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Compound Detail

CHEMBL594320

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COc1ccccc1C(=Cc1coc2nc(=N)[nH]c(N)c12)C1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL594320
Phase Preclinical
Structure Type MOL
InChI Key PUOLMVSSUQSKAQ-UHFFFAOYSA-N
7
Targets
10
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

322.4
MW (Da)
3.18
ALogP
5
HBA
3
HBD
100.9
PSA (Ų)
0.69
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 C18H18N4O2
MW 322.37
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.14

Activity Summary

IC50 7 meas. best 5.34
Ki 3 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL4564
 Ki 7.1 7.1 80.0 1
Dihydrofolate reductase
CHEMBL2363
 Ki 5.96 5.96 1100.0 1
Dihydrofolate reductase
CHEMBL202
 Ki 5.89 5.89 1300.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 5.34 5.34 4600.0 1
Dihydrofolate reductase
CHEMBL4564
 IC50 5.33 5.33 4640.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.3 5.3 5000.0 1
A-431
CHEMBL614069
 IC50 5.02 5.02 9500.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 4.99 4.99 10200.0 1
Dihydrofolate reductase
CHEMBL2363
 IC50 4.99 4.99 10340.0 1
Unchecked
CHEMBL612545
 IC50 4.65 4.65 22200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 80.0 nM 7.1 Competitive inhibition of mouse DHFR by enzyme kinetics assay in presence of var... 19748785
Dihydrofolate reductase Ki = 1100.0 nM 5.96 Inhibition of rat liver DHFR by enzyme kinetics assay in presence of variable DH... 19748785
Dihydrofolate reductase Ki = 1300.0 nM 5.89 Inhibition of human DHFR in presence of variable DHFA level by enzyme kinetics a... 19748785
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4600.0 nM 5.34 Inhibition of Toxoplasma gondii DHFR in presence of saturating levels of NADPH a... 19748785
Dihydrofolate reductase IC50 = 4640.0 nM 5.33 Inhibition of mouse DHFR in presence of saturating levels of NADPH and DHFA 19748785
NON-PROTEIN TARGET IC50 = 5000.0 nM 5.3 Antiangiogenic activity in chicken embryo chorioallantoic membrane assessed as i... 19748785
A-431 IC50 = 9500.0 nM 5.02 Cytotoxicity against human A431 cells after 48 hrs by CYQUANT cell proliferation... 19748785
Dihydrofolate reductase IC50 = 10200.0 nM 4.99 Inhibition of human DHFR in presence of saturating levels of NADPH and DHFA 19748785
Dihydrofolate reductase IC50 = 10340.0 nM 4.99 Inhibition of rat liver DHFR in presence of saturating levels of NADPH and DHFA 19748785
Unchecked IC50 = 22200.0 nM 4.65 Inhibition of Pneumocystis carinii DHFR in presence of saturating levels of NADP... 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