Record Information |
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Version | 1.0 |
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Created at | 2022-09-07 04:53:27 UTC |
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Updated at | 2022-09-07 04:53:27 UTC |
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NP-MRD ID | NP0244165 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,4r,5r,7s,8r,9r,10r,11s,12r)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-5,7-bis({[(2e)-2-methylbut-2-enoyl]oxy})-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate |
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Description | Nimbolidin D 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,4r,5r,7s,8r,9r,10r,11s,12r)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-5,7-bis({[(2e)-2-methylbut-2-enoyl]oxy})-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate is found in Melia azedarach. Based on a literature review very few articles have been published on Nimbolidin D. |
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Structure | COC(=O)C[C@@H]1[C@]2(C)[C@H]3[C@@H](OC[C@]3(C)[C@@H](C[C@@H]2OC(=O)C(\C)=C\C)OC(=O)C(\C)=C\C)[C@@H](OC(=O)C(\C)=C\C)[C@@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(C)=O)C1=COC=C1 InChI=1S/C44H58O12/c1-13-23(4)39(47)54-32-20-33(55-40(48)24(5)14-2)43(10)31(19-34(46)50-12)44(11,35-26(7)29(28-16-17-51-21-28)18-30(35)53-27(8)45)38(56-41(49)25(6)15-3)36-37(43)42(32,9)22-52-36/h13-17,21,29-33,36-38H,18-20,22H2,1-12H3/b23-13+,24-14+,25-15+/t29-,30+,31-,32-,33+,36-,37+,38-,42-,43+,44-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C44H58O12 |
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Average Mass | 778.9360 Da |
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Monoisotopic Mass | 778.39283 Da |
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IUPAC Name | (1R,4R,5R,7S,8R,9R,10R,11S,12R)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-5,7-bis({[(2E)-2-methylbut-2-enoyl]oxy})-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl (2E)-2-methylbut-2-enoate |
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Traditional Name | (1R,4R,5R,7S,8R,9R,10R,11S,12R)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-5,7-bis({[(2E)-2-methylbut-2-enoyl]oxy})-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl (2E)-2-methylbut-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | COC(=O)C[C@@H]1[C@]2(C)[C@H]3[C@@H](OC[C@]3(C)[C@@H](C[C@@H]2OC(=O)C(\C)=C\C)OC(=O)C(\C)=C\C)[C@@H](OC(=O)C(\C)=C\C)[C@@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(C)=O)C1=COC=C1 |
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InChI Identifier | InChI=1S/C44H58O12/c1-13-23(4)39(47)54-32-20-33(55-40(48)24(5)14-2)43(10)31(19-34(46)50-12)44(11,35-26(7)29(28-16-17-51-21-28)18-30(35)53-27(8)45)38(56-41(49)25(6)15-3)36-37(43)42(32,9)22-52-36/h13-17,21,29-33,36-38H,18-20,22H2,1-12H3/b23-13+,24-14+,25-15+/t29-,30+,31-,32-,33+,36-,37+,38-,42-,43+,44-/m1/s1 |
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InChI Key | QCFBMZLALFSLDU-BRTRSVSESA-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
- Pentacarboxylic acid or derivatives
- Fatty acid ester
- Fatty acyl
- Heteroaromatic compound
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Methyl ester
- Tetrahydrofuran
- Furan
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- 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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