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Compound Detail

CHEMBL4540298

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Nc1nc2[nH]c(CCCCc3ccc(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 CHEMBL4540298
Phase Preclinical
Structure Type MOL
InChI Key BDXBDXZHMOFNOY-INIZCTEOSA-N
5
Targets
9
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

473.5
MW (Da)
1.59
ALogP
6
HBA
6
HBD
191.3
PSA (Ų)
0.23
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 C22H24FN5O6
MW 473.46
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -0.26

Activity Summary

IC50 8 meas. best 9.24
Ki 1 meas. best 6.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Folate receptor alpha
CHEMBL2121
 IC50 9.24 9.24 0.6 1
Folate receptor beta
CHEMBL5064
 IC50 8.8 8.455 1.6 2
Proton-coupled folate transporter
CHEMBL1795188
 IC50 8.34 7.99 4.6 2
IGROV-1
CHEMBL613984
 IC50 8.26 8.21 5.4 2
A2780
CHEMBL614004
 IC50 7.87 7.87 13.6 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.77 6.77 170.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Folate receptor alpha IC50 = 0.58 nM 9.24 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
Folate receptor beta IC50 = 1.6 nM 8.8 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
Proton-coupled folate transporter IC50 = 4.57 nM 8.34 Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ... 29701475
IGROV-1 IC50 = 5.44 nM 8.26 Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ... 29701475
IGROV-1 IC50 = 6.89 nM 8.16 Antiproliferative activity against human IGROV1 cells harboring non targeted con... 29701475
Folate receptor beta IC50 = 7.78 nM 8.11 Binding affinity to human FR2 expressed in human HeLa R1-11 cells assessed as an... 29701475
A2780 IC50 = 13.6 nM 7.87 Antiproliferative activity against human A2780 cells after 96 hrs by Cell-Titer ... 29701475
Proton-coupled folate transporter IC50 = 23.0 nM 7.64 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 29701475
Proton-coupled folate transporter Ki = 170.0 nM 6.77 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 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