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Compound Detail

CHEMBL439973

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Cc1nc(N)nc2[nH]cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL439973
Phase Preclinical
Structure Type MOL
InChI Key FICRNCFTTZHHPO-HNNXBMFYSA-N
14
Targets
25
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

425.4
MW (Da)
1.68
ALogP
6
HBA
5
HBD
171.3
PSA (Ų)
0.34
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 C21H23N5O5
MW 425.45
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.08

Activity Summary

IC50 15 meas. best 7.62
EC50 10 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
carcinoma cell line
CHEMBL614380
 EC50 8.15 8.025 7.0 2
CCRF-CEM
CHEMBL382
 EC50 7.9 7.314 12.5 5
R30dm-CCRF-CEM
CHEMBL614143
 EC50 7.73 7.73 18.5 1
Dihydrofolate reductase
CHEMBL2902
 IC50 7.62 7.62 24.0 2
R1-CCRF-CEM
CHEMBL614384
 EC50 6.8 6.8 158.0 1
R2-CCRF-CEM
CHEMBL613523
 EC50 6.24 6.24 575.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 6.1 6.01 800.0 2
Thymidylate synthase
CHEMBL1952
 IC50 6.0 6.0 1000.0 2
Dihydrofolate reductase
CHEMBL1926
 IC50 5.92 5.92 1200.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 5.92 5.92 1200.0 1
Dihydrofolate reductase
CHEMBL1809
 IC50 5.75 5.75 1800.0 2
Thymidylate synthase
CHEMBL4341
 IC50 5.7 5.7 2000.0 1
Thymidylate synthase
CHEMBL6137
 IC50 5.7 5.7 2000.0 2
Thymidylate synthase
CHEMBL5328
 IC50 5.05 5.05 9000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
carcinoma cell line EC50 = 7.0 nM 8.15 Tested for their inhibition of growth of FaDu head on carcinoma cell lines. 11052789
CCRF-CEM EC50 = 12.5 nM 7.9 Growth inhibition of CCRF-CEM Human Leukemia Cell was determined 12570380
carcinoma cell line EC50 = 12.5 nM 7.9 Tested for their inhibition of growth of CCRF-CEM human leukemia on carcinoma ce... 11052789
CCRF-CEM EC50 = 12.5 nM 7.9 Concentration required to inhibit growth against CCRF-CEM cell 11052789
R30dm-CCRF-CEM EC50 = 18.5 nM 7.73 Growth inhibition of MTX-resistant subline R30dm-CCRF-CEM Human Leukemia Cell wa... 12570380
CCRF-CEM EC50 = 18.5 nM 7.73 Tested for their growth inhibition of CCRF-CEM human leukemia subline resistant ... 11052789
Dihydrofolate reductase IC50 = 24.0 nM 7.62 Compound was evaluated as inhibitor of Lactobacillus casei Dihydrofolate reducta... 12570380
Dihydrofolate reductase IC50 = 24.0 nM 7.62 Inhibitory concentration against isolated Lactobacillus casei Dihydrofolate redu... 11052789
R1-CCRF-CEM EC50 = 158.0 nM 6.8 Growth inhibition of MTX-resistant subline R1-CCRF-CEM Human Leukemia Cell was d... 12570380
CCRF-CEM EC50 = 158.0 nM 6.8 Tested for their growth inhibition of CCRF-CEM human leukemia subline resistant ... 11052789
R2-CCRF-CEM EC50 = 575.0 nM 6.24 Growth inhibition of MTX-resistant subline R2-CCRF-CEM Human Leukemia Cell was d... 12570380
CCRF-CEM EC50 = 575.0 nM 6.24 Tested for their growth inhibition of CCRF-CEM human leukemia subline resistant ... 11052789
Dihydrofolate reductase IC50 = 800.0 nM 6.1 Inhibitory concentration against isolated human Dihydrofolate reductase 11052789
Thymidylate synthase IC50 = 1000.0 nM 6.0 Compound was evaluated as inhibitor of human thymidylate synthase 12570380
Thymidylate synthase IC50 = 1000.0 nM 6.0 Inhibitory concentration against isolated Thymidylate synthase 11052789
Dihydrofolate reductase IC50 = 1200.0 nM 5.92 Compound was evaluated as inhibitor of human Dihydrofolate reductase 12570380
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1200.0 nM 5.92 Inhibitory concentration against isolated Toxoplasma gondii DHFR (dihydrofolate ... 11052789
Dihydrofolate reductase IC50 = 1200.0 nM 5.92 Inhibitory concentration against isolated Pneumocystis carinii DHFR (Dihydrofola... 11052789
Dihydrofolate reductase IC50 = 1800.0 nM 5.75 Compound was evaluated as inhibitor of Escherichia coli Dihydrofolate reductase 12570380
Dihydrofolate reductase IC50 = 1800.0 nM 5.75 Inhibitory concentration against isolated Escherichia coli Dihydrofolate reducta... 11052789

Literature References

PubMed DOI Target Context # Activities
11052789 10.1021/jm000200l CCRF-CEM 8
11052789 10.1021/jm000200l Thymidylate synthase 4
11052789 10.1021/jm000200l Dihydrofolate reductase 4
11052789 10.1021/jm000200l Unchecked 4
11052789 10.1021/jm000200l FaDu 4
12570380 10.1021/jm0203534 Thymidylate synthase 3
12570380 10.1021/jm0203534 Dihydrofolate reductase 3
12570380 10.1021/jm0203534 Folylpolyglutamate synthase, mitochondrial 2
11052789 10.1021/jm000200l carcinoma cell line 2
12570380 10.1021/jm0203534 HL-60 1
12570380 10.1021/jm0203534 MOLT-4 1
12570380 10.1021/jm0203534 R2-CCRF-CEM 1
12570380 10.1021/jm0203534 A549 1
12570380 10.1021/jm0203534 NCI-H226 1
12570380 10.1021/jm0203534 NCI-H460 1
12570380 10.1021/jm0203534 HCT-15 1
12570380 10.1021/jm0203534 HT-29 1
11052789 10.1021/jm000200l MCF7 1
12570380 10.1021/jm0203534 LOX IMVI 1
12570380 10.1021/jm0203534 UACC-257 1

Data from ChEMBL 36 via Core Engine