| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-07 16:04:49 UTC |
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| Updated at | 2022-09-07 16:04:49 UTC |
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| NP-MRD ID | NP0252534 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 4-(acetyloxy)-20-(furan-3-yl)-2,3,17-trihydroxy-5,14,19-trimethyl-8,22-dioxo-9,13,15,21,25-pentaoxaoctacyclo[12.10.1.1⁵,¹².0¹,¹⁶.0³,¹².0⁶,¹¹.0¹¹,¹⁶.0¹⁹,²⁴]hexacosan-18-yl acetate |
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| Description | 18-(Acetyloxy)-20-(furan-3-yl)-2,3,17-trihydroxy-5,14,19-trimethyl-8,22-dioxo-9,13,15,21,25-pentaoxaoctacyclo[12.10.1.1⁵,¹².0¹,¹⁶.0³,¹².0⁶,¹¹.0¹¹,¹⁶.0¹⁹,²⁴]Hexacosan-4-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. 4-(acetyloxy)-20-(furan-3-yl)-2,3,17-trihydroxy-5,14,19-trimethyl-8,22-dioxo-9,13,15,21,25-pentaoxaoctacyclo[12.10.1.1⁵,¹².0¹,¹⁶.0³,¹².0⁶,¹¹.0¹¹,¹⁶.0¹⁹,²⁴]hexacosan-18-yl acetate is found in Chukrasia tabularis. 18-(Acetyloxy)-20-(furan-3-yl)-2,3,17-trihydroxy-5,14,19-trimethyl-8,22-dioxo-9,13,15,21,25-pentaoxaoctacyclo[12.10.1.1⁵,¹².0¹,¹⁶.0³,¹².0⁶,¹¹.0¹¹,¹⁶.0¹⁹,²⁴]Hexacosan-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| Structure | CC(=O)OC1C2(C)CC34OC5(C)OC6(C(O)C13O)C1CC(=O)OC(C3=COC=C3)C1(C)C(OC(C)=O)C(O)C6(O5)C41COC(=O)CC21 InChI=1S/C32H36O15/c1-13(33)42-22-20(37)32-28-12-41-18(35)8-16(28)25(3)11-29(28)30(39,24(25)43-14(2)34)23(38)31(32,46-27(5,45-29)47-32)17-9-19(36)44-21(26(17,22)4)15-6-7-40-10-15/h6-7,10,16-17,20-24,37-39H,8-9,11-12H2,1-5H3 |
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| Synonyms | | Value | Source |
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| 18-(Acetyloxy)-20-(furan-3-yl)-2,3,17-trihydroxy-5,14,19-trimethyl-8,22-dioxo-9,13,15,21,25-pentaoxaoctacyclo[12.10.1.1,.0,.0,.0,.0,.0,]hexacosan-4-yl acetic acid | Generator | | 18-(Acetyloxy)-20-(furan-3-yl)-2,3,17-trihydroxy-5,14,19-trimethyl-8,22-dioxo-9,13,15,21,25-pentaoxaoctacyclo[12.10.1.1⁵,¹².0¹,¹⁶.0³,¹².0⁶,¹¹.0¹¹,¹⁶.0¹⁹,²⁴]hexacosan-4-yl acetic acid | Generator |
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| Chemical Formula | C32H36O15 |
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| Average Mass | 660.6250 Da |
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| Monoisotopic Mass | 660.20542 Da |
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| IUPAC Name | 4-(acetyloxy)-20-(furan-3-yl)-2,3,17-trihydroxy-5,14,19-trimethyl-8,22-dioxo-9,13,15,21,25-pentaoxaoctacyclo[12.10.1.1⁵,¹².0¹,¹⁶.0³,¹².0⁶,¹¹.0¹¹,¹⁶.0¹⁹,²⁴]hexacosan-18-yl acetate |
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| Traditional Name | 4-(acetyloxy)-20-(furan-3-yl)-2,3,17-trihydroxy-5,14,19-trimethyl-8,22-dioxo-9,13,15,21,25-pentaoxaoctacyclo[12.10.1.1⁵,¹².0¹,¹⁶.0³,¹².0⁶,¹¹.0¹¹,¹⁶.0¹⁹,²⁴]hexacosan-18-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=O)OC1C2(C)CC34OC5(C)OC6(C(O)C13O)C1CC(=O)OC(C3=COC=C3)C1(C)C(OC(C)=O)C(O)C6(O5)C41COC(=O)CC21 |
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| InChI Identifier | InChI=1S/C32H36O15/c1-13(33)42-22-20(37)32-28-12-41-18(35)8-16(28)25(3)11-29(28)30(39,24(25)43-14(2)34)23(38)31(32,46-27(5,45-29)47-32)17-9-19(36)44-21(26(17,22)4)15-6-7-40-10-15/h6-7,10,16-17,20-24,37-39H,8-9,11-12H2,1-5H3 |
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| InChI Key | UYWNZTJHBWJEGR-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 | - Mexicanolide
- Limonoid skeleton
- Prostaglandin skeleton
- Eicosanoid
- Naphthopyran
- Tetracarboxylic acid or derivatives
- Naphthalene
- Ortho ester
- 1,3-dioxepane
- Carboxylic acid orthoester
- Delta valerolactone
- Delta_valerolactone
- Dioxepane
- Pyran
- Meta-dioxane
- Oxane
- Fatty acyl
- Meta-dioxolane
- Cyclic alcohol
- Heteroaromatic compound
- Furan
- Tertiary alcohol
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Orthocarboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Polyol
- Alcohol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- 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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