| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-09 19:00:52 UTC |
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| Updated at | 2022-09-09 19:00:52 UTC |
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| NP-MRD ID | NP0289024 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1s,3br,4r,5ar,7r,9as,9br,11as)-1-[(2r,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-ethoxyoxolan-3-yl]-4-hydroxy-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate |
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| Description | (1R,2S,5R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-ethoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-11-en-5-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. Based on a literature review very few articles have been published on (1R,2S,5R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-ethoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-11-en-5-yl acetate. |
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| Structure | CCO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H](OC(C)=O)C(C)(C)[C@@H]3C[C@@H](O)[C@@]21C)[C@H](O)C(C)(C)O InChI=1S/C34H56O7/c1-10-39-29-20(17-22(41-29)28(37)31(5,6)38)21-11-12-23-32(21,7)15-13-24-33(8)16-14-27(40-19(2)35)30(3,4)25(33)18-26(36)34(23,24)9/h12,20-22,24-29,36-38H,10-11,13-18H2,1-9H3/t20-,21-,22+,24+,25-,26+,27+,28-,29+,32-,33+,34-/m0/s1 |
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| Synonyms | | Value | Source |
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| (1R,2S,5R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1S)-1,2-Dihydroxy-2-methylpropyl]-2-ethoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0,.0,]heptadec-11-en-5-yl acetic acid | Generator |
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| Chemical Formula | C34H56O7 |
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| Average Mass | 576.8150 Da |
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| Monoisotopic Mass | 576.40260 Da |
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| IUPAC Name | (1R,2S,5R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-ethoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl acetate |
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| Traditional Name | (1R,2S,5R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-ethoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CCO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H](OC(C)=O)C(C)(C)[C@@H]3C[C@@H](O)[C@@]21C)[C@H](O)C(C)(C)O |
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| InChI Identifier | InChI=1S/C34H56O7/c1-10-39-29-20(17-22(41-29)28(37)31(5,6)38)21-11-12-23-32(21,7)15-13-24-33(8)16-14-27(40-19(2)35)30(3,4)25(33)18-26(36)34(23,24)9/h12,20-22,24-29,36-38H,10-11,13-18H2,1-9H3/t20-,21-,22+,24+,25-,26+,27+,28-,29+,32-,33+,34-/m0/s1 |
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| InChI Key | ASHVARJLPTVMFR-SPAWGUAVSA-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 | Not Available |
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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
- Dihydroxy bile acid, alcohol, or derivatives
- 24-hydroxysteroid
- Hydroxy bile acid, alcohol, or derivatives
- Bile acid, alcohol, or derivatives
- Steroid ester
- 7-hydroxysteroid
- Hydroxysteroid
- Steroid
- Cyclic alcohol
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- 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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