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Avicularin

CAT: 0013-GTR19158776-06Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19158776-06Size:10 mg
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Description
Avicularin exhibits anti-inflammatory activity through the suppression of ERK signaling pathway in LPS-stimulated RAW 264.7 macrophage cells. Avicularin inhibits the accumulation of the intracellular lipids by decreasing C/EBPα-activated GLUT4-mediated glucose uptake in adipocytes and potently inhibiting fatty acid synthase.
CAS Number
572-30-5
Purity
>98% (HPLC)
Solubility
In Vitro: DMSO : 100 mg/mL (230.23 mM)
Smiles
C1=CC (=C (C=C1C2=C (C (=O) C3=C (C=C (C=C3O2) O) O) OC4C (C (C (O4) CO) O) O) O) O
Molecular Formula
C20H18O11
Molecular Weight
434.35
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

Avicularin

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.

CAS Number572-30-5
PubChem CID5490064
IUPAC Name3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Molecular FormulaC20H18O11
Molecular Weight434.3
XLogP1
Topological Polar Surface Area186
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count11
Rotatable Bond Count4
Heavy Atom Count31
Formal Charge0
Complexity711
SMILES
C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H](O4)CO)O)O)O)O
InChI
InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1
InChIKey
BDCDNTVZSILEOY-UXYNSRGZSA-N
Chemical Structure
2D Structure
2D structure of Avicularin
CAS: 572-30-5
CID: 5490064
Formula: C20H18O11
MW: 434.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight434.3
XLogP31
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count11
Rotatable Bond Count4
Exact Mass434.08491139
Monoisotopic Mass434.08491139
Topological Polar Surface Area186 Ų
Heavy Atom Count31
Formal Charge0
Complexity711
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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