| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-02 11:29:42 UTC |
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| Updated at | 2022-09-02 11:29:42 UTC |
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| NP-MRD ID | NP0154562 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1s,4s,5r,6r,7s,11r,16s,17s,18r,19r)-5,16,17-trihydroxy-6,14,18-trimethyl-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-13-en-9-one |
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| Description | (1S,4S,5R,6R,7S,11R,16S,17S,18R,19R)-5,16,17-trihydroxy-6,14,18-trimethyl-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]Nonadec-13-en-9-one 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,4s,5r,6r,7s,11r,16s,17s,18r,19r)-5,16,17-trihydroxy-6,14,18-trimethyl-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-13-en-9-one is found in Castela tortuosa. Based on a literature review very few articles have been published on (1S,4S,5R,6R,7S,11R,16S,17S,18R,19R)-5,16,17-trihydroxy-6,14,18-trimethyl-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]Nonadec-13-en-9-one. |
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| Structure | C[C@H]1[C@@H](O)[C@]2(O[C@H]3O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]3O)OC[C@]34[C@H]2[C@@]2(C)[C@H](O)[C@@H](O)CC(C)=C2C[C@H]3OC(=O)C[C@@H]14 InChI=1S/C26H38O12/c1-9-4-13(28)21(34)24(3)11(9)5-15-25-8-35-26(23(24)25,20(33)10(2)12(25)6-16(29)37-15)38-22-19(32)18(31)17(30)14(7-27)36-22/h10,12-15,17-23,27-28,30-34H,4-8H2,1-3H3/t10-,12+,13+,14+,15-,17+,18-,19+,20-,21-,22-,23-,24-,25-,26-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C26H38O12 |
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| Average Mass | 542.5780 Da |
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| Monoisotopic Mass | 542.23633 Da |
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| IUPAC Name | (1S,4S,5R,6R,7S,11R,16S,17S,18R,19R)-5,16,17-trihydroxy-6,14,18-trimethyl-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0^{1,7}.0^{4,19}.0^{13,18}]nonadec-13-en-9-one |
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| Traditional Name | (1S,4S,5R,6R,7S,11R,16S,17S,18R,19R)-5,16,17-trihydroxy-6,14,18-trimethyl-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0^{1,7}.0^{4,19}.0^{13,18}]nonadec-13-en-9-one |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@H]1[C@@H](O)[C@]2(O[C@H]3O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]3O)OC[C@]34[C@H]2[C@@]2(C)[C@H](O)[C@@H](O)CC(C)=C2C[C@H]3OC(=O)C[C@@H]14 |
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| InChI Identifier | InChI=1S/C26H38O12/c1-9-4-13(28)21(34)24(3)11(9)5-15-25-8-35-26(23(24)25,20(33)10(2)12(25)6-16(29)37-15)38-22-19(32)18(31)17(30)14(7-27)36-22/h10,12-15,17-23,27-28,30-34H,4-8H2,1-3H3/t10-,12+,13+,14+,15-,17+,18-,19+,20-,21-,22-,23-,24-,25-,26-/m1/s1 |
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| InChI Key | YIOHSMSXXBECLM-HIHVQHTHSA-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
- Quassinoid
- Naphthopyran
- Hexose monosaccharide
- Glycosyl compound
- O-glycosyl compound
- Naphthalene
- Delta valerolactone
- Delta_valerolactone
- Ketal
- Oxepane
- Monosaccharide
- Oxane
- Pyran
- Cyclic alcohol
- Tetrahydrofuran
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Polyol
- Carboxylic acid derivative
- Organoheterocyclic compound
- Acetal
- Monocarboxylic acid or derivatives
- Oxacycle
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Alcohol
- Organic oxide
- Primary alcohol
- 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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