| Record Information |
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| Version | 2.0 |
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| Created at | 2021-06-19 21:39:49 UTC |
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| Updated at | 2021-06-29 23:58:08 UTC |
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| NP-MRD ID | NP0030266 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 1,3,7-tri-O-acetyl-14,15-deoxyhavanensin |
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| Provided By | JEOL Database |
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| Description | (13Alpha,17alpha)-1alpha,3alpha,7alpha-Triacetoxy-4,4,8-trimethyl-21,23-epoxy-24-nor-5alpha-chola-14,20,22-triene 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. 1,3,7-tri-O-acetyl-14,15-deoxyhavanensin is found in Trichilia havanensis. 1,3,7-tri-O-acetyl-14,15-deoxyhavanensin was first documented in 2003 (Rodriguez, B., et al.). Based on a literature review very few articles have been published on (13alpha,17alpha)-1alpha,3alpha,7alpha-Triacetoxy-4,4,8-trimethyl-21,23-epoxy-24-nor-5alpha-chola-14,20,22-triene. |
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| Structure | [H]C1=C([H])C(=C([H])O1)[C@]1([H])C([H])([H])C([H])=C2[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])[C@@]2(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@@]2([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]12C([H])([H])[H] InChI=1S/C32H44O7/c1-18(33)37-26-16-28(39-20(3)35)32(8)24-11-13-30(6)22(21-12-14-36-17-21)9-10-23(30)31(24,7)27(38-19(2)34)15-25(32)29(26,4)5/h10,12,14,17,22,24-28H,9,11,13,15-16H2,1-8H3/t22-,24-,25-,26+,27+,28-,30-,31-,32+/m0/s1 |
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| Synonyms | | Value | Source |
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| (13a,17a)-1a,3a,7a-Triacetoxy-4,4,8-trimethyl-21,23-epoxy-24-nor-5a-chola-14,20,22-triene | Generator | | (13Α,17α)-1α,3α,7α-triacetoxy-4,4,8-trimethyl-21,23-epoxy-24-nor-5α-chola-14,20,22-triene | Generator |
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| Chemical Formula | C32H44O7 |
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| Average Mass | 540.6970 Da |
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| Monoisotopic Mass | 540.30870 Da |
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| IUPAC Name | (1R,2S,3S,5R,7S,9R,10R,14R,15S)-3,5-bis(acetyloxy)-14-(furan-3-yl)-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-9-yl acetate |
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| Traditional Name | (1R,2S,3S,5R,7S,9R,10R,14R,15S)-3,5-bis(acetyloxy)-14-(furan-3-yl)-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-9-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | [H]C1=C([H])C(=C([H])O1)[C@]1([H])C([H])([H])C([H])=C2[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])[C@@]2(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@@]2([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]12C([H])([H])[H] |
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| InChI Identifier | InChI=1S/C32H44O7/c1-18(33)37-26-16-28(39-20(3)35)32(8)24-11-13-30(6)22(21-12-14-36-17-21)9-10-23(30)31(24,7)27(38-19(2)34)15-25(32)29(26,4)5/h10,12,14,17,22,24-28H,9,11,13,15-16H2,1-8H3/t22-,24-,25-,26+,27+,28-,30-,31-,32+/m0/s1 |
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| InChI Key | JFZWEEGAFRZPEY-TXQBVQDDSA-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 havanensis | JEOL database | - Rodriguez, B., et al, Magn. Reson. Chem. 41,206 (2003)
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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
- Steroid
- Tricarboxylic acid or derivatives
- Furan
- Heteroaromatic compound
- Carboxylic acid ester
- Oxacycle
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen 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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