Compound Identification
SMILES
COC1=CC2=C(C=C1)[C@]1(C[C@@H]3N[C@](CO)([C@@H](C)O)[C@@H]4C[C@H]1OC[C@H]34)C(=O)N2
InChIKey
InChIKey=JBRTYQXRZWKPBC-LXJIRDTFSA-N
Formula
C20H26N2O5
Mass
374.437
Taxonomic Classification
Taxonomy Tree
-
Kingdom
Organic compounds
-
Superclass
Alkaloids and derivatives
- Class Gelsemium alkaloids
-
Superclass
Alkaloids and derivatives
Kingdom
Organic compounds
Superclass
Alkaloids and derivatives
Class
Gelsemium alkaloids
Subclass
Not available
Intermediate Tree Nodes
Not available
Direct Parent
Gelsemium alkaloids
Alternative Parents
Indolines Anisoles Alkyl aryl ethers Aralkylamines Oxepanes Oxanes Pyrrolidines Lactams Secondary alcohols 1,2-aminoalcohols Secondary carboxylic acid amides Amino acids and derivatives Oxacyclic compounds Dialkylamines Dialkyl ethers Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Primary alcohols
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