Record Information |
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Version | 2.0 |
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Created at | 2022-09-08 20:13:08 UTC |
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Updated at | 2022-09-08 20:13:08 UTC |
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NP-MRD ID | NP0273243 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | [(1s,6s,7s,11r,13r,16r,17s)-7-hydroxy-6,10,16-trimethyl-4,8,15-trioxo-3,14-dioxatetracyclo[11.4.0.0¹,⁵.0⁶,¹¹]heptadec-9-en-17-yl]acetic acid |
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Description | Vilmorinine E belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. [(1s,6s,7s,11r,13r,16r,17s)-7-hydroxy-6,10,16-trimethyl-4,8,15-trioxo-3,14-dioxatetracyclo[11.4.0.0¹,⁵.0⁶,¹¹]heptadec-9-en-17-yl]acetic acid is found in Ailanthus altissima. It was first documented in 2022 (PMID: 36109150). Based on a literature review a significant number of articles have been published on Vilmorinine E (PMID: 36108986) (PMID: 36109008) (PMID: 36109086) (PMID: 36109054). |
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Structure | C[C@@H]1[C@H](CC(O)=O)[C@@]23COC(=O)C2[C@@]2(C)[C@H](O)C(=O)C=C(C)[C@H]2C[C@H]3OC1=O InChI=1S/C20H24O8/c1-8-4-12(21)16(24)19(3)10(8)5-13-20(7-27-18(26)15(19)20)11(6-14(22)23)9(2)17(25)28-13/h4,9-11,13,15-16,24H,5-7H2,1-3H3,(H,22,23)/t9-,10-,11+,13-,15?,16-,19+,20-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C20H24O8 |
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Average Mass | 392.4040 Da |
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Monoisotopic Mass | 392.14712 Da |
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IUPAC Name | 2-[(1S,6S,7S,11R,13R,16R,17S)-7-hydroxy-6,10,16-trimethyl-4,8,15-trioxo-3,14-dioxatetracyclo[11.4.0.0^{1,5}.0^{6,11}]heptadec-9-en-17-yl]acetic acid |
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Traditional Name | [(1S,6S,7S,11R,13R,16R,17S)-7-hydroxy-6,10,16-trimethyl-4,8,15-trioxo-3,14-dioxatetracyclo[11.4.0.0^{1,5}.0^{6,11}]heptadec-9-en-17-yl]acetic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1[C@H](CC(O)=O)[C@@]23COC(=O)C2[C@@]2(C)[C@H](O)C(=O)C=C(C)[C@H]2C[C@H]3OC1=O |
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InChI Identifier | InChI=1S/C20H24O8/c1-8-4-12(21)16(24)19(3)10(8)5-13-20(7-27-18(26)15(19)20)11(6-14(22)23)9(2)17(25)28-13/h4,9-11,13,15-16,24H,5-7H2,1-3H3,(H,22,23)/t9-,10-,11+,13-,15?,16-,19+,20-/m1/s1 |
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InChI Key | HEARPDWGNHOTSL-VRQCDGKKSA-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 quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. |
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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 | Terpene lactones |
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Direct Parent | Quassinoids |
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Alternative Parents | |
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Substituents | - Quassinoid
- Naphthopyran
- Naphthalene
- Tricarboxylic acid or derivatives
- Delta valerolactone
- Delta_valerolactone
- Cyclohexenone
- Gamma butyrolactone
- Oxane
- Pyran
- Oxolane
- Cyclic ketone
- Carboxylic acid ester
- Ketone
- Lactone
- Secondary alcohol
- Carboxylic acid derivative
- Oxacycle
- Carboxylic acid
- Organoheterocyclic compound
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Carbonyl group
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic 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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