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Compound Detail

CHEMBL303313

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CN1CCN([C@H]2Cc3ccccc3Sc3ccc(Cl)cc32)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL303313
Phase Preclinical
Structure Type MOL
InChI Key XRYLGRGAWQSVQW-KRWDZBQOSA-N
14
Targets
38
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

344.9
MW (Da)
4.34
ALogP
3
HBA
0
HBD
6.5
PSA (Ų)
0.76
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H21ClN2S
MW 344.91
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.77

Activity Summary

Ki 22 meas. best 10.12
IC50 16 meas. best 9.35

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-1D adrenergic receptor
CHEMBL326
 Ki 10.12 9.97 0.1 2
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 9.85 9.85 0.1 3
Alpha-1B adrenergic receptor
CHEMBL3122
 Ki 9.66 9.66 0.2 1
Alpha-1A adrenergic receptor
CHEMBL4892
 Ki 9.55 9.4 0.3 2
D(3) dopamine receptor
CHEMBL3138
 Ki 9.4 9.3933 0.4 3
D(2) dopamine receptor
CHEMBL339
 Ki 9.4 9.4 0.4 3
Adrenergic receptor alpha-1
CHEMBL1907610
 IC50 9.35 9.35 0.5 2
5-hydroxytryptamine receptor 2A
CHEMBL322
 IC50 9.32 9.32 0.5 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 IC50 9.32 9.32 0.5 2
Rattus norvegicus
CHEMBL376
 IC50 9.02 7.1267 1.0 3
D(2) dopamine receptor
CHEMBL217
 Ki 8.96 8.96 1.1 1
D(2) dopamine receptor
CHEMBL339
 IC50 8.89 8.782 1.3 5
D(4) dopamine receptor
CHEMBL219
 Ki 8.82 8.82 1.5 1
D(1A) dopamine receptor
CHEMBL265
 Ki 8.72 8.7167 1.9 3
D(1A) dopamine receptor
CHEMBL265
 IC50 8.66 8.66 2.2 3
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 8.54 8.54 2.9 1
Histamine H1 receptor
CHEMBL231
 Ki 7.82 7.82 15.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-1D adrenergic receptor Ki = 0.076 nM 10.12 Displacement of [3H]prozosin from rat cloned alpha1d receptor 20857909
5-hydroxytryptamine receptor 2A Ki = 0.14 nM 9.85 In vitro binding affinity towards 5-hydroxytryptamine 2A receptor in rat tissue ... 14695828
5-hydroxytryptamine receptor 2A Ki = 0.1413 nM 9.85 Half-maximal inhibition of [3H]- Ketanserin binding to 5-hydroxytryptamine 2A re... 11784139
5-hydroxytryptamine receptor 2A Ki = 0.14 nM 9.85 Half-maximal inhibition of [3H]ketanserin binding to 5-hydroxytryptamine 2A rece... 11784139
Alpha-1D adrenergic receptor Ki = 0.15 nM 9.82 Displacement of [3H]prazosin (0.3 nM) from rat Alpha-1D adrenergic receptor expr... 12519065
Alpha-1B adrenergic receptor Ki = 0.22 nM 9.66 Displacement of [3H]prazosin (0.5 nM) from hamster Alpha-1B adrenergic receptor ... 12519065
Alpha-1A adrenergic receptor Ki = 0.28 nM 9.55 Displacement of [3H]prozosin from bovine cloned Alpha-1A receptor expressed in B... 20857909
D(3) dopamine receptor Ki = 0.4 nM 9.4 In vitro binding affinity towards Dopamine receptor D3 in Sf9 cell membranes usi... 14695828
D(2) dopamine receptor Ki = 0.4 nM 9.4 In vitro binding affinity towards Dopamine receptor D2 in rat tissue homogenate ... 14695828
D(2) dopamine receptor Ki = 0.3981 nM 9.4 Half-maximal inhibition of [3H]spiperone binding to Dopamine receptor D2 in rat ... 11784139
D(3) dopamine receptor Ki = 0.4 nM 9.4 Half-maximal inhibition of [3H]-7-OH-DPAT binding to Dopamine receptor D3 in rat... 11784139
D(2) dopamine receptor Ki = 0.4 nM 9.4 Half-maximal inhibition of [3H]spiperone binding to Dopamine receptor D2 in rat ... 11784139
D(3) dopamine receptor Ki = 0.4169 nM 9.38 Half-maximal inhibition of [3H]7-OH-DPAT binding to Dopamine receptor D3 in rat ... 11784139
Adrenergic receptor alpha-1 IC50 = 0.45 nM 9.35 Ability to displace [3H]prazosin (0.25 nM) from whole brain of rat Alpha-1 adren... 12519065
Adrenergic receptor alpha-1 IC50 = 0.45 nM 9.35 Ability to inhibit binding of [3H]PRAZ to alpha-1 adrenergic receptor in rat bra... 1676758
5-hydroxytryptamine receptor 2A IC50 = 0.48 nM 9.32 Ability to displace [3H]ketanserin (0.5 nM) from cerebral cortex of rat 5-hydrox... 12519065
Serotonin 2 (5-HT2) receptor IC50 = 0.48 nM 9.32 Binding affinity at serotonin 5-hydroxytryptamine 2 receptor by [3H]ketanserin d... 8151622
Serotonin 2 (5-HT2) receptor IC50 = 0.48 nM 9.32 Ability to inhibit binding of [3H]KET to 5-hydroxytryptamine 2 receptor in rat c... 1676758
Alpha-1A adrenergic receptor Ki = 0.56 nM 9.25 Displacement of [3H]prazosin (0.3 nM) from bovine Alpha-1A adrenergic receptor e... 12519065
Rattus norvegicus IC50 = 0.96 nM 9.02 In vitro inhibition of the accumulation of [3H]-NE into rat brain synaptosomes 1676758

Literature References

PubMed DOI Target Context # Activities
1676758 10.1021/jm00111a015 Rattus norvegicus 9
11784139 10.1021/jm010982y 5-hydroxytryptamine receptor 2A 2
11784139 10.1021/jm010982y D(1A) dopamine receptor 2
11784139 10.1021/jm010982y D(2) dopamine receptor 2
11784139 10.1021/jm010982y D(3) dopamine receptor 2
20857909 10.1021/jm100652h Histamine H1 receptor 1
2892932 10.1021/jm00397a006 D(2) dopamine receptor 1
1676758 10.1021/jm00111a015 Mus musculus 1
1676758 10.1021/jm00111a015 Adrenergic receptor alpha-1 1
1676758 10.1021/jm00111a015 Serotonin 2 (5-HT2) receptor 1
1676758 10.1021/jm00111a015 D(2) dopamine receptor 1
1676758 10.1021/jm00111a015 D(1A) dopamine receptor 1
14695828 10.1021/jm0309811 ADMET 1
14695828 10.1021/jm0309811 Dopamine D2 receptor and Serotonin 2a receptor (D2 and 5HT2a) 1
14695828 10.1021/jm0309811 D(3) dopamine receptor 1
14695828 10.1021/jm0309811 D(2) dopamine receptor 1
14695828 10.1021/jm0309811 D(1A) dopamine receptor 1
14695828 10.1021/jm0309811 5-hydroxytryptamine receptor 2A 1
11784139 10.1021/jm010982y Unchecked 1
11784139 10.1021/jm010982y Dopamine receptors; D1 & D2 1

Data from ChEMBL 36 via Core Engine