Record Information |
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Version | 1.0 |
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Created at | 2022-09-06 06:22:36 UTC |
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Updated at | 2022-09-06 06:22:36 UTC |
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NP-MRD ID | NP0227139 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,2r,3ar,5s,9s,10s,11s,13r,13ar)-9,10,11-tris(acetyloxy)-1,3a-dihydroxy-2,5,8,8-tetramethyl-13-{[(2r)-2-methylbutanoyl]oxy}-12-methylidene-4-oxo-1h,3h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-2-yl pyridine-3-carboxylate |
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Description | (2R,3R,3aR,4R,6S,7S,8S,12S,13aR)-6,7,8-tris(acetyloxy)-3,13a-dihydroxy-2,9,9,12-tetramethyl-4-{[(2R)-2-methylbutanoyl]oxy}-5-methylidene-13-oxo-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,12H,13H,13aH-cyclopenta[12]annulen-2-yl pyridine-3-carboxylate 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. (1r,2r,3ar,5s,9s,10s,11s,13r,13ar)-9,10,11-tris(acetyloxy)-1,3a-dihydroxy-2,5,8,8-tetramethyl-13-{[(2r)-2-methylbutanoyl]oxy}-12-methylidene-4-oxo-1h,3h,5h,9h,10h,11h,13h,13ah-cyclopenta[12]annulen-2-yl pyridine-3-carboxylate is found in Euphorbia lamarckii. Based on a literature review very few articles have been published on (2R,3R,3aR,4R,6S,7S,8S,12S,13aR)-6,7,8-tris(acetyloxy)-3,13a-dihydroxy-2,9,9,12-tetramethyl-4-{[(2R)-2-methylbutanoyl]oxy}-5-methylidene-13-oxo-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,12H,13H,13aH-cyclopenta[12]annulen-2-yl pyridine-3-carboxylate. |
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Structure | CC[C@@H](C)C(=O)O[C@@H]1[C@H]2[C@@H](O)[C@@](C)(C[C@]2(O)C(=O)[C@@H](C)\C=C\C(C)(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)C1=C)OC(=O)C1=CC=CN=C1 InChI=1S/C37H49NO13/c1-11-19(2)33(44)50-27-21(4)28(47-22(5)39)29(48-23(6)40)32(49-24(7)41)35(8,9)15-14-20(3)30(42)37(46)18-36(10,31(43)26(27)37)51-34(45)25-13-12-16-38-17-25/h12-17,19-20,26-29,31-32,43,46H,4,11,18H2,1-3,5-10H3/b15-14+/t19-,20+,26+,27+,28+,29-,31-,32-,36-,37-/m1/s1 |
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Synonyms | Value | Source |
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(2R,3R,3AR,4R,6S,7S,8S,12S,13ar)-6,7,8-tris(acetyloxy)-3,13a-dihydroxy-2,9,9,12-tetramethyl-4-{[(2R)-2-methylbutanoyl]oxy}-5-methylidene-13-oxo-1H,2H,3H,3ah,4H,5H,6H,7H,8H,9H,12H,13H,13ah-cyclopenta[12]annulen-2-yl pyridine-3-carboxylic acid | Generator |
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Chemical Formula | C37H49NO13 |
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Average Mass | 715.7930 Da |
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Monoisotopic Mass | 715.32039 Da |
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IUPAC Name | (2R,3R,3aR,4R,6S,7S,8S,12S,13aR)-6,7,8-tris(acetyloxy)-3,13a-dihydroxy-2,9,9,12-tetramethyl-4-{[(2R)-2-methylbutanoyl]oxy}-5-methylidene-13-oxo-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,12H,13H,13aH-cyclopenta[12]annulen-2-yl pyridine-3-carboxylate |
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Traditional Name | (1R,2R,3aR,5S,9S,10S,11S,13R,13aR)-9,10,11-tris(acetyloxy)-1,3a-dihydroxy-2,5,8,8-tetramethyl-13-{[(2R)-2-methylbutanoyl]oxy}-12-methylidene-4-oxo-1H,3H,5H,9H,10H,11H,13H,13aH-cyclopenta[12]annulen-2-yl pyridine-3-carboxylate |
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CAS Registry Number | Not Available |
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SMILES | CC[C@@H](C)C(=O)O[C@@H]1[C@H]2[C@@H](O)[C@@](C)(C[C@]2(O)C(=O)[C@@H](C)\C=C\C(C)(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)C1=C)OC(=O)C1=CC=CN=C1 |
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InChI Identifier | InChI=1S/C37H49NO13/c1-11-19(2)33(44)50-27-21(4)28(47-22(5)39)29(48-23(6)40)32(49-24(7)41)35(8,9)15-14-20(3)30(42)37(46)18-36(10,31(43)26(27)37)51-34(45)25-13-12-16-38-17-25/h12-17,19-20,26-29,31-32,43,46H,4,11,18H2,1-3,5-10H3/b15-14+/t19-,20+,26+,27+,28+,29-,31-,32-,36-,37-/m1/s1 |
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InChI Key | LOFYLMVVNBTSKH-ZQCZKMAKSA-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
- Pentacarboxylic acid or derivatives
- Pyridine carboxylic acid
- Pyridine carboxylic acid or derivatives
- Fatty acid ester
- Fatty acyl
- Pyridine
- Heteroaromatic compound
- Cyclic alcohol
- Tertiary alcohol
- Carboxylic acid ester
- Ketone
- Secondary alcohol
- Azacycle
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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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