Record Information |
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Version | 1.0 |
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Created at | 2022-09-09 09:49:24 UTC |
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Updated at | 2022-09-09 09:49:24 UTC |
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NP-MRD ID | NP0282830 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | methyl 9,12,18-tris(acetyloxy)-6-(furan-3-yl)-14-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecane-15-carboxylate |
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Description | Methyl 9,12,18-tris(acetyloxy)-6-(furan-3-yl)-14-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadecane-15-carboxylate 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 9,12,18-tris(acetyloxy)-6-(furan-3-yl)-14-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecane-15-carboxylate is found in Turraea floribunda. Methyl 9,12,18-tris(acetyloxy)-6-(furan-3-yl)-14-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadecane-15-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CCC(C)C(=O)OC1C(OC(C)=O)C2C3(C)C(CC(O)C(C)(C3CC(OC(C)=O)C2(C)C23OC2CC(C2=COC=C2)C13C)C(=O)OC)OC(C)=O InChI=1S/C38H52O13/c1-11-18(2)32(43)50-31-29(49-21(5)41)30-35(7)24(34(6,33(44)45-10)25(42)16-26(35)47-19(3)39)15-27(48-20(4)40)37(30,9)38-28(51-38)14-23(36(31,38)8)22-12-13-46-17-22/h12-13,17-18,23-31,42H,11,14-16H2,1-10H3 |
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Synonyms | Value | Source |
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Methyl 9,12,18-tris(acetyloxy)-6-(furan-3-yl)-14-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-3-oxapentacyclo[8.8.0.0,.0,.0,]octadecane-15-carboxylic acid | Generator | Methyl 9,12,18-tris(acetyloxy)-6-(furan-3-yl)-14-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecane-15-carboxylic acid | Generator |
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Chemical Formula | C38H52O13 |
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Average Mass | 716.8210 Da |
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Monoisotopic Mass | 716.34079 Da |
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IUPAC Name | methyl 9,12,18-tris(acetyloxy)-6-(furan-3-yl)-14-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecane-15-carboxylate |
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Traditional Name | methyl 9,12,18-tris(acetyloxy)-6-(furan-3-yl)-14-hydroxy-1,7,11,15-tetramethyl-8-[(2-methylbutanoyl)oxy]-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecane-15-carboxylate |
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CAS Registry Number | Not Available |
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SMILES | CCC(C)C(=O)OC1C(OC(C)=O)C2C3(C)C(CC(O)C(C)(C3CC(OC(C)=O)C2(C)C23OC2CC(C2=COC=C2)C13C)C(=O)OC)OC(C)=O |
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InChI Identifier | InChI=1S/C38H52O13/c1-11-18(2)32(43)50-31-29(49-21(5)41)30-35(7)24(34(6,33(44)45-10)25(42)16-26(35)47-19(3)39)15-27(48-20(4)40)37(30,9)38-28(51-38)14-23(36(31,38)8)22-12-13-46-17-22/h12-13,17-18,23-31,42H,11,14-16H2,1-10H3 |
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InChI Key | UAYNGGCQOLGBJR-UHFFFAOYSA-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
- Prostaglandin skeleton
- 17-furanylsteroid skeleton
- Eicosanoid
- Steroid ester
- Steroid
- Pentacarboxylic acid or derivatives
- Naphthopyran
- Naphthalene
- Beta-hydroxy acid
- Fatty acid ester
- Fatty acyl
- Pyran
- Hydroxy acid
- Oxane
- Methyl ester
- Cyclic alcohol
- Furan
- Heteroaromatic compound
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organic oxide
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Organic oxygen compound
- 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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