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Structure Information
Structure

Compound Identification

SMILES

CN1C[C@@]2(C=C)[C@@H]3C[C@H]4OCC3C1[C@@H]2[C@@]41C(=O)NC2=CC=CC=C12

InChIKey

InChIKey=NFYYATWFXNPTRM-WKRGLROPSA-N

Formula

C20H22N2O2

Mass

322.408

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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

Gelsemium skeleton - Indole or derivatives - Dihydroindole - Isoindoline - Isoindole or derivatives - Aralkylamine - Oxepane - Benzenoid - N-alkylpyrrolidine - Piperidine - Oxane - Pyrrolidine - Carboxamide group - Amino acid or derivatives - Lactam - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Oxacycle - Azacycle - Carboxylic acid derivative - Dialkyl ether - Ether - Organoheterocyclic compound - Amine - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - 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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