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Compound Detail

CHEMBL490417

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Cc1ccc2c(N3CCN(CCc4ccc5c(c4)NC(=O)CO5)CC3)cccc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL490417
Phase Preclinical
Structure Type MOL
InChI Key KGVROJQOCQABGA-UHFFFAOYSA-N
10
Targets
27
Activities
2
Assay Types
18
PK Parameters
20
Publications
0
Known Names

Molecular Properties

402.5
MW (Da)
3.24
ALogP
5
HBA
1
HBD
57.7
PSA (Ų)
0.73
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 C24H26N4O2
MW 402.50
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.27

Activity Summary

Ki 25 meas. best 10.2
EC50 2 meas. best 9.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 10.2 9.84 0.1 5
5-hydroxytryptamine receptor 1D
CHEMBL1983
 Ki 9.8 9.65 0.2 4
5-hydroxytryptamine receptor 1B
CHEMBL1898
 Ki 9.7 8.3 0.2 5
5-hydroxytryptamine receptor 1D
CHEMBL1983
 EC50 9.3 9.3 0.5 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.9 8.8667 1.3 3
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 8.4 8.0 4.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 EC50 8.1 8.1 7.9 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 Ki 7.2 7.2 63.1 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.5 6.5 316.2 1
D(2) dopamine receptor
CHEMBL217
 Ki 6.5 6.5 316.2 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.9 5.9 1258.9 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 5.4 5.4 3981.1 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.3 mL.min-1.g-1 Rattus norvegicus
CL 0.5 mL.min-1.g-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.3 mL.min-1.g-1 Rattus norvegicus
CL 0.5 mL.min-1.g-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Rattus norvegicus
CL 7.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.3 mL.min-1.g-1 Rattus norvegicus
CL 0.5 mL.min-1.g-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 894.41 nM Rattus norvegicus
F 68.0 % Rattus norvegicus
F 68.0 % Rattus norvegicus
F 72.0 % Rattus norvegicus
F 68.0 % Rattus norvegicus
T1/2 5.1 hr Rattus norvegicus
T1/2 5.1 hr Rattus norvegicus
T1/2 5.1 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1A Ki = 0.0631 nM 10.2 Antagonist activity at human 5HT1A assessed as GTPgammaS binding by scintillatio... 19286377
5-hydroxytryptamine receptor 1A Ki = 0.0631 nM 10.2 Antagonist activity against human recombinant 5HT1A receptor expressed in HEK293... 20590088
5-hydroxytryptamine receptor 1D Ki = 0.1585 nM 9.8 Displacement of [3H]5HT from human 5HT1D receptor expressed in CHO cells 18799312
5-hydroxytryptamine receptor 1D Ki = 0.1585 nM 9.8 Displacement of [3H]5-HT from human recombinant 5-HT1D receptor expressed in CHO... 21053897
5-hydroxytryptamine receptor 1B Ki = 0.1995 nM 9.7 Displacement of [3H]5HT from human 5HT1B receptor expressed in CHO cells 18799312
5-hydroxytryptamine receptor 1D Ki = 0.1995 nM 9.7 Displacement of [3H]5HT from human cloned 5HT1D receptor expressed in CHO cells 18829312
5-hydroxytryptamine receptor 1A Ki = 0.2512 nM 9.6 Displacement of [3H]WAY-100635 from human 5HT1A receptor expressed in CHO cells 18799312
5-hydroxytryptamine receptor 1A Ki = 0.2512 nM 9.6 Displacement of [3H]5HT from human cloned 5HT1A receptor expressed in CHO cells 18829312
5-hydroxytryptamine receptor 1A Ki = 0.2512 nM 9.6 Displacement of [3H]WAY100635 from human recombinant 5-HT1A receptor expressed i... 21053897
5-hydroxytryptamine receptor 1D EC50 = 0.5012 nM 9.3 Agonist activity at human 5HT1D assessed as GTPgammaS binding by scintillation p... 19286377
5-hydroxytryptamine receptor 1B Ki = 0.5012 nM 9.3 Displacement of [3H]5-HT from human recombinant 5-HT1B receptor expressed in CHO... 21053897
5-hydroxytryptamine receptor 1D Ki = 0.5012 nM 9.3 Antagonist activity against human recombinant 5HT1D receptor expressed in CHO ce... 20590088
5-hydroxytryptamine receptor 1B Ki = 0.5012 nM 9.3 Displacement of [3H]5HT from human cloned 5HT1B receptor expressed in CHO cells 18829312
Sodium-dependent serotonin transporter Ki = 1.259 nM 8.9 Displacement of [3H]citalopram human SerT receptor expressed in LLCPK cells 19286377
Sodium-dependent serotonin transporter Ki = 1.259 nM 8.9 Displacement of [3H]citalopram from human recombinant SERT expressed in LLCPK ce... 20590088
Sodium-dependent serotonin transporter Ki = 1.585 nM 8.8 Displacement of [3H]citalopram from human SerT expressed pig LLCPK cells 18799312
Sodium-dependent serotonin transporter Ki = 3.981 nM 8.4 Inhibition of [3H]5HT reuptake at SERT in rat cortical synaptosomes 18829312
Voltage-gated inwardly rectifying potassium channel KCNH2 EC50 = 7.943 nM 8.1 Inhibition of human ERG current by whole cell electrophysiology study 19286377
Sodium-dependent serotonin transporter Ki = 25.12 nM 7.6 Inhibition of [3H]5-HT uptake at SERT in rat cortical synaptosomes 21053897
Voltage-gated inwardly rectifying potassium channel KCNH2 Ki = 63.1 nM 7.2 Displacement of [3H]dofetilide human ERG expressed in CHO cells 19286377

Literature References

PubMed DOI Target Context # Activities
18799312 10.1016/j.bmcl.2008.08.084 Rattus norvegicus 5
20590088 10.1021/jm100482n Rattus norvegicus 4
19286377 10.1016/j.bmcl.2009.02.056 Rattus norvegicus 4
18829312 10.1016/j.bmcl.2008.08.110 Rattus norvegicus 3
19286377 10.1016/j.bmcl.2009.02.056 Voltage-gated inwardly rectifying potassium channel KCNH2 2
20590088 10.1021/jm100482n 5-hydroxytryptamine receptor 1A 2
20590088 10.1021/jm100482n Liver microsomes 2
18829312 10.1016/j.bmcl.2008.08.110 5-hydroxytryptamine receptor 1D 2
18829312 10.1016/j.bmcl.2008.08.110 5-hydroxytryptamine receptor 1A 2
18829312 10.1016/j.bmcl.2008.08.110 5-hydroxytryptamine receptor 1B 2
20590088 10.1021/jm100482n 5-hydroxytryptamine receptor 1B 2
19286377 10.1016/j.bmcl.2009.02.056 Liver microsomes 2
18799312 10.1016/j.bmcl.2008.08.084 5-hydroxytryptamine receptor 1D 2
19286377 10.1016/j.bmcl.2009.02.056 5-hydroxytryptamine receptor 1D 2
19286377 10.1016/j.bmcl.2009.02.056 5-hydroxytryptamine receptor 1B 2
19286377 10.1016/j.bmcl.2009.02.056 5-hydroxytryptamine receptor 1A 2
18799312 10.1016/j.bmcl.2008.08.084 Liver microsomes 2
20590088 10.1021/jm100482n 5-hydroxytryptamine receptor 1D 2
18799312 10.1016/j.bmcl.2008.08.084 5-hydroxytryptamine receptor 1A 2
18799312 10.1016/j.bmcl.2008.08.084 5-hydroxytryptamine receptor 1B 2

Data from ChEMBL 36 via Core Engine