Structure Database (LMSD)
Common Name
Visnagin
Systematic Name
4-methoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one
Synonyms
3D model of Visnagin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Visnagin is a polyketide synthase-derived furanochromone originally isolated from A. visnaga that has diverse biological activities.1,2,3,4,5 It inhibits the germination and growth of ryegrass (IC50s = 502 and 214 µM, respectively).2 Visnagin (100 µg/ml) is cytotoxic to, and induces apoptosis in, HT-144 melanoma cells.3 It reduces LPS-stimulated increases in the secretion of TNF-α, IL-1β, and IFN-γ in BV-2 microglial cells when used at concentrations of 50 and 100 µM.4 Visnagin (25 mg/kg) protects against cardiomyopathy induced by doxorubicin in mice.5
This information has been provided by Cayman Chemical
References
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Ammi visnaga
(#1053409)
Magnoliopsida
(#3398)
Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides.,
J Agric Food Chem, 2016
J Agric Food Chem, 2016
Pubmed ID:
27936681
String Representations
InChiKey (Click to copy)
NZVQLVGOZRELTG-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3
SMILES (Click to copy)
C12C(=O)C=C(C)OC=1C=C1OC=CC1=C2OC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
17
Rings
3
Aromatic Rings
3
Rotatable Bonds
1
Van der Waals Molecular Volume
183.00
Topological Polar Surface Area
52.58
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
4
logP
3.76
Molar Refractivity
63.65
Admin
Created at
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Updated at
1st Aug 2024