Breviscapine
Basic information
- CAS
116122-36-2- Standard SMILES
O=C(O)C1OC(Oc2cc3oc(-c4ccc(O)cc4)cc(=O)c3c(O)c2O)C(O)C(O)C1O- InChIKey
DJSISFGPUUYILV-UHFFFAOYSA-N- Molecular formula
- C21H18O12
- Average molar mass
- 462.4 g/mol
- Monoisotopic mass
- 462.07982601
Overview
Breviscapine has been reported in Chamaemespilus alpina, Scutellaria lateriflora, and Aria edulis with data available.
Names & identifiers
- Preferred name
- Breviscapine
- IUPAC
- 6-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
- English name
- BREVISCAPIN
- Molecular formula
- C21H18O11.C21H18O12
- Molecular weight
- 908.723
Names & synonyms
Breviscapine116122-36-26-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acidDTXSID609219246-(5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acidRefChem:917552scutellarin [M+H]+CHEMBL5597057SCHEMBL16519697HMS5082G15s3810DB-047268
Show more names
Lamps,BREVISCAPINScutellarin hydrateBreviscapine,Erigeron BreviscapusA natural extract containing apigenin 7-glucuronide and scutellarein 7-glucuronide7-(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--D-glucopyranosiduronic acid hydrate(2S,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylicaci
H578095,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl-beta-D-glucopyranosiduronic acid
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 203 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 4
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 777
Physicochemical properties
- storage temp.
- 2 · 2-8°C
- form
- Solid
- color
- Light yellow to yellow
- InChIKey
- BYTLLPAZARDJBB-MKCAKFMMNA-N
- LogP
- 0.426 · 0.426 (est)
Chemistry & industry
Applications
UsesBreviscapine is a crude flavonoid extract of Breviscapine, which is more than 85% of the active ingredient, Breviscapine. Breviscapine has a wide range of cardiovascular pharmacological activities, such as increasing blood flow, improving microcirculation, dilating blood vessels, reducing blood viscosity, promoting fibrinolysis, inhibiting platelet aggregation and thrombosis. Breviscapine has been used in the study of cerebral infarction and its sequelae, cerebral thrombosis, coronary heart disease and angina pectoris[1][2].
Additional notes
DefinitionChEBI: 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 glycosyloxyflavone, a glucosiduronic acid, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a scutellarein. It is a conjugate acid of a scutellarin(1-).
Related reactions
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Compound notes
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