Structure Information
Structure

Compound Identification

SMILES

C[C@@H]1CCC2[C@@H](C)[C@H](OC(=O)CCC(=O)OC(C#N)C3=CC=C(C=C3)[N+]([O-])=O)O[C@@H]3O[C@]4(C)CCC1[C@@]23OO4

InChIKey

InChIKey=KHDVPARGEVOEGR-MUGBLMPISA-N

Formula

C27H32N2O10

Mass

544.557

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Taxonomic Classification

Taxonomy Tree

Kingdom

Organic compounds

Superclass

Lipids and lipid-like molecules

Class

Prenol lipids

Subclass

Sesquiterpenoids

Intermediate Tree Nodes

Not available

Direct Parent

Artemisinins

Alternative Parents

Molecular Framework

Aromatic heteropolycyclic compounds

Substituents

Artemisinin skeleton - Benzyloxycarbonyl - Nitrobenzene - Nitroaromatic compound - Fatty acid ester - Oxepane - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Oxane - 1,2,4-trioxane - Benzenoid - Fatty acyl - Organic nitro compound - Dialkyl peroxide - Carboxylic acid ester - C-nitro compound - Oxacycle - Organic 1,3-dipolar compound - Organoheterocyclic compound - Carboxylic acid derivative - Propargyl-type 1,3-dipolar organic compound - Carbonitrile - Nitrile - Allyl-type 1,3-dipolar organic compound - Organic oxoazanium - Acetal - Hydrocarbon derivative - Organic salt - Carbonyl group - Cyanide - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Organic oxide - Organopnictogen compound - Organic zwitterion - Organic oxygen compound - Aromatic heteropolycyclic compound

Description

This compound belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins.

External Descriptors

Not available

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