Record Information |
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Version | 2.0 |
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Created at | 2022-04-29 03:42:21 UTC |
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Updated at | 2022-04-29 03:42:21 UTC |
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NP-MRD ID | NP0082626 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Taxawallin F |
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Description | (2S,3aS,4aS,6R,8R,8aR,9S,10S)-8,9-bis(acetyloxy)-6,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-2-yl acetate belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system. Taxawallin F is found in Taxus wallichiana . Based on a literature review very few articles have been published on (2S,3aS,4aS,6R,8R,8aR,9S,10S)-8,9-bis(acetyloxy)-6,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-2-yl acetate. |
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Structure | CC(=O)O[C@H]1C[C@]2(C[C@H]3C(=C)[C@H](O)C[C@@H](OC(C)=O)[C@]3(C)[C@H](OC(C)=O)[C@@H](O)C2=C1C)C(C)(C)O InChI=1S/C26H38O9/c1-12-17-10-26(24(6,7)32)11-19(33-14(3)27)13(2)21(26)22(31)23(35-16(5)29)25(17,8)20(9-18(12)30)34-15(4)28/h17-20,22-23,30-32H,1,9-11H2,2-8H3/t17-,18+,19-,20+,22-,23+,25+,26-/m0/s1 |
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Synonyms | Value | Source |
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(2S,3AS,4as,6R,8R,8ar,9S,10S)-8,9-bis(acetyloxy)-6,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2H,3H,3ah,4H,4ah,5H,6H,7H,8H,8ah,9H,10H-cyclohexa[F]azulen-2-yl acetic acid | Generator |
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Chemical Formula | C26H38O9 |
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Average Mass | 494.5810 Da |
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Monoisotopic Mass | 494.25158 Da |
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IUPAC Name | (2S,3aS,4aS,6R,8R,8aR,9S,10S)-8,9-bis(acetyloxy)-6,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-2-yl acetate |
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Traditional Name | (2S,3aS,4aS,6R,8R,8aR,9S,10S)-8,9-bis(acetyloxy)-6,10-dihydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2H,3H,4H,4aH,6H,7H,8H,9H,10H-cyclohexa[f]azulen-2-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)O[C@H]1C[C@]2(C[C@H]3C(=C)[C@H](O)C[C@@H](OC(C)=O)[C@]3(C)[C@H](OC(C)=O)[C@@H](O)C2=C1C)C(C)(C)O |
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InChI Identifier | InChI=1S/C26H38O9/c1-12-17-10-26(24(6,7)32)11-19(33-14(3)27)13(2)21(26)22(31)23(35-16(5)29)25(17,8)20(9-18(12)30)34-15(4)28/h17-20,22-23,30-32H,1,9-11H2,2-8H3/t17-,18+,19-,20+,22-,23+,25+,26-/m0/s1 |
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InChI Key | SGZHKJOBEGSWHS-HUVABCBLSA-N |
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Experimental Spectra |
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| Not Available |
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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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
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Chemical Shift Submissions |
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| Not Available |
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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 taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system. |
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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 | Taxanes and derivatives |
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Alternative Parents | |
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Substituents | - 11(15->1)-abeotaxane diterpenoid
- Tricarboxylic acid or derivatives
- Tertiary alcohol
- Cyclic alcohol
- Secondary 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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