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Compound Detail

CHEMBL389051

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C#CCN(Cc1ccc2[nH]c(N)nc(=O)c2c1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL389051
Phase Preclinical
Structure Type MOL
InChI Key LTKHPMDRMUCUEB-IBGZPJMESA-N
16
Targets
65
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

477.5
MW (Da)
1.19
ALogP
7
HBA
5
HBD
178.7
PSA (Ų)
0.27
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C24H23N5O6
MW 477.48
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -0.62

Activity Summary

IC50 55 meas. best 8.05
Ki 10 meas. best 8.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thymidylate synthase
CHEMBL3160
 Ki 8.47 7.235 3.4 2
Thymidylate synthase
CHEMBL1952
 Ki 8.15 6.79 7.0 3
Thymidylate synthase
CHEMBL5328
 IC50 8.05 7.5025 9.0 4
Thymidylate synthase
CHEMBL5328
 Ki 8.0 7.61 10.0 2
Thymidylate synthase
CHEMBL6137
 IC50 7.72 7.0013 19.0 8
Thymidylate synthase
CHEMBL3160
 IC50 7.7 7.7 20.0 4
Thymidylate synthase
CHEMBL1952
 IC50 7.7 6.9564 19.9 14
Thymidylate synthase (EC 2.1.1.45) (TS) (TSase)
CHEMBL1795153
 IC50 7.32 7.32 48.0 1
Thymidylate synthase
CHEMBL6137
 Ki 7.22 7.22 60.0 1
L1210
CHEMBL386
 Ki 7.22 7.22 60.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 7.14 6.6875 72.0 4
Dihydrofolate reductase
CHEMBL2363
 Ki 7.12 7.12 75.0 1
Unchecked
CHEMBL612545
 IC50 6.66 6.08 220.0 4
Thymidylate synthase
CHEMBL4341
 IC50 6.44 6.44 360.0 1
WIL2
CHEMBL612809
 IC50 6.36 6.36 440.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 5.72 5.4667 1900.0 3
L1210
CHEMBL386
 IC50 5.47 5.426 3400.0 5
L1210 (1565)
CHEMBL614000
 IC50 5.44 5.35 3600.0 2
Dihydrofolate reductase
CHEMBL1809
 IC50 4.96 4.8 11000.0 2
L1210 (RD1694)
CHEMBL614713
 IC50 4.89 4.89 13000.0 1
L1210 (R7A)
CHEMBL614712
 IC50 4.39 4.39 41000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thymidylate synthase Ki = 3.4 nM 8.47 Binding affinity against Thymidylate synthase was measured in vitro 2231606
Thymidylate synthase Ki = 7.0 nM 8.15 Inhibitory constant of thymidylate synthase was determined in human AML cells 3470522
Thymidylate synthase IC50 = 9.0 nM 8.05 Inhibition of Lactobacillus casei thymidylate synthase 15615538
Thymidylate synthase Ki = 10.0 nM 8.0 Compound was tested for inhibition of Thymidylate Synthase in Lactobacillus case... 3754285
Thymidylate synthase IC50 = 19.0 nM 7.72 Inhibition of Escherichia coli thymidylate synthase 19719239
Thymidylate synthase IC50 = 19.0 nM 7.72 Inhibition of Escherichia coli thymidylate synthase 18072727
Thymidylate synthase IC50 = 20.0 nM 7.7 Concentration required for in vitro inhibition of thymidylate synthase 2231606
Thymidylate synthase IC50 = 20.0 nM 7.7 Inhibitory activity against thymidylate synthase (TS) 8230138
Thymidylate synthase IC50 = 20.0 nM 7.7 Inhibition of isolated thymidylate synthase partially purified from L1210 mouse ... 10508430
Thymidylate synthase IC50 = 20.0 nM 7.7 Concentration required to inhibit 50% activity of Thymidylate synthase was deter... 2231607
Thymidylate synthase IC50 = 19.95 nM 7.7 Inhibition of thymidylate synthase 20153089
Thymidylate synthase IC50 = 20.0 nM 7.7 In vitro inhibitory activity against thymidylate synthase (TS) from L1210 mouse ... 1495009
Thymidylate synthase Ki = 30.0 nM 7.52 Inhibition of human thymidylate synthase 17004711
Thymidylate synthase IC50 = 36.0 nM 7.44 Compound was evaluated for the inhibition at a given concentration against recom... 10377234
Thymidylate synthase IC50 = 36.0 nM 7.44 Compound was evaluated for the inhibition at a given concentration against Lacto... 10377234
Thymidylate synthase IC50 = 37.0 nM 7.43 Ability to inhibit thymidylate synthase derived from human leukemia K562 cells 3470522
Thymidylate synthase (EC 2.1.1.45) (TS) (TSase) IC50 = 48.0 nM 7.32 Inhibition of Escherichia coli TS assessed as oxidation of tetrahydrofolate to d... 21550809
Thymidylate synthase IC50 = 55.0 nM 7.26 Inhibitory concentration against isolated Lactobacillus casei Thymidylate syntha... 11052789
Thymidylate synthase IC50 = 55.0 nM 7.26 Compound was evaluated as inhibitor of Lactobacillus casei thymidylate synthase 12570380
Thymidylate synthase Ki = 60.0 nM 7.22 Inhibition of Escherichia coli thymidylate synthase 17004711

Literature References

PubMed DOI Target Context # Activities
20485427 10.1038/nature09107 Plasmodium falciparum 4
11052789 10.1021/jm000200l Thymidylate synthase 4
3470522 10.1021/jm00387a016 Thymidylate synthase 4
18072727 10.1021/jm701052u Unchecked 4
17004711 10.1021/jm051187d Thymidylate synthase 3
11384244 10.1021/jm0100382 Thymidylate synthase 3
15615538 10.1021/jm040123k Dihydrofolate reductase 3
15615538 10.1021/jm040123k Thymidylate synthase 3
12570380 10.1021/jm0203534 Thymidylate synthase 3
18072727 10.1021/jm701052u Thymidylate synthase 2
2231607 10.1021/jm00173a025 L1210 2
2231607 10.1021/jm00173a025 L1210 (R7A) 2
10508430 10.1021/jm9803727 L1210 (RD1694) 2
10377234 10.1021/jm980586o Thymidylate synthase 2
10508430 10.1021/jm9803727 L1210 2
17004711 10.1021/jm051187d Unchecked 2
2231606 10.1021/jm00173a024 Thymidylate synthase 2
15615522 10.1021/jm040144e Thymidylate synthase 2
16451071 10.1021/jm058276a Thymidylate synthase 2
10508430 10.1021/jm9803727 L1210 (1565) 2

Data from ChEMBL 36 via Core Engine