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Compound Detail

CHEMBL540612

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COc1ccccc1N1CCN(CCCCNC(=O)c2ccc3ccccc3c2)CC1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL540612
Phase Preclinical
Structure Type MOL
InChI Key KFWJGUZIZAPFMX-UHFFFAOYSA-N
Parent Compound CHEMBL25236
Active Moiety CHEMBL25236
32
Targets
53
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

417.6
MW (Da)
4.18
ALogP
4
HBA
1
HBD
44.8
PSA (Ų)
0.56
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 C26H32ClN3O2
MW 454.01
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.24

Activity Summary

Ki 42 meas. best 9.05
IC50 8 meas. best 9.39
EC50 3 meas. best 8.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(3) dopamine receptor
CHEMBL3138
 IC50 9.39 9.265 0.4 2
D(3) dopamine receptor
CHEMBL234
 Ki 9.05 8.775 0.9 4
Dopamine receptor D2 and D3
CHEMBL2111342
 IC50 8.99 8.275 1.0 2
D(3) dopamine receptor
CHEMBL3138
 Ki 8.92 8.92 1.2 1
D(3) dopamine receptor
CHEMBL234
 EC50 8.57 8.57 2.7 1
Adrenergic receptor alpha-1
CHEMBL2094251
 Ki 8.3 8.3 5.0 1
Alpha-1A adrenergic receptor
CHEMBL229
 Ki 7.98 7.98 10.5 1
D(3) dopamine receptor
CHEMBL234
 IC50 7.89 7.89 13.0 1
D(2) dopamine receptor
CHEMBL339
 IC50 7.62 7.585 24.2 2
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 7.53 7.53 29.8 1
D(4) dopamine receptor
CHEMBL219
 Ki 7.36 6.7667 44.0 3
D(4) dopamine receptor
CHEMBL219
 EC50 7.31 7.31 49.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.25 7.17 56.2 2
D(2) dopamine receptor
CHEMBL217
 Ki 7.21 6.804 61.0 5
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 7.08 7.08 83.6 1
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 6.95 6.95 113.0 1
Histamine H1 receptor
CHEMBL231
 Ki 6.9 6.9 125.3 1
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 6.88 6.88 131.7 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
 Ki 6.78 6.78 166.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 6.66 6.445 218.0 2
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 6.6 6.6 253.3 1
Mu-type opioid receptor
CHEMBL233
 Ki 6.6 6.6 249.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 6.59 6.59 255.5 1
Alpha-1B adrenergic receptor
CHEMBL232
 Ki 6.57 6.57 268.8 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 6.52 6.52 303.9 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 6.38 6.165 412.0 2
D(2) dopamine receptor
CHEMBL339
 Ki 6.33 6.33 468.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 6.13 6.13 733.7 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
 Ki 6.12 6.12 754.4 1
D(1A) dopamine receptor
CHEMBL5067
 Ki 6.12 6.12 760.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2095200
 Ki 6.08 6.08 840.0 1
Unchecked
CHEMBL612545
 Ki 5.98 5.98 1042.0 1
Translocator protein
CHEMBL5742
 Ki 5.93 5.93 1179.9 1
D(1B) dopamine receptor
CHEMBL1850
 Ki 5.91 5.795 1223.0 2
Free fatty acid receptor 4
CHEMBL5339
 EC50 5.83 5.83 1479.7 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 5.78 5.78 1672.8 1
SARS-CoV-2
CHEMBL4303835
 IC50 4.72 4.72 18950.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(3) dopamine receptor IC50 = 0.41 nM 9.39 Displacement of [3H]nemonapride from Rattus norvegicus (rat) wild type dopamine ... -
D(3) dopamine receptor IC50 = 0.72 nM 9.14 Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D... -
D(3) dopamine receptor Ki = 0.9 nM 9.05 Displacement of [125I]ABN from human dopamine D3 receptor expressed in HEK293 ce... 23618707
Dopamine receptor D2 and D3 IC50 = 1.02 nM 8.99 Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D... -
D(3) dopamine receptor Ki = 1.2 nM 8.92 Displacement of [3H]R-(+)-7-OHDPAT from dopamine D3 receptor in Sprague-Dawley r... 24848155
D(3) dopamine receptor Ki = 1.3 nM 8.89 Inhibition of [3H]spiperone binding to human dopamine receptor D3 expressed in C... 15916420
D(3) dopamine receptor Ki = 2.213 nM 8.65 PDSP Secondary Binding target: DRD3 - Compounds are tested at 10 uM concentratio... -
D(3) dopamine receptor EC50 = 2.7 nM 8.57 Effective concentration in [3H]thymidine uptake assay by CHO dhfr- mutant cells ... 15916420
D(3) dopamine receptor Ki = 3.1 nM 8.51 Displacement of [3H]-N-methylspiperone from recombinant human D3 receptor (unkno... 32282200
Adrenergic receptor alpha-1 Ki = 5.0 nM 8.3 Inhibition of [3H]prazosin binding to porcine adrenergic receptor alpha1 15916420
Alpha-1A adrenergic receptor Ki = 10.48 nM 7.98 PDSP Secondary Binding target: ADRA1A - Compounds are tested at 10 uM concentrat... -
D(3) dopamine receptor IC50 = 13.0 nM 7.89 Antagonist activity at human dopamine D3 receptor expressed in human U2OS cells ... 24848155
D(2) dopamine receptor IC50 = 24.2 nM 7.62 Displacement of [3H]nemonapride from Rattus norvegicus (rat) wild type dopamine ... -
Dopamine receptor D2 and D3 IC50 = 27.5 nM 7.56 Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D... -
D(2) dopamine receptor IC50 = 28.3 nM 7.55 Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D... -
5-hydroxytryptamine receptor 7 Ki = 29.83 nM 7.53 PDSP Secondary Binding target: HTR7 - Compounds are tested at 10 uM concentratio... -
D(4) dopamine receptor Ki = 44.0 nM 7.36 Inhibition of [3H]spiperone binding to human dopamine receptor D4.4 expressed in... 15916420
D(4) dopamine receptor EC50 = 49.0 nM 7.31 Effective concentration from [3H]thymidine uptake assay in CHO10001 cells expres... 15916420
5-hydroxytryptamine receptor 1A Ki = 56.16 nM 7.25 PDSP Secondary Binding target: HTR1A - Compounds are tested at 10 uM concentrati... -
D(2) dopamine receptor Ki = 61.0 nM 7.21 Displacement of [125I]ABN from human dopamine D2L receptor expressed in HEK293 c... 23618707

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5724801 Fibroblast 304
- 10.6019/CHEMBL5058577 HEK-293T 304
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5058564 Fibroblast 10
- 10.6019/CHEMBL5058564 U2OS 9
- 10.6019/CHEMBL5058564 HEK-293T 9
15916420 10.1021/jm050170s D(4) dopamine receptor 5
32282200 10.1021/acs.jmedchem.9b01835 Unchecked 5
15916420 10.1021/jm050170s D(3) dopamine receptor 3
24848155 10.1021/jm401798r D(3) dopamine receptor 3
24848155 10.1021/jm401798r Unchecked 3
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 2
- 10.1007/s00044-004-0006-x D(2) dopamine receptor 2
- 10.1007/s00044-004-0006-x Dopamine receptor D2 and D3 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 2
22871578 10.1016/j.bmcl.2012.07.003 Unchecked 2
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 2

Data from ChEMBL 36 via Core Engine