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Compound Detail

CHEMBL460491

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CC1(C)CN2C(CS/C(=N\C3CCCCC3)NC3CCCCC3)=CSC2=N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL460491
Phase Preclinical
Structure Type MOL
InChI Key OOSUDWRRWZVFEB-UHFFFAOYSA-N
8
Targets
25
Activities
2
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

406.7
MW (Da)
5.37
ALogP
5
HBA
1
HBD
40.0
PSA (Ų)
0.50
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H34N4S2
MW 406.67
Aromatic Rings 0
Heavy Atoms 27
NP-Likeness -0.56

Activity Summary

IC50 24 meas. best 8.96
EC50 1 meas. best 7.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-X-C chemokine receptor type 4
CHEMBL2107
 IC50 8.96 6.7241 1.1 17
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.15 8.15 7.0 1
C-X-C chemokine receptor type 4
CHEMBL5556
 IC50 7.96 7.96 11.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 EC50 7.66 7.66 22.0 1
Unchecked
CHEMBL612545
 IC50 6.79 6.79 164.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 6.4 6.4 400.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 5.28 5.28 5200.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.88 4.88 13240.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 105.0 ng/ml Rattus norvegicus
CL 149.0 mL.min-1.g-1 Homo sapiens
CL 342.0 mL.min-1.g-1 Rattus norvegicus
Cmax 44.26 nM Rattus norvegicus
F 32.0 % Rattus norvegicus
Fu 0.2 - Homo sapiens
Fu 0.46 - Rattus norvegicus
T1/2 7.6 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-X-C chemokine receptor type 4 IC50 = 1.1 nM 8.96 Activity at CXCR4 in human CEM cells assessed as inhibition of CXCL12-induced ca... 19053768
C-X-C chemokine receptor type 4 IC50 = 1.1 nM 8.96 Inhibition of wild type CXCR4 (unknown origin) 28165741
Human immunodeficiency virus 1 IC50 = 7.0 nM 8.15 Antiviral activity against X4-tropic HIV1 3B assessed as inhibition of viral att... 19053768
C-X-C chemokine receptor type 4 IC50 = 8.0 nM 8.1 Displacement of [125I]CXCL12 from CXCR4 in human CEM cells 19053768
C-X-C chemokine receptor type 4 IC50 = 10.0 nM 8.0 Displacement of [125I]-CXCL12 from human CXCR4 receptor expressed in HEK293T cel... 30476826
C-X-C chemokine receptor type 4 IC50 = 10.0 nM 8.0 Displacement of CXCL12-red from human NLuc-tagged CXCR4 receptor expressed in HE... 30476826
C-X-C chemokine receptor type 4 IC50 = 11.0 nM 7.96 Displacement of [125I]CXCL12 from CXCR4 in rat IR983F cells 19053768
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 22.0 nM 7.66 Inhibition of HIV1 3B reverse transcriptase infected in human GHOST CXCR4 cells ... 33214847
C-X-C chemokine receptor type 4 IC50 = 32.5 nM 7.49 Antagonist activity at CXCR4 (unknown origin) expressed in CHO cells assessed as... 33214847
C-X-C chemokine receptor type 4 IC50 = 50.12 nM 7.3 Antagonist activity at human DEF3-fused CXCR4 receptor expressed in HEK293T cell... 30476826
C-X-C chemokine receptor type 4 IC50 = 50.12 nM 7.3 Antagonist activity at human DEF3-RLuc fused CXCR4 receptor expressed in HEK293T... 30476826
Unchecked IC50 = 164.0 nM 6.79 Inhibition of HIV1 3B Tat infected in human TZM-bl cells assessed as reduction i... 33214847
C-X-C chemokine receptor type 4 IC50 = 223.0 nM 6.65 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949
C-X-C chemokine receptor type 4 IC50 = 326.0 nM 6.49 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949
Cytochrome P450 2D6 IC50 = 400.0 nM 6.4 Inhibition of CYP2D6 19053768
C-X-C chemokine receptor type 4 IC50 = 430.0 nM 6.37 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949
C-X-C chemokine receptor type 4 IC50 = 967.0 nM 6.01 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949
Cytochrome P450 2C19 IC50 = 5200.0 nM 5.28 Inhibition of CYP2C19 19053768
C-X-C chemokine receptor type 4 IC50 = 6370.0 nM 5.2 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949
C-X-C chemokine receptor type 4 IC50 = 7190.0 nM 5.14 Antagonist activity at recombinant human N-terminal MDSKGSSQKGSRLLLLLVVSNLLLCQGV... 30655949

Literature References

PubMed DOI Target Context # Activities
30655949 10.1021/acsmedchemlett.8b00441 C-X-C chemokine receptor type 4 7
30655949 10.1021/acsmedchemlett.8b00441 Unchecked 6
19053768 10.1021/jm801065q No relevant target 5
19053768 10.1021/jm801065q C-X-C chemokine receptor type 4 5
19053768 10.1021/jm801065q Rattus norvegicus 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
30476826 10.1016/j.ejmech.2018.10.060 C-X-C chemokine receptor type 4 4
33214847 10.1021/acsmedchemlett.0c00444 Human immunodeficiency virus 1 3
19053768 10.1021/jm801065q Serum 2
33479612 10.1039/c9md00433e C-X-C chemokine receptor type 4 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
33214847 10.1021/acsmedchemlett.0c00444 C-X-C chemokine receptor type 4 2
29777988 10.1016/j.ejmech.2018.05.013 C-X-C chemokine receptor type 4 2
19053768 10.1021/jm801065q Human immunodeficiency virus 1 2
19053768 10.1021/jm801065q Liver microsomes 2
19053768 10.1021/jm801065q Voltage-gated inwardly rectifying potassium channel KCNH2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19053768 10.1021/jm801065q Blood 2
36944083 10.1021/acs.jmedchem.3c00151 C-X-C chemokine receptor type 4 1
19053768 10.1021/jm801065q Cytochrome P450 2D6 1

Data from ChEMBL 36 via Core Engine