Compound Detail

CHEMBL496739

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Cc1cccc(N2CCN(CCCCNC(=O)c3cc4ccccc4o3)CC2)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL496739
Phase	Preclinical
Structure Type	MOL
InChI Key	DIJKUIXRAWOVGJ-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

391.5

MW (Da)

4.07

ALogP

HBA

HBD

48.7

PSA (Å²)

0.62

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C24H29N3O2
MW	391.52
Aromatic Rings	3
Heavy Atoms	29
NP-Likeness	-1.57

Activity Summary

Ki 22 meas. best 8.35

IC50 5 meas. best 6.84

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
D(2) dopamine receptor CHEMBL339	Ki	8.35	7.465	4.5	2
D(3) dopamine receptor CHEMBL234	Ki	8.35	8.35	4.5	2
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	8.22	8.22	6.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.92	7.92	11.9	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	7.92	7.92	11.9	2
Histamine H1 receptor CHEMBL3943	Ki	7.82	7.82	15.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.82	7.82	15.3	1
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	7.82	7.82	15.3	2
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	7.37	7.37	43.0	1
Unchecked CHEMBL612545	Ki	6.86	6.7467	138.0	3
D(3) dopamine receptor CHEMBL234	IC50	6.84	6.84	143.0	1
Unchecked CHEMBL612545	IC50	6.75	6.75	180.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.69	6.69	206.0	1
5-hydroxytryptamine receptor 2A CHEMBL322	IC50	6.64	6.64	230.0	1
D(1A) dopamine receptor CHEMBL265	Ki	6.58	6.03	263.0	2
D(2) dopamine receptor CHEMBL217	Ki	6.58	6.58	263.0	1
D(2) dopamine receptor CHEMBL217	IC50	6.23	6.07	584.0	2
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	6.03	6.03	930.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	128.0	ng.hr.mL-1	Mus musculus
Cmax	395.89	nM	Mus musculus
Tmax	0.5	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
D(3) dopamine receptor	Ki	=	4.5	nM	8.35	Displacement of [3H]7OH-DPAT from dopamine D3 receptor expressed in Sf9 cells by...	19072656
D(2) dopamine receptor	Ki	=	4.5	nM	8.35	Displacement of [3H]spiperone from dopamine D2 receptor in CRL:CD(SD)BR-COBS rat...	20481570
D(3) dopamine receptor	Ki	=	4.5	nM	8.35	Binding affinity to dopamine D3 receptor (unknown origin)	25343529
Adrenergic receptor alpha-1	Ki	=	6.0	nM	8.22	Displacement of [3H]prazosin from adrenergic alpha1 receptor in rat cerebral cor...	19072656
5-hydroxytryptamine receptor 1A	Ki	=	11.9	nM	7.92	Displacement of [3H]8OH-DPAT from 5HT1A receptor in CRL:CD(SD)BR-COBS rat hippoc...	19072656
5-hydroxytryptamine receptor 1A	Ki	=	11.9	nM	7.92	Displacement of [3H]8OH-DPAT from 5HT1A receptor in rat CRL:CD(SD)BR-COBS hippoc...	20481570
5-hydroxytryptamine receptor 1A	Ki	=	11.9	nM	7.92	Binding affinity to 5HT1A receptor (unknown origin)	25343529
5-hydroxytryptamine receptor 2A	Ki	=	15.3	nM	7.82	Binding affinity to 5HT2A receptor (unknown origin)	25343529
Histamine H1 receptor	Ki	=	15.0	nM	7.82	Displacement of [3H]pyrilamine from histamine H1 receptor in guinea pig cerebell...	19072656
5-hydroxytryptamine receptor 2A	Ki	=	15.3	nM	7.82	Displacement of [3H]ketanserin from 5HT2A receptor in CRL:CD(SD)BR-COBS rat cort...	19072656
5-hydroxytryptamine receptor 2A	Ki	=	15.3	nM	7.82	Displacement of [3H]ketanserin from 5HT2A receptor in CRL:CD(SD)BR-COBS rat cort...	20481570
Adrenergic receptor alpha-2	Ki	=	43.0	nM	7.37	Displacement of [3H]clonidine from adrenergic alpha2 receptor in rat cerebral co...	19072656
Unchecked	Ki	=	138.0	nM	6.86	Displacement of [3H]idazoxan from imidazole I2 receptor in rabbit kidney by filt...	19072656
D(3) dopamine receptor	IC50	=	143.0	nM	6.84	Antagonist activity at human dopamine D3 receptor expressed in CHO-K1 cells by [...	19072656
Unchecked	IC50	=	180.0	nM	6.75	Intrinsic activity at 5HT1A receptor in Duncan Hartley guinea pig ileum	19072656
Unchecked	Ki	=	206.0	nM	6.69	Displacement of [3H]mesulergine from 5HT2C receptor in CRL:(HA) BR albino guinea...	19072656
Unchecked	Ki	=	206.0	nM	6.69	Displacement of [3H]mesulergine from 5HT2C receptor in CRL:(HA) BR albino guinea...	20481570
5-hydroxytryptamine receptor 2C	Ki	=	206.0	nM	6.69	Binding affinity to 5HT2C receptor (unknown origin)	25343529
5-hydroxytryptamine receptor 2A	IC50	=	230.0	nM	6.64	Intrinsic activity at 5HT2A receptor in Wistar rat aorta	19072656
D(2) dopamine receptor	Ki	=	263.0	nM	6.58	Displacement of [3H]spiperone from dopamine D2 receptor in CRL:CD(SD)BR-COBS rat...	19072656

Literature References

PubMed	DOI	Target Context	# Activities
19072656	10.1021/jm800689g	Mus musculus	14
19072656	10.1021/jm800689g	Rattus norvegicus	5
20481570	10.1021/jm100294b	Mus musculus	5
19072656	10.1021/jm800689g	Unchecked	4
19072656	10.1021/jm800689g	D(2) dopamine receptor	3
19072656	10.1021/jm800689g	5-hydroxytryptamine receptor 2A	2
19072656	10.1021/jm800689g	D(3) dopamine receptor	2
25343529	10.1021/jm501119j	5-hydroxytryptamine receptor 2C	1
25343529	10.1021/jm501119j	D(2) dopamine receptor	1
20481570	10.1021/jm100294b	Voltage-gated inwardly rectifying potassium channel KCNH2	1
20481570	10.1021/jm100294b	Unchecked	1
20481570	10.1021/jm100294b	5-hydroxytryptamine receptor 2A	1
20481570	10.1021/jm100294b	5-hydroxytryptamine receptor 1A	1
20481570	10.1021/jm100294b	D(2) dopamine receptor	1
20481570	10.1021/jm100294b	D(1A) dopamine receptor	1
19072656	10.1021/jm800689g	Adrenergic receptor alpha-2	1
19072656	10.1021/jm800689g	Adrenergic receptor alpha-1	1
19072656	10.1021/jm800689g	D(1A) dopamine receptor	1
19072656	10.1021/jm800689g	5-hydroxytryptamine receptor 1A	1
19072656	10.1021/jm800689g	Voltage-gated inwardly rectifying potassium channel KCNH2	1

Data from ChEMBL 36 via Core Engine