Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 21:14:01 UTC |
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Updated at | 2022-04-28 21:14:01 UTC |
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NP-MRD ID | NP0076050 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-3-Dehydroxyl-20-acetylpresinularolide B |
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Description | [(3AR,15aS)-10,14-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-6-yl]methyl acetate 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). (+)-3-Dehydroxyl-20-acetylpresinularolide B is found in Lobophytum crassum. Based on a literature review very few articles have been published on [(3aR,15aS)-10,14-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-6-yl]methyl acetate. |
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Structure | CC(=O)OC\C1=C/C[C@H]2[C@H](C\C(C)=C\CC\C(C)=C/CC1)OC(=O)C2=C InChI=1S/C22H30O4/c1-15-7-5-9-16(2)13-21-20(17(3)22(24)26-21)12-11-19(10-6-8-15)14-25-18(4)23/h8-9,11,20-21H,3,5-7,10,12-14H2,1-2,4H3/b15-8-,16-9+,19-11-/t20-,21+/m1/s1 |
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Synonyms | Value | Source |
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[(3AR,15as)-10,14-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,7H,8H,11H,12H,15H,15ah-cyclotetradeca[b]furan-6-yl]methyl acetic acid | Generator |
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Chemical Formula | C22H30O4 |
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Average Mass | 358.4780 Da |
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Monoisotopic Mass | 358.21441 Da |
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IUPAC Name | [(3aR,15aS)-10,14-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-6-yl]methyl acetate |
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Traditional Name | [(3aR,15aS)-10,14-dimethyl-3-methylidene-2-oxo-3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-6-yl]methyl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)OC\C1=C/C[C@H]2[C@H](C\C(C)=C\CC\C(C)=C/CC1)OC(=O)C2=C |
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InChI Identifier | InChI=1S/C22H30O4/c1-15-7-5-9-16(2)13-21-20(17(3)22(24)26-21)12-11-19(10-6-8-15)14-25-18(4)23/h8-9,11,20-21H,3,5-7,10,12-14H2,1-2,4H3/b15-8-,16-9+,19-11-/t20-,21+/m1/s1 |
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InChI Key | WVUIGZJAERAWJE-GBSATCBFSA-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 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
- Dicarboxylic acid or derivatives
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- 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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