Record Information |
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Version | 2.0 |
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Created at | 2022-04-28 22:25:56 UTC |
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Updated at | 2022-04-28 22:25:56 UTC |
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NP-MRD ID | NP0077267 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Toosendanin |
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Description | (1S,2R,4R,5R,6R,8R,10R,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-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. Toosendanin is found in Melia azedarach , Melia toosendan Sieb.et Zuce. , Toona sinensis and Turnera ulmifolia . Based on a literature review very few articles have been published on (1S,2R,4R,5R,6R,8R,10R,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-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(=O)O[C@@H]1C[C@H](O)[C@@]23CO[C@@H](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/C30H38O11/c1-13(31)39-20-10-19(34)29-12-38-25(36)26(20,3)17(29)9-18(33)28(5)23(29)22(35)24(40-14(2)32)27(4)16(15-6-7-37-11-15)8-21-30(27,28)41-21/h6-7,11,16-21,23-25,33-34,36H,8-10,12H2,1-5H3/t16-,17-,18+,19-,20+,21+,23-,24-,25+,26+,27+,28+,29+,30-/m0/s1 |
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Synonyms | Value | Source |
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(1S,2R,4R,5R,6R,8R,10R,11S,12R,14R,15R,16R,19S,21R)-21-(Acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0,.0,.0,.0,]henicosan-4-yl acetic acid | Generator |
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Chemical Formula | C30H38O11 |
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Average Mass | 574.6230 Da |
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Monoisotopic Mass | 574.24141 Da |
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IUPAC Name | (1S,2R,4R,5R,6R,8R,10R,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-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,10R,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-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(=O)O[C@@H]1C[C@H](O)[C@@]23CO[C@@H](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/C30H38O11/c1-13(31)39-20-10-19(34)29-12-38-25(36)26(20,3)17(29)9-18(33)28(5)23(29)22(35)24(40-14(2)32)27(4)16(15-6-7-37-11-15)8-21-30(27,28)41-21/h6-7,11,16-21,23-25,33-34,36H,8-10,12H2,1-5H3/t16-,17-,18+,19-,20+,21+,23-,24-,25+,26+,27+,28+,29+,30-/m0/s1 |
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InChI Key | NAHTXVIXCMUDLF-DUJPAFNYSA-N |
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Experimental Spectra |
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| Not Available |
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Predicted Spectra |
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| Not Available |
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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
- Pyran
- Oxane
- Dicarboxylic acid or derivatives
- Heteroaromatic compound
- Furan
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Hemiacetal
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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