number | Not Available |
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| SMILES | C\C1=C\CC\C(C)=C\C[C@H]2[C@@H](C\C(C)=C\CC1)OC(=O)C2=C |
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| InChI Identifier | InChI=1S/C20H28O2/c1-14-7-5-9-15(2)11-12-18-17(4)20(21)22-19(18)13-16(3)10-6-8-14/h7,10-11,18-19H,4-6,8-9,12-13H2,1-3H3/b14-7-,15-11+,16-10+/t18-,19-/m1/s1 |
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| InChI Key | XDYGLOIAEQJWFP-MXLIOEFTSA-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 | | Species Name | Source | Reference |
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| Lobophytum sp. | - | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as cembranolides. These are diterpenoids with a structure based on a cembrane skeleton fused to a lactone ring (5- or 6-membered). |
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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 | Cembranolides |
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| Alternative Parents | |
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| Substituents | - Cembranolide-skeleton
- Diterpenoid
- Cembrane diterpenoid
- Gamma butyrolactone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen 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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