1.0 2010-04-08 22:07:53 UTC 2025-11-18 23:06:08 UTC FDB008016 Irigenin Irigenin, also known as 5,7,3'-trihydroxy-6,4',5'-trimethoxyisoflavone, is a member of the class of compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. 3'-hydroxy,4'-methoxyisoflavonoids are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Thus, irigenin is considered to be a flavonoid lipid molecule. Irigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Irigenin can be synthesized from isoflavone. Irigenin can also be synthesized into iridin. Irigenin can be found in lima bean, which makes irigenin a potential biomarker for the consumption of this food product. Irigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily (Belamcanda chinensis), and Iris kemaonensis . 5,7,3'-Trimethoxy-6,4',5'-trimethoxyisoflavone Irigenin C18H16O8 360.3148 360.084517488 5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one irigenin 548-76-5 COC1=CC(=CC(O)=C1OC)C1=COC2=CC(O)=C(OC)C(O)=C2C1=O InChI=1S/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3 TUGWPJJTQNLKCL-UHFFFAOYSA-N belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. 3'-hydroxy,4'-methoxyisoflavonoids Organic compounds Phenylpropanoids and polyketides Isoflavonoids O-methylated isoflavonoids Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-O-methylisoflavones 4'-O-methylisoflavones Alkyl aryl ethers Anisoles Chromones Dimethoxybenzenes Heteroaromatic compounds Hydrocarbon derivatives Hydroxyisoflavonoids Isoflavones 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'-hydroxy,4'-methoxyisoflavonoid 3p-methoxyisoflavone 4p-o-methylisoflavone Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Dimethoxybenzene Ether Heteroaromatic compound Hydrocarbon derivative Hydroxyisoflavonoid Isoflavone Methoxybenzene Methoxyphenol Monocyclic benzene moiety O-dimethoxybenzene Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Pyran Pyranone Vinylogous acid Isoflavonoids Isoflavonoids hydroxyisoflavone methoxyisoflavone logp 2.74 ALOGPS logs -3.74 ALOGPS solubility 6.62e-02 g/l ALOGPS melting_point 185 oC logp 2.6 ChemAxon pka_strongest_acidic 7.12 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac 5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one ChemAxon average_mass 360.3148 ChemAxon mono_mass 360.084517488 ChemAxon smiles COC1=CC(=CC(O)=C1OC)C1=COC2=CC(O)=C(OC)C(O)=C2C1=O ChemAxon formula C18H16O8 ChemAxon inchi InChI=1S/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3 ChemAxon inchikey TUGWPJJTQNLKCL-UHFFFAOYSA-N ChemAxon polar_surface_area 114.68 ChemAxon refractivity 91.07 ChemAxon polarizability 35.6 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 101784 Specdb::MsMs 101785 Specdb::MsMs 101786 Specdb::MsMs 167469 Specdb::MsMs 167470 Specdb::MsMs 167471 Specdb::MsMs 3604661 Specdb::MsMs 3604662 Specdb::MsMs 3604663 Specdb::MsMs 3605464 Specdb::MsMs 3605465 Specdb::MsMs 3605466 Lima bean Type 1 specific Phaseolus lunatus 3884 cAMP-phosphodiesterase inhibitor 753 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Cholinergic 804 Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons. Hepatoprotective 981 Any compound that is able to prevent damage to the liver. RNA-genic 1297