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Compound Detail

CHEMBL124444

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COc1ccccc1N1CCN(CCCCNC(=O)c2cc3ccccc3o2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL124444
Phase Preclinical
Structure Type MOL
InChI Key SIIDHHZTVIEQJK-UHFFFAOYSA-N
15
Targets
28
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

407.5
MW (Da)
3.77
ALogP
5
HBA
1
HBD
58.0
PSA (Ų)
0.58
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H29N3O3
MW 407.51
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.35

Activity Summary

Ki 25 meas. best 9.04
IC50 2 meas. best 8.62
EC50 1 meas. best 8.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(3) dopamine receptor
CHEMBL234
 Ki 9.04 8.9775 0.9 4
D(3) dopamine receptor
CHEMBL234
 EC50 8.82 8.82 1.5 1
D(3) dopamine receptor
CHEMBL3138
 Ki 8.8 8.8 1.6 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 8.67 8.67 2.1 1
D(3) dopamine receptor
CHEMBL234
 IC50 8.62 8.62 2.4 1
Unchecked
CHEMBL612545
 IC50 8.09 8.09 8.2 1
Adrenergic receptor alpha-1
CHEMBL2094251
 Ki 8.07 8.07 8.6 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.77 7.77 17.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 7.52 7.52 30.0 3
Alpha-1A adrenergic receptor
CHEMBL319
 Ki 7.44 7.44 36.0 1
Unchecked
CHEMBL612545
 Ki 7.44 7.44 36.5 1
Alpha-2A adrenergic receptor
CHEMBL327
 Ki 7.27 7.27 54.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 7.08 6.946 84.0 5
D(2) dopamine receptor
CHEMBL339
 Ki 7.06 7.06 87.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2095200
 Ki 6.18 6.18 660.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.96 5.96 1100.0 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 5.96 5.83 1100.0 2
D(1A) dopamine receptor
CHEMBL265
 Ki 5.59 5.59 2565.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(3) dopamine receptor Ki = 0.92 nM 9.04 Displacement of [125]IABN from human D3 receptor expressed in HEK293 cells 19331412
D(3) dopamine receptor Ki = 1.1 nM 8.96 Binding affinity for human Dopamine receptor D3 by [3H]- spiperone displacement. 12361386
D(3) dopamine receptor Ki = 1.1 nM 8.96 Binding affinity for human dopamine receptor D3 15689154
D(3) dopamine receptor Ki = 1.122 nM 8.95 Displacement of [3H]spiperone from human dopamine D3 expressed in CHO cell membr... 17266201
D(3) dopamine receptor EC50 = 1.5 nM 8.82 Intrinsic activity in mitogenesis assay using Dopamine receptor D3 expressing CH... 12361386
D(3) dopamine receptor Ki = 1.6 nM 8.8 Binding affinity for rat striatum Dopamine receptor D3 (sf9 cells) by [3H]7-OH-D... 12930145
5-hydroxytryptamine receptor 1A Ki = 2.14 nM 8.67 Binding affinity for rat hippocampus 5-hydroxytryptamine 1A receptor by inhibiti... 12930145
D(3) dopamine receptor IC50 = 2.39 nM 8.62 Antagonist activity at human D3 receptor expressed in HEK293 cells assessed as i... 19331412
Unchecked IC50 = 8.2 nM 8.09 Antagonist activity at human D2 like receptor expressed in HEK293 cells assessed... 19331412
Adrenergic receptor alpha-1 Ki = 8.6 nM 8.07 Displacement of [3H]- ketanserin from porcine Alpha-1 adrenergic receptor 12361386
5-hydroxytryptamine receptor 1A Ki = 17.0 nM 7.77 Displacement of [3H]- 8-OH-DPAT from porcine 5-hydroxytryptamine 1A receptor 12361386
D(4) dopamine receptor Ki = 30.0 nM 7.52 Binding affinity for human Dopamine receptor D4 by [3H]- spiperone displacement. 12361386
D(4) dopamine receptor Ki = 30.0 nM 7.52 Binding affinity for Dopamine receptor D4 15689154
D(4) dopamine receptor Ki = 30.2 nM 7.52 Displacement of [3H]spiperone from human dopamine D4.4 expressed in CHO cell mem... 17266201
Alpha-1A adrenergic receptor Ki = 36.0 nM 7.44 Binding affinity for rat cortex alpha-1 adrenergic receptor by inhibition of [3H... 12930145
Unchecked Ki = 36.5 nM 7.44 Displacement of [125]IABN from human cloned D2 like receptor expressed in HEK293... 19331412
Alpha-2A adrenergic receptor Ki = 54.0 nM 7.27 Binding affinity for rat cortex Alpha-2 adrenergic receptor was determined using... 12930145
D(2) dopamine receptor Ki = 84.0 nM 7.08 Binding affinity for human Dopamine receptor D2 (short) by [3H]- spiperone displ... 12361386
D(2) dopamine receptor Ki = 87.0 nM 7.06 Binding affinity for rat striatum Dopamine receptor D2 by [3H]spiperone displace... 12930145
D(2) dopamine receptor Ki = 110.0 nM 6.96 Binding affinity for human Dopamine receptor D2 (long) by [3H]- spiperone displa... 12361386

Literature References

PubMed DOI Target Context # Activities
12361386 10.1021/jm025558r D(3) dopamine receptor 3
19331412 10.1021/jm900095y Unchecked 3
12361386 10.1021/jm025558r D(2) dopamine receptor 2
19331412 10.1021/jm900095y D(3) dopamine receptor 2
12361386 10.1021/jm025558r Dopamine receptors; D2 & D3 2
12361386 10.1021/jm025558r Serotonin 2 (5-HT2) receptor 1
12361386 10.1021/jm025558r Adrenergic receptor alpha-1 1
12361386 10.1021/jm025558r 5-hydroxytryptamine receptor 1A 1
12361386 10.1021/jm025558r Dopamine receptors; D3 & D4 1
12930145 10.1021/jm0211220 D(1A) dopamine receptor 1
12930145 10.1021/jm0211220 D(2) dopamine receptor 1
12930145 10.1021/jm0211220 D(3) dopamine receptor 1
12930145 10.1021/jm0211220 5-hydroxytryptamine receptor 1A 1
12930145 10.1021/jm0211220 Alpha-1A adrenergic receptor 1
12930145 10.1021/jm0211220 Alpha-2A adrenergic receptor 1
12930145 10.1021/jm0211220 Dopamine receptors; D2 & D3 1
26299826 10.1016/j.bmc.2015.07.050 5-hydroxytryptamine receptor 2A 1
15689154 10.1021/jm049612a D(3) dopamine receptor 1
15689154 10.1021/jm049612a D(4) dopamine receptor 1
12361386 10.1021/jm025558r D(4) dopamine receptor 1

Data from ChEMBL 36 via Core Engine