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Compound Detail

CHEMBL308480

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O=C1CC(CN2CCC(C(=O)c3ccc(F)cc3)CC2)Cc2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL308480
Phase Preclinical
Structure Type MOL
InChI Key JFVJCLYJXOVMSI-UHFFFAOYSA-N
10
Targets
26
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

365.4
MW (Da)
4.17
ALogP
3
HBA
0
HBD
37.4
PSA (Ų)
0.76
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H24FNO2
MW 365.45
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.86

Activity Summary

Ki 20 meas. best 8.8
Kd 6 meas. best 7.86

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 8.8 8.8 1.6 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 8.8 8.266 1.6 5
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 8.8 8.8 1.6 3
5-hydroxytryptamine receptor 2A
CHEMBL322
 Kd 7.86 7.86 13.8 1
Rattus norvegicus
CHEMBL376
 Kd 7.86 7.4633 13.8 3
Unchecked
CHEMBL612545
 Kd 7.86 7.86 13.8 1
D(2) dopamine receptor
CHEMBL339
 Ki 7.68 7.68 20.9 2
5-hydroxytryptamine receptor 2B
CHEMBL323
 Kd 7.2 7.2 63.1 1
D(2) dopamine receptor
CHEMBL217
 Ki 6.98 6.7 104.7 3
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 6.63 6.3375 234.4 4
D(1A) dopamine receptor
CHEMBL265
 Ki 6.49 6.49 323.6 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 1.6 nM 8.8 Binding affinity to 5-HT2A receptor (unknown origin) assessed as inhibition cons... 34743062
Serotonin 2 (5-HT2) receptor Ki = 1.585 nM 8.8 Tested for the binding affinity towards 5-HT2 receptor measured by [3H]ketanseri... -
5-hydroxytryptamine receptor 2A Ki = 1.585 nM 8.8 Inhibitory constant on 5-hydroxytryptamine 2A receptor of Rat frontal cortex 11754579
5-hydroxytryptamine receptor 2A Ki = 1.585 nM 8.8 In vitro ability to displace [3H]ketanserin binding from 5-hydroxytryptamine 2A ... 10425088
5-hydroxytryptamine receptor 2A Ki = 1.585 nM 8.8 Kinetic inhibition constant evaluated by measuring serotonergic activity 10966742
5-hydroxytryptamine receptor 2A Ki = 1.622 nM 8.79 Binding affinity for 5-HT2A receptor (unknown origin) 24316025
5-hydroxytryptamine receptor 2A Ki = 5.888 nM 8.23 Binding affinity towards serotonin 5-hydroxytryptamine 2A receptor 14741248
5-hydroxytryptamine receptor 2A Ki = 13.18 nM 7.88 Binding affinity towards serotonin 5-hydroxytryptamine 2A receptor 14741248
Unchecked Kd = 13.8 nM 7.86 pA2 value was evaluated by measuring the inhibition of the 5-HT-induced contract... 10425088
Rattus norvegicus Kd = 13.8 nM 7.86 Tested for the antagonistic activity against serotonin-induced contractions in r... -
5-hydroxytryptamine receptor 2A Kd = 13.8 nM 7.86 Negative log concentration of antagonist on 5-hydroxytryptamine 2A receptor in r... 11754579
D(2) dopamine receptor Ki = 20.89 nM 7.68 Compound was evaluated for its affinity (pKi) to inhibit [3H]spiperone binding t... 1676759
D(2) dopamine receptor Ki = 20.89 nM 7.68 In vitro ability to displace [3H]spiperone binding from dopamine receptor D2 in ... 10425088
5-hydroxytryptamine receptor 2A Ki = 23.44 nM 7.63 Binding affinity towards serotonin 5-hydroxytryptamine 2A receptor 14741248
Rattus norvegicus Kd = 35.48 nM 7.45 Compound was evaluated for the pA2 values against Dopamine (DA)-induced contract... 1676759
5-hydroxytryptamine receptor 2B Kd = 63.1 nM 7.2 Negative log concentration of antagonist was determined on 5-hydroxytryptamine 2... 11754579
Rattus norvegicus Kd = 83.18 nM 7.08 Compound was evaluated for the pA2 values against Norepinephrine (NE)-induced co... 1676759
D(2) dopamine receptor Ki = 104.71 nM 6.98 Binding affinity towards dopamine receptor D2 14741248
D(2) dopamine receptor Ki = 223.87 nM 6.65 Binding affinity towards dopamine receptor D2 14741248
5-hydroxytryptamine receptor 2C Ki = 234.42 nM 6.63 Inhibitory constant was determined on 5-hydroxytryptamine 2C receptor of Bovine ... 11754579

Literature References

PubMed DOI Target Context # Activities
14741248 10.1016/j.bmcl.2003.11.064 Dopamine D2 receptor and serotonin 2a receptor 3
14741248 10.1016/j.bmcl.2003.11.064 Serotonin 2 receptors; 5-HT2a & 5-HT2c 3
14741248 10.1016/j.bmcl.2003.11.064 D(2) dopamine receptor 3
14741248 10.1016/j.bmcl.2003.11.064 5-hydroxytryptamine receptor 2C 3
14741248 10.1016/j.bmcl.2003.11.064 5-hydroxytryptamine receptor 2A 3
1676759 10.1021/jm00111a046 Rattus norvegicus 2
10425088 10.1021/jm981094e Unchecked 2
11754579 10.1021/jm011014y 5-hydroxytryptamine receptor 2A 2
10425088 10.1021/jm981094e D(1A) dopamine receptor 1
34743062 10.1016/j.ejmech.2021.113964 5-hydroxytryptamine receptor 2A 1
10966742 10.1021/jm000941m 5-hydroxytryptamine receptor 2A 1
10425088 10.1021/jm981094e 5-hydroxytryptamine receptor 2A 1
10425088 10.1021/jm981094e D(2) dopamine receptor 1
1676759 10.1021/jm00111a046 Unchecked 1
1676759 10.1021/jm00111a046 Mus musculus 1
1676759 10.1021/jm00111a046 D(1A) dopamine receptor 1
1676759 10.1021/jm00111a046 D(2) dopamine receptor 1
11754579 10.1021/jm011014y Serotonin receptor 2a and 2c (5HT2A and 5HT2C) 1
11754579 10.1021/jm011014y Serotonin receptor 2a and 2b (5HT2A and 5HT2B) 1
11754579 10.1021/jm011014y 5-hydroxytryptamine receptor 2C 1

Data from ChEMBL 36 via Core Engine