1.0 2010-04-08 22:13:20 UTC 2019-11-26 03:15:18 UTC FDB017830 Scolymoside Isolated from Capsella bursa-pastoris (shepherd's purse) Cynara scolymus (globe artichoke) Scolymoside is a minor flavonoid found in the leaves and leaf extracts of artichoke (Cynara scolymus L.). Artichoke and artichoke leaf extracts (ALE) have a long history as a traditional part of the Mediterranean diet as well as in folk medicine for the treatment of dyspeptic disorders. Although several biol. mechanisms of action have been suggested, e.g. increased biliary secretion leading to an increased cholesterol elimination and/or inhibition of 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) reductase activity resulting in a decreased cholesterol biosynthesis, convincing and conclusive human studies investigating the blood cholesterol lowering properties of artichoke or ALE are currently limited. (European Food Research and Technology (2002), 215(2), 149-157.) Lonicerin Luteolin 7-neohesperidoside Luteolin 7-O-neohesperidoside Luteolin 7-O-rutinoside Luteolin 7-rutinoside Luteolin-7-O-beta-D-rutinoside Luteolin-7-O-rhamnoside Luteolin-7-rutinoside Luteoline-7-rhamnoglucoside Scolymoside Skolimoside Veronicastroside C27H30O15 594.5181 594.15847029 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]chromen-4-one 25694-72-8 CC1OC(OCC2OC(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(O)C(O)=C3)C(O)C(O)C2O)C(O)C(O)C1O InChI=1S/C27H30O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-7,9,18,20-30,32-37H,8H2,1H3 MGYBYJXAXUBTQF-UHFFFAOYSA-N belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Flavonoid-7-O-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids Acetals Benzene and substituted derivatives Catechols Chromones Disaccharides Flavones Heteroaromatic compounds Hydrocarbon derivatives O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Pyranones and derivatives Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid Acetal Alcohol Aromatic heteropolycyclic compound Benzenoid Benzopyran Catechol Chromone Disaccharide Flavone Flavonoid-7-o-glycoside Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Pyran Pyranone Secondary alcohol Vinylogous acid Solid logp 0.01 ALOGPS logs -2.46 ALOGPS solubility 2.07e+00 g/l ALOGPS melting_point Mp 192-196° (186-189°) logp -0.59 ChemAxon pka_strongest_acidic 7.3 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one ChemAxon average_mass 594.5181 ChemAxon mono_mass 594.15847029 ChemAxon smiles CC1OC(OCC2OC(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(O)C(O)=C3)C(O)C(O)C2O)C(O)C(O)C1O ChemAxon formula C27H30O15 ChemAxon inchi InChI=1S/C27H30O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-7,9,18,20-30,32-37H,8H2,1H3 ChemAxon inchikey MGYBYJXAXUBTQF-UHFFFAOYSA-N ChemAxon polar_surface_area 245.29 ChemAxon refractivity 137.91 ChemAxon polarizability 57.76 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 15 ChemAxon donor_count 9 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 109632 Specdb::MsMs 109633 Specdb::MsMs 109634 Specdb::MsMs 177108 Specdb::MsMs 177109 Specdb::MsMs 177110 HMDB05799 31788 Amaranth Type 1 specific Amaranthus 3564 Annual wild rice Type 1 specific Zizania aquatica 75727 Barley Type 1 specific Hordeum vulgare 4513 Breakfast cereal Type 2 specific Bulgur Type 2 specific Cereals and cereal products Unknown generic Common buckwheat Type 1 specific Fagopyrum esculentum 3617 Common wheat Type 1 specific Triticum aestivum 4565 Corn Type 1 specific Zea mays 4577 Date Type 1 specific Phoenix dactylifera 42345 Flour Type 2 specific Fruits Unknown generic Globe artichoke Type 1 specific Cynara scolymus 59895 0.0 0.0 0.0 mg/100 g Green vegetables Unknown generic Hard wheat Type 1 specific Triticum durum 4567 Herbs and Spices Unknown generic Lemon Type 1 specific Citrus limon 2708 1.85 1.850000024 1.850000024 mg/100 g Millet Type 1 specific Panicum miliaceum 4540 Oat Type 1 specific Avena sativa 4498 Orange mint Type 1 specific Mentha aquatica 190902 Oriental wheat Type 1 specific Triticum turanicum 376534 Pear Type 1 specific Pyrus communis 23211 Peppermint Type 1 specific Mentha X piperita 34256 591.175926 1170.351851781 12.0 mg/100 g Quinoa Type 1 specific Chenopodium quinoa 63459 Red rice Type 1 specific Oryza rufipogon 4529 Rice Type 1 specific Oryza sativa 4530 Rye Type 1 specific Secale cereale 4550 Sorghum Type 1 specific Sorghum bicolor 4558 Soy bean Type 1 specific Glycine max 3847 Spearmint Type 1 specific Mentha spicata 29719 Spelt Type 1 specific Triticum spelta 58933 Sweet orange Type 1 specific Citrus sinensis 2711 Tartary buckwheat Type 1 specific Fagopyrum tataricum 62330 Teff Type 1 specific Eragrostis tef 110835 Triticale Type 1 specific X Triticosecale rimpaui Wheat Type 1 specific Triticum 4564 Wild rice Type 1 specific Zizania 15949