Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 00:52:58 UTC |
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Updated at | 2021-06-30 00:19:11 UTC |
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NP-MRD ID | NP0043484 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | aphanalide K |
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Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
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Description | (1S,2R,3S,8R,10R,11R,12S,15R,16S,17R,18R)-15-(furan-3-yl)-10,17,18-trihydroxy-2,7,7,11,16-pentamethyl-5,13-dioxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadecan-3-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. aphanalide K is found in Aphanamixis grandifolia. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on (1S,2R,3S,8R,10R,11R,12S,15R,16S,17R,18R)-15-(furan-3-yl)-10,17,18-trihydroxy-2,7,7,11,16-pentamethyl-5,13-dioxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadecan-3-yl acetate (PMID: 27466641) (PMID: 27253005) (PMID: 26389468) (PMID: 26389426). |
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Structure | [H]O[C@]1([H])C([H])([H])[C@]2([H])[C@@](C([H])([H])[H])([C@@]3([H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]4(C([H])([H])[H])[C@]([H])(C5=C([H])OC([H])=C5[H])C([H])([H])C(=O)[C@@]4([H])[C@]13C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C(=O)OC2(C([H])([H])[H])C([H])([H])[H] InChI=1S/C28H38O9/c1-13(29)36-19-11-20(32)37-25(2,3)17-10-18(31)28(6)22-16(30)9-15(14-7-8-35-12-14)26(22,4)24(34)21(33)23(28)27(17,19)5/h7-8,12,15,17-19,21-24,31,33-34H,9-11H2,1-6H3/t15-,17-,18+,19-,21+,22+,23+,24-,26-,27+,28-/m0/s1 |
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Synonyms | Value | Source |
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(1S,2R,3S,8R,10R,11R,12S,15R,16S,17R,18R)-15-(Furan-3-yl)-10,17,18-trihydroxy-2,7,7,11,16-pentamethyl-5,13-dioxo-6-oxatetracyclo[9.7.0.0,.0,]octadecan-3-yl acetic acid | Generator |
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Chemical Formula | C28H38O9 |
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Average Mass | 518.6030 Da |
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Monoisotopic Mass | 518.25158 Da |
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IUPAC Name | (1S,2R,3S,8R,10R,11R,12S,15R,16S,17R,18R)-15-(furan-3-yl)-10,17,18-trihydroxy-2,7,7,11,16-pentamethyl-5,13-dioxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadecan-3-yl acetate |
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Traditional Name | (1S,2R,3S,8R,10R,11R,12S,15R,16S,17R,18R)-15-(furan-3-yl)-10,17,18-trihydroxy-2,7,7,11,16-pentamethyl-5,13-dioxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadecan-3-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | [H]O[C@]1([H])C([H])([H])[C@]2([H])[C@@](C([H])([H])[H])([C@@]3([H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]4(C([H])([H])[H])[C@]([H])(C5=C([H])OC([H])=C5[H])C([H])([H])C(=O)[C@@]4([H])[C@]13C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C(=O)OC2(C([H])([H])[H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C28H38O9/c1-13(29)36-19-11-20(32)37-25(2,3)17-10-18(31)28(6)22-16(30)9-15(14-7-8-35-12-14)26(22,4)24(34)21(33)23(28)27(17,19)5/h7-8,12,15,17-19,21-24,31,33-34H,9-11H2,1-6H3/t15-,17-,18+,19-,21+,22+,23+,24-,26-,27+,28-/m0/s1 |
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InChI Key | NMUNZRHSVIUJQI-ORPHTWIOSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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
- Caprolactone
- Oxepane
- Dicarboxylic acid or derivatives
- Cyclic alcohol
- Heteroaromatic compound
- Furan
- Carboxylic acid ester
- Ketone
- Lactone
- Secondary alcohol
- Oxacycle
- Carboxylic acid derivative
- Organoheterocyclic compound
- Polyol
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organooxygen compound
- Carbonyl group
- 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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