Record Information |
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Version | 1.0 |
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Created at | 2022-09-07 20:27:38 UTC |
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Updated at | 2022-09-07 20:27:38 UTC |
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NP-MRD ID | NP0255829 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | {14-hydroxy-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl 6-(acetyloxy)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylate |
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Description | {14-Hydroxy-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-14-yl}methyl 6-(acetyloxy)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-14-carboxylate belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. {14-hydroxy-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl 6-(acetyloxy)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylate is found in Fritillaria anhuiensis. {14-Hydroxy-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-14-yl}methyl 6-(acetyloxy)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-14-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC(=O)OC1CCC2(C)C3CCC4CC3(CC4C(=O)OCC3(O)CC45CC3CCC4C3(C)CCCC(C)(C)C3CC5)CCC2C1(C)C InChI=1S/C42H66O5/c1-26(43)47-34-15-18-39(7)31(37(34,4)5)14-19-40-21-27(9-11-32(39)40)29(23-40)35(44)46-25-42(45)24-41-20-13-30-36(2,3)16-8-17-38(30,6)33(41)12-10-28(42)22-41/h27-34,45H,8-25H2,1-7H3 |
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Synonyms | Value | Source |
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{14-hydroxy-5,5,9-trimethyltetracyclo[11.2.1.0,.0,]hexadecan-14-yl}methyl 6-(acetyloxy)-5,5,9-trimethyltetracyclo[11.2.1.0,.0,]hexadecane-14-carboxylic acid | Generator | {14-hydroxy-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl 6-(acetyloxy)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylic acid | Generator |
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Chemical Formula | C42H66O5 |
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Average Mass | 650.9850 Da |
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Monoisotopic Mass | 650.49103 Da |
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IUPAC Name | {14-hydroxy-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl 6-(acetyloxy)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylate |
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Traditional Name | {14-hydroxy-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl 6-(acetyloxy)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)OC1CCC2(C)C3CCC4CC3(CC4C(=O)OCC3(O)CC45CC3CCC4C3(C)CCCC(C)(C)C3CC5)CCC2C1(C)C |
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InChI Identifier | InChI=1S/C42H66O5/c1-26(43)47-34-15-18-39(7)31(37(34,4)5)14-19-40-21-27(9-11-32(39)40)29(23-40)35(44)46-25-42(45)24-41-20-13-30-36(2,3)16-8-17-38(30,6)33(41)12-10-28(42)22-41/h27-34,45H,8-25H2,1-7H3 |
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InChI Key | DFIWBJWAOZVFBV-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 kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. |
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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 | Kaurane diterpenoids |
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Alternative Parents | |
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Substituents | - Kaurane diterpenoid
- Dicarboxylic acid or derivatives
- Tertiary alcohol
- Cyclic alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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