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Compound Detail

CHEMBL4867565

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O=S(=O)(c1cccc(F)c1)n1ccc2c(N3CCNCC3)nc3ccccc3c21

Basic Information

ChEMBL ID CHEMBL4867565
Phase Preclinical
Structure Type MOL
InChI Key QNKGTIWNFNPEJL-UHFFFAOYSA-N
26
Targets
30
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

410.5
MW (Da)
2.98
ALogP
6
HBA
1
HBD
67.2
PSA (Ų)
0.56
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H19FN4O2S
MW 410.47
Aromatic Rings 4
Heavy Atoms 29
NP-Likeness -1.54

Activity Summary

Ki 26 meas. best 9.03
IC50 4 meas. best 7.17

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 3A
CHEMBL1899
Ki 9.03 9.03 0.9 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 8.52 8.52 3.0 1
5-hydroxytryptamine receptor 3A
CHEMBL1899
IC50 7.17 7.17 67.6 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.96 6.96 110.0 1
Beta-1 adrenergic receptor
CHEMBL213
Ki 6.77 6.77 170.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.77 6.77 170.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.68 6.68 210.0 1
Histamine H1 receptor
CHEMBL231
Ki 6.66 6.66 220.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 6.36 6.36 437.0 1
Unchecked
CHEMBL612545
Ki 6.3 6.075 500.0 4
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.08 6.08 830.0 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
Ki 6.05 6.05 890.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
Ki 6.03 6.03 940.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.96 5.96 1090.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.91 5.91 1240.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 5.71 5.71 1940.0 1
Mu-type opioid receptor
CHEMBL233
Ki 5.54 5.54 2880.0 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
Ki 5.54 5.54 2870.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.52 5.52 3005.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 5.52 5.52 2997.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.49 5.49 3270.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 5.46 5.46 3500.0 1
D(2) dopamine receptor
CHEMBL217
Ki 5.36 5.36 4392.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.34 5.34 4610.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 5.0 5.0 10000.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 4.92 4.92 12000.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 4.24 4.24 57000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 12.8 mL.min-1.g-1 Rattus norvegicus
CL 8.2 mL.min-1.g-1 Homo sapiens
Cmax 220.0 nM Rattus norvegicus
Cmax 220.0 nM Rattus norvegicus
Cmax 370.0 nM Rattus norvegicus
Cmax 370.0 nM Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 3A Ki = 0.93 nM 9.03 Binding affinity to 5HT3 receptor (unknown origin) 34467765
5-hydroxytryptamine receptor 6 Ki = 3.0 nM 8.52 Displacement of [3H]-LSD from human 5HT6 receptor expressed in HEK293 cell membr... 34467765
5-hydroxytryptamine receptor 3A IC50 = 67.6 nM 7.17 Antagonist activity at human 5-HT3 receptor expressed in CHO-K1 cells assessed a... 34467765
Alpha-2A adrenergic receptor Ki = 110.0 nM 6.96 Binding affinity to human adrenergic alpha 2A receptor 34467765
5-hydroxytryptamine receptor 2B Ki = 170.0 nM 6.77 Binding affinity to human 5-HT2B receptor 34467765
Beta-1 adrenergic receptor Ki = 170.0 nM 6.77 Binding affinity to human adrenergic beta1 receptor 34467765
D(3) dopamine receptor Ki = 210.0 nM 6.68 Binding affinity to human dopamine D3 receptor 34467765
Histamine H1 receptor Ki = 220.0 nM 6.66 Binding affinity to human histamine H1 receptor 34467765
5-hydroxytryptamine receptor 1A Ki = 437.0 nM 6.36 Displacement of [3H]-8-OH-DPAT from human 5HT1A receptor expressed in HEK293 cel... 34467765
Unchecked Ki = 500.0 nM 6.3 Binding affinity to rat L-type calcium channel dihydropyridine site 34467765
Unchecked Ki = 710.0 nM 6.15 Binding affinity to rat sodium channel site 2 34467765
5-hydroxytryptamine receptor 2C Ki = 830.0 nM 6.08 Binding affinity to human 5-HT2C receptor 34467765
5-hydroxytryptamine receptor 1B Ki = 890.0 nM 6.05 Binding affinity to human 5-HT1B receptor 34467765
Voltage-gated inwardly rectifying potassium channel KCNH2 Ki = 940.0 nM 6.03 Binding affinity to human ERG 34467765
Unchecked Ki = 1080.0 nM 5.97 Binding affinity to rat L-type calcium channel benzothiazepine site 34467765
Sodium-dependent dopamine transporter Ki = 1090.0 nM 5.96 Binding affinity to human DAT 34467765
Sodium-dependent noradrenaline transporter Ki = 1240.0 nM 5.91 Binding affinity to human NET 34467765
Unchecked Ki = 1320.0 nM 5.88 Binding affinity to rat L-type calcium channel phenylalkylamine site 34467765
Muscarinic acetylcholine receptor M1 Ki = 1940.0 nM 5.71 Binding affinity to human M1 receptor 34467765
5-hydroxytryptamine receptor 5A Ki = 2870.0 nM 5.54 Binding affinity to human 5-HT5A receptor 34467765

Literature References

PubMed DOI Target Context # Activities
34467765 10.1021/acs.jmedchem.1c00224 ADMET 11
34467765 10.1021/acs.jmedchem.1c00224 5-hydroxytryptamine receptor 6 5
34467765 10.1021/acs.jmedchem.1c00224 5-hydroxytryptamine receptor 3A 5
34467765 10.1021/acs.jmedchem.1c00224 Unchecked 5
34467765 10.1021/acs.jmedchem.1c00224 No relevant target 3
34467765 10.1021/acs.jmedchem.1c00224 Rattus norvegicus 3
34467765 10.1021/acs.jmedchem.1c00224 5-hydroxytryptamine receptor 2B 2
34467765 10.1021/acs.jmedchem.1c00224 5-hydroxytryptamine receptor 7 1
34467765 10.1021/acs.jmedchem.1c00224 Alpha-2A adrenergic receptor 1
34467765 10.1021/acs.jmedchem.1c00224 Beta-1 adrenergic receptor 1
34467765 10.1021/acs.jmedchem.1c00224 D(3) dopamine receptor 1
34467765 10.1021/acs.jmedchem.1c00224 Histamine H1 receptor 1
34467765 10.1021/acs.jmedchem.1c00224 D(2) dopamine receptor 1
34467765 10.1021/acs.jmedchem.1c00224 5-hydroxytryptamine receptor 2C 1
34467765 10.1021/acs.jmedchem.1c00224 5-hydroxytryptamine receptor 1B 1
34467765 10.1021/acs.jmedchem.1c00224 Voltage-gated inwardly rectifying potassium channel KCNH2 1
34467765 10.1021/acs.jmedchem.1c00224 Sodium-dependent dopamine transporter 1
34467765 10.1021/acs.jmedchem.1c00224 Sodium-dependent noradrenaline transporter 1
34467765 10.1021/acs.jmedchem.1c00224 Muscarinic acetylcholine receptor M1 1
34467765 10.1021/acs.jmedchem.1c00224 5-hydroxytryptamine receptor 2A 1

Data from ChEMBL 36 via Core Engine