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Compound Detail

CHEMBL4556281

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Cl.Cl.N[C@@H](Cc1c[nH]c2ccccc12)C(=O)NCCCCCCNc1c2c(nc3cc(Cl)ccc13)CCCC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4556281
Phase Preclinical
Structure Type MOL
InChI Key JDPFLTTTZILSHX-WLOLSGMKSA-N
Parent Compound CHEMBL4596071
Active Moiety CHEMBL4596071
7
Targets
10
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

518.1
MW (Da)
5.91
ALogP
4
HBA
4
HBD
95.8
PSA (Ų)
0.19
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H38Cl3N5O
MW 591.03
Aromatic Rings 4
Heavy Atoms 37
NP-Likeness -0.59

Activity Summary

IC50 9 meas. best 8.2
Kd 1 meas. best 5.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL220
 IC50 8.2 8.2 6.3 2
Cholinesterase
CHEMBL1914
 IC50 8.04 8.04 9.1 2
Acetylcholinesterase
CHEMBL4078
 Kd 5.32 5.32 4820.0 1
HepG2
CHEMBL395
 IC50 5.31 5.31 4900.0 2
CHO-K1
CHEMBL614031
 IC50 4.68 4.68 21000.0 1
Nitric oxide synthase 3
CHEMBL1075230
 IC50 4.58 4.58 26000.0 1
Nitric oxide synthase 1
CHEMBL3568
 IC50 4.58 4.58 26000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase IC50 = 6.3 nM 8.2 Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate... 30851693
Acetylcholinesterase IC50 = 6.31 nM 8.2 Inhibition of recombinant human AChE using acetylthiocholine as substrate by DTN... 33984470
Cholinesterase IC50 = 9.1 nM 8.04 Inhibition of human recombinant BChE using butyrylthiocholine iodide as substrat... 30851693
Cholinesterase IC50 = 9.07 nM 8.04 Inhibition of recombinant human BuChE using butyrylthiocholine as substrate by E... 33984470
Acetylcholinesterase Kd = 4820.0 nM 5.32 Displacement of propidium iodide from peripheral binding site of electric eel AC... 30851693
HepG2 IC50 = 4900.0 nM 5.31 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i... 30851693
HepG2 IC50 = 4900.0 nM 5.31 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability m... 33984470
CHO-K1 IC50 = 21000.0 nM 4.68 Cytotoxicity against CHOK1 cells assessed as reduction in cell viability incubat... 30851693
Nitric oxide synthase 3 IC50 = 26000.0 nM 4.58 Inhibition of nNOS in Wistar rat cortical homogenates incubated for 30 mins 30851693
Nitric oxide synthase 1 IC50 = 26000.0 nM 4.58 Inhibition of recombinant human nNOS 33984470

Literature References

PubMed DOI Target Context # Activities
30851693 10.1016/j.ejmech.2019.02.021 ADMET 13
30851693 10.1016/j.ejmech.2019.02.021 Rattus norvegicus 12
30851693 10.1016/j.ejmech.2019.02.021 Acetylcholinesterase 4
33984470 10.1016/j.bmcl.2021.128100 Nitric oxide synthase 1 2
30851693 10.1016/j.ejmech.2019.02.021 Cholinesterase 1
30851693 10.1016/j.ejmech.2019.02.021 Cholinesterases; ACHE & BCHE 1
30851693 10.1016/j.ejmech.2019.02.021 Amyloid-beta precursor protein 1
30851693 10.1016/j.ejmech.2019.02.021 No relevant target 1
30851693 10.1016/j.ejmech.2019.02.021 CHO-K1 1
30851693 10.1016/j.ejmech.2019.02.021 HepG2 1
30851693 10.1016/j.ejmech.2019.02.021 Nitric oxide synthase 3 1
33984470 10.1016/j.bmcl.2021.128100 Acetylcholinesterase 1
33984470 10.1016/j.bmcl.2021.128100 Cholinesterase 1
33984470 10.1016/j.bmcl.2021.128100 Unchecked 1
33984470 10.1016/j.bmcl.2021.128100 HepG2 1

Data from ChEMBL 36 via Core Engine