Compound: Scutellarin
SMILES: O=c1c2c(O)c(O)c(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@@H]([C@H]3O)O)cc2oc(c1)-c4ccc(O)cc4
InChIKey: DJSISFGPUUYILV-ZFORQUDYSA-N
Synonyms: Scutellarin, 27740-01-8, Breviscapin, Scutellarein-7-glucuronide, Scutellarin B, Scutellarein-7beta-D-glucuronide, Scutellarein-7beta-D-glucuronoside, Scutellarein-7-O-beta-D-glucuronide, Scutellarein 7-beta-D-glucuronide, Scutellarein 7-O-beta-D-glucuronide, 16IGP0ML9A, scutellarein-7-O-glucuronide, beta-D-Glucopyranosiduronic acid, 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl, Scutellarein 7-glucuronide, (2S,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid, CHEBI:61278, DTXSID101336184, Flavone, 4',5,6,7-tetrahydroxy-, 7-beta-D-glucopyranuronoside, 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranosiduronic acid, Glucopyranosiduronic acid, 5,6-dihydroxy-2-(p-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl, beta-D-, scutellarein-7-O-beta-glucuronide, (2S,3S,4S,5R,6S)-6-(5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid, scutellarein 7-beta-D-glucuronoside, RefChem:182033, DTXCID901350813, (3S,4S,6S)-6-(5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid, 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranosiduronate, scutellarein 7-O-beta-D-glucuronate, (2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid, CHEMBL487805, (2S,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-7-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid, SCUTELLAREIN 7-O-GLUCURONIDE, UNII-16IGP0ML9A, dengzhanhua, new-breviscapine, Scutellarin (Standard), MEGxp0_000554, orb1305016, orb3140825, SCHEMBL4211849, Scutellarin, analytical standard, SCHEMBL29397540, GTPL13075, HY-N0751R, DJSISFGPUUYILV-ZFORQUDYSA-N, S-7-G, HY-N0751, MSK40014, BDBM50242284, s3810, SCUTELLAREIN GLUCURONIDE [MI], AKOS016009652, AC-6073, CCG-269364, CCG-269365, CS-4273, EBC-466047, MS08111, 5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-4-one-7-b-D-glucuronide, NCGC00480778-01, NCGC00480778-02, SCUTELLAREIN GLUCURONIDE [WHO-DD], (2S,3S,4S,5R,6S)-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid, BS-16838, 5,6,4'-trihydroxyflavone-7-O-glucoronide, SCUTELLAREIN 7-.BETA.-D-GLUCURONIDE, SCUTELLAREIN 7-O-.BETA.-GLUCURONIDE, NS00015058, SCUTELLAREIN 7-.BETA.-D-GLUCURONOSIDE, SCUTELLAREIN 7-O-.BETA.-D-GLUCURONIDE, F808061, Q410712, FLAVONE, 4',5,6,7-TETRAHYDROXY-, 7-.BETA.-D-GLUCOPYRANURONOSIDE, 7-(beta-d-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one, (2S,3S,4S,5R,6S)-6-[5,6-DIHYDROXY-2-(4-HYDROXYPHENYL)-4-OXO-CHROMEN-7-YL]OXY-3,4,5-TRIHYDROXY-OXANE-2-CARBOXYLIC ACID, (2S,3S,4S,5R,6S)-6-{[4,6-dihydroxy-2-(4-hydroxyphenyl)-5-oxo-5H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid, .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 5,6-DIHYDROXY-2-(4-HYDROXYPHENYL)-4-OXO-4H-1-BENZOPYRAN-7-YL, |A-D-Glucopyranosiduronic acid, 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl, 4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-, GLUCOPYRANOSIDURONIC ACID, 5,6-DIHYDROXY-2-(P-HYDROXYPHENYL)-4-OXO-4H-1-BENZOPYRAN-7-YL, .BETA.-D-
Theoretical properties:
molecular_formula: C21H18O12
molecular_weight: 462.4 g/mol
exact_mass: 462.07982601 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 4
heavy_atom_count: 33
topological_polar_surface_area: 203 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Scutellarin is the glycosyloxyflavone which is the 7-O-glucuronide of scutellarein. It has a role as an antineoplastic agent and a proteasome inhibitor. It is a glucosiduronic acid, a trihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to a scutellarein. It is a conjugate acid of a scutellarin(1-).", "chebi": "The glycosyloxyflavone which is the 7-<em>O</em>-glucuronide of scutellarein.", "chembl": "SCUTELLARIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Scutellarin is a flavone, a type of phenolic chemical compound. It can be found in the Asian \"barbed skullcap\" Scutellaria barbata and the North American plant S. lateriflora both of which have been used in traditional medicine. The compound is found only in trace amounts in the \"Chinese skullcap\" Scutellaria baicalensis, another plant used in traditional Chinese medicine.\nThe determination of the structure of scutellarin took Guido Goldschmiedt many years: after the first publication on that topic in 1901, only in 1910 he managed to obtain enough starting material for more detailed studies.\nScutellarin has anticancer properties. It has been found to induce apoptosis of ovarian and breast tumor cells in vitro. One mechanism of scutellarin's antitumor action is to bind to TNF receptor II (TNFR2) in tumor-associated CD4+Foxp3+ regulatory T cells. These tumor \"helper\" cells show high expression of TNFR2 and are inhibited when it is blocked by scutellarin.\nScutellarin also shows protective effects for nerve cells that are affected by estrogen.\nScutellarin has been shown as a potential treatment for diabetic retinopathy, which could prevent diabetic blindness. In laboratory studies, scutellarin inhibits hypoxia-induced and moderately high glucose-induced proliferation and vascular endothelial growth factor (VEGF) expression in human retinal endothelial cells; thus, it could be a potential therapy for diabetic retinopathy. However, how scutellarin inhibits VEGF is unknown.\nScutellarin has anti-HIV-1 effects as well. In laboratory studies, a drug-resistant type HIV-1 cell-to-cell infection was inhibited with significant potency. The scutellarin compound was found to inhibit several strains of HIV-1 replication with different potencies, by preventing HIV-1 particle attachment and cell fusion, as well as inhibiting HIV-1 retransmission."}