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Structure Information
Structure

Compound Identification

SMILES

COC1=CC2=C(C=C1)[C@]1(CC3N[C@@](CO)([C@@H](C)O)[C@@H]4C[C@@H]1OC[C@H]34)C(=O)N2

InChIKey

InChIKey=JBRTYQXRZWKPBC-YVPRTTNYSA-N

Formula

C20H26N2O5

Mass

374.437

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Taxonomic Classification

Taxonomy Tree

Kingdom

Organic compounds

Superclass

Alkaloids and derivatives

Class

Gelsemium alkaloids

Subclass

Not available

Intermediate Tree Nodes

Not available

Direct Parent

Gelsemium alkaloids

Alternative Parents

Molecular Framework

Aromatic heteropolycyclic compounds

Substituents

C21-norgelsemium skeleton - Indole or derivatives - Dihydroindole - Anisole - Phenol ether - Alkyl aryl ether - Oxepane - Aralkylamine - Oxane - Benzenoid - Pyrrolidine - Secondary carboxylic acid amide - Secondary alcohol - 1,2-aminoalcohol - Amino acid or derivatives - Carboxamide group - Lactam - Secondary amine - Organoheterocyclic compound - Azacycle - Oxacycle - Carboxylic acid derivative - Dialkyl ether - Ether - Secondary aliphatic amine - Primary alcohol - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Carbonyl group - Organic oxygen compound - Organooxygen compound - Amine - Organic nitrogen compound - Alcohol - Aromatic heteropolycyclic compound

Description

This compound belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21.

External Descriptors

Not available

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