Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 01:53:19 UTC |
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Updated at | 2022-09-12 01:53:19 UTC |
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NP-MRD ID | NP0322855 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,2s,4s,5r,9r,10r,13r,15s)-2,10,15-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid |
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Description | (1R,2S,4S,5R,9R,10R,13R,15S)-2,10,15-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[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. (1r,2s,4s,5r,9r,10r,13r,15s)-2,10,15-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid is found in Helichrysum dasyanthum. Based on a literature review very few articles have been published on (1R,2S,4S,5R,9R,10R,13R,15S)-2,10,15-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylic acid. |
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Structure | C[C@]1(CCC[C@]2(C)[C@@H]1C[C@H](O)[C@@]13C[C@@H](CC[C@@]21O)C(=C)[C@@H]3O)C(O)=O InChI=1S/C20H30O5/c1-11-12-5-8-20(25)18(3)7-4-6-17(2,16(23)24)13(18)9-14(21)19(20,10-12)15(11)22/h12-15,21-22,25H,1,4-10H2,2-3H3,(H,23,24)/t12-,13-,14+,15+,17-,18-,19-,20-/m1/s1 |
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Synonyms | Value | Source |
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(1R,2S,4S,5R,9R,10R,13R,15S)-2,10,15-Trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0,.0,]hexadecane-5-carboxylate | Generator |
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Chemical Formula | C20H30O5 |
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Average Mass | 350.4550 Da |
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Monoisotopic Mass | 350.20932 Da |
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IUPAC Name | (1R,2S,4S,5R,9R,10R,13R,15S)-2,10,15-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid |
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Traditional Name | (1R,2S,4S,5R,9R,10R,13R,15S)-2,10,15-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[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@]1(CCC[C@]2(C)[C@@H]1C[C@H](O)[C@@]13C[C@@H](CC[C@@]21O)C(=C)[C@@H]3O)C(O)=O |
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InChI Identifier | InChI=1S/C20H30O5/c1-11-12-5-8-20(25)18(3)7-4-6-17(2,16(23)24)13(18)9-14(21)19(20,10-12)15(11)22/h12-15,21-22,25H,1,4-10H2,2-3H3,(H,23,24)/t12-,13-,14+,15+,17-,18-,19-,20-/m1/s1 |
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InChI Key | QPCQAXAGGHUPGC-VJDBPIJISA-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
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- 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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