Compound Identification
SMILES
COC1=CC2=C(C=C1)[C@]1(CC3[C@H]4CO[C@H]1C[C@H]4[C@@]1(CN31)[C@@H](C)O)C(=O)N2
InChIKey
InChIKey=BINNTLDJZAZYMH-ULQBSYSVSA-N
Formula
C20H24N2O4
Mass
356.422
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 Piperidines N-alkylpyrrolidines 1,3-aminoalcohols Secondary alcohols 1,2-aminoalcohols Amino acids and derivatives Trialkylamines Secondary carboxylic acid amides Lactams Azacyclic compounds Aziridines Dialkyl ethers Oxacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides
Molecular Framework
Aromatic heteropolycyclic compounds
Substituents
Gelsemium skeleton - C21-norgelsemium skeleton - Indole or derivatives - Dihydroindole - Anisole - Phenol ether - Alkyl aryl ether - Oxepane - Aralkylamine - Oxane - Benzenoid - N-alkylpyrrolidine - Piperidine - 1,3-aminoalcohol - Pyrrolidine - Carboxamide group - Amino acid or derivatives - Lactam - 1,2-aminoalcohol - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Secondary alcohol - Azacycle - Oxacycle - Aziridine - Organoheterocyclic compound - Carboxylic acid derivative - Dialkyl ether - Ether - Alcohol - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Amine - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - 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