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Compound Detail

CHEMBL594810

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

Basic Information

ChEMBL ID CHEMBL594810
Phase Preclinical
Structure Type MOL
InChI Key ZBHMLBFDTQKTKI-UHFFFAOYSA-N
7
Targets
11
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

324.4
MW (Da)
3.42
ALogP
5
HBA
3
HBD
100.9
PSA (Ų)
0.68
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H20N4O2
MW 324.38
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.19

Activity Summary

IC50 8 meas. best 5.38
Ki 3 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL4564
 Ki 7.16 7.16 70.0 1
Dihydrofolate reductase
CHEMBL202
 Ki 6.08 6.08 830.0 1
Dihydrofolate reductase
CHEMBL2363
 Ki 5.89 5.89 1300.0 1
Dihydrofolate reductase
CHEMBL4564
 IC50 5.38 5.38 4140.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.23 5.23 5900.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 5.2 5.2 6350.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 5.12 5.12 7500.0 1
Dihydrofolate reductase
CHEMBL2363
 IC50 4.92 4.92 11900.0 1
Unchecked
CHEMBL612545
 IC50 4.47 4.47 34000.0 1
A-431
CHEMBL614069
 IC50 4.32 4.32 48300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 70.0 nM 7.16 Competitive inhibition of mouse DHFR by enzyme kinetics assay in presence of var... 19748785
Dihydrofolate reductase Ki = 830.0 nM 6.08 Inhibition of human DHFR in presence of variable DHFA level by enzyme kinetics a... 19748785
Dihydrofolate reductase Ki = 1300.0 nM 5.89 Inhibition of rat liver DHFR by enzyme kinetics assay in presence of variable DH... 19748785
Dihydrofolate reductase IC50 = 4140.0 nM 5.38 Inhibition of mouse DHFR in presence of saturating levels of NADPH and DHFA 19748785
NON-PROTEIN TARGET IC50 = 5900.0 nM 5.23 Antiangiogenic activity in chicken embryo chorioallantoic membrane assessed as i... 19748785
Dihydrofolate reductase IC50 = 6350.0 nM 5.2 Inhibition of human DHFR in presence of saturating levels of NADPH and DHFA 19748785
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 7500.0 nM 5.12 Inhibition of Toxoplasma gondii DHFR in presence of saturating levels of NADPH a... 19748785
Dihydrofolate reductase IC50 = 11900.0 nM 4.92 Inhibition of rat liver DHFR in presence of saturating levels of NADPH and DHFA 19748785
Unchecked IC50 = 34000.0 nM 4.47 Inhibition of Pneumocystis carinii DHFR in presence of saturating levels of NADP... 19748785
A-431 IC50 = 48300.0 nM 4.32 Cytotoxicity against human A431 cells after 48 hrs by CYQUANT cell proliferation... 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 Epidermal growth factor receptor 1
19748785 10.1016/j.bmc.2009.08.044 Bifunctional dihydrofolate reductase-thymidylate synthase 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