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Compound Detail

CHEMBL4557278

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Nc1nc2[nH]c(CCCCc3cnc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c(F)c3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4557278
Phase Preclinical
Structure Type MOL
InChI Key STQPVYHCDNSBIJ-AWEZNQCLSA-N
7
Targets
11
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

474.4
MW (Da)
0.98
ALogP
7
HBA
6
HBD
204.2
PSA (Ų)
0.22
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H23FN6O6
MW 474.45
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -0.18

Activity Summary

IC50 10 meas. best 9.36
Ki 1 meas. best 6.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Folate receptor beta
CHEMBL5064
 IC50 9.36 8.51 0.4 2
Folate receptor alpha
CHEMBL2121
 IC50 9.16 9.16 0.7 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.7 8.7 2.0 1
IGROV-1
CHEMBL613984
 IC50 8.29 8.245 5.2 2
A2780
CHEMBL614004
 IC50 7.8 7.8 15.7 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 7.67 7.42 21.6 2
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.34 6.34 460.0 1
Reduced folate transporter
CHEMBL4833
 IC50 6.33 6.33 468.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Folate receptor beta IC50 = 0.44 nM 9.36 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
Folate receptor alpha IC50 = 0.69 nM 9.16 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 2.0 nM 8.7 Inhibition of GARFTase in human IGROV1 cells assessed as decrease in incorporati... 29701475
IGROV-1 IC50 = 5.17 nM 8.29 Antiproliferative activity against human IGROV1 cells harboring non targeted con... 29701475
IGROV-1 IC50 = 6.36 nM 8.2 Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ... 29701475
A2780 IC50 = 15.7 nM 7.8 Antiproliferative activity against human A2780 cells after 96 hrs by Cell-Titer ... 29701475
Proton-coupled folate transporter IC50 = 21.57 nM 7.67 Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ... 29701475
Folate receptor beta IC50 = 21.7 nM 7.66 Binding affinity to human FR2 expressed in human HeLa R1-11 cells assessed as an... 29701475
Proton-coupled folate transporter IC50 = 67.0 nM 7.17 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 29701475
Proton-coupled folate transporter Ki = 460.0 nM 6.34 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 29701475
Reduced folate transporter IC50 = 468.0 nM 6.33 Binding affinity to human RFC expressed in Chinese hamster PC43-10 cells assesse... 29701475

Literature References

PubMed DOI Target Context # Activities
29701475 10.1021/acs.jmedchem.8b00408 IGROV-1 7
29701475 10.1021/acs.jmedchem.8b00408 Proton-coupled folate transporter 6
29701475 10.1021/acs.jmedchem.8b00408 Reduced folate transporter 4
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor beta 3
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor alpha 2
29701475 10.1021/acs.jmedchem.8b00408 Unchecked 1
29701475 10.1021/acs.jmedchem.8b00408 A2780 1
29701475 10.1021/acs.jmedchem.8b00408 Trifunctional purine biosynthetic protein adenosine-3 1

Data from ChEMBL 36 via Core Engine