| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-05 20:21:11 UTC |
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| Updated at | 2022-09-05 20:21:11 UTC |
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| NP-MRD ID | NP0219382 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (3ar,4r,6s,6ar,9ar,9br)-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-4-hydroxy-2-methylbut-2-enoate |
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| Description | (3AR,4R,6S,6aR,9aR,9bR)-9-methyl-3-methylidene-2-oxo-3,3a,4,5,6a,7,9a,9b-octahydro-2H-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (3ar,4r,6s,6ar,9ar,9br)-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3ah-spiro[azuleno[4,5-b]furan-6,2'-oxiran]-4-yl (2e)-4-hydroxy-2-methylbut-2-enoate is found in Picradeniopsis pringlei. Based on a literature review very few articles have been published on (3aR,4R,6S,6aR,9aR,9bR)-9-methyl-3-methylidene-2-oxo-3,3a,4,5,6a,7,9a,9b-octahydro-2H-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate. |
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| Structure | C\C(=C/CO)C(=O)O[C@@H]1C[C@@]2(CO2)[C@@H]2CC=C(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 InChI=1S/C20H24O6/c1-10-4-5-13-15(10)17-16(12(3)19(23)26-17)14(8-20(13)9-24-20)25-18(22)11(2)6-7-21/h4,6,13-17,21H,3,5,7-9H2,1-2H3/b11-6+/t13-,14-,15+,16-,17-,20-/m1/s1 |
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| Synonyms | | Value | Source |
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| (3AR,4R,6S,6ar,9ar,9BR)-9-methyl-3-methylidene-2-oxo-3,3a,4,5,6a,7,9a,9b-octahydro-2H-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2E)-4-hydroxy-2-methylbut-2-enoic acid | Generator |
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| Chemical Formula | C20H24O6 |
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| Average Mass | 360.4060 Da |
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| Monoisotopic Mass | 360.15729 Da |
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| IUPAC Name | (3aR,4R,6S,6aR,9aR,9bR)-9-methyl-3-methylidene-2-oxo-3,3a,4,5,6a,7,9a,9b-octahydro-2H-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate |
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| Traditional Name | (3aR,4R,6S,6aR,9aR,9bR)-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate |
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| CAS Registry Number | Not Available |
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| SMILES | C\C(=C/CO)C(=O)O[C@@H]1C[C@@]2(CO2)[C@@H]2CC=C(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12 |
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| InChI Identifier | InChI=1S/C20H24O6/c1-10-4-5-13-15(10)17-16(12(3)19(23)26-17)14(8-20(13)9-24-20)25-18(22)11(2)6-7-21/h4,6,13-17,21H,3,5,7-9H2,1-2H3/b11-6+/t13-,14-,15+,16-,17-,20-/m1/s1 |
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| InChI Key | BAEQZLZMQQHROD-IYBHTPDWSA-N |
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| Experimental Spectra |
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| Not Available | | 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 guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. |
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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 | Terpene lactones |
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| Direct Parent | Guaianolides and derivatives |
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| Alternative Parents | |
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| Substituents | - Guaianolide-skeleton
- Sesquiterpenoid
- Fatty acid ester
- Dicarboxylic acid or derivatives
- Gamma butyrolactone
- Fatty acyl
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Lactone
- Carboxylic acid ester
- Organoheterocyclic compound
- Oxacycle
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Primary alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic 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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