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Compound Detail

CHEMBL595757

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COc1ccccc1C(Cc1coc2nc(N)nc(N)c12)C(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL595757
Phase Preclinical
Structure Type MOL
InChI Key AALMZTNNZVHOAS-UHFFFAOYSA-N
8
Targets
12
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

326.4
MW (Da)
3.38
ALogP
6
HBA
2
HBD
100.2
PSA (Ų)
0.75
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 C18H22N4O2
MW 326.40
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.32

Activity Summary

IC50 9 meas. best 5.5
Ki 3 meas. best 7.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL4564
 Ki 7.22 7.22 60.0 1
Dihydrofolate reductase
CHEMBL202
 Ki 6.11 6.11 770.0 1
Dihydrofolate reductase
CHEMBL2363
 Ki 5.85 5.85 1400.0 1
Dihydrofolate reductase
CHEMBL4564
 IC50 5.5 5.5 3200.0 1
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 5.3 5.3 5000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.3 5.3 5000.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 5.29 5.29 5090.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 5.16 5.16 7000.0 1
Dihydrofolate reductase
CHEMBL2363
 IC50 4.9 4.9 12600.0 1
Epidermal growth factor receptor
CHEMBL203
 IC50 4.74 4.74 18200.0 1
Unchecked
CHEMBL612545
 IC50 4.27 4.27 53600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 60.0 nM 7.22 Competitive inhibition of mouse DHFR by enzyme kinetics assay in presence of var... 19748785
Dihydrofolate reductase Ki = 770.0 nM 6.11 Inhibition of human DHFR in presence of variable DHFA level by enzyme kinetics a... 19748785
Dihydrofolate reductase Ki = 1400.0 nM 5.85 Inhibition of rat liver DHFR by enzyme kinetics assay in presence of variable DH... 19748785
Dihydrofolate reductase IC50 = 3200.0 nM 5.5 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
Vascular endothelial growth factor receptor 2 IC50 = 5000.0 nM 5.3 Inhibition of VEGFR2 in human U251 cells by phosphotyrosine ELISA 19748785
Dihydrofolate reductase IC50 = 5090.0 nM 5.29 Inhibition of human DHFR in presence of saturating levels of NADPH and DHFA 19748785
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 7000.0 nM 5.16 Inhibition of Toxoplasma gondii DHFR in presence of saturating levels of NADPH a... 19748785
Dihydrofolate reductase IC50 = 12600.0 nM 4.9 Inhibition of rat liver DHFR in presence of saturating levels of NADPH and DHFA 19748785
Epidermal growth factor receptor IC50 = 18200.0 nM 4.74 Inhibition of EGFR in human A431 cells by phosphotyrosine ELISA 19748785
Unchecked IC50 = 53600.0 nM 4.27 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 Vascular endothelial growth factor receptor 2 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 Bifunctional dihydrofolate reductase-thymidylate synthase 1
19748785 10.1016/j.bmc.2009.08.044 A-431 1

Data from ChEMBL 36 via Core Engine