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
Taxonomic Classification
Taxonomy Tree
-
Kingdom
Organic compounds
-
Superclass
Lipids and lipid-like molecules
-
Class
Prenol lipids
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Subclass
Sesquiterpenoids
- Level 5 Artemisinins
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Subclass
Sesquiterpenoids
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Class
Prenol lipids
-
Superclass
Lipids and lipid-like molecules
Kingdom
Organic compounds
Superclass
Lipids and lipid-like molecules
Class
Prenol lipids
Subclass
Sesquiterpenoids
Intermediate Tree Nodes
Not available
Direct Parent
Artemisinins
Alternative Parents
Benzyloxycarbonyls Nitrobenzenes Nitroaromatic compounds Fatty acid esters Oxepanes Trioxanes Dicarboxylic acids and derivatives Oxanes Dialkyl peroxides Carboxylic acid esters Organic oxoazanium compounds Oxacyclic compounds Nitriles Propargyl-type 1,3-dipolar organic compounds Acetals Carbonyl compounds Hydrocarbon derivatives Organic salts Organic zwitterions Organopnictogen compounds
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