| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-10 08:08:23 UTC |
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| Updated at | 2022-09-10 08:08:23 UTC |
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| NP-MRD ID | NP0297624 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 7-[2-(acetyloxy)-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-en-20-yl acetate |
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| Description | 7-[2-(Acetyloxy)-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icos-13-en-20-yl acetate 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. 7-[2-(acetyloxy)-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-en-20-yl acetate is found in Trichilia elegans. 7-[2-(Acetyloxy)-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icos-13-en-20-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| Structure | CC(=O)OC1OC(=O)C=C1C1OC(=O)C2OC22C1(C)CCC1C3(C)C=CC(=O)OC(C)(C)C3CC(OC(C)=O)C21C InChI=1S/C30H36O11/c1-14(31)36-19-13-18-26(3,4)40-20(33)9-10-27(18,5)17-8-11-28(6)22(16-12-21(34)38-25(16)37-15(2)32)39-24(35)23-30(28,41-23)29(17,19)7/h9-10,12,17-19,22-23,25H,8,11,13H2,1-7H3 |
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| Synonyms | | Value | Source |
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| 7-[2-(Acetyloxy)-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0,.0,.0,]icos-13-en-20-yl acetic acid | Generator | | 7-[2-(Acetyloxy)-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-en-20-yl acetic acid | Generator |
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| Chemical Formula | C30H36O11 |
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| Average Mass | 572.6070 Da |
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| Monoisotopic Mass | 572.22576 Da |
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| IUPAC Name | 7-[2-(acetyloxy)-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-en-20-yl acetate |
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| Traditional Name | 7-[2-(acetyloxy)-5-oxo-2H-furan-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-en-20-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=O)OC1OC(=O)C=C1C1OC(=O)C2OC22C1(C)CCC1C3(C)C=CC(=O)OC(C)(C)C3CC(OC(C)=O)C21C |
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| InChI Identifier | InChI=1S/C30H36O11/c1-14(31)36-19-13-18-26(3,4)40-20(33)9-10-27(18,5)17-8-11-28(6)22(16-12-21(34)38-25(16)37-15(2)32)39-24(35)23-30(28,41-23)29(17,19)7/h9-10,12,17-19,22-23,25H,8,11,13H2,1-7H3 |
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| InChI Key | QYUWVWXIYMIDCZ-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
- Pentacarboxylic acid or derivatives
- Naphthopyran
- Naphthalene
- 1,4-dioxepane
- Delta valerolactone
- Dioxepane
- Delta_valerolactone
- Acylal
- Oxane
- Pyran
- 2-furanone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Dihydrofuran
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Carboxylic acid derivative
- Dialkyl ether
- Acetal
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- 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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