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Record Information
Version2.0
Created at2021-06-19 17:13:48 UTC
Updated at2021-06-29 23:49:39 UTC
NP-MRD IDNP0024992
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,3'-dihydroxy-6,7,4'-trimethoxyflavone
Provided ByJEOL DatabaseJEOL Logo
DescriptionEupatorin 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).
Structure
Thumb
Synonyms
ValueSource
3',5-Dihydroxy-4',6,7-trimethoxyflavoneChEBI
EupatorineChEBI
Chemical FormulaC18H16O7
Average Mass344.3154 Da
Monoisotopic Mass344.08960 Da
IUPAC Name5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one
Traditional Nameeupatorin
CAS Registry NumberNot Available
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
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
InChI KeyKLAOKWJLUQKWIF-UHFFFAOYSA-N
Experimental Spectra
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.95ALOGPS
logP2.54ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.93ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.32 m³·mol⁻¹ChemAxon
Polarizability35.01 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0252128
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001539
KNApSAcK IDC00003894
Chemspider ID87743
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound97214
PDB IDNot Available
ChEBI ID136666
Good Scents IDrw1700781
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Park, Y., et al. (2007). Park, Y., et al, Magn. Reson. Chem. 45, 1072 (2007). Mag. Reson. Chem..