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Compound Detail

CHEMBL208599

HUPRINE X
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CCC1=CC2Cc3nc4cc(Cl)ccc4c(N)c3[C@@H](C1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL208599
Name HUPRINE X
Phase Preclinical
Structure Type MOL
InChI Key QTPHSDHUHXUYFE-KIYNQFGBSA-N
4
Targets
22
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

298.8
MW (Da)
4.86
ALogP
2
HBA
1
HBD
38.9
PSA (Ų)
0.76
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H19ClN2
MW 298.82
Aromatic Rings 2
Heavy Atoms 21

Activity Summary

IC50 16 meas. best 10.17
Ki 6 meas. best 10.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL220
 Ki 10.59 10.1167 0.0 3
Acetylcholinesterase
CHEMBL4768
 IC50 10.17 8.2067 0.1 9
Acetylcholinesterase
CHEMBL4780
 Ki 9.89 9.89 0.1 1
Acetylcholinesterase
CHEMBL220
 IC50 9.49 8.8025 0.3 4
Cholinesterase
CHEMBL1914
 IC50 7.8 7.2767 15.8 3
Cholinesterase
CHEMBL1914
 Ki 6.92 6.92 120.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase Ki = 0.026 nM 10.59 Inhibition of human AChE 16722663
Acetylcholinesterase Ki = 0.026 nM 10.59 Inhibitory activity against human AChE 12502352
Acetylcholinesterase IC50 = 0.0674 nM 10.17 Compound was evaluated for the inhibition of acetylcholinesterase activity from ... 11101357
Acetylcholinesterase Ki = 0.13 nM 9.89 Inhibition of Torpedo californica AChE 18479118
Acetylcholinesterase IC50 = 0.23 nM 9.64 Compound was evaluated for the inhibition of acetylcholinesterase activity from ... 11101357
Acetylcholinesterase IC50 = 0.32 nM 9.49 Inhibition of acetylcholinesterase isolated from Human erythrocytes. 11101357
Acetylcholinesterase Ki = 0.67 nM 9.17 Binding affinity to human AChE 18479118
Acetylcholinesterase IC50 = 0.75 nM 9.12 Inhibition of acetylcholinesterase isolated from Human erythrocytes. 11101357
Acetylcholinesterase IC50 = 1.1 nM 8.96 Inhibition of human recombinant AChE in erythrocytes by Ellman's assay 19473849
Acetylcholinesterase IC50 = 1.3 nM 8.89 Compound was evaluated for the inhibition of acetylcholinesterase of bovine eryt... 11101357
Acetylcholinesterase IC50 = 2.31 nM 8.64 Compound was evaluated for the inhibition of acetylcholinesterase activity from ... 11101357
Acetylcholinesterase IC50 = 2.77 nM 8.56 Compound was evaluated for the inhibition of acetylcholinesterase of bovine eryt... 11101357
Acetylcholinesterase IC50 = 3.34 nM 8.48 Compound was evaluated for the inhibition of acetylcholinesterase activity from ... 11101357
Cholinesterase IC50 = 15.8 nM 7.8 Inhibition of butyrylcholinesterase (BChE) in human serum 11101357
Acetylcholinesterase IC50 = 23.1 nM 7.64 Inhibition of acetylcholinesterase isolated from Human erythrocytes. 11101357
Cholinesterase IC50 = 58.3 nM 7.23 Inhibition of butyrylcholinesterase (BChE) in human serum 11101357
Cholinesterase Ki = 120.0 nM 6.92 Inhibitory activity against Equine Butyrylcholinesterase 12502352
Cholinesterase Ki = 120.0 nM 6.92 Inhibition of human BuChE 16722663
Cholinesterase IC50 = 159.0 nM 6.8 Inhibition of butyrylcholinesterase (BChE) in human serum 11101357
Acetylcholinesterase IC50 = 240.0 nM 6.62 Compound was evaluated for the inhibition of acetylcholinesterase activity from ... 11101357

Literature References

PubMed DOI Target Context # Activities
11101357 10.1021/jm000980y Acetylcholinesterase 15
11101357 10.1021/jm000980y Unchecked 9
11101357 10.1021/jm000980y Cholinesterase 3
18479118 10.1021/jm701253t Acetylcholinesterase 2
12502352 10.1021/jm0255668 Acetylcholinesterase 1
12502352 10.1021/jm0255668 Cholinesterase 1
16722663 10.1021/jm060257t Acetylcholinesterase 1
16722663 10.1021/jm060257t Cholinesterase 1
19473849 10.1016/j.bmc.2009.05.005 Acetylcholinesterase 1

Data from ChEMBL 36 via Core Engine