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Compound Detail

CHEMBL305177

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Nc1nc(N)c2cc(CNc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)ccc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL305177
Phase Preclinical
Structure Type MOL
InChI Key IOLLERXPKZGYRA-UHFFFAOYSA-N
7
Targets
13
Activities
2
Assay Types
0
PK Parameters
12
Publications
0
Known Names

Molecular Properties

438.4
MW (Da)
1.45
ALogP
8
HBA
6
HBD
193.6
PSA (Ų)
0.28
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H22N6O5
MW 438.44
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.59

Activity Summary

IC50 11 meas. best 8.46
Ki 2 meas. best 11.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL202
 Ki 11.0 11.0 0.0 1
Unchecked
CHEMBL612545
 IC50 8.46 8.4225 3.5 4
Dihydrofolate reductase
CHEMBL202
 IC50 8.35 8.35 4.5 1
Dihydrofolate reductase
CHEMBL2363
 IC50 8.32 8.32 4.8 1
L1210
CHEMBL386
 IC50 7.68 6.68 21.0 2
Dihydrofolate reductase
CHEMBL4564
 IC50 7.32 7.32 48.0 1
Thymidylate synthase
CHEMBL3160
 IC50 5.3 5.3 5000.0 1
L1210 ( R81)
CHEMBL614710
 IC50 4.34 4.34 46000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 0.01 nM 11.0 Inhibitory activity against Leu22-Phe mutant human Dihydrofolate reductase 7877140
Unchecked IC50 = 3.5 nM 8.46 Evaluated for the inhibition of human gastrointestinal adenocarcinoma cells in v... 3968685
Unchecked IC50 = 3.7 nM 8.43 Evaluated for the inhibition of human gastrointestinal adenocarcinoma cells in v... 3968685
Unchecked IC50 = 3.8 nM 8.42 Evaluated for the inhibition of human gastrointestinal adenocarcinoma cells in v... 3968685
Unchecked IC50 = 4.2 nM 8.38 Evaluated for the inhibition of human gastrointestinal adenocarcinoma cells in v... 3968685
Dihydrofolate reductase IC50 = 4.5 nM 8.35 Inhibitory activity against dihydrofolate reductase (DHFR) obtained from human W... 3339615
Dihydrofolate reductase IC50 = 4.8 nM 8.32 Inhibition of rat liver dihydrofolate reductase assayed spectrophotometrically a... 3968685
L1210 IC50 = 21.0 nM 7.68 Evaluated for the growth inhibition of L1210 /S cells 3968685
Dihydrofolate reductase IC50 = 48.0 nM 7.32 Evaluated for the inhibition of dihydrofolate reductase from L1210 mouse leukemi... 3968685
L1210 IC50 = 2100.0 nM 5.68 Evaluated for the uptake of Methotrexate in L1210 leukemia cells 3968685
Thymidylate synthase IC50 = 5000.0 nM 5.3 Inhibitory activity against thymidylate synthase isolated from L1210 leukemia ce... 3339615
L1210 ( R81) IC50 = 46000.0 nM 4.34 Evaluated for 50% inhibition of growth of L1210 / R81 cells (48 h), relative to ... 3968685

Literature References

PubMed DOI Target Context # Activities
3968685 10.1021/jm00380a011 Unchecked 4
7877140 10.1021/jm00005a002 Dihydrofolate reductase 3
3968685 10.1021/jm00380a011 Dihydrofolate reductase 2
3968685 10.1021/jm00380a011 L1210 2
110930 10.1021/jm00191a005 Thymidylate synthase 2
3339615 10.1021/jm00397a031 Thymidylate synthase 1
3339615 10.1021/jm00397a031 Dihydrofolate reductase 1
7392027 10.1021/jm00180a004 Dihydrofolate reductase 1
7120278 10.1021/jm00350a003 Dihydrofolate reductase 1
3968685 10.1021/jm00380a011 L1210 ( R81) 1
110930 10.1021/jm00191a005 Dihydrofolate reductase 1
319234 10.1021/jm00211a020 Dihydrofolate reductase 1

Data from ChEMBL 36 via Core Engine