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).
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2D Structure
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Physico-chemical Properties
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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
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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
Selectivity at enzymes
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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]