Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 00:52:23 UTC |
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Updated at | 2021-06-30 00:19:10 UTC |
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NP-MRD ID | NP0043470 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | turrapubin A |
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Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
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Description | TURRAPUBIN A 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. turrapubin A is found in Turraea pubescens. It was first documented in 2021 (PMID: 34125202). Based on a literature review very few articles have been published on TURRAPUBIN A (PMID: 34122252) (PMID: 34100190) (PMID: 34098671) (PMID: 34098168). |
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Structure | [H]C([H])=C1[C@]([H])([C@@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2(C([H])([H])[H])[C@]([H])(C3=C([H])OC([H])=C3[H])C([H])([H])[C@@]3([H])O[C@@]123)[C@@]1(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])C([H])([H])C(=O)OC([H])([H])[H] InChI=1S/C33H42O11/c1-16-27(31(7)22(13-26(38)39-9)30(5,6)23(37)14-24(31)41-17(2)34)28(42-18(3)35)29(43-19(4)36)32(8)21(20-10-11-40-15-20)12-25-33(16,32)44-25/h10-11,15,21-22,24-25,27-29H,1,12-14H2,2-9H3/t21-,22-,24+,25+,27+,28+,29-,31+,32+,33+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C33H42O11 |
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Average Mass | 614.6880 Da |
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Monoisotopic Mass | 614.27271 Da |
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IUPAC Name | methyl 2-[(1R,2S,3R)-2-[(3R,3aR,4R,5R,6R,7aS,7bR)-4,5-bis(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-octahydroindeno[3,3a-b]oxiren-6-yl]-3-(acetyloxy)-2,6,6-trimethyl-5-oxocyclohexyl]acetate |
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Traditional Name | methyl [(1R,2S,3R)-2-[(3R,3aR,4R,5R,6R,7aS,7bR)-4,5-bis(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[3,3a-b]oxiren-6-yl]-3-(acetyloxy)-2,6,6-trimethyl-5-oxocyclohexyl]acetate |
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CAS Registry Number | Not Available |
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SMILES | [H]C([H])=C1[C@]([H])([C@@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2(C([H])([H])[H])[C@]([H])(C3=C([H])OC([H])=C3[H])C([H])([H])[C@@]3([H])O[C@@]123)[C@@]1(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])C([H])([H])C(=O)OC([H])([H])[H] |
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InChI Identifier | InChI=1S/C33H42O11/c1-16-27(31(7)22(13-26(38)39-9)30(5,6)23(37)14-24(31)41-17(2)34)28(42-18(3)35)29(43-19(4)36)32(8)21(20-10-11-40-15-20)12-25-33(16,32)44-25/h10-11,15,21-22,24-25,27-29H,1,12-14H2,2-9H3/t21-,22-,24+,25+,27+,28+,29-,31+,32+,33+/m0/s1 |
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InChI Key | VXKJLBGAQIDBPO-YILSLSMRSA-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, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, 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 | Species Name | Source | Reference |
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Turraea pubescens | JEOL database | - Yuan, C. -M., et al, J. Nat. Prod. 76, 1166 (2013)
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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
- Tetracarboxylic acid or derivatives
- Oxane
- Furan
- Heteroaromatic compound
- Methyl ester
- Carboxylic acid ester
- Ketone
- Cyclic ketone
- Carboxylic acid derivative
- Dialkyl ether
- Oxirane
- Ether
- Oxacycle
- Organoheterocyclic compound
- 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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