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Compound Detail

CHEMBL389643

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Cc1c(Sc2ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc2)[nH]c2nc(N)nc(N)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL389643
Phase Preclinical
Structure Type MOL
InChI Key LLAPFSUYQVWFDD-NSHDSACASA-N
5
Targets
15
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

444.5
MW (Da)
1.63
ALogP
8
HBA
6
HBD
197.3
PSA (Ų)
0.30
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H20N6O5S
MW 444.47
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.42

Activity Summary

IC50 10 meas. best 7.8
EC50 5 meas. best 6.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL1809
 IC50 7.8 7.8 16.0 2
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 6.77 6.26 170.0 4
CCRF-CEM
CHEMBL382
 EC50 6.72 5.984 190.0 5
Dihydrofolate reductase
CHEMBL202
 IC50 6.68 6.68 210.0 2
Thymidylate synthase
CHEMBL1952
 IC50 6.27 6.27 540.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase IC50 = 16.0 nM 7.8 Inhibition of Escherichia coli DHFR 16279780
Dihydrofolate reductase IC50 = 16.0 nM 7.8 Inhibition of Escherichia coli DHFR at 30 degC under pH 7.4 by spectrophotometry 20056546
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 170.0 nM 6.77 Inhibition of Toxoplasma gondii DHFR 16279780
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 170.0 nM 6.77 Inhibition of Toxoplasma gondii DHFR at 30 degC under pH 7.4 by spectrophotometr... 20056546
CCRF-CEM EC50 = 190.0 nM 6.72 Growth inhibition of human CCRF-CEM cells 16279780
CCRF-CEM EC50 = 190.0 nM 6.72 Cytotoxicity against human CCRF-CEM cells 18605720
Dihydrofolate reductase IC50 = 210.0 nM 6.68 Inhibition of human DHFR 16279780
Dihydrofolate reductase IC50 = 210.0 nM 6.68 Inhibition of human DHFR at 30 degC under pH 7.4 by spectrophotometry 20056546
CCRF-CEM EC50 = 515.0 nM 6.29 Growth inhibition of methotrexate-resistant human CCRF-CEM R30dm cells expressin... 16279780
Thymidylate synthase IC50 = 540.0 nM 6.27 Inhibition of human thymidylate synthase 16279780
Thymidylate synthase IC50 = 540.0 nM 6.27 Inhibition of human thymidylate synthase at 30 degC under pH 7.4 by spectrophoto... 20056546
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1800.0 nM 5.75 Inhibition of Toxoplasma gondii thymidylate synthase 16279780
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1800.0 nM 5.75 Inhibition of Toxoplasma gondii TS at 30 degC under pH 7.4 by spectrophotometry 20056546
CCRF-CEM EC50 = 7750.0 nM 5.11 Growth inhibition of methotrexate-transport-resistant human CCRF-CEM R2 cells af... 16279780
CCRF-CEM EC50 = 8300.0 nM 5.08 Growth inhibition of methotrexate-resistant human CCRF-CEM R1 cells overproducin... 16279780

Literature References

PubMed DOI Target Context # Activities
16279780 10.1021/jm058234m CCRF-CEM 10
16279780 10.1021/jm058234m Folylpolyglutamate synthase, mitochondrial 3
16279780 10.1021/jm058234m Dihydrofolate reductase 2
16279780 10.1021/jm058234m Bifunctional dihydrofolate reductase-thymidylate synthase 2
16279780 10.1021/jm058234m Thymidylate synthase 2
20056546 10.1016/j.bmc.2009.11.029 Dihydrofolate reductase 2
20056546 10.1016/j.bmc.2009.11.029 Bifunctional dihydrofolate reductase-thymidylate synthase 2
20056546 10.1016/j.bmc.2009.11.029 Thymidylate synthase 1
20056546 10.1016/j.bmc.2009.11.029 Unchecked 1
18605720 10.1021/jm800244v CCRF-CEM 1
16279780 10.1021/jm058234m PC-3 1
16279780 10.1021/jm058234m LOX IMVI 1
16279780 10.1021/jm058234m U-251 1
16279780 10.1021/jm058234m SW-620 1
16279780 10.1021/jm058234m NCI-H460 1
16279780 10.1021/jm058234m ADMET 1
16279780 10.1021/jm058234m MOLT-4 1
16279780 10.1021/jm058234m K562 1
16279780 10.1021/jm058234m HL-60 1
16279780 10.1021/jm058234m HT-29 1

Data from ChEMBL 36 via Core Engine