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Compound Detail

CHEMBL522257

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

Basic Information

ChEMBL ID CHEMBL522257
Phase Preclinical
Structure Type MOL
InChI Key JAELRPUWEUXJPW-UHFFFAOYSA-N
5
Targets
14
Activities
1
Assay Types
15
PK Parameters
20
Publications
0
Known Names

Molecular Properties

416.5
MW (Da)
3.26
ALogP
5
HBA
0
HBD
48.9
PSA (Ų)
0.65
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 C25H28N4O2
MW 416.53
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.26

Activity Summary

Ki 14 meas. best 10.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 10.1 9.8667 0.1 3
5-hydroxytryptamine receptor 1D
CHEMBL1983
 Ki 10.0 9.8333 0.1 3
5-hydroxytryptamine receptor 1B
CHEMBL1898
 Ki 9.3 8.9 0.5 3
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 7.7 7.7 19.9 3
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 Ki 6.1 6.1 794.3 2

Pharmacokinetic Data

Parameter Value Units Species
CL 0.8 mL.min-1.g-1 Rattus norvegicus
CL 1.1 mL.min-1.g-1 Homo sapiens
CL 8.0 mL.min-1.kg-1 Rattus norvegicus
CL 0.8 mL.min-1.g-1 Rattus norvegicus
CL 1.1 mL.min-1.g-1 Homo sapiens
CL 8.0 mL.min-1.kg-1 Rattus norvegicus
CL 0.8 mL.min-1.g-1 Rattus norvegicus
CL 1.1 mL.min-1.g-1 Homo sapiens
CL 8.0 mL.min-1.kg-1 Rattus norvegicus
F 59.0 % Rattus norvegicus
F 59.0 % Rattus norvegicus
F 59.0 % Rattus norvegicus
T1/2 4.4 hr Rattus norvegicus
T1/2 4.4 hr Rattus norvegicus
T1/2 4.4 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1A Ki = 0.07943 nM 10.1 Antagonist activity at human 5HT1A assessed as GTPgammaS binding by scintillatio... 19286377
5-hydroxytryptamine receptor 1A Ki = 0.07943 nM 10.1 Antagonist activity against human recombinant 5HT1A receptor expressed in HEK293... 20590088
5-hydroxytryptamine receptor 1D Ki = 0.1 nM 10.0 Antagonist activity at human 5HT1D assessed as GTPgammaS binding by scintillatio... 19286377
5-hydroxytryptamine receptor 1D Ki = 0.1 nM 10.0 Antagonist activity against human recombinant 5HT1D receptor expressed in CHO ce... 20590088
5-hydroxytryptamine receptor 1D Ki = 0.3162 nM 9.5 Displacement of [3H]5HT from human 5HT1D receptor expressed in CHO cells 18799312
5-hydroxytryptamine receptor 1A Ki = 0.3981 nM 9.4 Displacement of [3H]WAY-100635 from human 5HT1A receptor expressed in CHO cells 18799312
5-hydroxytryptamine receptor 1B Ki = 0.5012 nM 9.3 Displacement of [3H]5HT from human 5HT1B receptor expressed in CHO cells 18799312
5-hydroxytryptamine receptor 1B Ki = 1.995 nM 8.7 Antagonist activity at human 5HT1B assessed as GTPgammaS binding by scintillatio... 19286377
5-hydroxytryptamine receptor 1B Ki = 1.995 nM 8.7 Antagonist activity against human recombinant 5HT1B receptor expressed in CHO ce... 20590088
Sodium-dependent serotonin transporter Ki = 19.95 nM 7.7 Displacement of [3H]citalopram from human SerT expressed pig LLCPK cells 18799312
Sodium-dependent serotonin transporter Ki = 19.95 nM 7.7 Displacement of [3H]citalopram human SerT receptor expressed in LLCPK cells 19286377
Sodium-dependent serotonin transporter Ki = 19.95 nM 7.7 Displacement of [3H]citalopram from human recombinant SERT expressed in LLCPK ce... 20590088
Voltage-gated inwardly rectifying potassium channel KCNH2 Ki = 794.33 nM 6.1 Displacement of [3H]dofetilide human ERG expressed in CHO cells 19286377
Voltage-gated inwardly rectifying potassium channel KCNH2 Ki = 794.33 nM 6.1 Displacement of [3H]-dofetilide from human ERG by scintillation proximity assay 20590088

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
18799312 10.1016/j.bmcl.2008.08.084 5-hydroxytryptamine receptor 1B 2
20590088 10.1021/jm100482n Liver microsomes 2
20590088 10.1021/jm100482n 5-hydroxytryptamine receptor 1D 2
20590088 10.1021/jm100482n 5-hydroxytryptamine receptor 1B 2
20590088 10.1021/jm100482n 5-hydroxytryptamine receptor 1A 2
19286377 10.1016/j.bmcl.2009.02.056 Liver microsomes 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
18799312 10.1016/j.bmcl.2008.08.084 5-hydroxytryptamine receptor 1A 2
18799312 10.1016/j.bmcl.2008.08.084 5-hydroxytryptamine receptor 1D 2
19286377 10.1016/j.bmcl.2009.02.056 Sodium-dependent serotonin transporter 1
19286377 10.1016/j.bmcl.2009.02.056 Voltage-gated inwardly rectifying potassium channel KCNH2 1
19286377 10.1016/j.bmcl.2009.02.056 ADMET 1
18799312 10.1016/j.bmcl.2008.08.084 Sodium-dependent serotonin transporter 1
20590088 10.1021/jm100482n Sodium-dependent serotonin transporter 1

Data from ChEMBL 36 via Core Engine