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Compound Detail

CHEMBL323565

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Nc1nc(N)c2c(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)coc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL323565
Phase Preclinical
Structure Type MOL
InChI Key XMILWEOSKUGJJX-ZDUSSCGKSA-N
6
Targets
29
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

427.4
MW (Da)
1.22
ALogP
8
HBA
5
HBD
194.7
PSA (Ų)
0.33
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H21N5O6
MW 427.42
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness 0.02

Activity Summary

IC50 17 meas. best 7.0
EC50 12 meas. best 6.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL2902
 IC50 7.0 7.0 100.0 4
FaDu
CHEMBL612250
 EC50 6.75 6.75 180.0 2
Dihydrofolate reductase
CHEMBL202
 IC50 6.66 6.21 220.0 6
CCRF-CEM
CHEMBL382
 EC50 6.54 6.0386 290.0 7
Unchecked
CHEMBL612545
 EC50 6.37 6.37 425.0 1
A253 cell line
CHEMBL614255
 EC50 6.27 6.27 540.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase IC50 = 100.0 nM 7.0 Inhibition of Lactobacillus casei DHFR 15615538
Dihydrofolate reductase IC50 = 100.0 nM 7.0 Inhibition of Lactobacillus casei dihydrofolate reductase at 37 degree C pH 7.4 16078850
Dihydrofolate reductase IC50 = 100.0 nM 7.0 Inhibitory concentration against Lactobacillus casei DHFR(Dihydro folate reducta... 7562910
Dihydrofolate reductase IC50 = 100.0 nM 7.0 Inhibitory concentration against Lactobacillus casei Dihydrofolate reductase 10956221
FaDu EC50 = 180.0 nM 6.75 The compound was tested for Growth inhibition of the human squamous cell carcino... 7562910
FaDu EC50 = 180.0 nM 6.75 Growth inhibition of human squamous cell carcinoma FaDu cells during continuous ... 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 = 250.0 nM 6.6 Inhibitory concentration against CCRF-CEM leukemic cell DHFR(Dihydro folate redu... 7562910
CCRF-CEM EC50 = 290.0 nM 6.54 Growth inhibition of human CCRF-CEM cells 15615538
CCRF-CEM EC50 = 290.0 nM 6.54 Growth inhibitory activity against CCRF-CEM human lymphoblastic leukemia cells 16078850
CCRF-CEM EC50 = 290.0 nM 6.54 Compound was tested for Growth inhibition of the Human T-lymphoblastic Leukemia ... 7562910
CCRF-CEM EC50 = 290.0 nM 6.54 Growth inhibition of CCRF-CEM human leukemia cells. 10956221
Unchecked EC50 = 425.0 nM 6.37 Growth inhibition of MTX-resistant R30dm sublines. 10956221
A253 cell line EC50 = 540.0 nM 6.27 Growth inhibition of human squamous cell carcinoma A253 cells during continuous ... 10956221
A253 cell line EC50 = 540.0 nM 6.27 The compound was tested for Growth inhibition of the human squamous cell carcino... 7562910
Dihydrofolate reductase IC50 = 1000.0 nM 6.0 Inhibition of human dihydrofolate reductase at 37 degree C pH 7.4 16078850
Dihydrofolate reductase IC50 = 1000.0 nM 6.0 Inhibitory concentration against recombinant human DHFR(Dihydro folate reductase... 7562910
Dihydrofolate reductase IC50 = 1000.0 nM 6.0 Inhibition of human recombinant DHFR 15615538
Dihydrofolate reductase IC50 = 1000.0 nM 6.0 Inhibitory concentration against recombinant human (rh) Dihydrofolate reductase 10956221
CCRF-CEM EC50 = 4250.0 nM 5.37 Growth inhibition of methotrexate-resistant human CCRF-CEM R30dm cells expressin... 15615538

Literature References

PubMed DOI Target Context # Activities
7562910 10.1021/jm00019a009 FaDu 6
10956221 10.1021/jm000130i Thymidylate synthase 4
10956221 10.1021/jm000130i Unchecked 4
15615538 10.1021/jm040123k CCRF-CEM 4
16078850 10.1021/jm058213s CCRF-CEM 4
15615538 10.1021/jm040123k Dihydrofolate reductase 3
16078850 10.1021/jm058213s Thymidylate synthase 3
16078850 10.1021/jm058213s ADMET 3
16078850 10.1021/jm058213s Dihydrofolate reductase 3
7562910 10.1021/jm00019a009 Dihydrofolate reductase 3
10956221 10.1021/jm000130i Dihydrofolate reductase 3
15615538 10.1021/jm040123k Thymidylate synthase 3
15615538 10.1021/jm040123k Folylpolyglutamate synthase, mitochondrial 3
7562910 10.1021/jm00019a009 Thymidylate synthase 2
7562910 10.1021/jm00019a009 CCRF-CEM 2
7562910 10.1021/jm00019a009 Folylpolyglutamate synthase, mitochondrial 2
10956221 10.1021/jm000130i Folylpolyglutamate synthase, mitochondrial 2
11052789 10.1021/jm000200l CCRF-CEM 1
10956221 10.1021/jm000130i FaDu 1
10956221 10.1021/jm000130i CCRF-CEM 1

Data from ChEMBL 36 via Core Engine