| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 01:00:14 UTC |
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| Updated at | 2022-04-28 01:00:14 UTC |
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| NP-MRD ID | NP0054751 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Derricidin |
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| Description | Derricidin belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, derricidin is considered to be a flavonoid. Derricidin is found in Derris floribunda , Derris sericea, Lonchocarpus guatemalensis, Lonchocarpus neuroscapha, Lonchocarpus sericeus, Lonchocarpus xuul and Millettia erythrocalyx. Derricidin was first documented in 2015 (PMID: 25973483). Based on a literature review a small amount of articles have been published on Derricidin (PMID: 32530447) (PMID: 25775405). |
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| Structure | CC(C)=CCOC1=CC(O)=C(C=C1)C(=O)\C=C\C1=CC=CC=C1 InChI=1S/C20H20O3/c1-15(2)12-13-23-17-9-10-18(20(22)14-17)19(21)11-8-16-6-4-3-5-7-16/h3-12,14,22H,13H2,1-2H3/b11-8+ |
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| Synonyms | Not Available |
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| Chemical Formula | C20H20O3 |
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| Average Mass | 308.3770 Da |
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| Monoisotopic Mass | 308.14124 Da |
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| IUPAC Name | (2E)-1-{2-hydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3-phenylprop-2-en-1-one |
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| Traditional Name | derricidin |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)=CCOC1=CC(O)=C(C=C1)C(=O)\C=C\C1=CC=CC=C1 |
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| InChI Identifier | InChI=1S/C20H20O3/c1-15(2)12-13-23-17-9-10-18(20(22)14-17)19(21)11-8-16-6-4-3-5-7-16/h3-12,14,22H,13H2,1-2H3/b11-8+ |
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| InChI Key | DGUGLZYULGVSIZ-DHZHZOJOSA-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 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Linear 1,3-diarylpropanoids |
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| Sub Class | Chalcones and dihydrochalcones |
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| Direct Parent | 2'-Hydroxychalcones |
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| Alternative Parents | |
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| Substituents | - 2'-hydroxychalcone
- Cinnamylphenol
- Phenoxy compound
- Benzoyl
- Phenol ether
- Styrene
- Aryl ketone
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Acryloyl-group
- Enone
- Vinylogous acid
- Alpha,beta-unsaturated ketone
- Ketone
- Ether
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic 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 | - Nabekura T, Kawasaki T, Kato Y, Kawai K, Fiorito S, Epifano F, Genovese S, Uwai Y: Citrus auraptene induces drug efflux transporter P-glycoprotein expression in human intestinal cells. Food Funct. 2020 Jun 24;11(6):5017-5023. doi: 10.1039/d0fo00315h. [PubMed:32530447 ]
- Taddeo VA, Epifano F, Genovese S, Fiorito S: Inhibition of soybean 15-lipoxygenase by naturally occurring acetophenones and derricidin. Nat Prod Commun. 2015 Apr;10(4):589-90. [PubMed:25973483 ]
- Fonseca BF, Predes D, Cerqueira DM, Reis AH, Amado NG, Cayres MC, Kuster RM, Oliveira FL, Mendes FA, Abreu JG: Derricin and derricidin inhibit Wnt/beta-catenin signaling and suppress colon cancer cell growth in vitro. PLoS One. 2015 Mar 16;10(3):e0120919. doi: 10.1371/journal.pone.0120919. eCollection 2015. [PubMed:25775405 ]
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