| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-03 12:52:49 UTC |
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| Updated at | 2022-09-03 12:52:49 UTC |
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| NP-MRD ID | NP0175417 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2,7-dioxo-3ah,4h,5h,6h,8bh-indeno[1,2-b]furan-4-yl acetate |
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| Description | 7-Oxoorobanchyl acetate belongs to the class of organic compounds known as strigolactones. These are terpene lactones structurally characterized by the presence of an indeno[1,2-b]furan and a 2,5-dihydrofuran-2-one linked together to form a 3-methyl-5-{8-methyl-2-oxo-indeno[1,2-b]furan-3-ylidene]methoxy}-2,5-dihydrofuran-2-one skeleton. (3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2,7-dioxo-3ah,4h,5h,6h,8bh-indeno[1,2-b]furan-4-yl acetate is found in Linum usitatissimum. (3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2,7-dioxo-3ah,4h,5h,6h,8bh-indeno[1,2-b]furan-4-yl acetate was first documented in 2009 (PMID: 19502732). Based on a literature review a small amount of articles have been published on 7-Oxoorobanchyl acetate (PMID: 30280444) (PMID: 23204500). |
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| Structure | CC(=O)O[C@H]1[C@H]2[C@H](OC(=O)\C2=C\O[C@@H]2OC(=O)C(C)=C2)C2=C1CCC(=O)C2(C)C InChI=1S/C21H22O8/c1-9-7-14(28-19(9)24)26-8-12-15-17(27-10(2)22)11-5-6-13(23)21(3,4)16(11)18(15)29-20(12)25/h7-8,14-15,17-18H,5-6H2,1-4H3/b12-8+/t14-,15+,17-,18+/m1/s1 |
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| Synonyms | | Value | Source |
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| 7-Oxoorobanchyl acetic acid | Generator | | Acetate-(3as,4S,8BS,e)-8,8-dimethyl-3-(((R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy)methylene)-2,7-dioxo-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno(1,2-b)furan-4-yl acetate | MeSH |
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| Chemical Formula | C21H22O8 |
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| Average Mass | 402.3990 Da |
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| Monoisotopic Mass | 402.13147 Da |
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| IUPAC Name | (3E,3aS,4S,8bS)-8,8-dimethyl-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylidene)-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-4-yl acetate |
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| Traditional Name | (3E,3aS,4S,8bS)-8,8-dimethyl-3-({[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxy}methylidene)-2,7-dioxo-3aH,4H,5H,6H,8bH-indeno[1,2-b]furan-4-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=O)O[C@H]1[C@H]2[C@H](OC(=O)\C2=C\O[C@@H]2OC(=O)C(C)=C2)C2=C1CCC(=O)C2(C)C |
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| InChI Identifier | InChI=1S/C21H22O8/c1-9-7-14(28-19(9)24)26-8-12-15-17(27-10(2)22)11-5-6-13(23)21(3,4)16(11)18(15)29-20(12)25/h7-8,14-15,17-18H,5-6H2,1-4H3/b12-8+/t14-,15+,17-,18+/m1/s1 |
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| InChI Key | GHBVBPVXEMMTGY-RMXVWQQMSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | 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 strigolactones. These are terpene lactones structurally characterized by the presence of an indeno[1,2-b]furan and a 2,5-dihydrofuran-2-one linked together to form a 3-methyl-5-{8-methyl-2-oxo-indeno[1,2-b]furan-3-ylidene]methoxy}-2,5-dihydrofuran-2-one skeleton. |
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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 | Strigolactones |
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| Alternative Parents | |
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| Substituents | - Strigolactone
- Tricarboxylic acid or derivatives
- Cyclohexenone
- 2-furanone
- Gamma butyrolactone
- Dihydrofuran
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Vinylogous ester
- Lactone
- Ketone
- Carboxylic acid ester
- Cyclic ketone
- Oxacycle
- Acetal
- Carboxylic acid derivative
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- 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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