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Compound Detail

CHEMBL171480

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C#CCN(Cc1ccc2ncnc(O)c2c1)c1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL171480
Phase Preclinical
Structure Type MOL
InChI Key AOGOUTMDEVCZHA-UHFFFAOYSA-N
7
Targets
10
Activities
2
Assay Types
0
PK Parameters
12
Publications
0
Known Names

Molecular Properties

462.5
MW (Da)
2.02
ALogP
7
HBA
4
HBD
152.9
PSA (Ų)
0.33
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H22N4O6
MW 462.46
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -0.85

Activity Summary

IC50 7 meas. best 6.89
Ki 3 meas. best 7.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thymidylate synthase
CHEMBL1952
 Ki 7.58 7.58 26.0 1
Thymidylate synthase
CHEMBL3160
 IC50 6.89 6.845 130.0 2
Thymidylate synthase
CHEMBL5328
 IC50 6.8 6.8 160.0 1
L1210
CHEMBL386
 IC50 6.57 5.6967 270.0 3
Dihydrofolate reductase
CHEMBL2363
 Ki 5.65 5.65 2250.0 1
Dihydrofolate reductase
CHEMBL2902
 Ki 5.6 5.6 2500.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 5.16 5.16 7000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thymidylate synthase Ki = 26.0 nM 7.58 Binding affinity against thymidylate synthase 1995868
Thymidylate synthase IC50 = 130.0 nM 6.89 Inhibition of L1210 leukemia thymidylate synthase (TS) enzyme 2704031
Thymidylate synthase IC50 = 160.0 nM 6.8 Inhibitory concentration of compound to inhibit Thymidylate synthase (TS) in L12... 2704030
Thymidylate synthase IC50 = 160.0 nM 6.8 The compound was not tested for inhibition of L1210 Thymidylate synthase due to ... 2362285
L1210 IC50 = 270.0 nM 6.57 Inhibition of the growth of methotrexate sensitive L1210 leukemia/S cells in cul... 2704031
L1210 IC50 = 400.0 nM 6.4 Tested for 50% inhibition of L1210 cell growth in vitro 2362285
Dihydrofolate reductase Ki = 2250.0 nM 5.65 Compound was evaluated for the inhibition of partially purified rat liver Dihydr... 2704030
Dihydrofolate reductase Ki = 2500.0 nM 5.6 Binding affinity against Dihydrofolate reductase 1995868
Dihydrofolate reductase IC50 = 7000.0 nM 5.16 Inhibition of human WIL2/dihydrofolate reductase activity 2704031
L1210 IC50 = 75000.0 nM 4.12 Inhibition of the growth of methotrexate resistant L1210 leukemia/R 81 cells in ... 2704031

Literature References

PubMed DOI Target Context # Activities
2704030 10.1021/jm00124a018 No relevant target 2
2704031 10.1021/jm00124a019 L1210 2
2704030 10.1021/jm00124a018 Thymidylate synthase 1
2704030 10.1021/jm00124a018 Dihydrofolate reductase 1
2704030 10.1021/jm00124a018 L1210 1
1995868 10.1021/jm00106a001 Thymidylate synthase 1
1995868 10.1021/jm00106a001 Dihydrofolate reductase 1
1995868 10.1021/jm00106a001 Mus musculus 1
2704031 10.1021/jm00124a019 Dihydrofolate reductase 1
2704031 10.1021/jm00124a019 Thymidylate synthase 1
2362285 10.1021/jm00169a040 Thymidylate synthase 1
2362285 10.1021/jm00169a040 L1210 1

Data from ChEMBL 36 via Core Engine