physostigmine   Click here for help

GtoPdb Ligand ID: 6598

Synonyms: Antilirium® | eserine | physostigmine salicylate
Approved drug
physostigmine is an approved drug
Comment: Physostigmine, originally isolated from the Calabar bean, is a parasympathomimetic alkaloid, acting as a reversible cholinesterase inhibitor (the enzyme responsible for the breakdown of acetylcholine in the synaptic cleft of the neuromuscular junction).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: physostigmine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 44.81
Molecular weight 275.16
XLogP 1.87
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CNC(=O)Oc1ccc2c(c1)C1(C)CCN(C1N2C)C
Isomeric SMILES CNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN([C@@H]1N2C)C
InChI InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1
InChI Key PIJVFDBKTWXHHD-HIFRSBDPSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes
IUPAC Name Click here for help
[(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
Synonyms Click here for help
Antilirium® | eserine | physostigmine salicylate
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9635029
Reactome Reaction Reactome logo R-HSA-9634834
Other databases
CAS Registry No. 57-47-6
ChEBI CHEBI:27953
ChEMBL Ligand CHEMBL94
DrugBank Ligand DB00981
DrugCentral Ligand 2159
GtoPdb PubChem SID 178103211
PubChem CID 5983
Search Google for chemical match using the InChIKey PIJVFDBKTWXHHD-HIFRSBDPSA-N
Search Google for chemicals with the same backbone PIJVFDBKTWXHHD
Search UniChem for chemical match using the InChIKey PIJVFDBKTWXHHD-HIFRSBDPSA-N
Search UniChem for chemicals with the same backbone PIJVFDBKTWXHHD
Wikipedia Physostigmine