Record Information |
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Version | 1.0 |
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Created at | 2022-09-04 00:08:04 UTC |
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Updated at | 2022-09-04 00:08:04 UTC |
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NP-MRD ID | NP0184890 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1'r,2s,4's,5'r,9's,10's,13'r,15'r)-5',9'-dimethyl-15'-{[(2z)-2-methylbut-2-enoyl]oxy}spiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane]-5'-carboxylic acid |
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Description | (1'R,2S,4'S,5'R,9'S,10'S,13'R,15'R)-5',9'-dimethyl-15'-{[(2Z)-2-methylbut-2-enoyl]oxy}spiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane]-5'-carboxylic acid 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. (1'r,2s,4's,5'r,9's,10's,13'r,15'r)-5',9'-dimethyl-15'-{[(2z)-2-methylbut-2-enoyl]oxy}spiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane]-5'-carboxylic acid is found in Smallanthus fruticosus. Based on a literature review very few articles have been published on (1'R,2S,4'S,5'R,9'S,10'S,13'R,15'R)-5',9'-dimethyl-15'-{[(2Z)-2-methylbut-2-enoyl]oxy}spiro[oxirane-2,14'-tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane]-5'-carboxylic acid. |
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Structure | C\C=C(\C)C(=O)O[C@H]1[C@@]2(CO2)[C@H]2C[C@@]11CC[C@H]3[C@@](C)(CCC[C@@]3(C)C(O)=O)[C@@H]1CC2 InChI=1S/C25H36O5/c1-5-15(2)19(26)30-20-24-12-9-17-22(3,10-6-11-23(17,4)21(27)28)18(24)8-7-16(13-24)25(20)14-29-25/h5,16-18,20H,6-14H2,1-4H3,(H,27,28)/b15-5-/t16-,17+,18+,20-,22-,23-,24-,25-/m1/s1 |
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Synonyms | Value | Source |
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(1'r,2S,4's,5'r,9's,10's,13'r,15'r)-5',9'-Dimethyl-15'-{[(2Z)-2-methylbut-2-enoyl]oxy}spiro[oxirane-2,14'-tetracyclo[11.2.1.0,.0,]hexadecane]-5'-carboxylate | Generator |
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Chemical Formula | C25H36O5 |
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Average Mass | 416.5580 Da |
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Monoisotopic Mass | 416.25627 Da |
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IUPAC Name | (1'R,2S,4'S,5'R,9'S,10'S,13'R,15'R)-5',9'-dimethyl-15'-{[(2Z)-2-methylbut-2-enoyl]oxy}spiro[oxirane-2,14'-tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane]-5'-carboxylic acid |
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Traditional Name | (1'R,2S,4'S,5'R,9'S,10'S,13'R,15'R)-5',9'-dimethyl-15'-{[(2Z)-2-methylbut-2-enoyl]oxy}spiro[oxirane-2,14'-tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane]-5'-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | C\C=C(\C)C(=O)O[C@H]1[C@@]2(CO2)[C@H]2C[C@@]11CC[C@H]3[C@@](C)(CCC[C@@]3(C)C(O)=O)[C@@H]1CC2 |
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InChI Identifier | InChI=1S/C25H36O5/c1-5-15(2)19(26)30-20-24-12-9-17-22(3,10-6-11-23(17,4)21(27)28)18(24)8-7-16(13-24)25(20)14-29-25/h5,16-18,20H,6-14H2,1-4H3,(H,27,28)/b15-5-/t16-,17+,18+,20-,22-,23-,24-,25-/m1/s1 |
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InChI Key | KTPSVDHGTNWZOZ-ZYRZPXLGSA-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
- Fatty acid ester
- Dicarboxylic acid or derivatives
- Fatty acyl
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Carboxylic acid ester
- Carboxylic acid derivative
- Carboxylic acid
- Dialkyl ether
- Oxirane
- Ether
- Oxacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- 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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