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Compound Detail

CHEMBL4538151

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Nc1nc2[nH]c(CCCc3ccc(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 CHEMBL4538151
Phase Preclinical
Structure Type MOL
InChI Key VEKHZPVGFDPVJG-HNNXBMFYSA-N
8
Targets
15
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

459.4
MW (Da)
1.20
ALogP
6
HBA
6
HBD
191.3
PSA (Ų)
0.26
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H22FN5O6
MW 459.43
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -0.26

Activity Summary

IC50 14 meas. best 9.0
Ki 1 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 9.0 9.0 1.0 1
Folate receptor alpha
CHEMBL2121
 IC50 8.95 8.95 1.1 1
IGROV-1
CHEMBL613984
 IC50 8.94 8.2075 1.1 4
A2780
CHEMBL614004
 IC50 8.67 8.67 2.1 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 8.42 8.34 3.8 2
Folate receptor beta
CHEMBL5064
 IC50 8.41 8.345 3.9 2
Reduced folate transporter
CHEMBL4833
 IC50 7.21 6.75 62.0 2
Unchecked
CHEMBL612545
 IC50 6.85 6.85 140.0 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.58 6.58 260.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.0 nM 9.0 Inhibition of GARFTase in human IGROV1 cells assessed as decrease in incorporati... 29701475
Folate receptor alpha IC50 = 1.12 nM 8.95 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
IGROV-1 IC50 = 1.14 nM 8.94 Antiproliferative activity against human IGROV1 cells harboring non targeted con... 29701475
IGROV-1 IC50 = 1.67 nM 8.78 Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ... 29701475
A2780 IC50 = 2.14 nM 8.67 Antiproliferative activity against human A2780 cells after 96 hrs by Cell-Titer ... 29701475
Proton-coupled folate transporter IC50 = 3.82 nM 8.42 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 29701475
Folate receptor beta IC50 = 3.87 nM 8.41 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
Folate receptor beta IC50 = 5.22 nM 8.28 Binding affinity to human FR2 expressed in human HeLa R1-11 cells assessed as an... 29701475
Proton-coupled folate transporter IC50 = 5.54 nM 8.26 Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ... 29701475
IGROV-1 IC50 = 19.2 nM 7.72 Antiproliferative activity against FRalpha knockout human IGROV1 KD10 cells afte... 29701475
IGROV-1 IC50 = 41.0 nM 7.39 Antiproliferative activity against FRalpha knockout human IGROV1 KD4 cells after... 29701475
Reduced folate transporter IC50 = 62.0 nM 7.21 Binding affinity to human RFC expressed in Chinese hamster PC43-10 cells assesse... 29701475
Unchecked IC50 = 140.0 nM 6.85 Antiproliferative activity in Chinese hamster R2 cells deficient in RFC, PCFT, a... 29701475
Proton-coupled folate transporter Ki = 260.0 nM 6.58 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 29701475
Reduced folate transporter IC50 = 507.0 nM 6.29 Binding affinity to human RFC2 expressed in human HeLa R1-11 cells assessed as a... 29701475

Literature References

PubMed DOI Target Context # Activities
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 IGROV-1 4
29701475 10.1021/acs.jmedchem.8b00408 Unchecked 3
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor beta 2
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor alpha 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