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Compound Detail

CHEMBL392760

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NCCc1cn(S(=O)(=O)c2c(Cl)nc3sccn23)c2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL392760
Phase Preclinical
Structure Type MOL
InChI Key RYBOXBBYCVOYNO-UHFFFAOYSA-N
6
Targets
18
Activities
3
Assay Types
21
PK Parameters
20
Publications
0
Known Names

Molecular Properties

380.9
MW (Da)
2.74
ALogP
7
HBA
1
HBD
82.4
PSA (Ų)
0.59
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 C15H13ClN4O2S2
MW 380.88
Aromatic Rings 4
Heavy Atoms 24
NP-Likeness -1.43

Activity Summary

Ki 10 meas. best 8.7
IC50 5 meas. best 4.48
EC50 3 meas. best 8.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 8.7 8.6886 2.0 7
5-hydroxytryptamine receptor 6
CHEMBL3371
 EC50 8.19 8.19 6.5 3
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 6.91 6.91 124.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.34 6.34 458.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 6.17 6.17 679.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.48 4.48 33000.0 1
Cytochrome P450 2A6
CHEMBL5282
 IC50 4.39 4.39 41000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 140.0 ng.hr.mL-1 Rattus norvegicus
AUC 190.0 ng.hr.mL-1 Rattus norvegicus
AUC 520.0 ng.hr.mL-1 Canis lupus familiaris
AUC 1430.0 ng.hr.mL-1 Canis lupus familiaris
CL 30.0 mL.min-1.kg-1 Canis lupus familiaris
CL 123.33 mL.min-1.kg-1 Rattus norvegicus
Cmax 128.65 nM Rattus norvegicus
Cmax 341.31 nM Canis lupus familiaris
F 23.0 % Rattus norvegicus
F 55.0 % Canis lupus familiaris
T1/2 1.0 hr Mus musculus
T1/2 0.1333 hr Rattus norvegicus
T1/2 0.4333 hr Canis lupus familiaris
T1/2 0.1067 hr Macaca mulatta
T1/2 1.0 hr Homo sapiens
T1/2 5.4 hr Rattus norvegicus
T1/2 3.1 hr Rattus norvegicus
T1/2 2.9 hr Canis lupus familiaris
T1/2 6.6 hr Canis lupus familiaris
Tmax 1.7 hr Rattus norvegicus
Tmax 2.3 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 6 Ki = 2.0 nM 8.7 Displacement of [3H]LSD from human 5HT6 receptor expressed in HeLa cells 17948978
5-hydroxytryptamine receptor 6 Ki = 2.0 nM 8.7 Displacement of [3H]LSD from human 5HT6 receptor expressed in HEK293 cells by li... 19159187
5-hydroxytryptamine receptor 6 Ki = 2.0 nM 8.7 Displacement of [3H]LSD from human cloned 5HT6 receptor expressed in human HeLa ... 19739674
5-hydroxytryptamine receptor 6 Ki = 2.0 nM 8.7 Binding affinity to 5HT6 receptor 19758807
5-hydroxytryptamine receptor 6 Ki = 2.0 nM 8.7 Displacement of [3H]lysergic acid diethylamide from human 5-HT6 receptor express... 26099069
5-hydroxytryptamine receptor 6 Ki = 2.2 nM 8.66 Binding affinity to 5-HT6R (unknown origin) assessed as inhibition constant 34311086
5-hydroxytryptamine receptor 6 Ki = 2.2 nM 8.66 Displacement of [3H]-LSD from human 5-HT6 receptor expressed in human HeLa cells... 38190615
5-hydroxytryptamine receptor 6 EC50 = 6.5 nM 8.19 Agonist activity at human 5HT6 receptor expressed in HeLa cells assessed as cAMP... 17948978
5-hydroxytryptamine receptor 6 EC50 = 6.5 nM 8.19 Agonist activity at human 5HT6 receptor expressed in HeLa cells assessed as indu... 19739674
5-hydroxytryptamine receptor 6 EC50 = 6.5 nM 8.19 Agonist activity at 5HT6 receptor 19758807
5-hydroxytryptamine receptor 2C Ki = 124.0 nM 6.91 Inhibition of human 5HT2C receptor expressed in CHO cells 17948978
5-hydroxytryptamine receptor 2B Ki = 458.0 nM 6.34 Inhibition of human 5HT2B receptor expressed in CHO cells 17948978
5-hydroxytryptamine receptor 7 Ki = 679.0 nM 6.17 Displacement of [3H]LSD from human 5HT7 receptor expressed in CHO cells 17948978
Cytochrome P450 3A4 IC50 = 33000.0 nM 4.48 Inhibition of human CYP3A4 17948978
Cytochrome P450 2A6 IC50 = 41000.0 nM 4.39 Inhibition of human CYP2A6 17948978

Literature References

PubMed DOI Target Context # Activities
17948978 10.1021/jm070521y Rattus norvegicus 23
17948978 10.1021/jm070521y Brain 10
17948978 10.1021/jm070521y Plasma 10
17948978 10.1021/jm070521y Canis familiaris 9
17948978 10.1021/jm070521y Unchecked 9
19739674 10.1021/jm900796p 5-hydroxytryptamine receptor 6 3
17948978 10.1021/jm070521y 5-hydroxytryptamine receptor 6 3
17948978 10.1021/jm070521y Beta-1 adrenergic receptor 2
17948978 10.1021/jm070521y Beta-2 adrenergic receptor 2
17948978 10.1021/jm070521y Alpha-2B adrenergic receptor 2
17948978 10.1021/jm070521y ADMET 2
17948978 10.1021/jm070521y No relevant target 2
17948978 10.1021/jm070521y Liver 2
19758807 10.1016/j.bmc.2009.08.006 5-hydroxytryptamine receptor 6 2
17948978 10.1021/jm070521y Liver microsomes 2
17948978 10.1021/jm070521y Alpha-2A adrenergic receptor 2
17948978 10.1021/jm070521y 5-hydroxytryptamine receptor 2C 2
17948978 10.1021/jm070521y 5-hydroxytryptamine receptor 2A 1
38190615 10.1021/acs.jmedchem.3c02148 5-hydroxytryptamine receptor 6 1
17948978 10.1021/jm070521y 5-hydroxytryptamine receptor 4 1

Data from ChEMBL 36 via Core Engine