Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 01:04:16 UTC |
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Updated at | 2021-06-30 00:19:37 UTC |
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NP-MRD ID | NP0043748 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | trichinenlide D |
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Provided By | JEOL Database |
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Description | Quivisianolide B 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. trichinenlide D is found in Trichilia sinensis. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on Quivisianolide B (PMID: 27466641) (PMID: 15924915) (PMID: 27253005) (PMID: 26389468). |
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Structure | [H]O[C@]12C(=O)[C@@](C3=C([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[C@@]4([H])[C@]33O[C@]13[H])C1=C([H])OC([H])=C1[H])(C([H])([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H] InChI=1S/C32H38O10/c1-8-16(2)24(35)41-26-28(3,4)19(13-21(33)38-7)30(6)18-9-11-29(5)20(32(18)27(42-32)31(26,37)25(30)36)14-22(34)40-23(29)17-10-12-39-15-17/h8-10,12,15,19-20,23,26-27,37H,11,13-14H2,1-7H3/b16-8+/t19-,20+,23-,26-,27+,29+,30+,31-,32+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C32H38O10 |
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Average Mass | 582.6460 Da |
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Monoisotopic Mass | 582.24650 Da |
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IUPAC Name | (1S,2R,4S,5R,9R,10R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadec-12-en-17-yl (2E)-2-methylbut-2-enoate |
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Traditional Name | (1S,2R,4S,5R,9R,10R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadec-12-en-17-yl (2E)-2-methylbut-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | [H]O[C@]12C(=O)[C@@](C3=C([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[C@@]4([H])[C@]33O[C@]13[H])C1=C([H])OC([H])=C1[H])(C([H])([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H] |
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InChI Identifier | InChI=1S/C32H38O10/c1-8-16(2)24(35)41-26-28(3,4)19(13-21(33)38-7)30(6)18-9-11-29(5)20(32(18)27(42-32)31(26,37)25(30)36)14-22(34)40-23(29)17-10-12-39-15-17/h8-10,12,15,19-20,23,26-27,37H,11,13-14H2,1-7H3/b16-8+/t19-,20+,23-,26-,27+,29+,30+,31-,32+/m0/s1 |
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InChI Key | KZECPRHFICCVSV-SJORWXJISA-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, 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, 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, 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, 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, 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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Trichilia sinensis | JEOL database | - Xu, J. -B., et al, J. Nat. Prod. 76, 1872 (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
- Mexicanolide
- Naphthopyran
- Naphthalene
- Tricarboxylic acid or derivatives
- Delta valerolactone
- Fatty acid ester
- Delta_valerolactone
- Oxepane
- Fatty acyl
- Oxane
- Pyran
- Cyclic alcohol
- Furan
- Heteroaromatic compound
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Methyl ester
- Tertiary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Ether
- Oxirane
- Dialkyl ether
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen 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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