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Compound Detail

CHEMBL183460

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Cc1ccc2c(OCCN3CCC(Cc4ccc5c(c4)NC(=O)CO5)CC3)cccc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL183460
Phase Preclinical
Structure Type MOL
InChI Key PJSUYRBCBFPCQW-UHFFFAOYSA-N
11
Targets
32
Activities
1
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

431.5
MW (Da)
4.21
ALogP
5
HBA
1
HBD
63.7
PSA (Ų)
0.63
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 C26H29N3O3
MW 431.54
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.95

Activity Summary

Ki 32 meas. best 9.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 9.5 9.0 0.3 9
5-hydroxytryptamine receptor 1D
CHEMBL1983
 Ki 8.8 8.8 1.6 5
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 8.4 8.1333 4.0 6
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.2 8.2 6.3 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
 Ki 8.0 8.0 10.0 5
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 6.7 6.7 199.5 1
D(3) dopamine receptor
CHEMBL234
 Ki 6.2 6.2 631.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 5.9 5.9 1258.9 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 5.8 5.8 1584.9 1
Beta-1 adrenergic receptor
CHEMBL213
 Ki 5.6 5.6 2511.9 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.5 5.5 3162.3 1

Pharmacokinetic Data

Parameter Value Units Species
CL 50.0 mL.min-1.kg-1 Rattus norvegicus
CL 3.4 mL.min-1.g-1 Rattus norvegicus
CL 1.2 mL.min-1.g-1 Homo sapiens
CL 50.0 mL.min-1.kg-1 Rattus norvegicus
F 45.0 % Rattus norvegicus
F 40.0 % Rattus norvegicus
T1/2 1.3 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1A Ki = 0.3162 nM 9.5 Negative logarithm causing 50% receptor occupancy against 5-hydroxytryptamine 1A... 16220969
5-hydroxytryptamine receptor 1A Ki = 0.3162 nM 9.5 Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in... 17629698
5-hydroxytryptamine receptor 1A Ki = 0.3162 nM 9.5 Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor 18433113
5-hydroxytryptamine receptor 1A Ki = 0.3162 nM 9.5 Mean negative logarithim of binding affinity was measured for the human 5-hydrox... 15664848
5-hydroxytryptamine receptor 1D Ki = 1.585 nM 8.8 Displacement of [3H]5-HT from human 5-hydroxytryptamine 1D receptor expressed in... 15887956
5-hydroxytryptamine receptor 1D Ki = 1.585 nM 8.8 Displacement of [3H]5-HT from human cloned 5HT1D receptor expressed in CHO cells 17129726
5-hydroxytryptamine receptor 1D Ki = 1.585 nM 8.8 Displacement of [3H]5-HT from human recombinant 5HT1D receptor expressed in CHO ... 17629698
5-hydroxytryptamine receptor 1D Ki = 1.585 nM 8.8 Displacement of [3H]5HT from human recombinant 5HT1D receptor 18433113
5-hydroxytryptamine receptor 1D Ki = 1.585 nM 8.8 Displacement of [3H]5HT from human cloned 5HT1D receptor expressed in CHO cells 18829312
5-hydroxytryptamine receptor 1A Ki = 2.512 nM 8.6 Displacement of [3H]WAY-100635 from human 5-hydroxytryptamine 1A receptor expres... 15887956
5-hydroxytryptamine receptor 1A Ki = 2.512 nM 8.6 Displacement of [3H]WAY-100635 from human cloned 5HT1A receptor expressed in CHO... 17129726
5-hydroxytryptamine receptor 1A Ki = 2.512 nM 8.6 Displacement of [3H]WAY 100635 from human recombinant 5HT1A receptor expressed i... 17629698
5-hydroxytryptamine receptor 1A Ki = 2.512 nM 8.6 Displacement of [3H]WAY100635 from human recombinant 5HT1A receptor 18433113
5-hydroxytryptamine receptor 1A Ki = 2.512 nM 8.6 Displacement of [3H]5HT from human cloned 5HT1A receptor expressed in CHO cells 18829312
Sodium-dependent serotonin transporter Ki = 3.981 nM 8.4 Inhibition of [3H]5-HT binding to serotonin transporter in rat cortical synaptos... 15887956
Sodium-dependent serotonin transporter Ki = 6.31 nM 8.2 Negative logarithm causing 50% receptor occupancy against serotonin transporter 16220969
Sodium-dependent serotonin transporter Ki = 6.31 nM 8.2 Mean negative logarithim of binding affinity was measured for the rat serotonin ... 15664848
Sodium-dependent serotonin transporter Ki = 7.943 nM 8.1 Inhibition of [3H]5-HT uptake at SERT in rat cortical synaptosomes 17129726
Sodium-dependent serotonin transporter Ki = 7.943 nM 8.1 Inhibition of [3H]5HT reuptake at SERT in rat cortical synaptosomes 18829312
5-hydroxytryptamine receptor 1B Ki = 10.0 nM 8.0 Displacement of [3H]5-HT from human 5-hydroxytryptamine 1B receptor expressed in... 15887956

Literature References

PubMed DOI Target Context # Activities
17629698 10.1016/j.bmcl.2007.06.078 Rattus norvegicus 4
17629698 10.1016/j.bmcl.2007.06.078 5-hydroxytryptamine receptor 1A 3
18433113 10.1021/jm8001444 5-hydroxytryptamine receptor 1A 3
17129726 10.1016/j.bmcl.2006.11.031 Rattus norvegicus 2
18829312 10.1016/j.bmcl.2008.08.110 5-hydroxytryptamine receptor 1B 2
18829312 10.1016/j.bmcl.2008.08.110 5-hydroxytryptamine receptor 1D 2
17629698 10.1016/j.bmcl.2007.06.078 Liver microsomes 2
17629698 10.1016/j.bmcl.2007.06.078 5-hydroxytryptamine receptor 1B 2
17629698 10.1016/j.bmcl.2007.06.078 5-hydroxytryptamine receptor 1D 2
15664848 10.1016/j.bmcl.2004.11.030 5-hydroxytryptamine receptor 1A 2
18829312 10.1016/j.bmcl.2008.08.110 5-hydroxytryptamine receptor 1A 2
17129726 10.1016/j.bmcl.2006.11.031 5-hydroxytryptamine receptor 1A 1
17129726 10.1016/j.bmcl.2006.11.031 Sodium-dependent serotonin transporter 1
17129726 10.1016/j.bmcl.2006.11.031 5-hydroxytryptamine receptor 1D 1
17129726 10.1016/j.bmcl.2006.11.031 5-hydroxytryptamine receptor 1B 1
16220969 10.1021/jm058225d Sodium-dependent serotonin transporter 1
16220969 10.1021/jm058225d 5-hydroxytryptamine receptor 1A 1
15887956 10.1021/jm049039v Sodium-dependent serotonin transporter 1
15887956 10.1021/jm049039v 5-hydroxytryptamine receptor 1D 1
18829312 10.1016/j.bmcl.2008.08.110 Sodium-dependent serotonin transporter 1

Data from ChEMBL 36 via Core Engine