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Compound Detail

CHEMBL395280

HUPERZINE A
🧪 Phase II
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🧪 Phase II
C/C=C1\[C@H]2C=C(C)C[C@]1(N)c1ccc(=O)[nH]c1C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL395280
Name HUPERZINE A
Phase Phase II
Structure Type MOL
InChI Key ZRJBHWIHUMBLCN-YQEJDHNASA-N

Known Names

(-)-huperzine a (-)-selagine Huperzine a L-huperzine a Selagine
9
Targets
74
Activities
3
Assay Types
1
PK Parameters
20
Publications
5
Known Names
4
Indications
1
Mechanisms

Molecular Properties

242.3
MW (Da)
2.00
ALogP
2
HBA
2
HBD
58.9
PSA (Ų)
0.68
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C15H18N2O
MW 242.32
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness 2.32

Mechanism of Action

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

Indications

Alzheimer Disease Brain Injuries Cocaine-Related Disorders Substance-Related Disorders

Activity Summary

IC50 63 meas. best 9.27
Ki 10 meas. best 8.23
Kd 1 meas. best 7.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL220
 IC50 9.27 7.0961 0.5 23
Acetylcholinesterase
CHEMBL4768
 Ki 8.23 7.9275 5.9 4
Acetylcholinesterase
CHEMBL4780
 IC50 7.94 7.94 11.4 1
Acetylcholinesterase
CHEMBL220
 Kd 7.77 7.77 17.0 1
Acetylcholinesterase
CHEMBL3199
 Ki 7.62 7.62 24.0 1
Acetylcholinesterase
CHEMBL3199
 IC50 7.35 7.0881 44.5 16
Acetylcholinesterase
CHEMBL220
 Ki 7.33 7.33 47.0 1
Acetylcholinesterase
CHEMBL4768
 IC50 7.28 7.1325 53.0 8
Acetylcholinesterase
CHEMBL3198
 IC50 7.09 7.09 82.0 1
Cholinesterase
CHEMBL1914
 IC50 7.0 7.0 100.0 1
Acetylcholinesterase
CHEMBL4078
 IC50 6.92 5.7233 120.0 3
Unchecked
CHEMBL612545
 IC50 6.92 5.1633 120.0 3
Acetylcholinesterase
CHEMBL4780
 Ki 6.76 6.76 175.0 2
Unchecked
CHEMBL612545
 Ki 5.25 5.135 5600.0 2
Butyrylcholinesterase
CHEMBL3403
 IC50 4.44 4.282 36400.0 5

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.5833 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase IC50 = 0.54 nM 9.27 Inhibition of acetylcholinesterase (unknown origin) assessed as inhibition of ac... 25222040
Acetylcholinesterase IC50 = 5.0 nM 8.3 In vitro inhibitory activity against Acetylcholinesterase (AChE). -
Acetylcholinesterase IC50 = 5.0 nM 8.3 Inhibition of AChE (unknown origin) 26159481
Acetylcholinesterase IC50 = 5.0 nM 8.3 Inhibition of AChE-induced amyloid beta aggregation 21216144
Acetylcholinesterase Ki = 5.9 nM 8.23 Dissociation constant for the inhibition of fetal bovine serum acetylcholinester... -
Acetylcholinesterase Ki = 5.9 nM 8.23 Binding affinity towards Acetylcholinesterase from fetal bovine serum 11078202
Acetylcholinesterase IC50 = 11.4 nM 7.94 Inhibition of Torpedo california AChE by Ellman's method 19726199
Acetylcholinesterase IC50 = 12.0 nM 7.92 Inhibition of human AChE pre-incubated for 10 mins before acetylthiocholine iodi... 22775474
Acetylcholinesterase Kd = 17.0 nM 7.77 Binding affinity to CM5 sensor chip immobilized recombinant human AChE assessed ... 33570950
Acetylcholinesterase IC50 = 21.0 nM 7.68 Inhibition of human AChE by Ellman's method 19726199
Acetylcholinesterase Ki = 23.6 nM 7.63 Dissociation constant for the inhibition of fetal bovine serum acetylcholinester... -
Acetylcholinesterase Ki = 24.0 nM 7.62 Compound was tested for its ability to inhibit acetylcholinesterase (AChE) in ra... 11551765
Acetylcholinesterase Ki = 24.0 nM 7.62 Inhibitory constant against fetal bovine serum (FBS) acetylcholinesterase 12031333
Acetylcholinesterase IC50 = 29.0 nM 7.54 DRUGMATRIX: Acetylcholinesterase enzyme inhibition (substrate: acetylthiocholine... -
Acetylcholinesterase IC50 = 33.0 nM 7.48 Inhibition of human AChE using acetylthiocholine iodide as substrate measured fo... 30701972
Acetylcholinesterase IC50 = 45.0 nM 7.35 Inhibition of AChE (unknown origin) 23395652
Acetylcholinesterase IC50 = 44.5 nM 7.35 Compound was tested for its ability to inhibit the action of acetylcholinesteras... 1766006
Acetylcholinesterase Ki = 47.0 nM 7.33 Inhibition of human AChE 16722663
Acetylcholinesterase IC50 = 47.0 nM 7.33 Ex vivo inhibition of human erythrocyte Acetylcholinesterase. 12166941
Acetylcholinesterase IC50 = 47.0 nM 7.33 Anticholinesterase activity against human erythrocyte AChE 16570913

Literature References

PubMed DOI Target Context # Activities
19726199 10.1016/j.bmc.2009.08.017 Acetylcholinesterase 10
25453793 10.1016/j.bmcl.2014.10.049 Mus musculus 8
33120080 10.1016/j.bmc.2020.115820 Unchecked 8
- 10.1016/0960-894X(96)00012-1 Acetylcholinesterase 6
18479118 10.1021/jm701253t Acetylcholinesterase 4
33570950 10.1021/acs.jmedchem.0c01863 Acetylcholinesterase 3
11101357 10.1021/jm000980y Unchecked 3
11804518 10.1021/jf0106087 Eurhopalus australis 3
17154513 10.1021/jm060945c Acetylcholinesterase 3
33120080 10.1016/j.bmc.2020.115820 Rattus norvegicus 3
11741490 10.1021/jm010949b Acetylcholinesterase 3
27552582 10.1021/acs.jmedchem.6b00636 Unchecked 2
11804518 10.1021/jf0106087 Tineola bisselliella 2
- 10.1039/C4MD00305E Caenorhabditis elegans 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.1016/0960-894X(96)00102-3 Acetylcholinesterase 2
1766006 10.1021/jm00116a010 Acetylcholinesterase 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
11804518 10.1021/jf0106087 Lucilia cuprina 2
27552582 10.1021/acs.jmedchem.6b00636 NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine