CAS 27740-01-8|Scutellarein-7-O-beta-D-glucuronide|Breviscapin|Scutellarein-7-glucuronide|Scutellarein-7beta-D-glucuronide|(2S,3S,4S,5R,6S)-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-y...

General Information

Structure

Molecular Formula

C₂₁H₁₈O₁₂

Molecular Mass

462.36042

Exact Mass

462.07982602

Charge

InChI

InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1

InChIKey

DJSISFGPUUYILV-ZFORQUDYSA-N

Canonic Smiles

OC(=O)[C@H]1O[C@@H](Oc2cc3oc(cc(=O)c3c(c2O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O

Isomeric Smiles

O=c1cc(oc2cc(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c(O)c(O)c12)c1ccc(O)cc1

Calculated Properties

JChem

Acid pKa

2.6182313

H Acceptors

H Donor

LogD (pH = 5.5)

-2.3393724

LogD (pH = 7.4)

-3.091061

Log P

0.45533025

Molar Refractivity

106.9066

Polarizability

41.499382

Polar Surface Area

203.44

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

Scutellarein-7-O-beta-D-glucuronideBreviscapinScutellarein-7-glucuronideScutellarein-7beta-D-glucuronideBreviscapine7-(β-D-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneScutellarein-7beta-D-glucuronosideScutellarinScutellarin hydrate5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl-β-D-glucopyranosiduronic acid7-(β-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneScutellarin7-(β-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one hydrate5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl-β-D-glucopyranosiduronic acid hydrateScutellarein-7-O-β-D-glucuronide5,6-Dihydroxy-2-(p-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid4',5,6,7-Tetrahydroxyflavone 7-β-D-GlucopyranuronosideScutellarein 7-β-D-GlucuronosideScutellarein 7-O-β-D-GlucuronideScutellarin B

IUPAC name

(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

IUPAC Traditional name

scutellarin

Names and Identifiers

Registration numbers

Chemspider ID

Wikipedia Title

PubChem CID

CHEMBL

CAS Number

Beilstein Number

MDL Number

PubChem SID

Registration numbers

Properties

Safety Information

Physical Property

Solubility

DMSO: ≥10 mg/mL

Apperance

yellow powder

Product Information

Empirical Formula (Hill Notation)

C21H18O12 · xH2O

C21H18O12

Purity

≥98% (HPLC)

≥98.0% (HPLC)

Grade

analytical standard

Shelf Life

(limited shelf life, expiry date on the label)

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Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

SML0014

Biochem/physiol Actions
Scutellarin is a flavonoid that exhibits a number of cardio- and neuro-protective effects. Scutellarin inhibits p38 activity, ERK phosphorylation, and TGF-β expression and fibrosis in a rat myocardial infarct model. In a cerebral ischemia-reperfusion model, the compound reduced infarct volume and neurological deficits by increasing eNOS expression while inhibiting the induction of iNOS.

73577

Wikipedia

Scutellarin

TRC

S201900

Scutellarin is an active flavonoid component from the medical plant Erigeron breviscapus (Vant) Hand-Mazz. Scutellarin is used as a micrpcirculation promoter for the treatment of cardio-cerebrovascular diseases. Studies suggest that Scutellarin has anti-c

Molecule Details

References

PubChem Literature

From Data Sources

• Chan, J.Y. et al.: Anticancer Res., 29, 3043 (2011)

• Gao, C. et al.: Drug Metab. Dispos., 39, 2034 (2011)

• Wang, C.-Z. et al.: Phytomedicine, 17, 63 (2011)

References

Bioactivity

PubChem BioAssay

Bioactivity