Record Information |
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Version | 2.0 |
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Created at | 2022-04-27 22:50:29 UTC |
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Updated at | 2022-04-27 22:50:29 UTC |
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NP-MRD ID | NP0051497 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5,7,4'-Trihydroxy-6-prenylisoflavone |
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Description | Wighteone, also known as erythrinin b, belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, wighteone is considered to be a flavonoid lipid molecule. 5,7,4'-Trihydroxy-6-prenylisoflavone is found in Anthyllis hermanniae, Argyrocytisus battandieri, Bolusanthus speciosus, Cudrania cochinchinensis var. gerontogea , Erythrina fusca, Erythrina latissima, Erythrina lysistemon , Erythrina mildbraedii, Erythrina orientalis, Erythrina poeppigiana , Erythrina suberosa, Erythrina suberosa var. glabrescences , Erythrina indica , Ficus glumosa, Ficus mucuso, Flemingia macrophylla, Flemingia philippinensis, Genista ephedroides, Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza uralensis , Laburnum anagyroides , Lupinus albus , Lupinus angustifolius , Lupinus luteus, Lupinus polyphyllus, Maclura cochinchinensis, Maclura pomifera, Maclura tricuspidata, Neonotonia wightii, Sophora flavescens and Sophora tomentosa. It was first documented in 2002 (PMID: 12150799). Wighteone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 21619045) (PMID: 16369693) (PMID: 22837700) (PMID: 23850732). |
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Structure | CC(C)=CCC1=C(O)C=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C=C1 InChI=1S/C20H18O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3 |
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Synonyms | Value | Source |
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5,7,4'-Trihydroxy-6-prenylisoflavone | ChEBI | 5,7-Dihydroxy-3-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one | ChEBI | Erythrinin b | ChEBI |
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Chemical Formula | C20H18O5 |
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Average Mass | 338.3590 Da |
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Monoisotopic Mass | 338.11542 Da |
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IUPAC Name | 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one |
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Traditional Name | wighteone |
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CAS Registry Number | Not Available |
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SMILES | CC(C)=CCC1=C(O)C=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C20H18O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3 |
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InChI Key | KIMDVVKVNNSHGZ-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. |
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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 | Isoflavans |
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Direct Parent | 6-prenylated isoflavanones |
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Alternative Parents | |
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Substituents | - 6-prenylated isoflavanone
- Isoflavone
- Hydroxyisoflavonoid
- Chromone
- 1-benzopyran
- Benzopyran
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Pyranone
- Phenol
- Benzenoid
- Pyran
- Monocyclic benzene moiety
- Heteroaromatic compound
- Vinylogous acid
- Oxacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | - Bankeu JJ, Khayala R, Lenta BN, Noungoue DT, Ngouela SA, Mustafa SA, Asaad K, Choudhary MI, Prigge ST, Hasanov R, Nkengfack AE, Tsamo E, Ali MS: Isoflavone dimers and other bioactive constituents from the figs of Ficus mucuso. J Nat Prod. 2011 Jun 24;74(6):1370-8. doi: 10.1021/np100896w. Epub 2011 May 27. [PubMed:21619045 ]
- el-Masry S, Amer ME, Abdel-Kader MS, Zaatout HH: Prenylated flavonoids of Erythrina lysistemon grown in Egypt. Phytochemistry. 2002 Aug;60(8):783-7. doi: 10.1016/s0031-9422(02)00202-9. [PubMed:12150799 ]
- Yin H, Zhao Y, Zhang Y, Zhang H, Xu L, Zou Z, Yang W, Cheng J, Zhou Y: Genome-wide analysis of the expression profile of Saccharomyces cerevisiae in response to treatment with the plant isoflavone, wighteone, as a potential antifungal agent. Biotechnol Lett. 2006 Jan;28(2):99-105. doi: 10.1007/s10529-005-4954-0. [PubMed:16369693 ]
- Wei S, Wu W, Ji Z: New antifungal pyranoisoflavone from Ficus tikoua Bur. Int J Mol Sci. 2012;13(6):7375-82. doi: 10.3390/ijms13067375. Epub 2012 Jun 14. [PubMed:22837700 ]
- Kumar S, Pathania AS, Saxena AK, Vishwakarma RA, Ali A, Bhushan S: The anticancer potential of flavonoids isolated from the stem bark of Erythrina suberosa through induction of apoptosis and inhibition of STAT signaling pathway in human leukemia HL-60 cells. Chem Biol Interact. 2013 Sep 25;205(2):128-37. doi: 10.1016/j.cbi.2013.06.020. Epub 2013 Jul 9. [PubMed:23850732 ]
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