Record Information |
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Version | 2.0 |
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Created at | 2021-06-19 17:13:48 UTC |
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Updated at | 2021-06-29 23:49:39 UTC |
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NP-MRD ID | NP0024992 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5,3'-dihydroxy-6,7,4'-trimethoxyflavone |
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Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
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Description | Eupatorin belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, eupatorin is considered to be a flavonoid. Eupatorin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 5,3'-dihydroxy-6,7,4'-trimethoxyflavone is found in Achillea collina, Achillea formosa, Achillea nobilis, Achillea setacea, Ageratina pichinchensis, Aloysia citrodora, Artemisia annua, Artemisia argyi, Baccharis genistelloides, Baccharis sagittalis, Brickellia dentata, Carphochaete bigelovii, Centaurea aggregata, Centaurea arenaria, Centaurea cadmea, Centaurea cuneifolia, Centaurea decipiens, Centaurea inermis, Chrysanthemum morifolium, Citrus reticulata, Condea tomentosa, Eupatorium album, Ageratina altissima, Ferula aucheri, Isodon umbrosus, Lantana montevidensis, Liatris aspera, Mentha piperita, Merillia caloxylon, Merrillia caloxylon, Ocimum basilicum, Phyla dulcis, Rudbeckia subtomentosa, Salvia limbata, Salvia mirzayanii, Salvia sahendica, Sideritis ferrensis, Sideritis nutans, Stevia origanoides, Tanacetum parthenium, Tanacetum vulgare, Teucrium nudicaule, Teucrium oliverianum, Teucrium orientale, Teucrium polium, Thymus vulgaris, Veronica officinalis , Veronica orchidea, Veronica teucrium and Vitex agnus-castus. 5,3'-dihydroxy-6,7,4'-trimethoxyflavone was first documented in 2008 (PMID: 18454852). Based on a literature review a small amount of articles have been published on Eupatorin (PMID: 19601638) (PMID: 22227008) (PMID: 22516932) (PMID: 22698713). |
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Structure | [H]OC1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C1=C([H])C(=O)C2=C(O[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C2O1 InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3 |
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Synonyms | Value | Source |
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3',5-Dihydroxy-4',6,7-trimethoxyflavone | ChEBI | Eupatorine | ChEBI |
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Chemical Formula | C18H16O7 |
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Average Mass | 344.3154 Da |
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Monoisotopic Mass | 344.08960 Da |
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IUPAC Name | 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one |
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Traditional Name | eupatorin |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C1=C([H])C(=O)C2=C(O[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C2O1 |
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InChI Identifier | InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3 |
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InChI Key | KLAOKWJLUQKWIF-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
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Predicted Spectra |
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| Not Available |
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Chemical Shift Submissions |
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| Not Available |
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Species |
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Species of Origin | | Show more...
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | O-methylated flavonoids |
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Direct Parent | 7-O-methylated flavonoids |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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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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External Links |
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HMDB ID | HMDB0252128 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB001539 |
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KNApSAcK ID | C00003894 |
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Chemspider ID | 87743 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 97214 |
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PDB ID | Not Available |
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ChEBI ID | 136666 |
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Good Scents ID | rw1700781 |
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References |
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General References | - Androutsopoulos V, Arroo RR, Hall JF, Surichan S, Potter GA: Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism. Breast Cancer Res. 2008;10(3):R39. doi: 10.1186/bcr2090. Epub 2008 May 2. [PubMed:18454852 ]
- Androutsopoulos VP, Li N, Arroo RR: The methoxylated flavones eupatorin and cirsiliol induce CYP1 enzyme expression in MCF7 cells. J Nat Prod. 2009 Aug;72(8):1390-4. doi: 10.1021/np900051s. [PubMed:19601638 ]
- Salmela AL, Pouwels J, Kukkonen-Macchi A, Waris S, Toivonen P, Jaakkola K, Maki-Jouppila J, Kallio L, Kallio MJ: The flavonoid eupatorin inactivates the mitotic checkpoint leading to polyploidy and apoptosis. Exp Cell Res. 2012 Mar 10;318(5):578-92. doi: 10.1016/j.yexcr.2011.12.014. Epub 2011 Dec 29. [PubMed:22227008 ]
- Laavola M, Nieminen R, Yam MF, Sadikun A, Asmawi MZ, Basir R, Welling J, Vapaatalo H, Korhonen R, Moilanen E: Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta Med. 2012 May;78(8):779-86. doi: 10.1055/s-0031-1298458. Epub 2012 Apr 19. [PubMed:22516932 ]
- Doleckova I, Rarova L, Gruz J, Vondrusova M, Strnad M, Krystof V: Antiproliferative and antiangiogenic effects of flavone eupatorin, an active constituent of chloroform extract of Orthosiphon stamineus leaves. Fitoterapia. 2012 Sep;83(6):1000-7. doi: 10.1016/j.fitote.2012.06.002. Epub 2012 Jun 12. [PubMed:22698713 ]
- Park, Y., et al. (2007). Park, Y., et al, Magn. Reson. Chem. 45, 1072 (2007). Mag. Reson. Chem..
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