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Compound Detail

CHEMBL140872

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O=C(CCCN1CCN(c2ncccn2)CC1)c1ccc(F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL140872
Phase Preclinical
Structure Type MOL
InChI Key WEVJMQOBCRCIPF-UHFFFAOYSA-N
13
Targets
18
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

328.4
MW (Da)
2.40
ALogP
5
HBA
0
HBD
49.3
PSA (Ų)
0.76
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 C18H21FN4O
MW 328.39
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -1.78

Activity Summary

Ki 15 meas. best 8.19
IC50 3 meas. best 8.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adrenergic receptor alpha-1
CHEMBL1907610
 IC50 8.22 8.22 6.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 8.19 8.19 6.5 1
D(4) dopamine receptor
CHEMBL3361
 Ki 8.19 8.19 6.5 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 7.66 7.66 22.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.52 7.52 30.5 2
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 7.1 7.1 80.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 7.01 7.01 98.0 2
D(3) dopamine receptor
CHEMBL234
 Ki 6.61 6.61 244.1 2
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 IC50 6.37 6.37 430.0 1
D(2) dopamine receptor
CHEMBL339
 IC50 6.17 6.17 679.0 1
Histamine H1 receptor
CHEMBL231
 Ki 6.04 6.04 911.8 2
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 5.38 5.38 4132.0 1
5-hydroxytryptamine receptor 2C
CHEMBL324
 Ki 5.38 5.38 4132.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adrenergic receptor alpha-1 IC50 = 6.0 nM 8.22 Inhibition of [3H]WB-4101 binding to rat cortical Alpha-1 adrenergic receptor in... 1361578
D(4) dopamine receptor Ki = 6.53 nM 8.19 Binding affinity to human cloned dopamine D4 receptor 18595716
D(4) dopamine receptor Ki = 6.5 nM 8.19 Displacement of [3H]N-methylspiperone from rat dopamine D4 receptor by liquid sc... 22245230
5-hydroxytryptamine receptor 2A Ki = 22.0 nM 7.66 Binding affinity to human cloned 5HT2A receptor 18595716
5-hydroxytryptamine receptor 2A Ki = 22.0 nM 7.66 Displacement of [3H]DOI from human 5HT2A receptor after 1 hr by liquid scintilla... 22245230
5-hydroxytryptamine receptor 1A Ki = 30.5 nM 7.52 Binding affinity to human cloned 5HT1A receptor 18595716
5-hydroxytryptamine receptor 1A Ki = 30.5 nM 7.52 Displacement of [3H]8-OH-DPAT from human 5HT1A receptor by liquid scintillation ... 22245230
Alpha-2C adrenergic receptor Ki = 80.0 nM 7.1 Displacement of [3H]clonidine from human Alpha-2C receptor by liquid scintillati... 22245230
D(2) dopamine receptor Ki = 98.0 nM 7.01 Binding affinity to human cloned dopamine D2 receptor 18595716
D(2) dopamine receptor Ki = 98.0 nM 7.01 Displacement of [3H]N-methylspiperone from human dopamine D2 receptor by liquid ... 22245230
D(3) dopamine receptor Ki = 244.1 nM 6.61 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor by liquid ... 22245230
D(3) dopamine receptor Ki = 244.1 nM 6.61 Binding affinity to human cloned dopamine D3 receptor 18595716
Sigma non-opioid intracellular receptor 1 IC50 = 430.0 nM 6.37 Displacement of (+)-[3H]-3-PPP from rat cortical sigma site 1361578
D(2) dopamine receptor IC50 = 679.0 nM 6.17 In vitro inhibitory against radioligand [3H]spiperone binding to rat striatal Do... 1361578
Histamine H1 receptor Ki = 911.8 nM 6.04 Binding affinity to human cloned histamine H1 receptor 18595716
Histamine H1 receptor Ki = 912.0 nM 6.04 Displacement of [3H]pyrilamine from human H1 receptor by liquid scintillation co... 22245230
5-hydroxytryptamine receptor 2C Ki = 4132.0 nM 5.38 Binding affinity to human cloned 5HT2C receptor 18595716
5-hydroxytryptamine receptor 2C Ki = 4132.0 nM 5.38 Displacement of [3H]mesulergine from rat 5HT2C receptor by liquid scintillation ... 22245230

Literature References

PubMed DOI Target Context # Activities
1361578 10.1021/jm00102a002 Rattus norvegicus 3
18595716 10.1016/j.bmc.2008.06.030 5-hydroxytryptamine receptor 2C 1
22245230 10.1016/j.bmc.2011.12.019 Alpha-2C adrenergic receptor 1
22245230 10.1016/j.bmc.2011.12.019 Histamine H1 receptor 1
22245230 10.1016/j.bmc.2011.12.019 5-hydroxytryptamine receptor 7 1
22245230 10.1016/j.bmc.2011.12.019 5-hydroxytryptamine receptor 2C 1
22245230 10.1016/j.bmc.2011.12.019 5-hydroxytryptamine receptor 2A 1
22245230 10.1016/j.bmc.2011.12.019 5-hydroxytryptamine receptor 1A 1
22245230 10.1016/j.bmc.2011.12.019 D(4) dopamine receptor 1
22245230 10.1016/j.bmc.2011.12.019 D(3) dopamine receptor 1
22245230 10.1016/j.bmc.2011.12.019 D(2) dopamine receptor 1
1361578 10.1021/jm00102a002 D(2) dopamine receptor 1
18595716 10.1016/j.bmc.2008.06.030 5-hydroxytryptamine receptor 2A 1
18595716 10.1016/j.bmc.2008.06.030 5-hydroxytryptamine receptor 1A 1
18595716 10.1016/j.bmc.2008.06.030 D(4) dopamine receptor 1
18595716 10.1016/j.bmc.2008.06.030 D(2) dopamine receptor 1
18595716 10.1016/j.bmc.2008.06.030 D(3) dopamine receptor 1
18595716 10.1016/j.bmc.2008.06.030 Histamine H1 receptor 1
1361578 10.1021/jm00102a002 Sigma non-opioid intracellular receptor 1 1
1361578 10.1021/jm00102a002 Adrenergic receptor alpha-1 1

Data from ChEMBL 36 via Core Engine