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Compound Detail

CHEMBL4084262

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COc1ccccc1N1CCC2(CCN(CCCSc3nnc(-c4ccccc4)n3C)CC2)CC1

Basic Information

ChEMBL ID CHEMBL4084262
Phase Preclinical
Structure Type MOL
InChI Key KVHHUZUNLIGTBY-UHFFFAOYSA-N
16
Targets
22
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

491.7
MW (Da)
5.36
ALogP
7
HBA
0
HBD
46.4
PSA (Ų)
0.31
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H37N5OS
MW 491.71
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -1.59

Activity Summary

Ki 20 meas. best 8.1
IC50 2 meas. best 7.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Ki 8.1 8.1 8.0 1
D(3) dopamine receptor
CHEMBL234
Ki 7.92 7.6233 12.0 3
D(3) dopamine receptor
CHEMBL234
IC50 7.38 7.38 41.4 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 7.28 7.28 52.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.53 6.53 295.0 1
Histamine H3 receptor
CHEMBL264
Ki 6.29 6.29 509.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 6.29 6.29 514.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.23 6.23 590.0 1
Histamine H2 receptor
CHEMBL1941
Ki 6.22 6.22 596.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 6.03 6.03 931.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 6.03 5.96 931.0 2
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 5.81 5.81 1557.0 1
D(2) dopamine receptor
CHEMBL217
IC50 5.79 5.79 1616.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.67 5.67 2144.0 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 5.66 5.66 2178.0 1
Alpha-1B adrenergic receptor
CHEMBL232
Ki 5.66 5.66 2173.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
Ki 5.07 5.07 8523.0 1
D(2) dopamine receptor
CHEMBL217
Ki 4.96 4.96 10895.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Ki = 8.0 nM 8.1 Displacement of [3H]-pyrilamine from recombinant human H1 receptor stably expres... 31021617
D(3) dopamine receptor Ki = 12.0 nM 7.92 Displacement of [125I]ABN from human dopamine D3 receptor expressed in HEK293 ce... 29125762
D(3) dopamine receptor Ki = 12.0 nM 7.92 Displacement of [125I]IABN from recombinant human D3 receptor stably expressed i... 31021617
D(3) dopamine receptor IC50 = 41.4 nM 7.38 Antagonist activity at recombinant human D3 receptor expressed in CHOK1 cells as... 31021617
Muscarinic acetylcholine receptor M2 Ki = 52.0 nM 7.28 Displacement of [3H]-QNB/[3H]-NMS from human muscarinic M2 receptor expressed in... 31021617
D(3) dopamine receptor Ki = 94.0 nM 7.03 Displacement of [3H]N-methylspiperone from D3 receptor (unknown origin) measured... 31021617
Sodium-dependent serotonin transporter Ki = 295.0 nM 6.53 Displacement of [3H]-citalopram from recombinant human SERT stably expressed in ... 31021617
Histamine H3 receptor Ki = 509.0 nM 6.29 Displacement of [3H]-alpha-methylhistamine from human histamine H3 receptor stab... 31021617
Muscarinic acetylcholine receptor M3 Ki = 514.0 nM 6.29 Displacement of [3H]-QNB/[3H]-NMS from human muscarinic M3 receptor expressed in... 31021617
Muscarinic acetylcholine receptor M4 Ki = 590.0 nM 6.23 Displacement of [3H]-QNB/[3H]-NMS from human muscarinic M4 receptor expressed in... 31021617
Histamine H2 receptor Ki = 596.0 nM 6.22 Displacement of [125I]-Iodo-aminopotentidine from human histamine H2 receptor ex... 31021617
5-hydroxytryptamine receptor 1A Ki = 931.0 nM 6.03 Displacement of [3H]8-OH-DPAT from human 5-HT1A receptor expressed in CHO-K1 cel... 29125762
Sodium-dependent noradrenaline transporter Ki = 931.0 nM 6.03 Displacement of [3H]-nisoxetine from recombinant human NET stably expressed in H... 31021617
5-hydroxytryptamine receptor 1A Ki = 1297.0 nM 5.89 Displacement of [3H]-Way100635 from recombinant human 5HT1A receptor transiently... 31021617
Alpha-2C adrenergic receptor Ki = 1557.0 nM 5.81 Displacement of [3H]-rauwolscine from recombinant human alpha2C adrenergic recep... 31021617
D(2) dopamine receptor IC50 = 1616.0 nM 5.79 Antagonist activity at recombinant human D2 receptor expressed in CHOK1 cells as... 31021617
5-hydroxytryptamine receptor 2B Ki = 2144.0 nM 5.67 Displacement of [3H]-LSD from recombinant human 5HT2B receptor stably expressed ... 31021617
Alpha-1A adrenergic receptor Ki = 2178.0 nM 5.66 Displacement of [3H]-prazosin from recombinant human alpha1A adrenergic receptor... 31021617
Alpha-1B adrenergic receptor Ki = 2173.0 nM 5.66 Displacement of [3H]-prazosin from recombinant human alpha1B adrenergic receptor... 31021617
Neuronal acetylcholine receptor; alpha3/beta4 Ki = 8523.0 nM 5.07 Displacement of [3H]-epibatidine from recombinant human alpha3beta4 nACHR stably... 31021617

Literature References

PubMed DOI Target Context # Activities
31021617 10.1021/acs.jmedchem.9b00412 D(3) dopamine receptor 4
31021617 10.1021/acs.jmedchem.9b00412 D(2) dopamine receptor 4
29125762 10.1021/acs.jmedchem.7b01248 D(3) dopamine receptor 2
31021617 10.1021/acs.jmedchem.9b00412 Unchecked 2
31021617 10.1021/acs.jmedchem.9b00412 D(1A) dopamine receptor 2
31021617 10.1021/acs.jmedchem.9b00412 GABA-A receptor; anion channel 1
29125762 10.1021/acs.jmedchem.7b01248 D(2) dopamine receptor 1
31021617 10.1021/acs.jmedchem.9b00412 5-hydroxytryptamine receptor 3A 1
31021617 10.1021/acs.jmedchem.9b00412 5-hydroxytryptamine receptor 2C 1
31021617 10.1021/acs.jmedchem.9b00412 5-hydroxytryptamine receptor 2B 1
31021617 10.1021/acs.jmedchem.9b00412 5-hydroxytryptamine receptor 2A 1
31021617 10.1021/acs.jmedchem.9b00412 5-hydroxytryptamine receptor 1E 1
31021617 10.1021/acs.jmedchem.9b00412 5-hydroxytryptamine receptor 1D 1
31021617 10.1021/acs.jmedchem.9b00412 5-hydroxytryptamine receptor 1B 1
31021617 10.1021/acs.jmedchem.9b00412 5-hydroxytryptamine receptor 1A 1
31021617 10.1021/acs.jmedchem.9b00412 D(1B) dopamine receptor 1
31021617 10.1021/acs.jmedchem.9b00412 D(4) dopamine receptor 1
29125762 10.1021/acs.jmedchem.7b01248 5-hydroxytryptamine receptor 2C 1
29125762 10.1021/acs.jmedchem.7b01248 5-hydroxytryptamine receptor 2A 1
29125762 10.1021/acs.jmedchem.7b01248 5-hydroxytryptamine receptor 1A 1

Data from ChEMBL 36 via Core Engine