Record Information |
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Version | 1.0 |
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Created at | 2022-09-02 02:04:00 UTC |
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Updated at | 2022-09-02 02:04:00 UTC |
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NP-MRD ID | NP0146631 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 2-methylbut-2-enoate |
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Description | 17,19-Bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]Icos-9-en-12-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. 17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 2-methylbut-2-enoate is found in Melia azedarach. 17,19-Bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]Icos-9-en-12-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC=C(C)C(=O)OC1C2OCC3(C)C2C(C)(C(CC3OC(C)=O)OC(C)=O)C2CC(=O)OC3CC(C(C)=C3C12C)C1=COC=C1 InChI=1S/C35H44O10/c1-9-17(2)32(39)45-31-29-30-33(6,16-41-29)25(42-19(4)36)14-26(43-20(5)37)34(30,7)24-13-27(38)44-23-12-22(21-10-11-40-15-21)18(3)28(23)35(24,31)8/h9-11,15,22-26,29-31H,12-14,16H2,1-8H3 |
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Synonyms | Value | Source |
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17,19-Bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0,.0,.0,]icos-9-en-12-yl 2-methylbut-2-enoic acid | Generator | 17,19-Bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 2-methylbut-2-enoic acid | Generator |
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Chemical Formula | C35H44O10 |
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Average Mass | 624.7270 Da |
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Monoisotopic Mass | 624.29345 Da |
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IUPAC Name | 17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 2-methylbut-2-enoate |
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Traditional Name | 17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 2-methylbut-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | CC=C(C)C(=O)OC1C2OCC3(C)C2C(C)(C(CC3OC(C)=O)OC(C)=O)C2CC(=O)OC3CC(C(C)=C3C12C)C1=COC=C1 |
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InChI Identifier | InChI=1S/C35H44O10/c1-9-17(2)32(39)45-31-29-30-33(6,16-41-29)25(42-19(4)36)14-26(43-20(5)37)34(30,7)24-13-27(38)44-23-12-22(21-10-11-40-15-21)18(3)28(23)35(24,31)8/h9-11,15,22-26,29-31H,12-14,16H2,1-8H3 |
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InChI Key | CSXRQWINVNDPIA-UHFFFAOYSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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 limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. |
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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 | Triterpenoids |
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Direct Parent | Limonoids |
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Alternative Parents | |
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Substituents | - Limonoid skeleton
- Tetracarboxylic acid or derivatives
- Caprolactone
- Fatty acid ester
- Oxepane
- Fatty acyl
- Furan
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Heteroaromatic compound
- Carboxylic acid ester
- Lactone
- Organoheterocyclic compound
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Oxacycle
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Organooxygen 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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