| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-09 03:16:26 UTC |
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| Updated at | 2022-09-09 03:16:27 UTC |
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| NP-MRD ID | NP0278301 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 2-(4-hydroxy-3-methoxyphenyl)-6-(2-hydroxy-4,6-dimethoxybenzoyl)-7-(4-methoxyphenyl)furo[3,2-g]chromen-4-one |
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| Description | Cissampeloflavone belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 2-(4-hydroxy-3-methoxyphenyl)-6-(2-hydroxy-4,6-dimethoxybenzoyl)-7-(4-methoxyphenyl)furo[3,2-g]chromen-4-one is found in Cissampelos pareira. 2-(4-hydroxy-3-methoxyphenyl)-6-(2-hydroxy-4,6-dimethoxybenzoyl)-7-(4-methoxyphenyl)furo[3,2-g]chromen-4-one was first documented in 2003 (PMID: 12943789). Based on a literature review a small amount of articles have been published on Cissampeloflavone (PMID: 28029072) (PMID: 19384282). |
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| Structure | COC1=CC=C(C=C1)C1=C(C=C2C(=O)C3=C(OC(=C3)C3=CC=C(O)C(OC)=C3)C=C2O1)C(=O)C1=C(O)C=C(OC)C=C1OC InChI=1S/C34H26O10/c1-39-19-8-5-17(6-9-19)34-23(33(38)31-25(36)12-20(40-2)13-30(31)42-4)14-21-28(44-34)16-27-22(32(21)37)15-26(43-27)18-7-10-24(35)29(11-18)41-3/h5-16,35-36H,1-4H3 |
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| Synonyms | Not Available |
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| Chemical Formula | C34H26O10 |
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| Average Mass | 594.5720 Da |
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| Monoisotopic Mass | 594.15260 Da |
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| IUPAC Name | 2-(4-hydroxy-3-methoxyphenyl)-6-(2-hydroxy-4,6-dimethoxybenzoyl)-7-(4-methoxyphenyl)-4H-furo[3,2-g]chromen-4-one |
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| Traditional Name | 2-(4-hydroxy-3-methoxyphenyl)-6-(2-hydroxy-4,6-dimethoxybenzoyl)-7-(4-methoxyphenyl)furo[3,2-g]chromen-4-one |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=CC=C(C=C1)C1=C(C=C2C(=O)C3=C(OC(=C3)C3=CC=C(O)C(OC)=C3)C=C2O1)C(=O)C1=C(O)C=C(OC)C=C1OC |
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| InChI Identifier | InChI=1S/C34H26O10/c1-39-19-8-5-17(6-9-19)34-23(33(38)31-25(36)12-20(40-2)13-30(31)42-4)14-21-28(44-34)16-27-22(32(21)37)15-26(43-27)18-7-10-24(35)29(11-18)41-3/h5-16,35-36H,1-4H3 |
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| InChI Key | CRGCVJNINHYLJP-UHFFFAOYSA-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 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | 2-arylbenzofuran flavonoids |
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| Sub Class | Not Available |
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| Direct Parent | 2-arylbenzofuran flavonoids |
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| Alternative Parents | |
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| Substituents | - 2-arylbenzofuran flavonoid
- Furanoflavonoid or dihydroflavonoid
- 4p-methoxyflavonoid-skeleton
- 2-phenylbenzofuran
- Phenylbenzofuran
- Aryl-phenylketone
- 1-benzopyran
- Benzopyran
- Methoxyphenol
- M-dimethoxybenzene
- Dimethoxybenzene
- Benzofuran
- Methoxybenzene
- Phenol ether
- Aryl ketone
- Anisole
- Benzoyl
- Phenoxy compound
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Furan
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Hydrocarbon derivative
- 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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| General References | - Alves MF, Scotti MT, Scotti L, Mendonca FJB, Filho JMB, de Melo SAL, Dos Santos SG, de F F M Diniz M: Secondary Metabolites from Cissampelos, A Possible Source for New Leads with Anti-Inflammatory Activity. Curr Med Chem. 2017;24(16):1629-1644. doi: 10.2174/0929867323666161227123411. [PubMed:28029072 ]
- Ogungbe IV, Setzer WN: Comparative molecular docking of antitrypanosomal natural products into multiple Trypanosoma brucei drug targets. Molecules. 2009 Apr 14;14(4):1513-36. doi: 10.3390/molecules14041513. [PubMed:19384282 ]
- Ramirez I, Carabot A, Melendez P, Carmona J, Jimenez M, Patel AV, Crabb TA, Blunden G, Cary PD, Croft SL, Costa M: Cissampeloflavone, a chalcone-flavone dimer from Cissampelos pareira. Phytochemistry. 2003 Sep;64(2):645-7. doi: 10.1016/s0031-9422(03)00241-3. [PubMed:12943789 ]
- LOTUS database [Link]
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