1.0 2010-04-08 22:04:58 UTC 2025-11-18 22:31:16 UTC FDB001442 (-)-Arctigenin Isolated from Cnicus benedictus, Forsythia viridissima, Arctium lappa, Ipomoea cairica and others (CCD) Arctigenin is a lignan found in certain plants of the Asteraceae , including the Greater burdock (Arctium lappa) and Saussurea heteromalla. It has shown antiviral and anticancer effects. It is the aglycone of arctiin. (-)-Arctigenin 2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R-trans)- 2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)- 4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanone 4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanone Arctigenin C21H24O6 372.4117 372.1572885 (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one (-)-arctigenin 7770-78-7 COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1 NQWVSMVXKMHKTF-JKSUJKDBSA-N belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Dibenzylbutyrolactone lignans Organic compounds Lignans, neolignans and related compounds Furanoid lignans Tetrahydrofuran lignans Aromatic heteromonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acid esters Dimethoxybenzenes Gamma butyrolactones Hydrocarbon derivatives Lignan lactones Methoxyphenols Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Phenoxy compounds Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic heteromonocyclic compound Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dibenzylbutyrolactone Dimethoxybenzene Ether Gamma butyrolactone Hydrocarbon derivative Lactone Lignan lactone Methoxybenzene Methoxyphenol Monocarboxylic acid or derivatives Monocyclic benzene moiety O-dimethoxybenzene Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Tetrahydrofuran Lignans lignan logp 3.20 ALOGPS logs -4.54 ALOGPS solubility 1.06e-02 g/l ALOGPS logp 3.44 ChemAxon pka_strongest_acidic 9.95 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one ChemAxon average_mass 372.4117 ChemAxon mono_mass 372.1572885 ChemAxon smiles COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC ChemAxon formula C21H24O6 ChemAxon inchi InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1 ChemAxon inchikey NQWVSMVXKMHKTF-JKSUJKDBSA-N ChemAxon polar_surface_area 74.22 ChemAxon refractivity 100.12 ChemAxon polarizability 38.87 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 5 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 23414 Specdb::CMs 41739 Specdb::CMs 134023 Specdb::CMs 141757 Specdb::MsMs 66333 Specdb::MsMs 66334 Specdb::MsMs 66335 Specdb::MsMs 123870 Specdb::MsMs 123871 Specdb::MsMs 123872 Specdb::MsMs 2230972 Specdb::MsMs 2231839 Specdb::MsMs 2232380 Specdb::MsMs 2252262 Specdb::MsMs 2252996 Specdb::MsMs 2253459 Specdb::MsMs 2254217 Specdb::MsMs 2254303 Specdb::MsMs 2255116 Specdb::MsMs 2255479 Specdb::MsMs 2256270 Specdb::MsMs 2256361 Specdb::MsMs 2257159 Specdb::MsMs 2257410 Specdb::MsMs 2258212 Specdb::MsMs 2258417 Specdb::MsMs 2259132 Specdb::MsMs 2259449 Specdb::MsMs 2260177 HMDB30087 #<Reference:0x000055ce30724288> Burdock Type 1 specific Arctium lappa 4217 16.66 16.66 16.66 mg/100 g Cardoon Type 1 specific Cynara cardunculus 4265 Grape wine Type 2 specific 0.0 0.0 0.0 mg/100 g Sesame Type 1 specific Sesamum orientale 4182 0.019 0.018999999 0.018999999 mg/100 g Anti HIV 333 A substance that destroys or inhibits replication of viruses. Anti leukemic 393 A substance that inhibits or prevents the proliferation of neoplasms. Anti proliferant 547 Anti TNF 659 A substance that diminishes the rate of a chemical reaction. Anti topoisomerase-II 661 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. Anti-integrase 374 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. Anti-lymphomic 414 Anti-viral 689 A substance that destroys or inhibits replication of viruses. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Differentiator 880 HIV-reverse-transcriptase inhibitor 994 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. Immunomodulator 1031 Biologically active substance whose activity affects or plays a role in the functioning of the immune system. 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. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Phosphodiesterase inhibitor 1215 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. Topoisomerase inhibitor 1370 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.