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Compound Detail

CHEMBL593154

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COc1ccccc1C(=Cc1coc2nc(=N)[nH]c(N)c12)CC(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL593154
Phase Preclinical
Structure Type MOL
InChI Key GSEWOBPWXZKJLQ-UHFFFAOYSA-N
7
Targets
10
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

338.4
MW (Da)
3.81
ALogP
5
HBA
3
HBD
100.9
PSA (Ų)
0.66
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H22N4O2
MW 338.41
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -0.10

Activity Summary

IC50 7 meas. best 4.78
Ki 3 meas. best 6.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL4564
 Ki 6.04 6.04 910.0 1
Dihydrofolate reductase
CHEMBL2363
 Ki 5.33 5.33 4700.0 1
Dihydrofolate reductase
CHEMBL202
 Ki 4.96 4.96 11000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.78 4.78 16700.0 1
A-431
CHEMBL614069
 IC50 4.73 4.73 18600.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 4.6 4.6 24900.0 1
Dihydrofolate reductase
CHEMBL2363
 IC50 4.36 4.36 43900.0 1
Dihydrofolate reductase
CHEMBL4564
 IC50 4.29 4.29 51900.0 1
Unchecked
CHEMBL612545
 IC50 4.28 4.28 52600.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 4.06 4.06 86500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 910.0 nM 6.04 Competitive inhibition of mouse DHFR by enzyme kinetics assay in presence of var... 19748785
Dihydrofolate reductase Ki = 4700.0 nM 5.33 Inhibition of rat liver DHFR by enzyme kinetics assay in presence of variable DH... 19748785
Dihydrofolate reductase Ki = 11000.0 nM 4.96 Inhibition of human DHFR in presence of variable DHFA level by enzyme kinetics a... 19748785
NON-PROTEIN TARGET IC50 = 16700.0 nM 4.78 Antiangiogenic activity in chicken embryo chorioallantoic membrane assessed as i... 19748785
A-431 IC50 = 18600.0 nM 4.73 Cytotoxicity against human A431 cells after 48 hrs by CYQUANT cell proliferation... 19748785
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 24900.0 nM 4.6 Inhibition of Toxoplasma gondii DHFR in presence of saturating levels of NADPH a... 19748785
Dihydrofolate reductase IC50 = 43900.0 nM 4.36 Inhibition of rat liver DHFR in presence of saturating levels of NADPH and DHFA 19748785
Dihydrofolate reductase IC50 = 51900.0 nM 4.29 Inhibition of mouse DHFR in presence of saturating levels of NADPH and DHFA 19748785
Unchecked IC50 = 52600.0 nM 4.28 Inhibition of Pneumocystis carinii DHFR in presence of saturating levels of NADP... 19748785
Dihydrofolate reductase IC50 = 86500.0 nM 4.06 Inhibition of human DHFR in presence of saturating levels of NADPH and DHFA 19748785

Literature References

PubMed DOI Target Context # Activities
19748785 10.1016/j.bmc.2009.08.044 Dihydrofolate reductase 6
19748785 10.1016/j.bmc.2009.08.044 Unchecked 3
19748785 10.1016/j.bmc.2009.08.044 NON-PROTEIN TARGET 1
19748785 10.1016/j.bmc.2009.08.044 A-431 1
19748785 10.1016/j.bmc.2009.08.044 Bifunctional dihydrofolate reductase-thymidylate synthase 1
19748785 10.1016/j.bmc.2009.08.044 Epidermal growth factor receptor 1
19748785 10.1016/j.bmc.2009.08.044 Platelet-derived growth factor receptor beta 1
19748785 10.1016/j.bmc.2009.08.044 Vascular endothelial growth factor receptor 2 1

Data from ChEMBL 36 via Core Engine