Record Information |
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Version | 1.0 |
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Created at | 2022-09-07 21:51:16 UTC |
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Updated at | 2022-09-07 21:51:17 UTC |
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NP-MRD ID | NP0256885 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 1-[5-(2-hydroxy-3,3-dimethyloxiran-2-yl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate |
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Description | 14-[5-(2-Hydroxy-3,3-dimethyloxiran-2-yl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-9-yl acetate 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. 1-[5-(2-hydroxy-3,3-dimethyloxiran-2-yl)oxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate is found in Xylocarpus granatum. 14-[5-(2-Hydroxy-3,3-dimethyloxiran-2-yl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-9-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC(=O)OC1CC2C(C)(C)C(=O)C=CC2(C)C2CCC3(C)C(CC=C3C12C)C1COC(C1)C1(O)OC1(C)C InChI=1S/C32H46O6/c1-18(33)37-25-16-23-27(2,3)24(34)12-14-30(23,7)22-11-13-29(6)20(9-10-21(29)31(22,25)8)19-15-26(36-17-19)32(35)28(4,5)38-32/h10,12,14,19-20,22-23,25-26,35H,9,11,13,15-17H2,1-8H3 |
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Synonyms | Value | Source |
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14-[5-(2-Hydroxy-3,3-dimethyloxiran-2-yl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadeca-3,11-dien-9-yl acetic acid | Generator | 14-[5-(2-Hydroxy-3,3-dimethyloxiran-2-yl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,11-dien-9-yl acetic acid | Generator |
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Chemical Formula | C32H46O6 |
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Average Mass | 526.7140 Da |
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Monoisotopic Mass | 526.32944 Da |
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IUPAC Name | 14-[5-(2-hydroxy-3,3-dimethyloxiran-2-yl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,11-dien-9-yl acetate |
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Traditional Name | 14-[5-(2-hydroxy-3,3-dimethyloxiran-2-yl)oxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,11-dien-9-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)OC1CC2C(C)(C)C(=O)C=CC2(C)C2CCC3(C)C(CC=C3C12C)C1COC(C1)C1(O)OC1(C)C |
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InChI Identifier | InChI=1S/C32H46O6/c1-18(33)37-25-16-23-27(2,3)24(34)12-14-30(23,7)22-11-13-29(6)20(9-10-21(29)31(22,25)8)19-15-26(36-17-19)32(35)28(4,5)38-32/h10,12,14,19-20,22-23,25-26,35H,9,11,13,15-17H2,1-8H3 |
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InChI Key | VAHZUXRWDAYHCB-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
- 24-hydroxysteroid
- Hydroxy bile acid, alcohol, or derivatives
- Monohydroxy bile acid, alcohol, or derivatives
- Bile acid, alcohol, or derivatives
- Steroid ester
- 3-oxo-delta-1-steroid
- 3-oxosteroid
- Oxosteroid
- Delta-1-steroid
- Steroid
- Cyclohexenone
- Tetrahydrofuran
- Cyclic ketone
- Carboxylic acid ester
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Dialkyl ether
- Oxirane
- Ether
- Oxacycle
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic 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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