Compound Detail

CHEMBL346389

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O=C1COc2cc(CN3CCN(c4ccc(Cl)cc4)CC3)ccc2N1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL346389
Phase	Preclinical
Structure Type	MOL
InChI Key	UFFHNEZNXKJHFB-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

357.8

MW (Da)

2.99

ALogP

HBA

HBD

44.8

PSA (Å²)

0.92

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C19H20ClN3O2
MW	357.84
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	-1.64

Activity Summary

Ki 26 meas. best 8.37

IC50 9 meas. best 6.54

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	Ki	8.37	8.37	4.3	1
D(4) dopamine receptor CHEMBL219	Ki	8.37	8.37	4.3	2
Alpha-1A adrenergic receptor CHEMBL319	Ki	6.69	6.69	203.0	1
Sigma intracellular receptor 2 CHEMBL4105907	Ki	6.64	6.64	231.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL3602	Ki	6.64	6.64	231.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.63	6.63	232.0	2
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	6.54	6.54	285.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.43	6.43	368.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL3602	IC50	6.43	6.43	375.0	1
Alpha-2B adrenergic receptor CHEMBL266	Ki	6.43	6.43	368.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.39	6.39	411.0	2
D(2) dopamine receptor CHEMBL217	Ki	6.38	6.38	413.0	3
Alpha-1A adrenergic receptor CHEMBL319	IC50	6.3	6.3	500.0	1
Alpha-2B adrenergic receptor CHEMBL266	IC50	6.2	6.2	630.0	1
D(3) dopamine receptor CHEMBL234	Ki	6.17	6.17	679.0	3
Alpha-1B adrenergic receptor CHEMBL232	Ki	6.1	6.1	787.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	6.1	6.1	792.0	2
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.1	6.1	787.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	6.02	6.02	964.0	2
Alpha-2A adrenergic receptor CHEMBL1867	IC50	5.96	5.96	1100.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	5.87	5.87	1340.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	5.85	5.85	1400.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	5.85	5.85	1425.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.78	5.78	1678.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	5.78	5.78	1678.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	IC50	5.57	5.57	2700.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
D(4) dopamine receptor	Ki	=	4.3	nM	8.37	Binding affinity at Dopamine receptor D4 in CHO cells by radioligand displacemen...	10602703
Unchecked	Ki	=	4.3	nM	8.37	Inhibition of human dopamine D4.4 receptor	28489950
D(4) dopamine receptor	Ki	=	4.3	nM	8.37	Displacement of [3H]-spiperone from human D4 receptor expressed in CHO cells ass...	33422983
Alpha-1A adrenergic receptor	Ki	=	203.0	nM	6.69	Inhibition of [3H]- prazosin binding against Alpha-1A adrenergic receptor from r...	10602703
Sigma intracellular receptor 2	Ki	=	231.0	nM	6.64	Inhibition of sigma2 receptor (unknown origin)	28489950
Sigma non-opioid intracellular receptor 1	Ki	=	231.0	nM	6.64	Inhibition of [3H]- Ifenprodil binding against rat brain Sigma opioid receptor t...	10602703
Sigma non-opioid intracellular receptor 1	Ki	=	232.0	nM	6.63	Inhibition of sigma1 receptor (unknown origin)	28489950
Sigma non-opioid intracellular receptor 1	Ki	=	232.0	nM	6.63	Inhibition of [3H]- pentazocine binding against guinea pig brain Sigma opioid re...	10602703
Sigma non-opioid intracellular receptor 1	IC50	=	285.0	nM	6.54	Inhibition of [3H]- pentazocine binding against guinea pig brain Sigma opioid re...	10602703
Sigma non-opioid intracellular receptor 1	IC50	=	375.0	nM	6.43	Inhibition of [3H]- Ifenprodil binding against rat brain Sigma opioid receptor t...	10602703
Alpha-2B adrenergic receptor	Ki	=	368.0	nM	6.43	Inhibition of alpha2B adrenergic receptor (unknown origin)	28489950
Alpha-2B adrenergic receptor	Ki	=	368.0	nM	6.43	Inhibition of [3H]- Yohimbine binding against rat kidney cortex Alpha-2B adrener...	10602703
Alpha-2A adrenergic receptor	Ki	=	411.0	nM	6.39	Inhibition of [3H]- MK-912 binding against human recombinant Alpha-2A adrenergic...	10602703
Alpha-2A adrenergic receptor	Ki	=	411.0	nM	6.39	Inhibition of alpha2A adrenergic receptor (unknown origin)	28489950
D(2) dopamine receptor	Ki	=	413.0	nM	6.38	Binding affinity at Dopamine receptor D2 in CHO cells by radioligand displacemen...	10602703
D(2) dopamine receptor	Ki	=	413.0	nM	6.38	Inhibition of human dopamine D2 receptor	28489950
D(2) dopamine receptor	Ki	=	413.0	nM	6.38	Binding affinity to human D2R assessed as inhibition constant	33422983
Alpha-1A adrenergic receptor	IC50	=	500.0	nM	6.3	Inhibition of [3H]- prazosin binding against Alpha-1A adrenergic receptor from r...	10602703
Alpha-2B adrenergic receptor	IC50	=	630.0	nM	6.2	Inhibition of [3H]- Yohimbine binding against rat kidney cortex Alpha-2B adrener...	10602703
D(3) dopamine receptor	Ki	=	679.0	nM	6.17	Binding affinity to human D3R assessed as inhibition constant	33422983

Literature References

PubMed	DOI	Target Context	# Activities
10602703	10.1021/jm990277d	Sigma non-opioid intracellular receptor 1	4
28489950	10.1021/acs.jmedchem.7b00151	Unchecked	3
10602703	10.1021/jm990277d	Rattus norvegicus	2
10602703	10.1021/jm990277d	Alpha-1A adrenergic receptor	2
10602703	10.1021/jm990277d	Alpha-1B adrenergic receptor	2
10602703	10.1021/jm990277d	Alpha-2A adrenergic receptor	2
10602703	10.1021/jm990277d	Alpha-2B adrenergic receptor	2
10602703	10.1021/jm990277d	5-hydroxytryptamine receptor 1A	2
10602703	10.1021/jm990277d	Serotonin 2 (5-HT2) receptor	2
10602703	10.1021/jm990277d	Muscarinic acetylcholine receptor M5	2
33422983	10.1016/j.ejmech.2020.113141	D(4) dopamine receptor	1
10602703	10.1021/jm990277d	D(4) dopamine receptor	1
28489950	10.1021/acs.jmedchem.7b00151	Alpha-1B adrenergic receptor	1
28489950	10.1021/acs.jmedchem.7b00151	Alpha-2B adrenergic receptor	1
28489950	10.1021/acs.jmedchem.7b00151	Alpha-2A adrenergic receptor	1
28489950	10.1021/acs.jmedchem.7b00151	5-hydroxytryptamine receptor 2A	1
28489950	10.1021/acs.jmedchem.7b00151	5-hydroxytryptamine receptor 1A	1
28489950	10.1021/acs.jmedchem.7b00151	D(3) dopamine receptor	1
28489950	10.1021/acs.jmedchem.7b00151	D(2) dopamine receptor	1
10602703	10.1021/jm990277d	D(2) dopamine receptor	1

Data from ChEMBL 36 via Core Engine