Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 11:39:10 UTC |
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Updated at | 2022-09-12 11:39:10 UTC |
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NP-MRD ID | NP0328303 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s,3r,4r,7r,10s,12s,13r,14r,15s,17r,19s,20r)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0²,¹⁰.0³,⁷.0¹⁴,¹⁹.0¹⁷,¹⁹]icosane-5,8-dione |
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Description | (2S,3R,4R,7R,10S,12S,13R,14R,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0²,¹⁰.0³,⁷.0¹⁴,¹⁹.0¹⁷,¹⁹]Icosane-5,8-dione 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. (2s,3r,4r,7r,10s,12s,13r,14r,15s,17r,19s,20r)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0²,¹⁰.0³,⁷.0¹⁴,¹⁹.0¹⁷,¹⁹]icosane-5,8-dione is found in Toona ciliata. Based on a literature review very few articles have been published on (2S,3R,4R,7R,10S,12S,13R,14R,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0²,¹⁰.0³,⁷.0¹⁴,¹⁹.0¹⁷,¹⁹]Icosane-5,8-dione. |
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Structure | C[C@@]12OC(=O)[C@H](O)[C@]1(O)[C@]1(C)[C@H](CC2=O)O[C@H]2C1[C@@](C)(O)[C@@]13O[C@@H]1C[C@@H](C1=COC=C1)[C@]3(C)[C@H]2O InChI=1S/C25H30O10/c1-20-11(10-5-6-32-9-10)7-14-25(20,34-14)22(3,30)16-15(17(20)27)33-13-8-12(26)23(4)24(31,21(13,16)2)18(28)19(29)35-23/h5-6,9,11,13-18,27-28,30-31H,7-8H2,1-4H3/t11-,13-,14+,15-,16?,17-,18-,20+,21+,22+,23-,24-,25+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C25H30O10 |
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Average Mass | 490.5050 Da |
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Monoisotopic Mass | 490.18390 Da |
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IUPAC Name | (2S,3R,4R,7R,10S,12S,13R,14R,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0^{2,10}.0^{3,7}.0^{14,19}.0^{17,19}]icosane-5,8-dione |
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Traditional Name | (2S,3R,4R,7R,10S,12S,13R,14R,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0^{2,10}.0^{3,7}.0^{14,19}.0^{17,19}]icosane-5,8-dione |
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CAS Registry Number | Not Available |
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SMILES | C[C@@]12OC(=O)[C@H](O)[C@]1(O)[C@]1(C)[C@H](CC2=O)O[C@H]2C1[C@@](C)(O)[C@@]13O[C@@H]1C[C@@H](C1=COC=C1)[C@]3(C)[C@H]2O |
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InChI Identifier | InChI=1S/C25H30O10/c1-20-11(10-5-6-32-9-10)7-14-25(20,34-14)22(3,30)16-15(17(20)27)33-13-8-12(26)23(4)24(31,21(13,16)2)18(28)19(29)35-23/h5-6,9,11,13-18,27-28,30-31H,7-8H2,1-4H3/t11-,13-,14+,15-,16?,17-,18-,20+,21+,22+,23-,24-,25+/m0/s1 |
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InChI Key | OMQBBQBLEKPHLY-QJTZMQFLSA-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
- Terpene lactone
- Alpha-acyloxy ketone
- Oxane
- Gamma butyrolactone
- Heteroaromatic compound
- Tetrahydrofuran
- Tertiary alcohol
- Furan
- Cyclic alcohol
- Secondary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Monocarboxylic acid or derivatives
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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