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Compound Detail

CHEMBL1256415

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COc1ccc2nc3c(c(N)c2c1)CCCC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1256415
Phase Preclinical
Structure Type MOL
InChI Key APQPVVOYBLOJDY-UHFFFAOYSA-N
5
Targets
31
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

228.3
MW (Da)
2.70
ALogP
3
HBA
1
HBD
48.1
PSA (Ų)
0.82
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H16N2O
MW 228.29
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -0.64

Activity Summary

IC50 27 meas. best 5.43
Ki 4 meas. best 5.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL220
 Ki 5.68 5.44 2090.0 4
Muscarinic acetylcholine receptor M1
CHEMBL216
 IC50 5.43 5.43 3710.0 1
Acetylcholinesterase
CHEMBL220
 IC50 5.1 4.94 8000.0 11
Cholinesterase
CHEMBL1914
 IC50 5.05 4.745 8860.0 10
HepG2
CHEMBL395
 IC50 4.94 4.5467 11500.0 3
CHO-K1
CHEMBL614031
 IC50 4.2 4.2 63000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase Ki = 2090.0 nM 5.68 Inhibition of human recombinant AChE assessed as dissociation constant for enzym... 25089370
Acetylcholinesterase Ki = 2090.0 nM 5.68 Inhibition of human recombinant AChE assessed as dissociation constant for enzym... 22818849
Muscarinic acetylcholine receptor M1 IC50 = 3710.0 nM 5.43 Antagonist activity at human M1 mAChR expressed in CHO cells assessed as inhibit... 29533874
Acetylcholinesterase Ki = 6340.0 nM 5.2 Inhibition of human recombinant AChE assessed as dissociation constant for enzym... 25089370
Acetylcholinesterase Ki = 6340.0 nM 5.2 Inhibition of human recombinant AChE assessed as dissociation constant for enzym... 22818849
Acetylcholinesterase IC50 = 8000.0 nM 5.1 Inhibition of recombinant human AChE using acetylthiocholine iodide as substrate... 33829779
Cholinesterase IC50 = 8860.0 nM 5.05 Inhibition of human serum BChE using butyrylthiocholine iodide as substrate prei... 33829779
Acetylcholinesterase IC50 = 10000.0 nM 5.0 Inhibition of recombinant human AChE using acetylthiocholine as substrate by DTN... 33984470
Acetylcholinesterase IC50 = 10000.0 nM 5.0 Inhibition of human recombinant AChE using acetylthiocholine as substrate preinc... 26503905
Acetylcholinesterase IC50 = 10000.0 nM 5.0 Inhibition of human erythrocyte AChE using acetylthiocholine iodide as substrate... 29533874
Acetylcholinesterase IC50 = 10000.0 nM 5.0 Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate... 30851693
Acetylcholinesterase IC50 = 10500.0 nM 4.98 Inhibition of human recombinant AChE after 5 mins using spectrophotometer by Ell... 21920739
Acetylcholinesterase IC50 = 10500.0 nM 4.98 Inhibition of human recombinant AChE after 5 mins by Ellman method 25259726
HepG2 IC50 = 11500.0 nM 4.94 Hepatotoxicity in human HepG2 cells assessed as cell viability after 24 hrs by M... 26503905
Acetylcholinesterase IC50 = 15000.0 nM 4.82 Inhibition of human erythrocyte AChE using acetylthiocholine as substrate preinc... 30017112
Acetylcholinesterase IC50 = 15000.0 nM 4.82 Inhibition of human recombinant AChE after 5 mins 20817518
Acetylcholinesterase IC50 = 15000.0 nM 4.82 Inhibition of human recombinant AChE using acetylthiocholine substrate preincuba... 22818849
Acetylcholinesterase IC50 = 15000.0 nM 4.82 Inhibition of human recombinant AChE pre-incubated for 5 mins before acetylthioc... 25089370
Cholinesterase IC50 = 17600.0 nM 4.75 Inhibition of recombinant human BuChE using butyrylthiocholine as substrate by E... 33984470
Cholinesterase IC50 = 18000.0 nM 4.75 Inhibition of human recombinant BChE using butyrylthiocholine iodide as substrat... 30851693

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
22818849 10.1016/j.ejmech.2012.06.051 Acetylcholinesterase 3
25089370 10.1021/jm5008648 Acetylcholinesterase 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4651402 Vero C1008 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
33984470 10.1016/j.bmcl.2021.128100 Nitric oxide synthase 1 2
25089370 10.1021/jm5008648 Cholinesterase 1
26503905 10.1021/acs.jmedchem.5b01325 Cholinesterases; ACHE & BCHE 1
26503905 10.1021/acs.jmedchem.5b01325 Cholinesterase 1
25259726 10.1021/jm5010804 Amyloid-beta precursor protein 1
25259726 10.1021/jm5010804 Cholinesterases; ACHE & BCHE 1
25259726 10.1021/jm5010804 Cholinesterase 1
25259726 10.1021/jm5010804 Acetylcholinesterase 1
25089370 10.1021/jm5008648 Unchecked 1
22818849 10.1016/j.ejmech.2012.06.051 Cholinesterases; ACHE & BCHE 1
33829779 10.1021/acs.jmedchem.1c00048 Acetylcholinesterase 1
21920739 10.1016/j.bmcl.2011.08.042 Cholinesterase 1
21920739 10.1016/j.bmcl.2011.08.042 Acetylcholinesterase 1
20817518 10.1016/j.bmcl.2010.08.044 Acetylcholinesterase 1

Data from ChEMBL 36 via Core Engine