Compound Detail

CHEMBL4465095

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Nc1nc2[nH]c(CCCCc3csc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c3F)cc2c(=O)[nH]1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4465095
Phase	Preclinical
Structure Type	MOL
InChI Key	JWZBILLJZHUAOY-LBPRGKRZSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

479.5

MW (Da)

1.65

ALogP

HBA

HBD

191.3

PSA (Å²)

0.22

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C20H22FN5O6S
MW	479.49
Aromatic Rings	3
Heavy Atoms	33
NP-Likeness	-0.26

Activity Summary

IC50 13 meas. best 9.44

Ki 1 meas. best 6.6

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Folate receptor alpha CHEMBL2121	IC50	9.44	9.44	0.4	1
Trifunctional purine biosynthetic protein adenosine-3 CHEMBL3972	IC50	9.15	9.15	0.7	1
Folate receptor beta CHEMBL5064	IC50	9.12	8.835	0.8	2
IGROV-1 CHEMBL613984	IC50	8.75	7.64	1.8	5
A2780 CHEMBL614004	IC50	8.51	8.51	3.1	1
Proton-coupled folate transporter CHEMBL1795188	IC50	8.3	8.26	5.0	2
Reduced folate transporter CHEMBL4833	IC50	6.67	6.67	213.0	1
Proton-coupled folate transporter CHEMBL1795188	Ki	6.6	6.6	250.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Folate receptor alpha	IC50	=	0.36	nM	9.44	Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess...	29701475
Trifunctional purine biosynthetic protein adenosine-3	IC50	=	0.7	nM	9.15	Inhibition of GARFTase in human IGROV1 cells assessed as decrease in incorporati...	29701475
Folate receptor beta	IC50	=	0.75	nM	9.12	Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ...	29701475
IGROV-1	IC50	=	1.79	nM	8.75	Antiproliferative activity against human IGROV1 cells harboring non targeted con...	29701475
IGROV-1	IC50	=	1.9	nM	8.72	Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ...	29701475
Folate receptor beta	IC50	=	2.84	nM	8.55	Binding affinity to human FR2 expressed in human HeLa R1-11 cells assessed as an...	29701475
A2780	IC50	=	3.11	nM	8.51	Antiproliferative activity against human A2780 cells after 96 hrs by Cell-Titer ...	29701475
Proton-coupled folate transporter	IC50	=	5.01	nM	8.3	Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ...	29701475
Proton-coupled folate transporter	IC50	=	6.0	nM	8.22	Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses...	29701475
IGROV-1	IC50	=	66.9	nM	7.17	Antiproliferative activity against FRalpha knockout human IGROV1 KD10 cells afte...	29701475
IGROV-1	IC50	=	138.0	nM	6.86	Antiproliferative activity against FRalpha knockout human IGROV1 KD4 cells after...	29701475
IGROV-1	IC50	=	200.0	nM	6.7	Anticlonogenic activity against human IGROV1 cells incubated for 24 hrs followed...	29701475
Reduced folate transporter	IC50	=	213.0	nM	6.67	Binding affinity to human RFC2 expressed in human HeLa R1-11 cells assessed as a...	29701475
Proton-coupled folate transporter	Ki	=	250.0	nM	6.6	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	10
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	ADMET	4
29701475	10.1021/acs.jmedchem.8b00408	Unchecked	3
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	A2780	1
29701475	10.1021/acs.jmedchem.8b00408	Trifunctional purine biosynthetic protein adenosine-3	1

Data from ChEMBL 36 via Core Engine