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Compound Detail

CHEMBL225180

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Cc1[nH]c2nc(N)[nH]c(=O)c2c1Sc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL225180
Phase Preclinical
Structure Type MOL
InChI Key DSIACOJIIGFHHZ-NSHDSACASA-N
8
Targets
22
Activities
2
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

445.5
MW (Da)
1.34
ALogP
7
HBA
6
HBD
191.3
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 C19H19N5O6S
MW 445.46
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.42

Activity Summary

IC50 20 meas. best 7.38
EC50 2 meas. best 6.35

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thymidylate synthase
CHEMBL1952
 IC50 7.38 7.314 42.0 5
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 7.05 6.845 90.0 2
Thymidylate synthase (EC 2.1.1.45) (TS) (TSase)
CHEMBL1795153
 IC50 6.68 6.68 210.0 1
Thymidylate synthase
CHEMBL6137
 IC50 6.57 6.57 270.0 3
CCRF-CEM
CHEMBL382
 EC50 6.35 6.22 450.0 2
Dihydrofolate reductase
CHEMBL202
 IC50 5.68 5.676 2100.0 5
Dihydrofolate reductase
CHEMBL1809
 IC50 4.68 4.67 21000.0 2
Unchecked
CHEMBL612545
 IC50 4.68 4.68 21000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thymidylate synthase IC50 = 42.0 nM 7.38 Inhibition of human thymidylate synthase 18800768
Thymidylate synthase IC50 = 42.0 nM 7.38 Inhibition of human TS assessed as oxidation of tetrahydrofolate to dihydrofolat... 21550809
Thymidylate synthase IC50 = 54.0 nM 7.27 Inhibition of recombinant human TS 16451071
Thymidylate synthase IC50 = 54.0 nM 7.27 Inhibition of human thymidylate synthase 15615522
Thymidylate synthase IC50 = 54.0 nM 7.27 Inhibition of human thymidylate synthase 18072727
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 90.0 nM 7.05 Inhibition of Toxoplasma gondii TS assessed as oxidation of tetrahydrofolate to ... 21550809
Thymidylate synthase (EC 2.1.1.45) (TS) (TSase) IC50 = 210.0 nM 6.68 Inhibition of Escherichia coli TS assessed as oxidation of tetrahydrofolate to d... 21550809
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 230.0 nM 6.64 Inhibition of Toxoplasma gondii DHFR by spectrophotometry 21550809
Thymidylate synthase IC50 = 270.0 nM 6.57 Inhibition of TS from Escherichia coli 16451071
Thymidylate synthase IC50 = 270.0 nM 6.57 Inhibition of Escherichia coli thymidylate synthase 15615522
Thymidylate synthase IC50 = 270.0 nM 6.57 Inhibition of Escherichia coli thymidylate synthase 18072727
CCRF-CEM EC50 = 450.0 nM 6.35 Inhibition of growth in CCRF-CEM cells 16451071
CCRF-CEM EC50 = 810.0 nM 6.09 Inhibition of growth in MTX-resistant CCRF-CEM cell line, R30dm cells 16451071
Dihydrofolate reductase IC50 = 2100.0 nM 5.68 Inhibition of recombinant human DHFR 16451071
Dihydrofolate reductase IC50 = 2100.0 nM 5.68 Inhibition of human DHFR 15615522
Dihydrofolate reductase IC50 = 2100.0 nM 5.68 Inhibition of human recombinant DHFR 18072727
Dihydrofolate reductase IC50 = 2100.0 nM 5.68 Inhibition of human DHFR by spectrophotometry 21550809
Dihydrofolate reductase IC50 = 2200.0 nM 5.66 Inhibition of human recombinant DHFR 18800768
Unchecked IC50 = 21000.0 nM 4.68 Inhibition of DHFR from Escherichia coli 16451071
Dihydrofolate reductase IC50 = 21000.0 nM 4.68 Inhibition of Escherichia coli DHFR 15615522

Literature References

PubMed DOI Target Context # Activities
18072727 10.1021/jm701052u Unchecked 4
21550809 10.1016/j.bmc.2011.03.067 Dihydrofolate reductase 2
16451071 10.1021/jm058276a Thymidylate synthase 2
21550809 10.1016/j.bmc.2011.03.067 Bifunctional dihydrofolate reductase-thymidylate synthase 2
18800768 10.1021/jm8006933 Dihydrofolate reductase 2
18800768 10.1021/jm8006933 Bifunctional dihydrofolate reductase-thymidylate synthase 2
18800768 10.1021/jm8006933 Thymidylate synthase 2
18072727 10.1021/jm701052u Thymidylate synthase 2
15615522 10.1021/jm040144e Dihydrofolate reductase 2
15615522 10.1021/jm040144e Thymidylate synthase 2
16451071 10.1021/jm058276a CCRF-CEM 2
18072727 10.1021/jm701052u Dihydrofolate reductase 1
16451071 10.1021/jm058276a R2-CCRF-CEM 1
16451071 10.1021/jm058276a R1-CCRF-CEM 1
18800768 10.1021/jm8006933 Unchecked 1
21550809 10.1016/j.bmc.2011.03.067 Thymidylate synthase 1
21550809 10.1016/j.bmc.2011.03.067 Thymidylate synthase (EC 2.1.1.45) (TS) (TSase) 1
16451071 10.1021/jm058276a Unchecked 1
16451071 10.1021/jm058276a Dihydrofolate reductase 1

Data from ChEMBL 36 via Core Engine