Record Information |
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Version | 2.0 |
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Created at | 2022-09-02 00:44:27 UTC |
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Updated at | 2022-09-02 00:44:27 UTC |
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NP-MRD ID | NP0145521 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,2r,4r,5r,6s,8r,10s,11s,12r,14r,15r,16r,19s,21r)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-4-yl acetate |
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Description | (1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-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. (1s,2r,4r,5r,6s,8r,10s,11s,12r,14r,15r,16r,19s,21r)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-4-yl acetate is found in Melia azedarach. Based on a literature review very few articles have been published on (1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-4-yl acetate. |
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Structure | CC(C)C(=O)[C@@H]1OC[C@]23[C@@H](O)C[C@@H](OC(C)=O)[C@@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@@H]3C(=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](C[C@H]3O[C@@]123)C1=COC=C1 InChI=1S/C34H44O11/c1-15(2)25(39)28-30(5)20-11-21(37)32(7)27(33(20,14-42-28)22(38)12-23(30)43-16(3)35)26(40)29(44-17(4)36)31(6)19(18-8-9-41-13-18)10-24-34(31,32)45-24/h8-9,13,15,19-24,27-29,37-38H,10-12,14H2,1-7H3/t19-,20-,21+,22-,23+,24+,27-,28-,29-,30+,31+,32+,33+,34+/m0/s1 |
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Synonyms | Value | Source |
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(1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19S,21R)-21-(Acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0,.0,.0,.0,]henicosan-4-yl acetic acid | Generator |
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Chemical Formula | C34H44O11 |
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Average Mass | 628.7150 Da |
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Monoisotopic Mass | 628.28836 Da |
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IUPAC Name | (1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-4-yl acetate |
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Traditional Name | (1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-4-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C(=O)[C@@H]1OC[C@]23[C@@H](O)C[C@@H](OC(C)=O)[C@@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@@H]3C(=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](C[C@H]3O[C@@]123)C1=COC=C1 |
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InChI Identifier | InChI=1S/C34H44O11/c1-15(2)25(39)28-30(5)20-11-21(37)32(7)27(33(20,14-42-28)22(38)12-23(30)43-16(3)35)26(40)29(44-17(4)36)31(6)19(18-8-9-41-13-18)10-24-34(31,32)45-24/h8-9,13,15,19-24,27-29,37-38H,10-12,14H2,1-7H3/t19-,20-,21+,22-,23+,24+,27-,28-,29-,30+,31+,32+,33+,34+/m0/s1 |
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InChI Key | XZVSQEQUTVXEMX-PDMXXUAHSA-N |
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Experimental Spectra |
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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 |
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Chemical Shift Submissions |
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| Not Available |
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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
- 17-furanylsteroid skeleton
- Steroid ester
- Naphthopyran
- Naphthalene
- Alpha-acyloxy ketone
- Dicarboxylic acid or derivatives
- Pyran
- Oxane
- Cyclic alcohol
- Furan
- Heteroaromatic compound
- Carboxylic acid ester
- Secondary alcohol
- Ketone
- Ether
- Oxirane
- Oxacycle
- Dialkyl ether
- Organoheterocyclic compound
- Carboxylic acid derivative
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- 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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