1.0 2010-04-08 22:05:00 UTC 2025-11-18 22:31:57 UTC FDB001539 Eupatorin Eupatorin, also known as 3',5-dihydroxy-4',6,7-trimethoxyflavone, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, eupatorin is considered to be a flavonoid lipid molecule. Eupatorin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eupatorin can be found in lemon verbena, mandarin orange (clementine, tangerine), and peppermint, which makes eupatorin a potential biomarker for the consumption of these food products. 3',5-Dihydroxy-4',6,7-trimethoxyflavone 5,3'-Dihydroxy-6,7,4'-trimethoxyflavone Eupatorine Flavone, 3',5-dihydroxy-4',6, 7-trimethoxy- Flavone, 3',5-dihydroxy-4',6,7-trimethoxy- Flavone, 3',5-dihydroxy-4',6,7-trimethoxy- (8CI) C18H16O7 344.3154 344.089602866 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one eupatorin 855-96-9 COC1=CC=C(C=C1O)C1=CC(=O)C2=C(O)C(OC)=C(OC)C=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 KLAOKWJLUQKWIF-UHFFFAOYSA-N 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. 7-O-methylated flavonoids Organic compounds Phenylpropanoids and polyketides Flavonoids O-methylated flavonoids Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 4'-O-methylated flavonoids 5-hydroxyflavonoids 6-O-methylated flavonoids Alkyl aryl ethers Anisoles Chromones Flavones Heteroaromatic compounds Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Organic oxides Oxacyclic compounds Phenoxy compounds Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4p-methoxyflavonoid-skeleton 5-hydroxyflavonoid 6-methoxyflavonoid-skeleton 7-methoxyflavonoid-skeleton Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Ether Flavone Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Pyran Pyranone Vinylogous acid Flavones and Flavonols logp 2.95 ALOGPS logs -3.89 ALOGPS solubility 4.47e-02 g/l ALOGPS logp 2.54 ChemAxon pka_strongest_acidic 8.99 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one ChemAxon average_mass 344.3154 ChemAxon mono_mass 344.089602866 ChemAxon smiles COC1=CC=C(C=C1O)C1=CC(=O)C2=C(O)C(OC)=C(OC)C=C2O1 ChemAxon formula C18H16O7 ChemAxon inchi 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 ChemAxon inchikey KLAOKWJLUQKWIF-UHFFFAOYSA-N ChemAxon polar_surface_area 94.45 ChemAxon refractivity 90.32 ChemAxon polarizability 35.01 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 7 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 111285 Specdb::CMs 124473 Specdb::CMs 880516 Specdb::CMs 880517 Specdb::CMs 880518 Specdb::CMs 880519 Specdb::CMs 880520 Specdb::CMs 880521 Specdb::MsMs 50637 Specdb::MsMs 50638 Specdb::MsMs 50639 Specdb::MsMs 133935 Specdb::MsMs 133936 Specdb::MsMs 133937 Specdb::MsMs 3433317 Specdb::MsMs 3433318 Specdb::MsMs 3433319 Specdb::MsMs 3433320 Specdb::MsMs 3433321 Lemon verbena Type 1 specific Aloysia triphylla 542672 11.650357 11.65035728 11.65035728 mg/100 g Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 Peppermint Type 1 specific Mentha X piperita 34256 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti carcinomic 162 A substance that inhibits or prevents the proliferation of neoplasms. Anti-malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Emetic 899 Immunostimulant 1032 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity. Parasiticide 1198 Plasmodicide 1233