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Compound Detail

CHEMBL2311578

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Cc1cc(OCc2nnc(SC3CCCC3)n2-c2cccnc2)ccc1-c1ccc(S(C)(=O)=O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2311578
Phase Preclinical
Structure Type MOL
InChI Key UJGTUKMAJVCBIS-UHFFFAOYSA-N
7
Targets
18
Activities
2
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

520.7
MW (Da)
5.65
ALogP
8
HBA
0
HBD
87.0
PSA (Ų)
0.30
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H28N4O3S2
MW 520.68
Aromatic Rings 4
Heavy Atoms 36
NP-Likeness -1.76

Activity Summary

IC50 10 meas. best 8.89
EC50 8 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
L929
CHEMBL612267
 IC50 8.89 8.89 1.3 1
Transitional endoplasmic reticulum ATPase
CHEMBL1075145
 IC50 7.96 7.5475 11.0 4
Influenza A virus
CHEMBL613740
 EC50 7.52 7.52 30.0 5
Human betaherpesvirus 5
CHEMBL371
 IC50 6.89 6.89 130.0 1
Cytomegalovirus
CHEMBL613134
 IC50 6.89 6.89 130.0 1
HCT-116
CHEMBL394
 IC50 6.42 6.385 380.0 2
Transitional endoplasmic reticulum ATPase
CHEMBL1075145
 EC50 5.85 5.76 1400.0 3
U-87 MG
CHEMBL614247
 IC50 5.21 5.21 6214.7 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 223.89 ng.hr.mL-1 Mus musculus
AUC 1176.74 ng.hr.mL-1 Mus musculus
CL 400.0 mL.min-1.kg-1 Homo sapiens
CL 115.0 mL.min-1.kg-1 Mus musculus
Cmax 60.0 nM Mus musculus
Cmax 300.0 nM Mus musculus
F 16.4 % Mus musculus
T1/2 6.0 hr Mus musculus
T1/2 0.9 hr Mus musculus
T1/2 0.1667 hr Mus musculus
T1/2 0.1667 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 0.15 hr Mus musculus
Tmax 0.8 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
L929 IC50 = 1.3 nM 8.89 Antiproliferative activity against mouse L929 cells assessed as inhibition of ce... 36893622
Transitional endoplasmic reticulum ATPase IC50 = 11.0 nM 7.96 Inhibition of recombinant human full length Avi-tagged p97 (1 to 806 residues) e... 26985295
Transitional endoplasmic reticulum ATPase IC50 = 20.0 nM 7.7 Inhibition of p97 (unknown origin) ATPase activity by Biomol Green Reagent based... 37465292
Transitional endoplasmic reticulum ATPase IC50 = 24.0 nM 7.62 Inhibition of human recombinant His-GST tagged VCP expressed in baculovirus infe... 23245311
Influenza A virus EC50 = 30.0 nM 7.52 Antiviral activity against Oseltamivir-resistant Influenza A virus (A/North Caro... 33873056
Influenza A virus EC50 = 30.0 nM 7.52 Antiviral activity against Amantadine-resistant Influenza A virus (A/WSN/1933 (H... 33873056
Influenza A virus EC50 = 30.0 nM 7.52 Antiviral activity against Influenza A virus (A/Denmark/528/2009 (H1N1)) infecte... 33873056
Influenza A virus EC50 = 30.0 nM 7.52 Antiviral activity against Influenza A virus (A/Texas/04/2009 (H1N1)) infected i... 33873056
Influenza A virus EC50 = 30.0 nM 7.52 Antiviral activity against Amantadine -resistant Influenza A virus (A/Washington... 33873056
Transitional endoplasmic reticulum ATPase IC50 = 123.3 nM 6.91 Covalent inhibition of p97 (unknown origin) ATPase activity incubated for 60 min... 36634454
Human betaherpesvirus 5 IC50 = 130.0 nM 6.89 Antiviral activity against Human Cytomegalovirus 31550150
Cytomegalovirus IC50 = 130.0 nM 6.89 Antiviral activity against human Cytomegalovirus infected in human fibroblast ce... 33873056
HCT-116 IC50 = 380.0 nM 6.42 Cytotoxicity against human HCT116 cells after 72 hrs by luciferase reporter gene... 23245311
HCT-116 IC50 = 450.0 nM 6.35 Antiproliferative activity against human HCT-116 cells assessed as reduction in ... 36893622
Transitional endoplasmic reticulum ATPase EC50 = 1400.0 nM 5.85 Inhibition of human p97 in human HeLa cells harboring UbG76V-GFP assessed as acc... 30429948
Transitional endoplasmic reticulum ATPase EC50 = 1800.0 nM 5.75 Inhibition of p97 in human HeLa cells expressing UbG76V-GFP/ODD-Luc assessed as ... 37465292
Transitional endoplasmic reticulum ATPase EC50 = 2100.0 nM 5.68 Inhibition of human p97 in human HeLa cells harboring UbG76V-GFP assessed as acc... 30429948
U-87 MG IC50 = 6214.67 nM 5.21 Cytotoxicity against human U87 cells assessed as reduction in cell viability inc... 36634454

Literature References

PubMed DOI Target Context # Activities
23245311 10.1021/jm3013213 Mus musculus 10
33873056 10.1016/j.ejmech.2021.113446 ADMET 5
23245311 10.1021/jm3013213 Transitional endoplasmic reticulum ATPase 5
33873056 10.1016/j.ejmech.2021.113446 Influenza A virus 5
30830772 10.1021/acs.jmedchem.9b00144 Transitional endoplasmic reticulum ATPase 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5724709 Fibroblast 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL5724709 HEK-293T 2
37465292 10.1021/acsmedchemlett.3c00163 Transitional endoplasmic reticulum ATPase 2
30429948 10.1021/acsmedchemlett.8b00372 Transitional endoplasmic reticulum ATPase 2
30429948 10.1021/acsmedchemlett.8b00372 ADMET 2
- 10.6019/CHEMBL5724709 U2OS 2
23245311 10.1021/jm3013213 HCT-116 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
30429948 10.1021/acsmedchemlett.8b00372 Panel NCI-60 (60 carcinoma cell lines) 1
23245311 10.1021/jm3013213 ATPase family gene 2 protein homolog A 1
23245311 10.1021/jm3013213 Vacuolar protein sorting-associated protein 4B 1
23245311 10.1021/jm3013213 Heat shock protein HSP90 1
23245311 10.1021/jm3013213 Liver microsomes 1

Data from ChEMBL 36 via Core Engine