Record Information |
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Version | 1.0 |
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Created at | 2022-09-09 19:59:11 UTC |
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Updated at | 2022-09-09 19:59:11 UTC |
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NP-MRD ID | NP0289678 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,2r,5s,6r,13s,14r,16s)-16-[(1r)-1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate |
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Description | (1R,2R,5S,6R,13S,14R,16S)-16-[(1R)-1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate 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. (1r,2r,5s,6r,13s,14r,16s)-16-[(1r)-1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate is found in Swietenia mahagoni. Based on a literature review very few articles have been published on (1R,2R,5S,6R,13S,14R,16S)-16-[(1R)-1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate. |
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Structure | COC(=O)[C@H](OC(C)=O)[C@H]1C(C)(C)[C@H](OC(=O)C(C)=C(C)C)[C@@H]2CC3=C4CC(=O)O[C@@H](C5=COC=C5)[C@@]4(C)CC[C@H]3[C@@]1(C)C2=O InChI=1S/C35H44O10/c1-17(2)18(3)31(39)45-30-22-14-21-23(10-12-34(7)24(21)15-25(37)44-29(34)20-11-13-42-16-20)35(8,28(22)38)27(33(30,5)6)26(32(40)41-9)43-19(4)36/h11,13,16,22-23,26-27,29-30H,10,12,14-15H2,1-9H3/t22-,23-,26-,27+,29+,30-,34+,35-/m1/s1 |
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Synonyms | Value | Source |
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(1R,2R,5S,6R,13S,14R,16S)-16-[(1R)-1-(Acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoic acid | Generator |
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Chemical Formula | C35H44O10 |
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Average Mass | 624.7270 Da |
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Monoisotopic Mass | 624.29345 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | COC(=O)[C@H](OC(C)=O)[C@H]1C(C)(C)[C@H](OC(=O)C(C)=C(C)C)[C@@H]2CC3=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/C35H44O10/c1-17(2)18(3)31(39)45-30-22-14-21-23(10-12-34(7)24(21)15-25(37)44-29(34)20-11-13-42-16-20)35(8,28(22)38)27(33(30,5)6)26(32(40)41-9)43-19(4)36/h11,13,16,22-23,26-27,29-30H,10,12,14-15H2,1-9H3/t22-,23-,26-,27+,29+,30-,34+,35-/m1/s1 |
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InChI Key | AYEZTOKCHWMCDA-LVIKVNAZSA-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
- Naphthopyran
- Tetracarboxylic acid or derivatives
- Naphthalene
- Delta valerolactone
- Fatty acid ester
- Delta_valerolactone
- Fatty acyl
- Oxane
- Pyran
- Heteroaromatic compound
- Furan
- Alpha,beta-unsaturated carboxylic ester
- Methyl ester
- Enoate ester
- Carboxylic acid ester
- Ketone
- Lactone
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- 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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