Structure Information
Structure

Compound Identification

SMILES

C[C@@H]1OC(=O)C(C[C@H](O)CCCCCCCCCC[C@@H](O)[C@H]2CCC(=O)O2)=C1

InChIKey

InChIKey=QCRUDDMRGHFGNR-MTFMMBMASA-N

Formula

C22H36O6

Mass

396.524

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Taxonomic Classification

Taxonomy Tree

Kingdom

Organic compounds

Superclass

Lipids and lipid-like molecules

Class

Fatty Acyls

Subclass

Fatty alcohols

Intermediate Tree Nodes

Not available

Direct Parent

Annonaceous acetogenins

Alternative Parents

Molecular Framework

Aliphatic heteromonocyclic compounds

Substituents

Annonaceae acetogenin skeleton - Long chain fatty alcohol - 2-furanone - Dicarboxylic acid or derivatives - Gamma butyrolactone - Dihydrofuran - Oxolane - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Lactone - Carboxylic acid ester - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Carboxylic acid derivative - Organooxygen compound - Alcohol - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Organic oxide - Aliphatic heteromonocyclic compound

Description

This compound belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

External Descriptors

Not available

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