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Compound Detail

CHEMBL297784

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Cn1ccc2cc3c(cc21)CCN3C(=O)Nc1cccnc1

Basic Information

ChEMBL ID CHEMBL297784
Phase Preclinical
Structure Type MOL
InChI Key QJQORSLQNXDVGE-UHFFFAOYSA-N
12
Targets
29
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

292.3
MW (Da)
3.17
ALogP
3
HBA
1
HBD
50.2
PSA (Ų)
0.75
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C17H16N4O
MW 292.34
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness -1.68

Activity Summary

Ki 21 meas. best 8.55
IC50 4 meas. best 8.03
EC50 2 meas. best 7.89
Kd 2 meas. best 8.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 8.55 8.0875 2.8 4
5-hydroxytryptamine receptor 2B
CHEMBL323
Kd 8.5 8.49 3.2 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 8.37 7.7967 4.3 9
5-hydroxytryptamine receptor 2C
CHEMBL324
Ki 8.3 8.3 5.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 8.03 8.03 9.4 1
5-hydroxytryptamine receptor 2C
CHEMBL3006
Ki 8.0 8.0 10.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
EC50 7.89 7.89 13.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 7.3 7.3 50.0 1
Histone deacetylase 6
CHEMBL1865
IC50 6.37 6.37 426.7 1
5-hydroxytryptamine receptor 2A
CHEMBL322
Ki 6.3 6.3 501.2 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
EC50 5.82 5.82 1500.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.79 5.745 1621.8 4
5-hydroxytryptamine receptor 4
CHEMBL4317
Ki 5.3 5.3 5011.9 1
Cytochrome P450 2D6
CHEMBL289
IC50 4.52 4.52 30000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2C Ki = 2.8 nM 8.55 Displacement of [3H]LSD from human recombinant 5-HT2C receptor expressed in HEK ... 34467758
5-hydroxytryptamine receptor 2B Kd = 3.162 nM 8.5 Inhibition of 5-HT binding to 5-HT2B receptor of Rat stomach fundus 8960557
5-hydroxytryptamine receptor 2B Kd = 3.311 nM 8.48 Inhibitory potency against rat stomach fundus 5-hydroxytryptamine 2B receptor 7629791
5-hydroxytryptamine receptor 2B Ki = 4.3 nM 8.37 Displacement of [3H]LSD from human cloned 5HT2B receptor expressed in CHO cells ... 20958049
5-hydroxytryptamine receptor 2C Ki = 5.012 nM 8.3 Displacement of [3H]mesulergine from rat 5-HT2C receptor expressed in HEK293 8960557
5-hydroxytryptamine receptor 2C IC50 = 9.4 nM 8.03 Antagonist activity at human recombinant 5-HT2C receptor assessed as inhibition ... 24805037
5-hydroxytryptamine receptor 2C Ki = 10.0 nM 8.0 Binding affinity against human 5-hydroxytryptamine 2C receptor expressed in 293 ... 7629791
5-hydroxytryptamine receptor 2C Ki = 10.0 nM 8.0 Binding affinity analysed on 5-HT 2C in human clone using [3H]mesulergine as rad... 8709108
5-hydroxytryptamine receptor 2B Ki = 12.0 nM 7.92 Displacement of [3H]LSD from 5-HT2B receptor (unknown origin) 24365159
5-hydroxytryptamine receptor 2B Ki = 12.02 nM 7.92 Displacement of [3H]LSD from 5-HT2B receptor (unknown origin) 24365159
5-hydroxytryptamine receptor 2C Ki = 12.59 nM 7.9 Binding affinity towards cloned human 5-hydroxytryptamine 2C receptor expressed ... 9572885
5-hydroxytryptamine receptor 2C Ki = 12.59 nM 7.9 Displacement of [3H]mesulergine from 5-hydroxytryptamine 2C receptor expressed i... 9357513
5-hydroxytryptamine receptor 2B EC50 = 13.0 nM 7.89 Antagonist activity at recombinant human 5-HT2B receptor expressed in CHOK1 cell... 32342685
5-hydroxytryptamine receptor 2B Ki = 18.5 nM 7.73 Inhibition of [3H]LSD binding to 5-HT2B receptor (unknown origin) 25728001
5-hydroxytryptamine receptor 2B Ki = 20.0 nM 7.7 Displacement of [3H]LSD from 5-HT2B receptor (unknown origin) assessed as inhibi... 36001775
5-hydroxytryptamine receptor 2B Ki = 21.0 nM 7.68 Displacement of [3H]LSD from human recombinant 5-HT2B receptor stably expressed ... -
5-hydroxytryptamine receptor 2B Ki = 22.2 nM 7.65 Displacement of [3H]LSD from human 5HT2B receptor expressed in HEK cells membran... 30108996
5-hydroxytryptamine receptor 2B Ki = 25.12 nM 7.6 Displacement of [3H]5-HT from 5-hydroxytryptamine 2B receptor expressed in HEK 2... 9357513
5-hydroxytryptamine receptor 2B Ki = 25.12 nM 7.6 Binding affinity towards cloned human 5-hydroxytryptamine 2B receptor expressed ... 9572885
Cytochrome P450 1A2 IC50 = 50.0 nM 7.3 Inhibition of heterologously expressed human Cytochrome P450 1A2 at 500 uM 9357513

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
21919481 10.1021/jm2007672 Neuronal acetylcholine receptor subunit alpha-7 2
24365159 10.1016/j.bmcl.2013.12.024 5-hydroxytryptamine receptor 2B 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
9357513 10.1021/jm970424c Serotonin receptor (2b and 2c) 1
7629791 10.1021/jm00014a004 5-hydroxytryptamine receptor 4 1
7629791 10.1021/jm00014a004 Serotonin 3 (5-HT3) receptor 1
7629791 10.1021/jm00014a004 5-hydroxytryptamine receptor 1D 1
7629791 10.1021/jm00014a004 5-hydroxytryptamine receptor 1A 1
7629791 10.1021/jm00014a004 5-hydroxytryptamine receptor 2B 1
7629791 10.1021/jm00014a004 5-hydroxytryptamine receptor 2C 1
7629791 10.1021/jm00014a004 5-hydroxytryptamine receptor 2A 1
25728001 10.1002/anie.201412154 5-hydroxytryptamine receptor 2B 1
9357513 10.1021/jm970424c Cytochrome P450 3A4 1
9357513 10.1021/jm970424c Cytochrome P450 2D6 1
9357513 10.1021/jm970424c Aromatase 1
9357513 10.1021/jm970424c Cytochrome P450 2C9 1
9357513 10.1021/jm970424c Cytochrome P450 1A2 1
9357513 10.1021/jm970424c Rattus norvegicus 1
9357513 10.1021/jm970424c 5-hydroxytryptamine receptor 2C 1

Data from ChEMBL 36 via Core Engine