Record Information |
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Version | 2.0 |
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Created at | 2022-09-11 22:32:48 UTC |
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Updated at | 2022-09-11 22:32:48 UTC |
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NP-MRD ID | NP0320725 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,2s,6s,7s,9r,13s,15r,16s,17s)-15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione |
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Description | (1S,2S,6S,7S,9R,13S,15R,16S,17S)-15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-ene-3,11-dione 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,2s,6s,7s,9r,13s,15r,16s,17s)-15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione is found in Quassia amara. Based on a literature review very few articles have been published on (1S,2S,6S,7S,9R,13S,15R,16S,17S)-15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-ene-3,11-dione. |
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Structure | COC1=C[C@@H](C)[C@@H]2C[C@H]3OC(=O)C[C@H]4C(=C)[C@@H](O)[C@@H](O)[C@@H]([C@@]34C)[C@@]2(C)C1=O InChI=1S/C21H28O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9,11-12,14,16-18,23-24H,2,7-8H2,1,3-5H3/t9-,11+,12+,14-,16-,17-,18+,20-,21+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C21H28O6 |
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Average Mass | 376.4490 Da |
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Monoisotopic Mass | 376.18859 Da |
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IUPAC Name | (1S,2S,6S,7S,9R,13S,15R,16S,17S)-15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-ene-3,11-dione |
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Traditional Name | (1S,2S,6S,7S,9R,13S,15R,16S,17S)-15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-ene-3,11-dione |
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CAS Registry Number | Not Available |
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SMILES | COC1=C[C@@H](C)[C@@H]2C[C@H]3OC(=O)C[C@H]4C(=C)[C@@H](O)[C@@H](O)[C@@H]([C@@]34C)[C@@]2(C)C1=O |
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InChI Identifier | InChI=1S/C21H28O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9,11-12,14,16-18,23-24H,2,7-8H2,1,3-5H3/t9-,11+,12+,14-,16-,17-,18+,20-,21+/m1/s1 |
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InChI Key | CKRHSGZMMGXRKZ-FPWAFXQNSA-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 | - Triterpenoid
- Polycyclic triterpenoid
- C-20 quassinoid skeleton
- Quassinoid
- Naphthopyran
- Naphthalene
- Delta valerolactone
- Delta_valerolactone
- Cyclohexenone
- Pyran
- Oxane
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid ester
- Lactone
- Ketone
- 1,2-diol
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Organooxygen compound
- 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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