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Compound Detail

CHEMBL5182943

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COc1cc(OC)c(C2NCCc3c2[nH]c2ccc(F)cc32)cc1OC.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5182943
Phase Preclinical
Structure Type MOL
InChI Key LWHOEIHANZIFDG-UHFFFAOYSA-N
Parent Compound CHEMBL5221893
Active Moiety CHEMBL5221893
12
Targets
18
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

356.4
MW (Da)
3.57
ALogP
4
HBA
2
HBD
55.5
PSA (Ų)
0.75
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H22ClFN2O3
MW 392.86
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness 0.02

Activity Summary

Ki 12 meas. best 7.25
EC50 6 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2B
CHEMBL1833
 EC50 8.0 7.98 10.0 2
5-hydroxytryptamine receptor 2C
CHEMBL225
 EC50 7.7 7.695 20.0 2
5-hydroxytryptamine receptor 2A
CHEMBL224
 EC50 7.41 7.405 39.0 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 7.25 7.25 55.7 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 6.6 6.6 249.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 6.28 6.28 530.0 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
 Ki 6.18 6.18 660.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 6.17 6.17 671.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 6.12 6.12 760.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 6.02 6.02 964.0 1
Beta-1 adrenergic receptor
CHEMBL213
 Ki 6.02 6.02 961.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 5.86 5.86 1367.0 1
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 5.63 5.63 2328.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.61 5.61 2445.0 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
 Ki 5.55 5.55 2839.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2B EC50 = 10.0 nM 8.0 Agonist activity at human 5HT2B receptor stably expressed in Flp-In-T-REx-293 ce... 35450369
5-hydroxytryptamine receptor 2B EC50 = 10.96 nM 7.96 Agonist activity at human 5HT2B receptor stably expressed in Flp-In-T-REx-293 ce... 35450369
5-hydroxytryptamine receptor 2C EC50 = 20.0 nM 7.7 Agonist activity at human 5HT2C receptor stably expressed in Flp-In-T-REx-293 ce... 35450369
5-hydroxytryptamine receptor 2C EC50 = 20.42 nM 7.69 Agonist activity at human 5HT2C receptor stably expressed in Flp-In-T-REx-293 ce... 35450369
5-hydroxytryptamine receptor 2A EC50 = 39.0 nM 7.41 Agonist activity at human 5HT2A receptor stably expressed in Flp-In-T-REx-293 ce... 35450369
5-hydroxytryptamine receptor 2A EC50 = 39.81 nM 7.4 Agonist activity at human 5HT2A receptor stably expressed in Flp-In-T-REx-293 ce... 35450369
5-hydroxytryptamine receptor 2B Ki = 55.7 nM 7.25 Binding affinity to 5HT2B receptor (unknown origin) assessed as inhibition const... 35450369
5-hydroxytryptamine receptor 7 Ki = 249.0 nM 6.6 Binding affinity to 5HT7 receptor (unknown origin) assessed as inhibition consta... 35450369
5-hydroxytryptamine receptor 6 Ki = 530.0 nM 6.28 Binding affinity to 5HT6 receptor (unknown origin) assessed as inhibition consta... 35450369
5-hydroxytryptamine receptor 1D Ki = 660.0 nM 6.18 Binding affinity to 5HT1D receptor (unknown origin) assessed as inhibition const... 35450369
5-hydroxytryptamine receptor 2C Ki = 671.0 nM 6.17 Binding affinity to 5HT2C receptor (unknown origin) assessed as inhibition const... 35450369
Sigma non-opioid intracellular receptor 1 Ki = 760.0 nM 6.12 Binding affinity to sigma 1 receptor (unknown origin) assessed as inhibition con... 35450369
Alpha-2C adrenergic receptor Ki = 964.0 nM 6.02 Binding affinity to alpha2c (unknown origin) assessed as inhibition constant 35450369
Beta-1 adrenergic receptor Ki = 961.0 nM 6.02 Binding affinity to beta1 receptor (unknown origin) assessed as inhibition const... 35450369
5-hydroxytryptamine receptor 1A Ki = 1367.0 nM 5.86 Binding affinity to 5HT1A receptor (unknown origin) assessed as inhibition const... 35450369
Sigma intracellular receptor 2 Ki = 2328.0 nM 5.63 Binding affinity to sigma 2 receptor (unknown origin) assessed as inhibition con... 35450369
5-hydroxytryptamine receptor 2A Ki = 2445.0 nM 5.61 Binding affinity to 5HT2A receptor (unknown origin) assessed as inhibition const... 35450369
5-hydroxytryptamine receptor 5A Ki = 2839.0 nM 5.55 Binding affinity to 5HT5A receptor (unknown origin) assessed as inhibition const... 35450369

Literature References

PubMed DOI Target Context # Activities
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 2C 4
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 2A 4
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 2B 4
35450369 10.1021/acsmedchemlett.1c00694 GABA-A receptor; anion channel 1
35450369 10.1021/acsmedchemlett.1c00694 Alpha-1A adrenergic receptor 1
35450369 10.1021/acsmedchemlett.1c00694 Sigma intracellular receptor 2 1
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 1A 1
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 1B 1
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 1D 1
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 1E 1
35450369 10.1021/acsmedchemlett.1c00694 Sigma non-opioid intracellular receptor 1 1
35450369 10.1021/acsmedchemlett.1c00694 Sodium-dependent serotonin transporter 1
35450369 10.1021/acsmedchemlett.1c00694 D(4) dopamine receptor 1
35450369 10.1021/acsmedchemlett.1c00694 D(3) dopamine receptor 1
35450369 10.1021/acsmedchemlett.1c00694 Beta-1 adrenergic receptor 1
35450369 10.1021/acsmedchemlett.1c00694 Alpha-2C adrenergic receptor 1
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 7 1
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 6 1
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 5A 1
35450369 10.1021/acsmedchemlett.1c00694 5-hydroxytryptamine receptor 3A 1

Data from ChEMBL 36 via Core Engine