Structure Database (LMSD)

Common Name
Visnagin
Systematic Name
4-methoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one
Synonyms
LM ID
LMPK13110003
Formula
Exact Mass
Calculate m/z
230.05791
Status
Curated


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
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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

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