physostigmine   Click here for help

GtoPdb Ligand ID: 6598

Synonyms: Antilirium® | eserine | physostigmine salicylate
Approved drug
physostigmine is an approved drug
Compound class: Natural product
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

References
1. Luo W, Yu QS, Kulkarni SS, Parrish DA, Holloway HW, Tweedie D, Shafferman A, Lahiri DK, Brossi A, Greig NH. (2006)
Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine.
J Med Chem, 49 (7): 2174-85. [PMID:16570913]