Structure Database (LMSD)

Common Name
Quassin
Systematic Name
2,12-Dimethoxypicrasa-2,12-diene-1,11,16-trione
Synonyms
LM ID
LMPR0106110002
Formula
Exact Mass
Calculate m/z
388.188591
Status
Curated

Classification

Biological Context

Quassin is a quassinoid that has been found in Q. amara and has diverse biological activities.1,2,3 It is active against chloroquine-sensitive and -resistant strains of P. falciparum (IC50 = 0.15 µM for both).1 Quassin has antifeedant and insecticidal activity against the diamondback moth (P. xylostella) when applied to dietary cabbage leaf discs at 16, 31.9, or 63.7 µg/cm2.2 It increases viability of SH-SY5Y cells in a model of hydrogen peroxide-induced neuronal injury when used at concentrations of 25, 50, or 100 µM.3

This information has been provided by Cayman Chemical

References

2. Daido, M., Fukamiya, N., Okano, M., et al. Antifeedant and insecticidal activity of quassinoids against diamondback moth (Plutella xylostella). Biosci. Biotechnol. Biochem. 57(2), 2440246 (1993).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Quassia amara (#43725)
Magnoliopsida (#3398)
Quassin and Neoquassin,
Tetrahedron, 1961

String Representations

InChiKey (Click to copy)
IOSXSVZRTUWBHC-LBTVDEKVSA-N
InChi (Click to copy)
InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3/t10-,12+,13+,15-,19+,21-,22+/m1/s1
SMILES (Click to copy)
[C@@]12(C)[C@@]3([H])CC(=O)O[C@]1([H])C[C@@]1([H])[C@H](C)C=C(OC)C(=O)[C@]1(C)[C@@]2([H])C(=O)C(=C3C)OC

Other Databases

Wikipedia
KEGG ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 4
Aromatic Rings 0
Rotatable Bonds 2
Van der Waals Molecular Volume 379.26
Topological Polar Surface Area 80.97
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 6
logP 3.11
Molar Refractivity 100.29

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Created at
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Updated at
11th Mar 2025