1.0 2010-04-08 22:05:05 UTC 2025-11-18 22:32:36 UTC FDB001706 Vitexin 6''-O-malonyl 2''-O-xyloside Vitexin, also known as apigenin 8-C-glucoside or 8-glycosylapigenin, belongs to the class of organic compounds known as flavonoid 8-C-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is also described as an apigenin flavone glucoside. Vitexin has been found in passion flower, chasteberry, bamboo leaves, millet and Hawthorn. Vitexin has shown a wide range of pharmacological effects, such as antioxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects (PMID: 27693342). Vitexin has also been shown to directly inhibit thyroid peroxidase and potentially contributes to goiter (PMID: 1696490). It is sometimes called a goitrogen. C21H20O10 432.3775 432.10564686 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one vitexin 205584-37-8 OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1 InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1 SGEWCQFRYRRZDC-VPRICQMDSA-N belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Flavonoid 8-C-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Benzene and substituted derivatives C-glycosyl compounds Chromones Dialkyl ethers Flavones Heteroaromatic compounds Hexoses Hydrocarbon derivatives Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Primary alcohols Pyranones and derivatives Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Alcohol Aromatic heteropolycyclic compound Benzenoid Benzopyran C-glycosyl compound Chromone Dialkyl ether Ether Flavone Flavonoid-8-c-glycoside Glycosyl compound Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Monosaccharide Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Primary alcohol Pyran Pyranone Secondary alcohol Vinylogous acid C-glycosyl compound Flavones and Flavonols flavones trihydroxyflavone logp 0.36 ALOGPS logs -2.40 ALOGPS solubility 1.73e+00 g/l ALOGPS logp -0.051 ChemAxon pka_strongest_acidic 6.17 ChemAxon pka_strongest_basic -3 ChemAxon iupac 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one ChemAxon average_mass 432.3775 ChemAxon mono_mass 432.10564686 ChemAxon smiles OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1 ChemAxon formula C21H20O10 ChemAxon inchi InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1 ChemAxon inchikey SGEWCQFRYRRZDC-VPRICQMDSA-N ChemAxon polar_surface_area 177.14 ChemAxon refractivity 106.03 ChemAxon polarizability 41.52 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 53442 Specdb::MsMs 53443 Specdb::MsMs 53444 Specdb::MsMs 142575 Specdb::MsMs 142576 Specdb::MsMs 142577 Specdb::MsMs 285832 Specdb::MsMs 285833 Specdb::MsMs 285834 Specdb::MsMs 285835 Specdb::MsMs 285836 Specdb::MsMs 285837 Specdb::MsMs 1470789 Specdb::MsMs 1470795 Specdb::MsMs 1470848 Specdb::MsMs 1470872 Specdb::MsMs 1470954 Specdb::MsMs 1470955 Specdb::MsMs 1470956 Specdb::MsMs 1473252 Specdb::MsMs 1473253 Specdb::MsMs 1473254 Specdb::MsMs 1473255 Specdb::MsMs 1473256 Specdb::MsMs 1473257 Common beet Type 1 specific Beta vulgaris 161934