| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-10 01:09:41 UTC |
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| Updated at | 2022-09-10 01:09:41 UTC |
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| NP-MRD ID | NP0293246 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (6r,21z)-10-hydroxy-16,17-dimethoxy-21-(methoxymethylidene)-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),3,8,10,14,16,18-heptaen-12-one |
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| Description | (6R,21Z)-10-hydroxy-16,17-dimethoxy-21-(methoxymethylidene)-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(13),3(11),4(8),9,14,16,18-heptaen-12-one belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. (6r,21z)-10-hydroxy-16,17-dimethoxy-21-(methoxymethylidene)-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),3,8,10,14,16,18-heptaen-12-one is found in Tephrosia villosa. Based on a literature review very few articles have been published on (6R,21Z)-10-hydroxy-16,17-dimethoxy-21-(methoxymethylidene)-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(13),3(11),4(8),9,14,16,18-heptaen-12-one. |
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| Structure | CO\C=C1/OC2=CC(OC)=C(OC)C=C2C2=C1OC1=C3C[C@@H](OC3=CC(O)=C1C2=O)C(C)=C InChI=1S/C25H22O8/c1-11(2)15-7-13-16(31-15)8-14(26)22-23(27)21-12-6-18(29-4)19(30-5)9-17(12)32-20(10-28-3)25(21)33-24(13)22/h6,8-10,15,26H,1,7H2,2-5H3/b20-10-/t15-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C25H22O8 |
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| Average Mass | 450.4430 Da |
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| Monoisotopic Mass | 450.13147 Da |
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| IUPAC Name | (6R,21Z)-10-hydroxy-16,17-dimethoxy-21-(methoxymethylidene)-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-1(13),3,8,10,14,16,18-heptaen-12-one |
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| Traditional Name | (6R,21Z)-10-hydroxy-16,17-dimethoxy-21-(methoxymethylidene)-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-1(13),3,8,10,14,16,18-heptaen-12-one |
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| CAS Registry Number | Not Available |
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| SMILES | CO\C=C1/OC2=CC(OC)=C(OC)C=C2C2=C1OC1=C3C[C@@H](OC3=CC(O)=C1C2=O)C(C)=C |
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| InChI Identifier | InChI=1S/C25H22O8/c1-11(2)15-7-13-16(31-15)8-14(26)22-23(27)21-12-6-18(29-4)19(30-5)9-17(12)32-20(10-28-3)25(21)33-24(13)22/h6,8-10,15,26H,1,7H2,2-5H3/b20-10-/t15-/m1/s1 |
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| InChI Key | GRAGCGUVWZEKFU-RKQRPNFGSA-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 rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Isoflavonoids |
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| Sub Class | Rotenoids |
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| Direct Parent | Rotenones |
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| Alternative Parents | |
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| Substituents | - Rotenone or derivatives
- Isoflavone
- Chromone
- Benzopyran
- 1-benzopyran
- Coumaran
- Anisole
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Oxacycle
- Ether
- Organoheterocyclic compound
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- 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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