Compound: Avicularin
SMILES: O=c1c(O[C@@H]2O[C@@H](CO)[C@@H]([C@H]2O)O)c(oc3c1c(O)cc(c3)O)-c4cc(O)c(O)cc4
InChIKey: BDCDNTVZSILEOY-UXYNSRGZSA-N
Synonyms: Avicularin, 572-30-5, Avicularoside, Quercetin 3-alpha-L-arabinofuranoside, TN38NQ38BQ, CHEBI:65460, DTXSID60205832, 4H-1-Benzopyran-4-one, 3-(alpha-L-arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-, RefChem:115784, DTXCID90128323, Fenicularin, quercetin-3-arabinoside, MFCD10566630, 3-(((2S,3R,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one, Quercetin 3-O-alpha-L-arabinofuranoside, Avicularine, Guaiaverin, 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one, Avicularin (Standard), UNII-TN38NQ38BQ, SCHEMBL151758, Avicularin, analytical standard, CHEMBL471282, orb1300263, orb3140784, quercetin 3-O-arabinofuranoside, quercetin-3-o-arabinofuranoside, SCHEMBL29505880, HY-N0222R, HY-N0222, BDBM50362887, LMPK12112167, MSK158866, AKOS015897125, EBC-615876, FQ65464, 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one, 3-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one, AC-34226, MS-27769, CS-0008260, NS00097554, C22608, QUERCETIN 3-O-.ALPHA.-L-ARABINOFURANOSIDE, Q9163056, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl alpha-L-arabinofuranoside, 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl alpha-L-arabinofuranoside, 3-(.ALPHA.-L-ARABINOFURANOSYLOXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE, 3-(?-L-Arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; Avicularine; Avicularoside;
Theoretical properties:
molecular_formula: C20H18O11
molecular_weight: 434.3 g/mol
exact_mass: 434.08491139 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 11
rotatable_bond_count: 4
heavy_atom_count: 31
topological_polar_surface_area: 186 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Avicularin is a quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and Foeniculum vulgare. It has a role as a hepatoprotective agent and a plant metabolite. It is an alpha-L-arabinofuranoside, a tetrahydroxyflavone, a monosaccharide derivative and a quercetin O-glycoside.
chebi: A quercetin <em>O</em>-glycoside in which an α-<small>L</small>-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from <em>Juglans regia</em> and <em>Foeniculum vulgare</em>.
chembl: AVICULARIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Avicularin is a bio-active flavonol isolated from a number of plants including Polygonum aviculare, Rhododendron aureum and Taxillus kaempferi.
It suppresses lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells.