Compound Detail

CHEMBL1687

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COc1cc2c3cc1Oc1cc(ccc1O)C[C@@H]1c4c(cc(OC)c(O)c4Oc4ccc(cc4)C[C@@H]3N(C)CC2)CC[N+]1(C)C.[Cl-]

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1687
Phase	Preclinical
Structure Type	MOL
InChI Key	MHXYWXHKLBMJKL-QBYKQQEBSA-N
Parent Compound	CHEMBL339427
Active Moiety	CHEMBL339427

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

609.7

MW (Da)

6.70

ALogP

HBA

HBD

80.6

PSA (Å²)

0.24

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C37H41ClN2O6
MW	645.20
Aromatic Rings	4
Heavy Atoms	45
NP-Likeness	2.26

Activity Summary

IC50 13 meas. best 6.2

Ki 3 meas. best 5.32

EC50 1 meas.

Kd 1 meas. best 4.8

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	6.2	5.76	636.0	4
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907594	IC50	5.7	5.435	2000.0	2
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL4980	Ki	5.32	5.32	4790.0	1
Acetylcholine receptor subunit alpha CHEMBL3097	IC50	5.22	5.22	6030.0	1
Small conductance calcium-activated potassium channel CHEMBL2096673	IC50	5.12	5.12	7500.0	1
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907589	IC50	5.04	5.04	9200.0	1
Small conductance calcium-activated potassium channel protein 3 CHEMBL3780	Ki	5.04	5.04	9200.0	1
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907596	Ki	5.01	5.01	9720.0	1
Plasmodium falciparum CHEMBL364	IC50	4.82	4.82	15300.0	1
Small conductance calcium-activated potassium channel protein 3 CHEMBL3780	Kd	4.8	4.8	16000.0	1
GABA-A receptor; anion channel CHEMBL2093872	IC50	4.24	4.24	58000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	3.4	mL.min-1.kg-1	Homo sapiens
CL	3.4	mL.min-1.kg-1	Homo sapiens
Fu	0.58	-	Homo sapiens
MRT	2.2	hr	Homo sapiens
T1/2	2.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	636.0	nM	6.2	Displacement of [3H]PCP from nAChR in Apis mellifera (honeybee0 head homogenates	-
Unchecked	IC50	=	1420.0	nM	5.85	Blockade of neuromuscular transmission activity in albino Sprague-Dawley rat hem...	6284880
Neuronal acetylcholine receptor; alpha3/beta4	IC50	=	2000.0	nM	5.7	Inhibitory activity against nicotinic acetylcholine receptor alpha3-beta4	15203153
Unchecked	IC50	=	3000.0	nM	5.52	Inhibition of apamin-sensitive SKCa channel of guinea-pig hepatocytes	15225721
Unchecked	IC50	=	3350.0	nM	5.47	Displacement of [3H]alpha-BGT from nAChR in Apis mellifera (honeybee) head homog...	-
Neuronal acetylcholine receptor subunit alpha-7	Ki	=	4790.0	nM	5.32	Binding affinity nicotinic acetylcholine receptor alpha-7 was evaluated by its a...	12372503
Acetylcholine receptor subunit alpha	IC50	=	6030.0	nM	5.22	Displacement of [3H]PCP from nAChR in Torpedo nobiliana electric organs membrane...	-
Neuronal acetylcholine receptor; alpha3/beta4	IC50	=	6800.0	nM	5.17	Antagonist activity at human alpha3beta4 nAChR expressed in HEK-tsA201 cells ass...	23757208
Small conductance calcium-activated potassium channel	IC50	=	7500.0	nM	5.12	The SKCa-blocking action was assessed by its ability to inhibit the after hyperp...	7658440
Neuronal acetylcholine receptor; alpha4/beta2	IC50	=	9200.0	nM	5.04	Antagonist activity at human alpha4beta2 nAChR expressed in HEK-tsA201 cells ass...	23757208
Small conductance calcium-activated potassium channel protein 3	Ki	=	9200.0	nM	5.04	Displacement of [I125]apamine from Wistar rat recombinant SK3 channel expressed ...	18998663
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	9720.0	nM	5.01	Binding affinity for nicotinic acetylcholine receptor alpha4-beta2 was evaluated...	12372503
Plasmodium falciparum	IC50	=	15300.0	nM	4.82	Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D6 i...	9917283
Small conductance calcium-activated potassium channel protein 3	Kd	=	16000.0	nM	4.8	Inhibition of Wistar rat recombinant SK3 channel expressed in HEK293 cells by wh...	18998663
GABA-A receptor; anion channel	IC50	=	58000.0	nM	4.24	Displacement of [3H]GABA from gamma-aminobutyric-acid A (GABA-A) receptor	1317920

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	467
-	10.1584/jpestics.20.49	Acetylcholine receptor subunit alpha	6
-	10.1016/S0960-894X(96)00429-5	Acetylcholine receptor subunit delta	4
18426954	10.1124/dmd.108.020479	ADMET	4
-	10.1584/jpestics.20.57	Unchecked	2
19445515	10.1021/jm900403j	Homo sapiens	2
9917283	10.1021/np980144f	Unchecked	2
9917283	10.1021/np980144f	Plasmodium falciparum	2
18998663	10.1021/jm800809f	Small conductance calcium-activated potassium channel protein 3	2
1317920	10.1021/jm00089a005	GABA-A receptor; anion channel	1
12372503	10.1016/s0960-894x(02)00687-x	Neuronal acetylcholine receptor; alpha4/beta2	1
18426954	10.1124/dmd.108.020479	NON-PROTEIN TARGET	1
2579237	10.1021/jm00381a019	Sodium channel alpha subunits; brain (Types I, II, III)	1
9917283	10.1021/np980144f	KB	1
6284880	10.1021/np50020a010	Unchecked	1
1710653	10.1021/np50073a012	Human immunodeficiency virus type 1 reverse transcriptase	1
7658440	10.1021/jm00018a013	Small conductance calcium-activated potassium channel	1
15225721	10.1016/j.bmcl.2004.05.031	Unchecked	1
1676426	10.1021/jm00110a007	Acetylcholine receptor	1
15203153	10.1016/j.bmcl.2004.05.001	Neuronal acetylcholine receptor; alpha3/beta4	1

Data from ChEMBL 36 via Core Engine