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Compound Detail

CHEMBL104829

FURO[2,3D]PYRIMIDINE ANTIFOLATE
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CN(Cc1coc2nc(N)nc(N)c12)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL104829
Name FURO[2,3D]PYRIMIDINE ANTIFOLATE
Phase Preclinical
Structure Type MOL
InChI Key WXINNGCGSCFUCR-ZDUSSCGKSA-N
6
Targets
9
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

442.4
MW (Da)
1.07
ALogP
9
HBA
5
HBD
197.9
PSA (Ų)
0.32
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H22N6O6
MW 442.43
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.49

Activity Summary

IC50 5 meas. best 6.66
EC50 4 meas. best 7.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CCRF-CEM
CHEMBL382
 EC50 7.33 7.33 47.0 1
FaDu
CHEMBL612250
 EC50 7.26 7.26 55.0 1
Dihydrofolate reductase
CHEMBL202
 IC50 6.66 6.66 220.0 3
Dihydrofolate reductase
CHEMBL2902
 IC50 6.66 6.66 220.0 1
Unchecked
CHEMBL612545
 EC50 6.09 6.04 807.0 2
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 4.7 4.7 19800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CCRF-CEM EC50 = 47.0 nM 7.33 Growth inhibition of CCRF-CEM human leukemia cells. 10956221
FaDu EC50 = 55.0 nM 7.26 Growth inhibition of human squamous cell carcinoma FaDu cells during continuous ... 10956221
Dihydrofolate reductase IC50 = 220.0 nM 6.66 Inhibitory concentration against recombinant human (rh) Dihydrofolate reductase 10956221
Dihydrofolate reductase IC50 = 220.0 nM 6.66 Inhibitory concentration against Lactobacillus casei Dihydrofolate reductase 10956221
Dihydrofolate reductase IC50 = 220.0 nM 6.66 Inhibitory concentration against human dihydrofolate reductase (DHFR) 11052789
Dihydrofolate reductase IC50 = 220.0 nM 6.66 Inhibition of human DHFR at 30 degC under pH 7.4 by spectrophotometry 20056546
Unchecked EC50 = 807.0 nM 6.09 Growth inhibition of MTX-resistant R1 sublines. 10956221
Unchecked EC50 = 1030.0 nM 5.99 Growth inhibition of MTX-resistant R30dm sublines. 10956221
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 19800.0 nM 4.7 Inhibitory concentration against Toxoplasma gondii Dihydrofolate reductase 10956221

Literature References

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

Data from ChEMBL 36 via Core Engine