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Compound Detail

CHEMBL338975

PHYSOSTIGMINE SALICYLATE
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CNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN(C)[C@@H]1N2C.O=C(O)c1ccccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL338975
Name PHYSOSTIGMINE SALICYLATE
Phase Preclinical
Structure Type MOL
InChI Key HZOTZTANVBDFOF-PBCQUBLHSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL94
Active Moiety CHEMBL94

Known Names

Antilirium NSC-757275 Physostigmine monosalicylate Physostigmine salicylate Physostigmini salicylas
4
Targets
4
Activities
2
Assay Types
0
PK Parameters
7
Publications
5
Known Names
1
Mechanisms

Molecular Properties

275.4
MW (Da)
1.77
ALogP
4
HBA
1
HBD
44.8
PSA (Ų)
0.85
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem sal-; -stigmine

Extended Properties

Molecular Formula C22H27N3O5
MW 413.47
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness 1.15

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Acetylcholinesterase inhibitor INHIBITOR Acetylcholinesterase ✓ ✓

Activity Summary

IC50 3 meas. best 7.8
Ki 1 meas. best 6.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cholinesterase
CHEMBL1914
 IC50 7.8 7.8 16.0 1
Acetylcholinesterase
CHEMBL4780
 IC50 7.67 7.67 21.3 1
Acetylcholinesterase
CHEMBL220
 IC50 7.55 7.55 28.0 1
Acetylcholinesterase
CHEMBL4078
 Ki 6.68 6.68 210.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cholinesterase IC50 = 16.0 nM 7.8 Ex vivo inhibition of human plasma Butyrylcholinesterase. 12166941
Acetylcholinesterase IC50 = 21.3 nM 7.67 Inhibition of Torpedo california AChE by Ellman's method 19726199
Acetylcholinesterase IC50 = 28.0 nM 7.55 Ex vivo inhibition of human erythrocyte Acetylcholinesterase. 12166941
Acetylcholinesterase Ki = 210.0 nM 6.68 Reversible mixed-type inhibition of electric eel acetylcholinesterase using acet... 592327

Literature References

PubMed DOI Target Context # Activities
19726199 10.1016/j.bmc.2009.08.017 Acetylcholinesterase 4
12166941 10.1021/jm010491d Acetylcholinesterase 1
12166941 10.1021/jm010491d Cholinesterase 1
12166941 10.1021/jm010491d Cholinesterases; ACHE & BCHE 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
592327 10.1021/jm00222a016 Acetylcholinesterase 1

Data from ChEMBL 36 via Core Engine