| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-04 19:33:54 UTC |
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| Updated at | 2022-09-04 19:33:54 UTC |
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| NP-MRD ID | NP0200675 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1r,2r,3r,5s,7s,8s,9r,10s,11s)-2,7,9,10,13-pentakis(acetyloxy)-11-hydroxy-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-12-en-5-yl (2e)-3-phenylprop-2-enoate |
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| Description | Taxuspine D 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. (1r,2r,3r,5s,7s,8s,9r,10s,11s)-2,7,9,10,13-pentakis(acetyloxy)-11-hydroxy-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-12-en-5-yl (2e)-3-phenylprop-2-enoate is found in Taxus canadensis, Taxus cuspidata and Taxus wallichiana. (1r,2r,3r,5s,7s,8s,9r,10s,11s)-2,7,9,10,13-pentakis(acetyloxy)-11-hydroxy-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0³,⁸]pentadec-12-en-5-yl (2e)-3-phenylprop-2-enoate was first documented in 2003 (PMID: 12539780). Based on a literature review very few articles have been published on Taxuspine D. |
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| Structure | CC(=O)O[C@H]1C[C@H](OC(=O)\C=C\C2=CC=CC=C2)C(=C)[C@H]2[C@H](OC(C)=O)[C@@H]3CC(OC(C)=O)=C(C)[C@](O)([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@]12C)C3(C)C InChI=1S/C39H48O13/c1-20-29(52-32(45)17-16-27-14-12-11-13-15-27)19-31(48-23(4)41)38(10)33(20)34(49-24(5)42)28-18-30(47-22(3)40)21(2)39(46,37(28,8)9)36(51-26(7)44)35(38)50-25(6)43/h11-17,28-29,31,33-36,46H,1,18-19H2,2-10H3/b17-16+/t28-,29-,31-,33-,34+,35-,36-,38+,39-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C39H48O13 |
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| Average Mass | 724.8000 Da |
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| Monoisotopic Mass | 724.30949 Da |
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| IUPAC Name | (1R,2R,3R,5S,7S,8S,9R,10S,11S)-2,7,9,10,13-pentakis(acetyloxy)-11-hydroxy-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-12-en-5-yl (2E)-3-phenylprop-2-enoate |
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| Traditional Name | (1R,2R,3R,5S,7S,8S,9R,10S,11S)-2,7,9,10,13-pentakis(acetyloxy)-11-hydroxy-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-12-en-5-yl (2E)-3-phenylprop-2-enoate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=O)O[C@H]1C[C@H](OC(=O)\C=C\C2=CC=CC=C2)C(=C)[C@H]2[C@H](OC(C)=O)[C@@H]3CC(OC(C)=O)=C(C)[C@](O)([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@]12C)C3(C)C |
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| InChI Identifier | InChI=1S/C39H48O13/c1-20-29(52-32(45)17-16-27-14-12-11-13-15-27)19-31(48-23(4)41)38(10)33(20)34(49-24(5)42)28-18-30(47-22(3)40)21(2)39(46,37(28,8)9)36(51-26(7)44)35(38)50-25(6)43/h11-17,28-29,31,33-36,46H,1,18-19H2,2-10H3/b17-16+/t28-,29-,31-,33-,34+,35-,36-,38+,39-/m0/s1 |
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| InChI Key | YQWATTVJPRZZEE-HWFKHETCSA-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 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 | - Hexacarboxylic acid or derivatives
- Taxane diterpenoid
- Cinnamic acid or derivatives
- Cinnamic acid ester
- Styrene
- Fatty acid ester
- Monocyclic benzene moiety
- Fatty acyl
- Benzenoid
- Enol ester
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tertiary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- 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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