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Compound Detail

CHEMBL1949930

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COc1cc(OC(C)C)cc(S(=O)(=O)c2ccc3c(c2)O[C@H]2CNCC[C@@H]32)c1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1949930
Phase Preclinical
Structure Type MOL
InChI Key IKXSPLZKOZXPFB-RQBPZYBGSA-N
Parent Compound CHEMBL1963007
Active Moiety CHEMBL1963007
12
Targets
16
Activities
2
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

403.5
MW (Da)
3.15
ALogP
6
HBA
1
HBD
73.9
PSA (Ų)
0.83
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H26ClNO5S
MW 439.96
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.10

Activity Summary

IC50 9 meas. best 7.35
Ki 7 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 8.4 8.16 4.0 2
5-hydroxytryptamine receptor 6
CHEMBL3372
 Ki 7.57 7.415 27.0 2
5-hydroxytryptamine receptor 6
CHEMBL3371
 IC50 7.35 7.26 45.0 2
Muscarinic acetylcholine receptor M1
CHEMBL216
 IC50 5.66 5.66 2200.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.48 5.48 3300.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.43 5.43 3700.0 1
Unchecked
CHEMBL612545
 IC50 5.41 5.41 3900.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 5.36 5.36 4400.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
 IC50 5.32 5.32 4800.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 5.21 5.21 6200.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.2 5.2 6300.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
 IC50 5.1 5.1 7900.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 4.72 4.72 19000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 41.0 mL.min-1.kg-1 Rattus norvegicus
CL 28.0 mL.min-1.kg-1 Rattus norvegicus
F 39.0 % Rattus norvegicus
F 11.0 % Rattus norvegicus
T1/2 2.5 hr Rattus norvegicus
T1/2 0.4 hr Rattus norvegicus
T1/2 0.6667 hr Mus musculus
T1/2 0.6667 hr Rattus norvegicus
T1/2 0.6667 hr Canis lupus familiaris
T1/2 0.6667 hr Homo sapiens
Vd 4.3 L.kg-1 Rattus norvegicus
Vd 1.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 6 Ki = 4.0 nM 8.4 Displacement of [3H]LSD from human recombinant 5HT6 receptor 22226656
5-hydroxytryptamine receptor 6 Ki = 12.0 nM 7.92 Displacement of [3H]LSD from human recombinant 5HT6 receptor 22226656
5-hydroxytryptamine receptor 6 Ki = 27.0 nM 7.57 Displacement of [3H]LSD from rat recombinant 5HT6 receptor 22226656
5-hydroxytryptamine receptor 6 IC50 = 45.0 nM 7.35 Antagonist activity at human 5HT6 receptor expressed in human astrocytoma cells ... 22226656
5-hydroxytryptamine receptor 6 Ki = 55.0 nM 7.26 Displacement of [3H]LSD from rat recombinant 5HT6 receptor 22226656
5-hydroxytryptamine receptor 6 IC50 = 67.0 nM 7.17 Antagonist activity at human 5HT6 receptor expressed in human astrocytoma cells ... 22226656
Muscarinic acetylcholine receptor M1 IC50 = 2200.0 nM 5.66 Inhibition of M1 receptor 22226656
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3300.0 nM 5.48 Inhibition of human ERG by patch clamp assay 22226656
5-hydroxytryptamine receptor 2A Ki = 3700.0 nM 5.43 Inhibition of human 5HT2A 22226656
Unchecked IC50 = 3900.0 nM 5.41 Inhibition of calcium channel-L type 22226656
Sodium-dependent noradrenaline transporter IC50 = 4400.0 nM 5.36 Inhibition of NA transporter 22226656
Muscarinic acetylcholine receptor M4 IC50 = 4800.0 nM 5.32 Inhibition of M4 receptor 22226656
5-hydroxytryptamine receptor 2B Ki = 6200.0 nM 5.21 Inhibition of human 5HT2B 22226656
Sodium-dependent dopamine transporter IC50 = 6300.0 nM 5.2 Inhibition of DA transporter 22226656
Muscarinic acetylcholine receptor M2 IC50 = 7900.0 nM 5.1 Inhibition of M2 receptor 22226656
5-hydroxytryptamine receptor 2C Ki = 19000.0 nM 4.72 Inhibition of human 5HT2C 22226656

Literature References

PubMed DOI Target Context # Activities
22226656 10.1016/j.bmcl.2011.12.026 Rattus norvegicus 14
22226656 10.1016/j.bmcl.2011.12.026 5-hydroxytryptamine receptor 6 6
22226656 10.1016/j.bmcl.2011.12.026 Muscarinic acetylcholine receptor M1 2
22226656 10.1016/j.bmcl.2011.12.026 Muscarinic acetylcholine receptor M2 2
22226656 10.1016/j.bmcl.2011.12.026 Sodium-dependent dopamine transporter 2
22226656 10.1016/j.bmcl.2011.12.026 5-hydroxytryptamine receptor 2C 2
22226656 10.1016/j.bmcl.2011.12.026 5-hydroxytryptamine receptor 2B 2
22226656 10.1016/j.bmcl.2011.12.026 5-hydroxytryptamine receptor 2A 2
22226656 10.1016/j.bmcl.2011.12.026 Sodium-dependent noradrenaline transporter 2
22226656 10.1016/j.bmcl.2011.12.026 Muscarinic acetylcholine receptor M4 2
22226656 10.1016/j.bmcl.2011.12.026 Unchecked 2
22226656 10.1016/j.bmcl.2011.12.026 Liver microsomes 2
22226656 10.1016/j.bmcl.2011.12.026 Liver 2
22226656 10.1016/j.bmcl.2011.12.026 Plasma 2
22226656 10.1016/j.bmcl.2011.12.026 ADMET 2
22226656 10.1016/j.bmcl.2011.12.026 No relevant target 2
22226656 10.1016/j.bmcl.2011.12.026 Nucleic Acid 2
22226656 10.1016/j.bmcl.2011.12.026 Cytochrome P450 2C19 1
22226656 10.1016/j.bmcl.2011.12.026 Cytochrome P450 2D6 1
22226656 10.1016/j.bmcl.2011.12.026 Cytochrome P450 3A4 1

Data from ChEMBL 36 via Core Engine