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Compound Detail

CHEMBL4293999

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O=C(CCCCN1CCC(c2noc3cc(F)ccc23)CC1)c1cc2c3c(c1)CCN3C(=O)CC2

Basic Information

ChEMBL ID CHEMBL4293999
Phase Preclinical
Structure Type MOL
InChI Key ACOZPXLCYUQMHS-UHFFFAOYSA-N
18
Targets
24
Activities
2
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

475.6
MW (Da)
5.03
ALogP
5
HBA
0
HBD
66.7
PSA (Ų)
0.35
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H30FN3O3
MW 475.56
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -1.15

Activity Summary

Ki 17 meas. best 9.14
IC50 7 meas. best 8.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 9.14 9.14 0.7 1
5-hydroxytryptamine receptor 2A
CHEMBL322
Ki 9.14 9.14 0.7 1
D(3) dopamine receptor
CHEMBL234
Ki 8.78 8.78 1.7 1
D(3) dopamine receptor
CHEMBL3138
Ki 8.78 8.78 1.7 1
D(2) dopamine receptor
CHEMBL339
Ki 8.54 8.54 2.9 1
D(2) dopamine receptor
CHEMBL217
Ki 8.54 8.54 2.9 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 8.26 8.26 5.5 2
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 8.07 8.07 8.6 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 8.07 8.07 8.6 1
D(2) dopamine receptor
CHEMBL217
IC50 8.04 8.04 9.0 1
D(3) dopamine receptor
CHEMBL234
IC50 7.59 7.59 25.6 1
D(1A) dopamine receptor
CHEMBL265
Ki 7.11 7.11 76.9 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 6.75 6.75 177.6 1
5-hydroxytryptamine receptor 7
CHEMBL3223
Ki 6.65 6.65 226.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 6.59 6.59 257.4 1
D(1A) dopamine receptor
CHEMBL2056
IC50 6.44 6.44 366.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
Ki 6.37 6.37 431.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
IC50 6.23 6.23 587.8 1
5-hydroxytryptamine receptor 2C
CHEMBL324
Ki 6.21 6.21 616.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.21 6.21 616.0 1
Histamine H1 receptor
CHEMBL231
Ki 6.2 6.2 630.3 1
Histamine H1 receptor
CHEMBL3943
Ki 6.2 6.2 630.3 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.54 5.54 2905.4 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3141.3 ng.hr.mL-1 Rattus norvegicus
AUC 18532.7 ng.hr.mL-1 Rattus norvegicus
AUC 3151.2 ng.hr.mL-1 Rattus norvegicus
AUC 18539.5 ng.hr.mL-1 Rattus norvegicus
CL 15.4 mL.min-1.kg-1 Rattus norvegicus
Cmax 7849.69 nM Rattus norvegicus
F 58.8 % Rattus norvegicus
T1/2 2.15 hr Rattus norvegicus
T1/2 2.02 hr Rattus norvegicus
Tmax 1.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.72 nM 9.14 Displacement of [3H]-ketanserine from serotonin 5-HT2A receptor in rat brain cor... 30383372
5-hydroxytryptamine receptor 2A Ki = 0.72 nM 9.14 Binding affinity to 5HT2A receptor (unknown origin) 32877805
D(3) dopamine receptor Ki = 1.66 nM 8.78 Displacement of [3H] 7-OH-DPAT from dopamine D3 receptor in rat olfactory tuberc... 30383372
D(3) dopamine receptor Ki = 1.66 nM 8.78 Binding affinity to D3 receptor (unknown origin) 32877805
D(2) dopamine receptor Ki = 2.9 nM 8.54 Binding affinity to D2 receptor (unknown origin) 32877805
D(2) dopamine receptor Ki = 2.9 nM 8.54 Displacement of [3H]-spiperone from dopamine D2 receptor in rat striatum homogen... 30383372
5-hydroxytryptamine receptor 6 Ki = 5.55 nM 8.26 Binding affinity to 5HT6 receptor (unknown origin) 32877805
5-hydroxytryptamine receptor 6 Ki = 5.55 nM 8.26 Displacement of [3H]-lysergic acid diethylamide from human serotonin 5-HT6 recep... 30383372
5-hydroxytryptamine receptor 1A Ki = 8.6 nM 8.07 Binding affinity to 5HT1A receptor (unknown origin) 32877805
5-hydroxytryptamine receptor 1A Ki = 8.6 nM 8.07 Displacement of [3H]-8-OH-DPAT from serotonin 5-HT1A receptor in rat brain corte... 30383372
D(2) dopamine receptor IC50 = 9.02 nM 8.04 Antagonist activity at dopamine D2 receptor long isoform (unknown origin) expres... 30383372
D(3) dopamine receptor IC50 = 25.6 nM 7.59 Antagonist activity at dopamine D3 receptor (unknown origin) expressed in HEK293... 30383372
D(1A) dopamine receptor Ki = 76.9 nM 7.11 Displacement of [3H]-SCH23390 from dopamine D1 receptor in rat strriatum homogen... 30383372
5-hydroxytryptamine receptor 6 IC50 = 177.6 nM 6.75 Antagonist activity at serotonin human 5-HT6 receptor expressed in HEK293 cells ... 30383372
5-hydroxytryptamine receptor 7 Ki = 226.0 nM 6.65 Displacement of [3H]-5-CT from 5-HT7 receptor in rat cerebral cortex homogenates... 30383372
5-hydroxytryptamine receptor 2A IC50 = 257.4 nM 6.59 Antagonist activity at serotonin 5-HT2A receptor (unknown origin) expressed in H... 30383372
D(1A) dopamine receptor IC50 = 366.0 nM 6.44 Antagonist activity at human dopamine D1 receptor expressed in HEK293T cells ass... 30383372
Adrenergic receptor alpha-1 Ki = 431.0 nM 6.37 Displacement of [3H]-prazosin from alpha-1 adrenergic receptor in rat cerebral c... 30383372
5-hydroxytryptamine receptor 1A IC50 = 587.8 nM 6.23 Antagonist activity at serotonin 5-HT1A receptor (unknown origin) expressed in H... 30383372
5-hydroxytryptamine receptor 2C Ki = 616.0 nM 6.21 Displacement of [3H]-mesulergine from serotonin 5-HT2C receptor in rat brain cer... 30383372

Literature References

PubMed DOI Target Context # Activities
30383372 10.1021/acs.jmedchem.8b01096 Rattus norvegicus 15
30383372 10.1021/acs.jmedchem.8b01096 Mus musculus 10
30383372 10.1021/acs.jmedchem.8b01096 5-hydroxytryptamine receptor 2A 4
30383372 10.1021/acs.jmedchem.8b01096 5-hydroxytryptamine receptor 1A 4
30383372 10.1021/acs.jmedchem.8b01096 D(2) dopamine receptor 4
30383372 10.1021/acs.jmedchem.8b01096 D(3) dopamine receptor 4
30383372 10.1021/acs.jmedchem.8b01096 5-hydroxytryptamine receptor 6 4
30383372 10.1021/acs.jmedchem.8b01096 D(1A) dopamine receptor 3
30383372 10.1021/acs.jmedchem.8b01096 Unchecked 2
30383372 10.1021/acs.jmedchem.8b01096 Adrenergic receptor alpha-1 1
30383372 10.1021/acs.jmedchem.8b01096 Voltage-gated inwardly rectifying potassium channel KCNH2 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 7 1
30383372 10.1021/acs.jmedchem.8b01096 Adrenergic receptor alpha-2 1
30383372 10.1021/acs.jmedchem.8b01096 Histamine H3 receptor 1
30383372 10.1021/acs.jmedchem.8b01096 Sodium-dependent serotonin transporter 1
30383372 10.1021/acs.jmedchem.8b01096 Sigma non-opioid intracellular receptor 1 1
30383372 10.1021/acs.jmedchem.8b01096 Muscarinic acetylcholine receptor M1 1
30383372 10.1021/acs.jmedchem.8b01096 Glutamate NMDA receptor 1

Data from ChEMBL 36 via Core Engine