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Compound Detail

CHEMBL25889

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C#CCN(Cc1ccc2nc(C)nc(O)c2c1)c1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL25889
Phase Preclinical
Structure Type MOL
InChI Key PMTUUSDTAKQWQJ-UHFFFAOYSA-N
17
Targets
27
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

476.5
MW (Da)
2.33
ALogP
7
HBA
4
HBD
152.9
PSA (Ų)
0.32
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 C25H24N4O6
MW 476.49
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -0.96

Activity Summary

IC50 25 meas. best 8.22
Ki 2 meas. best 8.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thymidylate synthase
CHEMBL6137
 Ki 8.32 8.32 4.8 1
Enterococcus faecium
CHEMBL357
 IC50 8.22 8.22 6.0 1
MCF7
CHEMBL387
 IC50 8.15 8.15 7.0 1
Thymidylate synthase
CHEMBL1952
 Ki 8.07 8.07 8.5 1
Thymidylate synthase
CHEMBL1952
 IC50 8.01 7.7433 9.8 3
Manca
CHEMBL614320
 IC50 7.89 7.89 13.0 1
Lymphoma cell line
CHEMBL614114
 IC50 7.89 7.89 13.0 1
Lacticaseibacillus casei
CHEMBL613075
 IC50 7.66 7.66 22.0 1
CCRF-CEM
CHEMBL382
 IC50 7.54 7.455 29.0 2
L1210
CHEMBL386
 IC50 7.35 7.1333 45.0 3
Thymidylate synthase
CHEMBL6137
 IC50 7.35 7.35 45.0 1
GC3/MTK-
CHEMBL614157
 IC50 7.32 7.315 48.0 2
SW480
CHEMBL612544
 IC50 7.3 7.3 50.0 1
Unchecked
CHEMBL612545
 IC50 7.3 6.5667 50.0 3
Thymidylate synthase
CHEMBL3160
 IC50 7.3 7.3 50.0 1
Thymidylate synthase
CHEMBL5328
 IC50 7.0 7.0 100.0 1
MOLT-4
CHEMBL614177
 IC50 5.82 5.82 1500.0 1
H35R0.3
CHEMBL614160
 IC50 5.65 5.65 2240.0 1
Dihydrofolate reductase
CHEMBL2902
 IC50 4.46 4.46 35000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thymidylate synthase Ki = 4.8 nM 8.32 Inhibition of Thymidylate synthase of Escherichia coli (Ki) 2066965
Enterococcus faecium IC50 = 6.0 nM 8.22 Inhibition of growth of Staphylococcus faecium 2542557
MCF7 IC50 = 7.0 nM 8.15 Compound was evaluated for inhibition of tumor cell growth in MCF-7 cell line 1895294
Thymidylate synthase Ki = 8.5 nM 8.07 Inhibition of human Thymidylate synthase (Ki) 2066965
Thymidylate synthase IC50 = 9.8 nM 8.01 Inhibition of purified human thymidylate synthase from a SV40-transformed human ... 2542557
Thymidylate synthase IC50 = 10.0 nM 8.0 Compound was evaluated for the inhibition of human Thymidylate Synthase 1895294
Lymphoma cell line IC50 = 13.0 nM 7.89 Inhibition of growth of tumor cells, manca human lymphoma cells 2542557
Manca IC50 = 13.0 nM 7.89 Compound was evaluated for inhibition of tumor cell growth in Manca human lympho... 1895294
Lacticaseibacillus casei IC50 = 22.0 nM 7.66 Inhibition of growth of Lactobacillus casei 2542557
CCRF-CEM IC50 = 29.0 nM 7.54 Activity for growth inhibition in tissue culture of human leukemias (CCRF-CEM) 8632414
CCRF-CEM IC50 = 43.0 nM 7.37 Inhibition of cellular growth against human (CCRF-CEM) leukemias (ATCC) deficien... 2066965
Thymidylate synthase IC50 = 45.0 nM 7.35 Compound was evaluated for the inhibition of Escherichia coli Thymidylate Syntha... 1895294
L1210 IC50 = 45.0 nM 7.35 Inhibition of murine L1210 cell line tissue culture growth 8632414
GC3/MTK- IC50 = 48.0 nM 7.32 Inhibition of GC3/M TK- (human adenocarcinoma) cell growth in vitro. 8632414
GC3/MTK- IC50 = 49.0 nM 7.31 Inhibition of cellular growth against human adenocarcinoma (GC3/M TK-) deficient... 2066965
SW480 IC50 = 50.0 nM 7.3 Compound was evaluated for inhibition of tumor cell growth in SW/480 cell line 1895294
Unchecked IC50 = 50.0 nM 7.3 Inhibition of growth of colon adenocarcinoma SW 480 cells 2542557
Thymidylate synthase IC50 = 50.0 nM 7.3 In vitro inhibitory activity against thymidylate synthase partially purified fro... 8576912
Unchecked IC50 = 55.0 nM 7.26 Inhibition of growth of H35N cells 2542557
L1210 IC50 = 59.0 nM 7.23 Inhibition of cellular growth against mouse (L1210) deficient in thymidine kinas... 2066965

Literature References

PubMed DOI Target Context # Activities
2542557 10.1021/jm00126a023 H35R0.3 15
2066965 10.1021/jm00111a001 Thymidylate synthase 4
8632414 10.1021/jm9502652 Thymidylate synthase 4
2542557 10.1021/jm00126a023 Unchecked 3
2542557 10.1021/jm00126a023 Thymidylate synthase 3
2542557 10.1021/jm00126a023 Bifunctional purine biosynthesis protein ATIC 2
2542557 10.1021/jm00126a023 Trifunctional purine biosynthetic protein adenosine-3 2
2542557 10.1021/jm00126a023 Dihydrofolate reductase 2
1895294 10.1021/jm00113a011 Thymidylate synthase 2
1895294 10.1021/jm00113a011 Folylpolyglutamate synthase, mitochondrial 2
1895294 10.1021/jm00113a011 MCF7 1
1895294 10.1021/jm00113a011 Unchecked 1
1895294 10.1021/jm00113a011 MOLT-4 1
1895294 10.1021/jm00113a011 Manca 1
1895294 10.1021/jm00113a011 SW480 1
2066965 10.1021/jm00111a001 GC3/MTK- 1
2066965 10.1021/jm00111a001 CCRF-CEM 1
2066965 10.1021/jm00111a001 L1210 1
8632414 10.1021/jm9502652 GC3/MTK- 1
8576912 10.1021/jm950645n L1210 1

Data from ChEMBL 36 via Core Engine