Structure Information
Structure

Compound Identification

SMILES

[H][C@]1(C)OC(=O)[C@@]23C(=C)[C@@](C)(CC4=C(C)[C@]5(C=CC(=O)OC5(C)C)[C@@]([H])(C[C@]24C)OC(C)=O)OC(=O)[C@]13O

InChIKey

InChIKey=SLCHGQPSMLGFMX-MCLJPEIISA-N

Formula

C27H32O9

Mass

500.544

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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 heteropolycyclic compounds

Substituents

Annonaceae acetogenin skeleton - Terpene lactone - Farsesane sesquiterpenoid - Sesquiterpenoid - Tetracarboxylic acid or derivatives - Fatty alcohol ester - Secoiridoid-skeleton - Furopyran - Delta_valerolactone - Fatty acid ester - Dihydropyranone - Delta valerolactone - Pyran - Oxane - Monosaccharide - Gamma butyrolactone - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Tetrahydrofuran - Tertiary alcohol - Furan - Lactone - Carboxylic acid ester - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic heteropolycyclic 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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