Record Information |
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Version | 1.0 |
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Created at | 2022-09-05 17:00:43 UTC |
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Updated at | 2022-09-05 17:00:43 UTC |
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NP-MRD ID | NP0216875 |
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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)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate |
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Description | Nimbolidin C 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)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl 2-methylpropanoate is found in Melia azedarach. It was first documented in 2001 (PMID: 11701014). Based on a literature review very few articles have been published on Nimbolidin C. |
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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(C)=O)OC(C)=O)[C@@H](OC(=O)C(C)C)[C@@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(C)=O)C1=COC=C1 InChI=1S/C37H50O12/c1-18(2)34(42)49-33-31-32-35(7,17-45-31)27(47-21(5)39)15-28(48-22(6)40)36(32,8)26(14-29(41)43-10)37(33,9)30-19(3)24(23-11-12-44-16-23)13-25(30)46-20(4)38/h11-12,16,18,24-28,31-33H,13-15,17H2,1-10H3/t24-,25+,26-,27-,28+,31-,32+,33-,35-,36+,37-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C37H50O12 |
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Average Mass | 686.7950 Da |
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Monoisotopic Mass | 686.33023 Da |
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IUPAC Name | (1R,4R,5R,7S,8R,9R,10R,11S,12R)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl 2-methylpropanoate |
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Traditional Name | (1R,4R,5R,7S,8R,9R,10R,11S,12R)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl 2-methylpropanoate |
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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(C)=O)OC(C)=O)[C@@H](OC(=O)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/C37H50O12/c1-18(2)34(42)49-33-31-32-35(7,17-45-31)27(47-21(5)39)15-28(48-22(6)40)36(32,8)26(14-29(41)43-10)37(33,9)30-19(3)24(23-11-12-44-16-23)13-25(30)46-20(4)38/h11-12,16,18,24-28,31-33H,13-15,17H2,1-10H3/t24-,25+,26-,27-,28+,31-,32+,33-,35-,36+,37-/m1/s1 |
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InChI Key | OVMLYMIACVFLEH-SDSCJSQRSA-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
- Furan
- Heteroaromatic compound
- Tetrahydrofuran
- Methyl ester
- Carboxylic acid ester
- Carboxylic acid derivative
- Dialkyl ether
- Ether
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxygen 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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