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Compound Detail

CHEMBL106628

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Nc1nc(N)c2c(CNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)coc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL106628
Phase Preclinical
Structure Type MOL
InChI Key ACXZKUHGYNILFP-LBPRGKRZSA-N
6
Targets
11
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

428.4
MW (Da)
1.05
ALogP
9
HBA
6
HBD
206.7
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 C19H20N6O6
MW 428.41
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.41

Activity Summary

IC50 7 meas. best 6.66
EC50 4 meas. best 6.9

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
FaDu
CHEMBL612250
 EC50 6.9 6.9 126.0 1
CCRF-CEM
CHEMBL382
 EC50 6.85 6.85 142.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 6.66 6.4275 220.0 4
Dihydrofolate reductase
CHEMBL2902
 IC50 6.25 6.25 560.0 2
Unchecked
CHEMBL612545
 EC50 6.18 6.0 663.0 2
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 6.16 6.16 700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
FaDu EC50 = 126.0 nM 6.9 Growth inhibition of human squamous cell carcinoma FaDu cells during continuous ... 10956221
CCRF-CEM EC50 = 142.0 nM 6.85 Growth inhibition of CCRF-CEM human leukemia cells. 10956221
Dihydrofolate reductase IC50 = 220.0 nM 6.66 Inhibition of human DHFR at 30 degC under pH 7.4 by spectrophotometry 20056546
Dihydrofolate reductase IC50 = 450.0 nM 6.35 Inhibitory concentration against recombinant human (rh) Dihydrofolate reductase 10956221
Dihydrofolate reductase IC50 = 450.0 nM 6.35 Inhibitory concentration against human dihydrofolate reductase (DHFR), 11052789
Dihydrofolate reductase IC50 = 450.0 nM 6.35 Inhibitory concentration against recombinant human DHFR(Dihydro folate reductase... 7562910
Dihydrofolate reductase IC50 = 560.0 nM 6.25 Inhibitory concentration against Lactobacillus casei Dihydrofolate reductase 10956221
Dihydrofolate reductase IC50 = 560.0 nM 6.25 inhibitory concentration against Lactobacillus casei DHFR(Dihydro folate reducta... 7562910
Unchecked EC50 = 663.0 nM 6.18 Growth inhibition of MTX-resistant R30dm sublines. 10956221
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 700.0 nM 6.16 Inhibitory concentration against Toxoplasma gondii Dihydrofolate reductase 10956221
Unchecked EC50 = 1523.0 nM 5.82 Growth inhibition of MTX-resistant R1 sublines. 10956221

Literature References

PubMed DOI Target Context # Activities
10956221 10.1021/jm000130i Thymidylate synthase 4
10956221 10.1021/jm000130i Unchecked 3
10956221 10.1021/jm000130i Dihydrofolate reductase 3
7562910 10.1021/jm00019a009 Thymidylate synthase 2
7562910 10.1021/jm00019a009 Dihydrofolate reductase 2
11052789 10.1021/jm000200l Thymidylate synthase 1
20056546 10.1016/j.bmc.2009.11.029 Dihydrofolate reductase 1
20056546 10.1016/j.bmc.2009.11.029 Thymidylate synthase 1
11052789 10.1021/jm000200l Bifunctional purine biosynthesis protein ATIC 1
11052789 10.1021/jm000200l Trifunctional purine biosynthetic protein adenosine-3 1
11052789 10.1021/jm000200l FaDu 1
11052789 10.1021/jm000200l CCRF-CEM 1
11052789 10.1021/jm000200l Dihydrofolate reductase 1
10956221 10.1021/jm000130i A253 cell line 1
10956221 10.1021/jm000130i FaDu 1
10956221 10.1021/jm000130i CCRF-CEM 1
10956221 10.1021/jm000130i Bifunctional dihydrofolate reductase-thymidylate synthase 1

Data from ChEMBL 36 via Core Engine