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Avicularin

Avicularin structure

Avicularin 

structure
  • CAS No:

    572-30-5

  • Formula:

    C20H18O11

  • Chemical Name:

    Avicularin

  • Synonyms:

    4H-1-Benzopyran-4-one,3-(α-L-arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-;Avicularin;3-(α-L-Arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one;Avicularoside;Quercetin 3-α-L-arabinofuranoside;Avicularine;Quercetin 3-O-α-L-arabinofuranoside;844831-83-0;887670-96-4;158560-11-3

  • Categories:

    Natural Products  >  Flavonoids

Description

Avicularin is a bio-active flavonoid from plants, anti-inflammatory, anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities. Avicularin exhibits anti-inflammatory activity through the suppression of ERK signaling pathway in LPS-stimulated RAW 264.7 macrophage cells. Avicularin ameliorates human hepatocellular carcinoma via the regulation of NF κB (p65), COX 2 and PPAR γ activities[1][2].


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 a monosaccharide derivative, an alpha-L-arabinofuranoside, a tetrahydroxyflavone and a quercetin O-glycoside.

Avicularin Basic Attributes

434.35

434.35

DTXSID60205832

Characteristics

186

2.06

White powder

1.9±0.1 g/cm3

207-208 °C

855.4±65.0 °C at 760 mmHg

305.8±27.8 °C

1.802

Safety Information

NONH for all modes of transport

3

Drug Information

avicularin

Avicularin Use and Manufacturing

Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]

Computed Properties

Molecular Weight:434.3
XLogP3:1
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:4
Exact Mass:434.08491139
Monoisotopic Mass:434.08491139
Topological Polar Surface Area:186
Heavy Atom Count:31
Complexity:711
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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