1.0 2010-04-08 22:05:22 UTC 2025-11-18 22:37:22 UTC FDB002422 Eupafolin Eupafolin, also known as 6-methoxy 5 or 73'4'-tetrahydroxyflavone, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, eupafolin is considered to be a flavonoid lipid molecule. Eupafolin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eupafolin can be found in common sage, lemon verbena, rosemary, and sesame, which makes eupafolin a potential biomarker for the consumption of these food products. 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one, 9CI 6-Methoxyluteolin Eupafolin Nepetin C16H12O7 316.2623 316.058302738 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one nepetin 520-11-6 COC1=C(O)C2=C(OC(=CC2=O)C2=CC(O)=C(O)C=C2)C=C1O InChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3 FHHSEFRSDKWJKJ-UHFFFAOYSA-N belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. 6-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'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Alkyl aryl ethers Anisoles Benzene and substituted derivatives Catechols Chromones Flavones Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Oxacyclic compounds Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 6-methoxyflavonoid-skeleton 7-hydroxyflavonoid Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzopyran Catechol Chromone Ether Flavone Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Pyran Pyranone Vinylogous acid Flavones and Flavonols logp 2.75 ALOGPS logs -3.43 ALOGPS solubility 1.17e-01 g/l ALOGPS logp 2.25 ChemAxon pka_strongest_acidic 7.09 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one ChemAxon average_mass 316.2623 ChemAxon mono_mass 316.058302738 ChemAxon smiles COC1=C(O)C2=C(OC(=CC2=O)C2=CC(O)=C(O)C=C2)C=C1O ChemAxon formula C16H12O7 ChemAxon inchi InChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3 ChemAxon inchikey FHHSEFRSDKWJKJ-UHFFFAOYSA-N ChemAxon polar_surface_area 116.45 ChemAxon refractivity 81.36 ChemAxon polarizability 30.8 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 88866 Specdb::MsMs 88867 Specdb::MsMs 88868 Specdb::MsMs 151674 Specdb::MsMs 151675 Specdb::MsMs 151676 Specdb::MsMs 285885 Specdb::MsMs 285886 Specdb::MsMs 285887 Specdb::MsMs 285888 Specdb::MsMs 1479246 Specdb::MsMs 1479344 Specdb::CMs 74311 Common sage Type 1 specific Salvia officinalis 38868 Lemon verbena Type 1 specific Aloysia triphylla 542672 2.599615 2.599615402 2.599615402 mg/100 g Rosemary Type 1 specific Rosmarinus officinalis 39367 Sesame Type 1 specific Sesamum orientale 4182 Aldose reductase inhibitor 40 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). Anti-cataract 168 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Xanthine oxidase inhibitor 1431 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).