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
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
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
acetylcholinesterase (Cartwright blood group) Primary target of this compound Hs Inhibitor Inhibition 7.6 – 7.8 pIC50 - 1
pIC50 7.6 – 7.8 [1]
butyrylcholinesterase Hs Inhibitor Inhibition 7.6 – 7.8 pIC50 - 1
pIC50 7.6 – 7.8 [1]