Record Information |
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Version | 2.0 |
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Created at | 2022-09-11 20:33:47 UTC |
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Updated at | 2022-09-11 20:33:47 UTC |
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NP-MRD ID | NP0319504 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,2r,5s,6r,10r,11s,12r,15r,16r,18s,19r)-16-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadec-8-en-18-yl (2e)-3-phenylprop-2-enoate |
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Description | 1-Cinnamoyl-3-acetylvilasinin belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (1r,2r,5s,6r,10r,11s,12r,15r,16r,18s,19r)-16-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadec-8-en-18-yl (2e)-3-phenylprop-2-enoate is found in Melia volkensii. Based on a literature review very few articles have been published on 1-Cinnamoyl-3-acetylvilasinin. |
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Structure | CC(=O)O[C@@H]1C[C@H](OC(=O)\C=C\C2=CC=CC=C2)[C@@]2(C)[C@H]3[C@@H](OC[C@]13C)[C@@H](O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](CC=C12)C1=COC=C1 InChI=1S/C37H44O7/c1-22(38)43-28-19-29(44-30(39)14-11-23-9-7-6-8-10-23)37(5)27-15-17-34(2)25(24-16-18-41-20-24)12-13-26(34)36(27,4)33(40)31-32(37)35(28,3)21-42-31/h6-11,13-14,16,18,20,25,27-29,31-33,40H,12,15,17,19,21H2,1-5H3/b14-11+/t25-,27-,28+,29-,31+,32-,33+,34-,35+,36-,37-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C37H44O7 |
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Average Mass | 600.7520 Da |
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Monoisotopic Mass | 600.30870 Da |
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IUPAC Name | (1R,2R,5S,6R,10R,11S,12R,15R,16R,18S,19R)-16-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadec-8-en-18-yl (2E)-3-phenylprop-2-enoate |
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Traditional Name | (1R,2R,5S,6R,10R,11S,12R,15R,16R,18S,19R)-16-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadec-8-en-18-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@@]2(C)[C@H]3[C@@H](OC[C@]13C)[C@@H](O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](CC=C12)C1=COC=C1 |
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InChI Identifier | InChI=1S/C37H44O7/c1-22(38)43-28-19-29(44-30(39)14-11-23-9-7-6-8-10-23)37(5)27-15-17-34(2)25(24-16-18-41-20-24)12-13-26(34)36(27,4)33(40)31-32(37)35(28,3)21-42-31/h6-11,13-14,16,18,20,25,27-29,31-33,40H,12,15,17,19,21H2,1-5H3/b14-11+/t25-,27-,28+,29-,31+,32-,33+,34-,35+,36-,37-/m0/s1 |
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InChI Key | URQZJLPVQSJQOL-ISWXVQJLSA-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 limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. |
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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 | Triterpenoids |
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Direct Parent | Limonoids |
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Alternative Parents | |
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Substituents | - Limonoid skeleton
- 17-furanylsteroid skeleton
- Steroid ester
- Steroid
- Naphthofuran
- Cinnamic acid or derivatives
- Cinnamic acid ester
- Styrene
- Fatty acid ester
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Fatty acyl
- Benzenoid
- Cyclic alcohol
- Heteroaromatic compound
- Furan
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Carboxylic acid ester
- Secondary alcohol
- Oxacycle
- Ether
- Dialkyl ether
- Organoheterocyclic compound
- Carboxylic acid derivative
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- 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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