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Compound Detail

CHEMBL4065484

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CS(=O)(=O)c1ccc(-c2cnc(NCc3ccco3)n3cnnc23)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4065484
Phase Preclinical
Structure Type MOL
InChI Key DYIRSNMPIZZNBK-UHFFFAOYSA-N
9
Targets
26
Activities
2
Assay Types
15
PK Parameters
20
Publications
0
Known Names

Molecular Properties

369.4
MW (Da)
2.40
ALogP
8
HBA
1
HBD
102.4
PSA (Ų)
0.58
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C17H15N5O3S
MW 369.41
Aromatic Rings 4
Heavy Atoms 26
NP-Likeness -1.83

Activity Summary

IC50 23 meas. best 7.91
Kd 3 meas. best 7.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polycomb protein EED
CHEMBL2189117
 IC50 7.91 7.488 12.2 10
Unchecked
CHEMBL612545
 IC50 7.66 7.1525 22.0 4
KARPAS-422
CHEMBL2366368
 IC50 7.1 6.9625 80.0 4
Polycomb protein EED
CHEMBL2189117
 Kd 7.09 7.09 82.0 1
EZH2/SUZ12/EED complex
CHEMBL3137286
 Kd 7.09 7.09 82.0 1
Histone-binding protein RBBP4/Histone-lysine N-methyltransferase EZH2/Polycomb protein EED/Polycomb protein SUZ12
CHEMBL6066587
 IC50 6.98 6.98 104.0 1
Unchecked
CHEMBL612545
 Kd 6.94 6.94 114.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
 IC50 4.85 4.85 14000.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 IC50 4.82 4.82 15000.0 1
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 4.7 4.7 20000.0 1
G-401
CHEMBL613509
 IC50 4.07 4.07 85000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 8.0 mL.min-1.kg-1 Mus musculus
CL 14.0 mL.min-1.kg-1 Rattus norvegicus
CL 16.0 mL.min-1.kg-1 Canis lupus familiaris
F 109.0 % Mus musculus
F 60.0 % Rattus norvegicus
F 68.0 % Canis lupus familiaris
F 10.0 % Mus musculus
F 62.0 % Rattus norvegicus
Fu 0.144 - Mus musculus
Fu 0.08 - Rattus norvegicus
Fu 0.24 - Canis lupus familiaris
Fu 0.13 - Homo sapiens
T1/2 2.2 hr Mus musculus
T1/2 2.2 hr Mus musculus
T1/2 1.6 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polycomb protein EED IC50 = 12.2 nM 7.91 Inhibition of biotinylated H3K27Me3 peptide (19 to 33 residues) binding to His-t... 34613724
Polycomb protein EED IC50 = 17.6 nM 7.75 Inhibition of EED ( 1 to 441 residues) (unknown origin) pre-incubated for 15 min... 32580550
Polycomb protein EED IC50 = 20.0 nM 7.7 Inhibition of EED (unknown origin) 35093670
Polycomb protein EED IC50 = 22.0 nM 7.66 Inhibition of recombinant N-terminal GST-tagged EED (76 to 441 residues) (unknow... 28092155
Unchecked IC50 = 22.0 nM 7.66 Inhibition of PRC2 (unknown origin) assessed as reduction in H3K27 trimethylatio... 35352560
Polycomb protein EED IC50 = 23.4 nM 7.63 Binding affinity to EED in PRC2 complex (unknown origin) using H3K27me0 (21 to 4... 33283516
Unchecked IC50 = 23.4 nM 7.63 Inhibition of PRC2 (unknown origin) using H3K27me0 as peptide substrate by LC-MS... 35224495
Polycomb protein EED IC50 = 30.0 nM 7.52 Inhibition of EED (unknown origin) 36724635
Polycomb protein EED IC50 = 45.0 nM 7.35 Displacement of UNC5114-biotin tracer ligand from N-terminal 6His-tagged EED (1 ... 33283516
Polycomb protein EED IC50 = 45.0 nM 7.35 Inhibition of full length N-terminal His-6x tagged EED (1 to 441 residues) (unkn... 35093670
Polycomb protein EED IC50 = 45.0 nM 7.35 Inhibition of His tagged EED (1 to 441) (unknown origin) using biotin-H3K27me3 p... 32871345
KARPAS-422 IC50 = 80.0 nM 7.1 Antiproliferative activity against human KARPAS422 cells harboring monoallelic Y... 28092155
KARPAS-422 IC50 = 80.0 nM 7.1 Antiproliferative activity against human KARPAS-422 cells expressing EZH2 Y641N ... 35093670
EZH2/SUZ12/EED complex Kd = 82.0 nM 7.09 Binding affinity to PRC2 complex of EZH2-EED-SUZ12 (unknown origin) assessed as ... 35224495
Polycomb protein EED Kd = 82.0 nM 7.09 Binding affinity to EED (unknown origin) by ITC method 28478342
Histone-binding protein RBBP4/Histone-lysine N-methyltransferase EZH2/Polycomb protein EED/Polycomb protein SUZ12 IC50 = 104.0 nM 6.98 TR-FRET Assay: The TR-FRET method was used to measure the PRC2 enzyme activity. ... -
Unchecked Kd = 114.0 nM 6.94 Binding affinity to PRC2 (unknown origin) by ITC method 28478342
KARPAS-422 IC50 = 125.4 nM 6.9 Growth inhibition of human KARPAS-422 cells assessed as cell growth incubated fo... 34613724
KARPAS-422 IC50 = 180.0 nM 6.75 Growth inhibition of human KARPAS422 cells incubated for 7 days by WST8 assay 32580550
Polycomb protein EED IC50 = 220.0 nM 6.66 Inhibition of EED in human G401 cells assessed as reduction in global H3K27me3 l... 28092155

Literature References

PubMed DOI Target Context # Activities
35352560 10.1021/acs.jmedchem.1c02148 ADMET 20
28092155 10.1021/acs.jmedchem.6b01576 Mus musculus 11
28092155 10.1021/acs.jmedchem.6b01576 ADMET 6
28092155 10.1021/acs.jmedchem.6b01576 No relevant target 5
38607318 10.1021/acs.jmedchem.4c00538 Unchecked 5
28092155 10.1021/acs.jmedchem.6b01576 Liver 4
28092155 10.1021/acs.jmedchem.6b01576 Plasma 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
38607318 10.1021/acs.jmedchem.4c00538 K562 3
28092155 10.1021/acs.jmedchem.6b01576 Rattus norvegicus 3
28092155 10.1021/acs.jmedchem.6b01576 Canis familiaris 3
35224495 10.1039/d1md00274k KARPAS-422 3
28092155 10.1021/acs.jmedchem.6b01576 Voltage-gated inwardly rectifying potassium channel KCNH2 2
33283516 10.1021/acs.jmedchem.0c01344 Polycomb protein EED 2
35093670 10.1016/j.ejmech.2022.114144 Polycomb protein EED 2
32580550 10.1021/acs.jmedchem.0c00479 KARPAS-422 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
35352560 10.1021/acs.jmedchem.1c02148 Unchecked 2
28092155 10.1021/acs.jmedchem.6b01576 Unchecked 2
28092155 10.1021/acs.jmedchem.6b01576 KARPAS-422 2

Data from ChEMBL 36 via Core Engine