Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 06:10:46 UTC |
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Updated at | 2022-09-12 06:10:46 UTC |
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NP-MRD ID | NP0325426 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | methyl (2r)-2-[(1r,2s,5r,6r,13r,14s,16s)-14-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]-2-hydroxyacetate |
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Description | Methyl (2R)-2-[(1R,2S,5R,6R,13R,14S,16S)-14-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-16-yl]-2-hydroxyacetate 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. methyl (2r)-2-[(1r,2s,5r,6r,13r,14s,16s)-14-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-16-yl]-2-hydroxyacetate is found in Khaya senegalensis. Based on a literature review very few articles have been published on methyl (2R)-2-[(1R,2S,5R,6R,13R,14S,16S)-14-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-16-yl]-2-hydroxyacetate. |
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Structure | COC(=O)[C@H](O)[C@H]1C(C)(C)[C@H](OC(C)=O)[C@]2(O)CC3=C4CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)CC[C@@H]3[C@@]1(C)C2=O InChI=1S/C29H36O10/c1-14(30)38-25-26(2,3)21(20(32)23(33)36-6)28(5)17-7-9-27(4)18(16(17)12-29(25,35)24(28)34)11-19(31)39-22(27)15-8-10-37-13-15/h8,10,13,17,20-22,25,32,35H,7,9,11-12H2,1-6H3/t17-,20+,21-,22-,25-,27+,28+,29-/m0/s1 |
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Synonyms | Value | Source |
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Methyl (2R)-2-[(1R,2S,5R,6R,13R,14S,16S)-14-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadec-10-en-16-yl]-2-hydroxyacetic acid | Generator |
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Chemical Formula | C29H36O10 |
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Average Mass | 544.5970 Da |
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Monoisotopic Mass | 544.23085 Da |
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IUPAC Name | methyl (2R)-2-[(1R,2S,5R,6R,13R,14S,16S)-14-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]-2-hydroxyacetate |
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Traditional Name | (R)-(methyl [(1R,2S,5R,6R,13R,14S,16S)-14-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl](hydroxy)acetate) |
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CAS Registry Number | Not Available |
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SMILES | COC(=O)[C@H](O)[C@H]1C(C)(C)[C@H](OC(C)=O)[C@]2(O)CC3=C4CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)CC[C@@H]3[C@@]1(C)C2=O |
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InChI Identifier | InChI=1S/C29H36O10/c1-14(30)38-25-26(2,3)21(20(32)23(33)36-6)28(5)17-7-9-27(4)18(16(17)12-29(25,35)24(28)34)11-19(31)39-22(27)15-8-10-37-13-15/h8,10,13,17,20-22,25,32,35H,7,9,11-12H2,1-6H3/t17-,20+,21-,22-,25-,27+,28+,29-/m0/s1 |
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InChI Key | JWYNOYIKTIPXBD-MWGBPSIWSA-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
- Mexicanolide
- Steroid lactone
- 12-hydroxysteroid
- Hydroxysteroid
- 12-alpha-hydroxysteroid
- Steroid
- Naphthopyran
- Naphthalene
- Tricarboxylic acid or derivatives
- Delta valerolactone
- Delta_valerolactone
- Oxane
- Pyran
- Methyl ester
- Heteroaromatic compound
- Cyclic alcohol
- Tertiary alcohol
- Furan
- Secondary alcohol
- Carboxylic acid ester
- Lactone
- Ketone
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- 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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