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
1. Abe, I. Engineering of plant polyketide biosynthesis. Chem. Pharm. Bull. (Tokyo) 56(11), 1505-1514 (2008).
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
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Created at
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Updated at
1st Aug 2024