Record Information |
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Version | 2.0 |
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Created at | 2022-09-05 17:07:57 UTC |
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Updated at | 2022-09-05 17:07:57 UTC |
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NP-MRD ID | NP0216960 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,2s,3ar,4r,5r,10r,11s,13r,13ar)-11,13-bis(acetyloxy)-3a,4,10-trihydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate |
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Description | (2S,4R,6S,7R,10E,12R,13R)-1,2,3,3abeta,4,5,6,7,9,12,13,13a-Dodecahydro-2alpha,9,9,12-tetramethyl-3alpha-(benzoyloxy)-4,6-diacetoxy-5-methylene-7,13,13aalpha-trihydroxy-8H-cyclopentacyclododecen-8-one belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton. (1s,2s,3ar,4r,5r,10r,11s,13r,13ar)-11,13-bis(acetyloxy)-3a,4,10-trihydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia hyberna. Based on a literature review very few articles have been published on (2S,4R,6S,7R,10E,12R,13R)-1,2,3,3abeta,4,5,6,7,9,12,13,13a-Dodecahydro-2alpha,9,9,12-tetramethyl-3alpha-(benzoyloxy)-4,6-diacetoxy-5-methylene-7,13,13aalpha-trihydroxy-8H-cyclopentacyclododecen-8-one. |
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Structure | C[C@H]1C[C@@]2(O)[C@H]([C@H]1OC(=O)C1=CC=CC=C1)[C@@H](OC(C)=O)C(=C)[C@H](OC(C)=O)[C@@H](O)C(=O)C(C)(C)\C=C\[C@@H](C)[C@H]2O InChI=1S/C31H40O10/c1-16-13-14-30(6,7)28(36)23(34)26(40-20(5)33)18(3)25(39-19(4)32)22-24(17(2)15-31(22,38)27(16)35)41-29(37)21-11-9-8-10-12-21/h8-14,16-17,22-27,34-35,38H,3,15H2,1-2,4-7H3/b14-13+/t16-,17+,22-,23-,24+,25+,26+,27-,31-/m1/s1 |
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Synonyms | Value | Source |
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(2S,4R,6S,7R,10E,12R,13R)-1,2,3,3Abeta,4,5,6,7,9,12,13,13a-dodecahydro-2a,9,9,12-tetramethyl-3a-(benzoyloxy)-4,6-diacetoxy-5-methylene-7,13,13aalpha-trihydroxy-8H-cyclopentacyclododecen-8-one | Generator | (2S,4R,6S,7R,10E,12R,13R)-1,2,3,3Abeta,4,5,6,7,9,12,13,13a-dodecahydro-2α,9,9,12-tetramethyl-3α-(benzoyloxy)-4,6-diacetoxy-5-methylene-7,13,13aalpha-trihydroxy-8H-cyclopentacyclododecen-8-one | Generator |
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Chemical Formula | C31H40O10 |
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Average Mass | 572.6510 Da |
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Monoisotopic Mass | 572.26215 Da |
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IUPAC Name | (1S,2S,3aR,4R,5R,10R,11S,13R,13aR)-11,13-bis(acetyloxy)-3a,4,10-trihydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate |
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Traditional Name | (1S,2S,3aR,4R,5R,10R,11S,13R,13aR)-11,13-bis(acetyloxy)-3a,4,10-trihydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,4H,5H,10H,11H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate |
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CAS Registry Number | Not Available |
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SMILES | C[C@H]1C[C@@]2(O)[C@H]([C@H]1OC(=O)C1=CC=CC=C1)[C@@H](OC(C)=O)C(=C)[C@H](OC(C)=O)[C@@H](O)C(=O)C(C)(C)\C=C\[C@@H](C)[C@H]2O |
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InChI Identifier | InChI=1S/C31H40O10/c1-16-13-14-30(6,7)28(36)23(34)26(40-20(5)33)18(3)25(39-19(4)32)22-24(17(2)15-31(22,38)27(16)35)41-29(37)21-11-9-8-10-12-21/h8-14,16-17,22-27,34-35,38H,3,15H2,1-2,4-7H3/b14-13+/t16-,17+,22-,23-,24+,25+,26+,27-,31-/m1/s1 |
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InChI Key | RCIQJDCADVYGLY-MFHFMUCMSA-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 jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton. |
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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 | Jatrophane and cyclojatrophane diterpenoids |
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Alternative Parents | |
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Substituents | - Jatrophane diterpenoid
- Benzoate ester
- Benzoic acid or derivatives
- Tricarboxylic acid or derivatives
- Benzoyl
- Benzenoid
- Monocyclic benzene moiety
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Cyclic ketone
- Ketone
- Carboxylic acid ester
- Polyol
- Carboxylic acid derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic 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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