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Compound Detail

CHEMBL340427

XANTHOSTIGMINE
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CNC(=O)Oc1cccc(CN(C)CCCOc2ccc3c(=O)c4ccccc4oc3c2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL340427
Name XANTHOSTIGMINE
Phase Preclinical
Structure Type MOL
InChI Key DNSUFPJFKSCBRT-UHFFFAOYSA-N
4
Targets
14
Activities
1
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

446.5
MW (Da)
4.57
ALogP
6
HBA
1
HBD
81.0
PSA (Ų)
0.32
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H26N2O5
MW 446.50
Aromatic Rings 4
Heavy Atoms 33
NP-Likeness -0.64

Activity Summary

IC50 14 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL220
 IC50 9.52 9.52 0.3 7
Acetylcholinesterase
CHEMBL3199
 IC50 9.52 8.61 0.3 2
Cholinesterase
CHEMBL1914
 IC50 7.32 6.32 48.0 3
Butyrylcholinesterase
CHEMBL3403
 IC50 7.32 7.32 48.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase IC50 = 0.3 nM 9.52 In vitro inhibition of human erythrocyte Acetylcholinesterase. 11689067
Acetylcholinesterase IC50 = 0.3 nM 9.52 Inhibition of rat acetylcholinesterase (AChE) 9767635
Acetylcholinesterase IC50 = 0.3 nM 9.52 Inhibition of human erythrocyte AchE 17008100
Acetylcholinesterase IC50 = 0.3 nM 9.52 Inhibition of human AchE 18181565
Acetylcholinesterase IC50 = 0.3 nM 9.52 Inhibition of AChE 20053484
Acetylcholinesterase IC50 = 0.3 nM 9.52 Inhibition of human AChE 24900454
Acetylcholinesterase IC50 = 0.3 nM 9.52 Inhibition of acetylcholinesterase (unknown origin) -
Acetylcholinesterase IC50 = 0.3 nM 9.52 Inhibition of human erythrocyte AChE using acetylthiocholine iodide as substrate... 35858523
Acetylcholinesterase IC50 = 20.0 nM 7.7 Inhibitory concentration against rat brain acetylcholinesterase AChE 9767635
Butyrylcholinesterase IC50 = 48.0 nM 7.32 Inhibition of isolated Butyrylcholinesterase (BuChE ) 9767635
Cholinesterase IC50 = 48.0 nM 7.32 Inhibition of human serum BuChE 17008100
Cholinesterase IC50 = 48.0 nM 7.32 Inhibition of human serum BChE using butyrylthiocholine as substrate by Ellman's... 35858523
Cholinesterase IC50 = 48000.0 nM 4.32 Inhibition of isolated human BuChE 15974596

Literature References

PubMed DOI Target Context # Activities
9767635 10.1021/jm9810046 Acetylcholinesterase 2
15974596 10.1021/jm049515h Acetylcholinesterase 2
17008100 10.1016/j.bmc.2006.09.026 Unchecked 2
18181565 10.1021/jm7009364 Acetylcholinesterase 2
35858523 10.1016/j.ejmech.2022.114606 Cholinesterases; ACHE & BCHE 1
11689067 10.1021/jm010914b Acetylcholinesterase 1
35858523 10.1016/j.ejmech.2022.114606 Cholinesterase 1
35858523 10.1016/j.ejmech.2022.114606 Acetylcholinesterase 1
- 10.1007/s00044-010-9373-7 Acetylcholinesterase 1
24900454 10.1021/ml200313p Acetylcholinesterase 1
20053484 10.1016/j.ejmech.2009.12.038 Acetylcholinesterase 1
17008100 10.1016/j.bmc.2006.09.026 Cholinesterase 1
17008100 10.1016/j.bmc.2006.09.026 Acetylcholinesterase 1
15974596 10.1021/jm049515h Cholinesterases; ACHE & BCHE 1
15974596 10.1021/jm049515h Cholinesterase 1
9767635 10.1021/jm9810046 Cholinesterases; ACHE & BCHE 1
9767635 10.1021/jm9810046 Butyrylcholinesterase 1

Data from ChEMBL 36 via Core Engine