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Compound Detail

CHEMBL4743159

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CC(C)C(=O)Nc1nc(-c2ccc(O)cc2O)cs1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4743159
Phase Preclinical
Structure Type MOL
InChI Key WIDNAJNXDPHROL-UHFFFAOYSA-N
3
Targets
21
Activities
2
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

278.3
MW (Da)
2.82
ALogP
5
HBA
3
HBD
82.5
PSA (Ų)
0.81
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H14N2O3S
MW 278.33
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -1.12

Activity Summary

IC50 15 meas. best 6.89
Ki 6 meas. best 6.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mushroom tyrosinase
CHEMBL6066154
 IC50 6.89 6.89 130.0 1
Tyrosinase
CHEMBL1973
 IC50 6.77 5.955 170.0 10
Tyrosinase
CHEMBL1973
 Ki 6.6 6.5067 250.0 6
MNT-1
CHEMBL5209890
 IC50 6.55 5.775 280.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mushroom tyrosinase IC50 = 130.0 nM 6.89 Inhibition of mushroom tyrosinase using L-DOPA as substrate by spectrophotometri... 38823727
Tyrosinase IC50 = 170.0 nM 6.77 Inhibition of tyrosinase in human MNT-1 cells using L-DOPA as substrate preincub... 38262119
Tyrosinase Ki = 250.0 nM 6.6 Competitive inhibition of His-tagged human tyrosinase expressed in HEK293 cells ... 37657271
Tyrosinase Ki = 250.0 nM 6.6 Binding affinity to His-tagged human tyrosinase expressed in HEK293 cells assess... 38262119
Tyrosinase Ki = 250.0 nM 6.6 Inhibition of truncated His-tagged human tyrosinase catalytic domain expressed i... 36462443
Tyrosinase Ki = 250.0 nM 6.6 Binding affinity to human His-tagged tyrosinase CD expressed in HEK293 cells ass... 35717871
Tyrosinase Ki = 250.0 nM 6.6 Inhibition of human His-tagged tyrosinase expressed in HEK 293 cells using L-DOP... 32787103
MNT-1 IC50 = 280.0 nM 6.55 Inhibition of melanogenesis in human MNT-1 cells incubated for 14 days 38262119
Tyrosinase IC50 = 900.0 nM 6.05 Inhibition of human His-tagged tyrosinase CD expressed in HEK293 cells assessed ... 35717871
Tyrosinase Ki = 920.0 nM 6.04 Binding affinity to human tyrosinase using l-DOPA as substrate assessed as inhib... 37657271
Tyrosinase IC50 = 1100.0 nM 5.96 Competitive inhibition of His-tagged human tyrosinase expressed in HEK293 cells 37657271
Tyrosinase IC50 = 1100.0 nM 5.96 Competitive inhibition of human tyrosinase using L-DOPA as substrate by spectrop... 38823727
Tyrosinase IC50 = 1100.0 nM 5.96 Inhibition of truncated His-tagged human tyrosinase catalytic domain expressed i... 36462443
Tyrosinase IC50 = 1100.0 nM 5.96 Inhibition of human his tagged tyrosinase expressed in HEK293 cells using L-DOPA... 34365131
Tyrosinase IC50 = 1100.0 nM 5.96 Inhibition of human His-tagged tyrosinase expressed in HEK 293 cells using L-DOP... 32787103
Tyrosinase IC50 = 1400.0 nM 5.85 Inhibition of human tyrosinase using L-DOPA as substrate incubated for 10 to 20 ... 35717871
Tyrosinase IC50 = 2200.0 nM 5.66 Inhibition of human tyrosinase assessed as reduction in L-dopaquinone-MBTH compl... 34041485
Tyrosinase IC50 = 3800.0 nM 5.42 Inhibition of human tyrosinase using L-DOPA as substrate by spectrophotometer an... 37657271
MNT-1 IC50 = 10000.0 nM 5.0 Inhibition of melanogenesis in human MNT-1 cells incubated for 4 days 38262119

Literature References

PubMed DOI Target Context # Activities
37657271 10.1016/j.ejmech.2023.115771 Tyrosinase 5
38262119 10.1016/j.ejmech.2024.116165 MNT-1 4
35717871 10.1016/j.ejmech.2022.114525 Tyrosinase 3
32787103 10.1021/acs.jmedchem.0c00994 Tyrosinase 2
34365131 10.1016/j.ejmech.2021.113744 Tyrosinase 2
36462443 10.1016/j.ejmech.2022.114972 Tyrosinase 2
38262119 10.1016/j.ejmech.2024.116165 Tyrosinase 2
37657271 10.1016/j.ejmech.2023.115771 Mushroom tyrosinase 2
34041485 10.1039/D0MD00310G Tyrosinase 1
38823727 10.1016/j.bmcl.2024.129823 Tyrosinase 1
38823727 10.1016/j.bmcl.2024.129823 Mushroom tyrosinase 1

Data from ChEMBL 36 via Core Engine