| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 14:28:29 UTC |
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| Updated at | 2022-09-12 14:28:30 UTC |
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| NP-MRD ID | NP0329768 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 19-(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-17-[(2-methylpropanoyl)oxy]-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 | 19-(Acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-17-[(2-methylpropanoyl)oxy]-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. 19-(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-17-[(2-methylpropanoyl)oxy]-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. 19-(Acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-17-[(2-methylpropanoyl)oxy]-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(=O)C(C)C)OC(C)=O)C2CC(=O)OC3CC(C(C)=C3C12C)C1=COC=C1 InChI=1S/C37H48O10/c1-10-19(4)34(41)47-32-30-31-35(7,17-43-30)26(46-33(40)18(2)3)15-27(44-21(6)38)36(31,8)25-14-28(39)45-24-13-23(22-11-12-42-16-22)20(5)29(24)37(25,32)9/h10-12,16,18,23-27,30-32H,13-15,17H2,1-9H3 |
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| Synonyms | | Value | Source |
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| 19-(Acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-17-[(2-methylpropanoyl)oxy]-4-oxo-5,14-dioxapentacyclo[11.6.1.0,.0,.0,]icos-9-en-12-yl 2-methylbut-2-enoic acid | Generator | | 19-(Acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-17-[(2-methylpropanoyl)oxy]-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 | C37H48O10 |
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| Average Mass | 652.7810 Da |
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| Monoisotopic Mass | 652.32475 Da |
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| IUPAC Name | 19-(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-17-[(2-methylpropanoyl)oxy]-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 | 19-(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-17-[(2-methylpropanoyl)oxy]-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(=O)C(C)C)OC(C)=O)C2CC(=O)OC3CC(C(C)=C3C12C)C1=COC=C1 |
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| InChI Identifier | InChI=1S/C37H48O10/c1-10-19(4)34(41)47-32-30-31-35(7,17-43-30)26(46-33(40)18(2)3)15-27(44-21(6)38)36(31,8)25-14-28(39)45-24-13-23(22-11-12-42-16-22)20(5)29(24)37(25,32)9/h10-12,16,18,23-27,30-32H,13-15,17H2,1-9H3 |
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| InChI Key | SICUEZAFVFZILZ-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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