1.0 2010-04-08 22:04:58 UTC 2025-11-18 22:31:17 UTC FDB001444 (-)-Arctiin (-)-arctiin is a member of the class of compounds known as lignan glycosides. Lignan glycosides are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones (-)-arctiin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-arctiin can be found in burdock, which makes (-)-arctiin a potential biomarker for the consumption of this food product. Arctigenin-4-glucoside Arctiin (8CI) C27H34O11 534.5523 534.21011193 (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one arctiin 20362-31-6 COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(OC)=C2)C=C1OC InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1 XOJVHLIYNSOZOO-SWOBOCGESA-N belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. Lignan glycosides Organic compounds Lignans, neolignans and related compounds Lignan glycosides Aromatic heteromonocyclic compounds Acetals Alkyl aryl ethers Alkyl glycosides Anisoles Carbonyl compounds Carboxylic acid esters Dibenzylbutyrolactone lignans Dimethoxybenzenes Fatty acyl glycosides of mono- and disaccharides Gamma butyrolactones Hydrocarbon derivatives Lignan lactones Monocarboxylic acids and derivatives Monosaccharides O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Phenoxy compounds Polyols Primary alcohols Secondary alcohols Tetrahydrofurans 9,9p-epoxylignan Acetal Alcohol Alkyl aryl ether Alkyl glycoside Anisole Aromatic heteromonocyclic compound Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dibenzylbutyrolactone Dimethoxybenzene Ether Fatty acyl Fatty acyl glycoside Fatty acyl glycoside of mono- or disaccharide Furanoid lignan Gamma butyrolactone Glycosyl compound Hydrocarbon derivative Lactone Lignan glycoside Lignan lactone Methoxybenzene Monocarboxylic acid or derivatives Monocyclic benzene moiety Monosaccharide O-dimethoxybenzene O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol ether Phenolic glycoside Phenoxy compound Polyol Primary alcohol Secondary alcohol Tetrahydrofuran Tetrahydrofuran lignan Lignan glycosides glycoside lignan logp 1.71 ALOGPS logs -3.45 ALOGPS solubility 1.92e-01 g/l ALOGPS logp 1.17 ChemAxon pka_strongest_acidic 12.2 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one ChemAxon average_mass 534.5523 ChemAxon mono_mass 534.21011193 ChemAxon smiles COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(OC)=C2)C=C1OC ChemAxon formula C27H34O11 ChemAxon inchi InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1 ChemAxon inchikey XOJVHLIYNSOZOO-SWOBOCGESA-N ChemAxon polar_surface_area 153.37 ChemAxon refractivity 132.26 ChemAxon polarizability 54.3 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 10 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 92397 Specdb::MsMs 92398 Specdb::MsMs 92399 Specdb::MsMs 156006 Specdb::MsMs 156007 Specdb::MsMs 156008 Specdb::MsMs 3597376 Specdb::MsMs 3597377 Specdb::MsMs 3597378 Specdb::MsMs 3597379 Specdb::MsMs 3597380 Specdb::MsMs 3597381 Burdock Type 1 specific Arctium lappa 4217 3000.0 3000.0 3000.0 mg/100 g Anti-cancer 159 A substance that inhibits or prevents the proliferation of neoplasms. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Diuretic 883 An agent that promotes the excretion of urine through its effects on kidney function. Narcotic 1139 A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.