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Compound Detail

CHEMBL4214638

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Nc1nc2[nH]c(CCCCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)nc3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4214638
Phase Preclinical
Structure Type MOL
InChI Key FSOJIOKMUXQEMI-HNNXBMFYSA-N
8
Targets
24
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

456.5
MW (Da)
0.84
ALogP
7
HBA
6
HBD
204.2
PSA (Ų)
0.23
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H24N6O6
MW 456.46
Aromatic Rings 3
Heavy Atoms 33

Activity Summary

IC50 22 meas. best 9.43
Ki 2 meas. best 6.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 9.43 7.93 0.4 2
Folate receptor beta
CHEMBL5064
 IC50 9.29 8.26 0.5 4
IGROV-1
CHEMBL613984
 IC50 9.17 7.915 0.7 6
Folate receptor alpha
CHEMBL2121
 IC50 8.9 7.9833 1.3 3
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.89 8.815 1.3 2
A2780
CHEMBL614004
 IC50 8.27 8.27 5.4 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 8.05 7.6033 9.0 3
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.62 6.55 240.0 2
Reduced folate transporter
CHEMBL4833
 IC50 6.2 6.2 634.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 0.37 nM 9.43 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 29425443
Folate receptor beta IC50 = 0.51 nM 9.29 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
Folate receptor beta IC50 = 0.58 nM 9.24 Binding affinity to human FR-beta receptor expressed in Chinese hamster D4 cells... 29425443
IGROV-1 IC50 = 0.68 nM 9.17 Antiproliferative activity against human IGROV1 cells expressing human FR-alpha/... 29425443
Folate receptor alpha IC50 = 1.27 nM 8.9 Binding affinity to human FR-alpha receptor expressed in Chinese hamster RT16 ce... 29425443
Folate receptor alpha IC50 = 1.3 nM 8.89 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.3 nM 8.89 Inhibition of GARFTase in human IGROV1 cells assessed as decrease in incorporati... 29701475
IGROV-1 IC50 = 1.55 nM 8.81 Antiproliferative activity against human IGROV1 cells harboring non targeted con... 29701475
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.8 nM 8.74 Inhibition of GARFTase in human KB cells assessed as decrease in [14C]formyl GAR... 29425443
IGROV-1 IC50 = 1.87 nM 8.73 Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ... 29701475
A2780 IC50 = 5.42 nM 8.27 Antiproliferative activity against human A2780 cells after 96 hrs by Cell-Titer ... 29701475
Folate receptor beta IC50 = 6.54 nM 8.18 Binding affinity to human FR2 expressed in human HeLa R1-11 cells assessed as an... 29701475
Proton-coupled folate transporter IC50 = 8.98 nM 8.05 Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ... 29701475
Proton-coupled folate transporter IC50 = 30.4 nM 7.52 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 29701475
IGROV-1 IC50 = 30.5 nM 7.52 Antiproliferative activity against FRalpha knockout human IGROV1 KD10 cells afte... 29701475
Proton-coupled folate transporter IC50 = 57.6 nM 7.24 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 29425443
IGROV-1 IC50 = 64.1 nM 7.19 Antiproliferative activity against FRalpha knockout human IGROV1 KD4 cells after... 29701475
Proton-coupled folate transporter Ki = 240.0 nM 6.62 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 29701475
Proton-coupled folate transporter Ki = 332.0 nM 6.48 Inhibition of [3H]MTX uptake at human PCFT expressed in Chinese hamster R2/PCFT4... 29425443
KB IC50 = 368.0 nM 6.43 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 29425443

Literature References

PubMed DOI Target Context # Activities
29425443 10.1021/acs.jmedchem.7b01708 Proton-coupled folate transporter 6
29701475 10.1021/acs.jmedchem.8b00408 Proton-coupled folate transporter 6
29425443 10.1021/acs.jmedchem.7b01708 KB 5
29425443 10.1021/acs.jmedchem.7b01708 IGROV-1 5
29701475 10.1021/acs.jmedchem.8b00408 IGROV-1 4
29701475 10.1021/acs.jmedchem.8b00408 Reduced folate transporter 4
29425443 10.1021/acs.jmedchem.7b01708 Folate receptor alpha 3
29425443 10.1021/acs.jmedchem.7b01708 Folate receptor beta 3
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor beta 3
29425443 10.1021/acs.jmedchem.7b01708 Unchecked 2
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor alpha 2
29701475 10.1021/acs.jmedchem.8b00408 Trifunctional purine biosynthetic protein adenosine-3 1
29425443 10.1021/acs.jmedchem.7b01708 Reduced folate transporter 1
29701475 10.1021/acs.jmedchem.8b00408 A2780 1
29701475 10.1021/acs.jmedchem.8b00408 Unchecked 1
29425443 10.1021/acs.jmedchem.7b01708 Mus musculus 1
29425443 10.1021/acs.jmedchem.7b01708 Trifunctional purine biosynthetic protein adenosine-3 1

Data from ChEMBL 36 via Core Engine