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Compound Detail

CHEMBL5400876

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c1ccc(N2CCN(CCCc3nc4ccccc4s3)CC2)nc1

Basic Information

ChEMBL ID CHEMBL5400876
Phase Preclinical
Structure Type MOL
InChI Key KZVXSSLUUGFVFR-UHFFFAOYSA-N
24
Targets
37
Activities
3
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

338.5
MW (Da)
3.45
ALogP
5
HBA
0
HBD
32.3
PSA (Ų)
0.71
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H22N4S
MW 338.48
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -2.57

Activity Summary

Ki 26 meas. best 8.66
IC50 6 meas. best 7.59
EC50 5 meas. best 7.97

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(4) dopamine receptor
CHEMBL219
Ki 8.66 8.34 2.2 2
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 8.24 8.24 5.8 1
D(4) dopamine receptor
CHEMBL219
EC50 7.97 7.97 10.6 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.89 7.89 13.0 1
D(4) dopamine receptor
CHEMBL219
IC50 7.59 7.375 25.6 2
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 7.34 7.34 46.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.14 7.14 72.0 1
Sigma intracellular receptor 2
CHEMBL4105907
Ki 7.14 7.14 72.7 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 6.97 6.97 107.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
Ki 6.6 6.6 252.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.45 6.45 358.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.45 6.45 356.0 1
Alpha-1B adrenergic receptor
CHEMBL232
Ki 6.4 6.4 397.0 1
Histamine H1 receptor
CHEMBL231
Ki 6.37 6.37 431.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.27 6.27 532.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.23 6.085 584.0 2
Alpha-1A adrenergic receptor
CHEMBL229
Ki 6.23 6.23 586.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 6.2 6.2 634.0 1
D(2) dopamine receptor
CHEMBL217
EC50 5.96 5.96 1110.0 1
Mu-type opioid receptor
CHEMBL233
Ki 5.9 5.9 1265.0 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
Ki 5.85 5.85 1423.0 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
Ki 5.64 5.64 2266.0 1
5-hydroxytryptamine receptor 1E
CHEMBL2182
Ki 5.56 5.56 2764.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 5.56 5.56 2736.0 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
Ki 5.54 5.54 2859.0 1
D(2) dopamine receptor
CHEMBL217
Ki 5.53 5.53 2930.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.45 5.45 3545.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 5.37 5.37 4262.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
EC50 5.34 5.34 4600.0 1
D(3) dopamine receptor
CHEMBL234
EC50 5.25 5.25 5560.0 1
D(2) dopamine receptor
CHEMBL217
IC50 5.17 5.085 6690.0 2
D(3) dopamine receptor
CHEMBL234
IC50 4.66 4.66 22000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 355.4 ng.hr.mL-1 Rattus norvegicus
AUC 1242.22 ng.hr.mL-1 Rattus norvegicus
Cmax 1450.0 nM Rattus norvegicus
Cmax 4520.0 nM Rattus norvegicus
T1/2 0.82 hr Rattus norvegicus
T1/2 1.09 hr Rattus norvegicus
Tmax 0.25 hr Rattus norvegicus
Tmax 0.25 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(4) dopamine receptor Ki = 2.2 nM 8.66 Displacement of [3H]N-methylspiperone from human D4 receptor stably expressed in... 37646374
5-hydroxytryptamine receptor 1A Ki = 5.8 nM 8.24 Binding affinity to 5-HT1A (unknown origin) assessed as inhibition constant 37646374
D(4) dopamine receptor Ki = 9.48 nM 8.02 Binding affinity to D4 receptor (unknown origin) assessed as inhibition constant 37646374
D(4) dopamine receptor EC50 = 10.6 nM 7.97 Agonist activity at human D4 receptor stably expressed in CHO-K1 cells assessed ... 37646374
5-hydroxytryptamine receptor 2B Ki = 13.0 nM 7.89 Binding affinity to 5-HT2B (unknown origin) assessed as inhibition constant 37646374
D(4) dopamine receptor IC50 = 25.6 nM 7.59 Antagonist activity at human D4 receptor stably expressed in CHO-K1 cells assess... 37646374
5-hydroxytryptamine receptor 2A Ki = 46.0 nM 7.34 Binding affinity to 5-HT2A (unknown origin) assessed as inhibition constant 37646374
D(4) dopamine receptor IC50 = 69.3 nM 7.16 Antagonist activity at human D4 receptor stably expressed in CHO-K1 cells assess... 37646374
Sigma intracellular receptor 2 Ki = 72.7 nM 7.14 Binding affinity to sigma 2 (unknown origin) assessed as inhibition constant 37646374
Alpha-2C adrenergic receptor Ki = 72.0 nM 7.14 Binding affinity to alpha2C adrenergic receptor (unknown origin) assessed as inh... 37646374
5-hydroxytryptamine receptor 7 Ki = 107.0 nM 6.97 Binding affinity to 5-HT7 (unknown origin) assessed as inhibition constant 37646374
Sigma non-opioid intracellular receptor 1 Ki = 252.0 nM 6.6 Binding affinity to guinea pig sigma 1 assessed as inhibition constant 37646374
Alpha-2B adrenergic receptor Ki = 358.0 nM 6.45 Binding affinity to alpha2B adrenergic receptor (unknown origin) assessed as inh... 37646374
Alpha-2A adrenergic receptor Ki = 356.0 nM 6.45 Binding affinity to alpha2A adrenergic receptor (unknown origin) assessed as inh... 37646374
Alpha-1B adrenergic receptor Ki = 397.0 nM 6.4 Binding affinity to alpha1B adrenergic receptor (unknown origin) assessed as inh... 37646374
Histamine H1 receptor Ki = 431.0 nM 6.37 Binding affinity to H1 receptor (unknown origin) assessed as inhibition constant 37646374
5-hydroxytryptamine receptor 2B IC50 = 532.0 nM 6.27 Antagonist activity at 5-HT2B receptor (unknown origin) by calcium flux assay 37646374
Alpha-1A adrenergic receptor Ki = 586.0 nM 6.23 Binding affinity to alpha1A adrenergic receptor (unknown origin) assessed as inh... 37646374
D(3) dopamine receptor Ki = 584.0 nM 6.23 Binding affinity to D3 receptor (unknown origin) assessed as inhibition constant 37646374
Sodium-dependent noradrenaline transporter Ki = 634.0 nM 6.2 Binding affinity to NET (unknown origin) assessed as inhibition constant 37646374

Literature References

PubMed DOI Target Context # Activities
37646374 10.1021/acs.jmedchem.3c00734 ADMET 13
37646374 10.1021/acs.jmedchem.3c00734 D(4) dopamine receptor 12
37646374 10.1021/acs.jmedchem.3c00734 Unchecked 12
37646374 10.1021/acs.jmedchem.3c00734 D(2) dopamine receptor 10
37646374 10.1021/acs.jmedchem.3c00734 D(3) dopamine receptor 7
37646374 10.1021/acs.jmedchem.3c00734 5-hydroxytryptamine receptor 2A 6
37646374 10.1021/acs.jmedchem.3c00734 5-hydroxytryptamine receptor 2B 6
37646374 10.1021/acs.jmedchem.3c00734 5-hydroxytryptamine receptor 1A 4
37646374 10.1021/acs.jmedchem.3c00734 Alpha-1A adrenergic receptor 2
37646374 10.1021/acs.jmedchem.3c00734 Alpha-1B adrenergic receptor 2
37646374 10.1021/acs.jmedchem.3c00734 Mu-type opioid receptor 2
37646374 10.1021/acs.jmedchem.3c00734 5-hydroxytryptamine receptor 7 2
37646374 10.1021/acs.jmedchem.3c00734 Alpha-1D adrenergic receptor 2
37646374 10.1021/acs.jmedchem.3c00734 Alpha-2A adrenergic receptor 2
37646374 10.1021/acs.jmedchem.3c00734 5-hydroxytryptamine receptor 5A 2
37646374 10.1021/acs.jmedchem.3c00734 5-hydroxytryptamine receptor 2C 2
37646374 10.1021/acs.jmedchem.3c00734 5-hydroxytryptamine receptor 1E 2
37646374 10.1021/acs.jmedchem.3c00734 5-hydroxytryptamine receptor 1D 2
37646374 10.1021/acs.jmedchem.3c00734 5-hydroxytryptamine receptor 1B 2
37646374 10.1021/acs.jmedchem.3c00734 D(1A) dopamine receptor 2

Data from ChEMBL 36 via Core Engine