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Compound Detail

CHEMBL4289498

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O=C(CCCN1CCC(c2noc3cc(F)ccc23)CC1)c1cc2c3c(c1)CCN3C(=O)CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4289498
Phase Preclinical
Structure Type MOL
InChI Key LFATXWJLBURBCJ-UHFFFAOYSA-N
16
Targets
17
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

461.5
MW (Da)
4.64
ALogP
5
HBA
0
HBD
66.7
PSA (Ų)
0.50
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H28FN3O3
MW 461.54
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -1.21

Activity Summary

Ki 16 meas. best 9.15
IC50 1 meas. best 6.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 9.15 9.15 0.7 1
D(3) dopamine receptor
CHEMBL234
 Ki 8.77 8.77 1.7 1
D(2) dopamine receptor
CHEMBL217
 Ki 8.54 8.54 2.9 1
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 8.25 7.435 5.6 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 8.07 8.07 8.6 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 8.0 8.0 9.9 1
D(2) dopamine receptor
CHEMBL339
 Ki 7.99 7.99 10.3 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 7.92 7.92 12.0 1
Alpha-1A adrenergic receptor
CHEMBL229
 Ki 7.37 7.37 43.1 1
D(3) dopamine receptor
CHEMBL3138
 Ki 7.21 7.21 61.3 1
Histamine H1 receptor
CHEMBL3943
 Ki 6.38 6.38 421.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 6.31 6.31 491.3 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 6.21 6.21 616.0 1
5-hydroxytryptamine receptor 2C
CHEMBL324
 Ki 6.21 6.21 610.3 1
Histamine H1 receptor
CHEMBL231
 Ki 6.2 6.2 630.1 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 6.08 6.08 823.7 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.7 nM 9.15 Binding affinity to 5-HT2A receptor (unknown origin) 33705900
D(3) dopamine receptor Ki = 1.7 nM 8.77 Binding affinity to dopamine D3 receptor (unknown origin) 33705900
D(2) dopamine receptor Ki = 2.9 nM 8.54 Binding affinity to dopamine D2 receptor (unknown origin) 33705900
5-hydroxytryptamine receptor 6 Ki = 5.6 nM 8.25 Binding affinity to 5-HT6 receptor (unknown origin) 33705900
5-hydroxytryptamine receptor 1A Ki = 8.6 nM 8.07 Binding affinity to 5-HT1A receptor (unknown origin) 33705900
5-hydroxytryptamine receptor 2A Ki = 9.9 nM 8.0 Displacement of [3H]-ketanserine from serotonin 5-HT2A receptor in rat brain cor... 30383372
D(2) dopamine receptor Ki = 10.3 nM 7.99 Displacement of [3H]-spiperone from dopamine D2 receptor in rat striatum homogen... 30383372
5-hydroxytryptamine receptor 1A Ki = 12.0 nM 7.92 Displacement of [3H]-8-OH-DPAT from serotonin 5-HT1A receptor in rat brain corte... 30383372
Alpha-1A adrenergic receptor Ki = 43.1 nM 7.37 Binding affinity to alpha1 adrenoceptor (unknown origin) 33705900
D(3) dopamine receptor Ki = 61.3 nM 7.21 Displacement of [3H] 7-OH-DPAT from dopamine D3 receptor in rat olfactory tuberc... 30383372
5-hydroxytryptamine receptor 6 Ki = 241.0 nM 6.62 Displacement of [3H]-lysergic acid diethylamide from human serotonin 5-HT6 recep... 30383372
Histamine H1 receptor Ki = 421.0 nM 6.38 Displacement of [3H]-mepyramine from histamine H1 receptor in guinea pig cerebel... 30383372
Adrenergic receptor alpha-1 Ki = 491.3 nM 6.31 Displacement of [3H]-prazosin from alpha-1 adrenergic receptor in rat cerebral c... 30383372
5-hydroxytryptamine receptor 2C Ki = 610.3 nM 6.21 Displacement of [3H]-mesulergine from serotonin 5-HT2C receptor in rat brain cer... 30383372
5-hydroxytryptamine receptor 2C Ki = 616.0 nM 6.21 Binding affinity to 5-HT2C receptor (unknown origin) 33705900
Histamine H1 receptor Ki = 630.1 nM 6.2 Binding affinity to histamine H1 receptor (unknown origin) 33705900
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 823.7 nM 6.08 Inhibition of human ERG expressed in HEK293 cells at -50 mV holding potential by... 30383372

Literature References

PubMed DOI Target Context # Activities
30383372 10.1021/acs.jmedchem.8b01096 Voltage-gated inwardly rectifying potassium channel KCNH2 1
33705900 10.1016/j.bmcl.2021.127909 Histamine H1 receptor 1
33705900 10.1016/j.bmcl.2021.127909 Alpha-1A adrenergic receptor 1
33705900 10.1016/j.bmcl.2021.127909 5-hydroxytryptamine receptor 6 1
33705900 10.1016/j.bmcl.2021.127909 5-hydroxytryptamine receptor 2C 1
33705900 10.1016/j.bmcl.2021.127909 5-hydroxytryptamine receptor 2A 1
33705900 10.1016/j.bmcl.2021.127909 5-hydroxytryptamine receptor 1A 1
33705900 10.1016/j.bmcl.2021.127909 D(3) dopamine receptor 1
33705900 10.1016/j.bmcl.2021.127909 D(2) dopamine receptor 1
30383372 10.1021/acs.jmedchem.8b01096 D(2) dopamine receptor 1
30383372 10.1021/acs.jmedchem.8b01096 D(3) dopamine receptor 1
30383372 10.1021/acs.jmedchem.8b01096 5-hydroxytryptamine receptor 6 1
30383372 10.1021/acs.jmedchem.8b01096 Adrenergic receptor alpha-1 1
30383372 10.1021/acs.jmedchem.8b01096 5-hydroxytryptamine receptor 2C 1
30383372 10.1021/acs.jmedchem.8b01096 Histamine H1 receptor 1
30383372 10.1021/acs.jmedchem.8b01096 5-hydroxytryptamine receptor 2A 1
30383372 10.1021/acs.jmedchem.8b01096 5-hydroxytryptamine receptor 1A 1

Data from ChEMBL 36 via Core Engine