| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-04 00:36:29 UTC |
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| Updated at | 2022-09-04 00:36:29 UTC |
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| NP-MRD ID | NP0185253 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 2,6,6-trimethyl-12-methylidenetetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-4-yl acetate |
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| Description | 2,6,6-Trimethyl-12-methylidenetetracyclo[11.2.1.0¹,¹⁰.0²,⁷]Hexadecan-4-yl acetate belongs to the class of organic compounds known as stemarane diterpenoids. These are diterpenoids with a structure characterized by a stemarane skeleton. Some characteristics include the bicyclic system C/D that is constituted by a bicyclo[3.2.1]Octane fused to the bicyclic A/B system in a different fashion with respect to other tetracyclic diterpenes possessing the bicyclo[3.2.1]Octane system. Moreover, the two contiguous quaternary carbon atoms, C(9) and C(10), are present, the former being a spirocyclic atom. Oxygenation can happen at positions C(2), C(7), C(13), C(17), C(18), and C(19). 2,6,6-trimethyl-12-methylidenetetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-4-yl acetate is found in Calceolaria dentata. 2,6,6-Trimethyl-12-methylidenetetracyclo[11.2.1.0¹,¹⁰.0²,⁷]Hexadecan-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| Structure | CC(=O)OC1CC(C)(C)C2CCC3CC(=C)C4CCC3(C4)C2(C)C1 InChI=1S/C22H34O2/c1-14-10-17-6-7-19-20(3,4)12-18(24-15(2)23)13-21(19,5)22(17)9-8-16(14)11-22/h16-19H,1,6-13H2,2-5H3 |
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| Synonyms | | Value | Source |
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| 2,6,6-Trimethyl-12-methylidenetetracyclo[11.2.1.0,.0,]hexadecan-4-yl acetic acid | Generator | | 2,6,6-Trimethyl-12-methylidenetetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-4-yl acetic acid | Generator |
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| Chemical Formula | C22H34O2 |
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| Average Mass | 330.5120 Da |
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| Monoisotopic Mass | 330.25588 Da |
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| IUPAC Name | 2,6,6-trimethyl-12-methylidenetetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-4-yl acetate |
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| Traditional Name | 2,6,6-trimethyl-12-methylidenetetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-4-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=O)OC1CC(C)(C)C2CCC3CC(=C)C4CCC3(C4)C2(C)C1 |
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| InChI Identifier | InChI=1S/C22H34O2/c1-14-10-17-6-7-19-20(3,4)12-18(24-15(2)23)13-21(19,5)22(17)9-8-16(14)11-22/h16-19H,1,6-13H2,2-5H3 |
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| InChI Key | VUFSOKZNTWNMLI-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 stemarane diterpenoids. These are diterpenoids with a structure characterized by a stemarane skeleton. Some characteristics include the bicyclic system C/D that is constituted by a bicyclo[3.2.1]Octane fused to the bicyclic A/B system in a different fashion with respect to other tetracyclic diterpenes possessing the bicyclo[3.2.1]Octane system. Moreover, the two contiguous quaternary carbon atoms, C(9) and C(10), are present, the former being a spirocyclic atom. Oxygenation can happen at positions C(2), C(7), C(13), C(17), C(18), and C(19). |
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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 | Diterpenoids |
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| Direct Parent | Stemarane diterpenoids |
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| Alternative Parents | |
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| Substituents | - Stemarane diterpenoid
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic 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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