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Compound Detail

CHEMBL2158681

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Nc1nc2[nH]c(CCCCc3csc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2158681
Phase Preclinical
Structure Type MOL
InChI Key VMGGIKVXYOZFJO-ZDUSSCGKSA-N
9
Targets
19
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

461.5
MW (Da)
1.51
ALogP
7
HBA
6
HBD
191.3
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 C20H23N5O6S
MW 461.50
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.15

Activity Summary

IC50 16 meas. best 9.77
Ki 3 meas. best 6.44

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 9.77 9.2167 0.2 3
Folate receptor beta
CHEMBL5064
 IC50 9.37 8.41 0.4 2
IGROV-1
CHEMBL613984
 IC50 9.32 7.99 0.5 3
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 9.22 8.985 0.6 2
Folate receptor alpha
CHEMBL2121
 IC50 8.6 8.6 2.5 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.6 8.6 2.5 1
A2780
CHEMBL614004
 IC50 7.54 7.54 28.8 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 7.38 7.26 41.5 2
R2
CHEMBL614385
 IC50 7.38 7.38 41.5 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.44 5.8 360.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 0.17 nM 9.77 Growth inhibition of human KB cells endogenously expressing RFC/FRalpha/PCFT inc... 22243528
KB IC50 = 0.39 nM 9.41 Inhibition of colony formation of human KB cells endogenously expressing RFC/FRa... 22243528
Folate receptor beta IC50 = 0.43 nM 9.37 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
IGROV-1 IC50 = 0.48 nM 9.32 Growth inhibition of human IGROV1 cells endogenously expressing RFC/FRalpha/PCFT... 22243528
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 0.6 nM 9.22 Inhibition of GARFTase in human IGROV1 cells assessed as decrease in incorporati... 29701475
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.79 nM 8.75 Inhibition of GARFTase in human IGROV1 cells assessed as reduction in [14C]glyci... 22243528
NON-PROTEIN TARGET IC50 = 2.54 nM 8.6 Growth inhibition of Chinese hamster RT16 cells expressing human folate receptor... 22243528
Folate receptor alpha IC50 = 2.5 nM 8.6 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
KB IC50 = 3.4 nM 8.47 Growth inhibition of human KB cells endogenously expressing RFC/FRalpha/PCFT in ... 22243528
A2780 IC50 = 28.8 nM 7.54 Antiproliferative activity against human A2780 cells after 96 hrs by Cell-Titer ... 29701475
Folate receptor beta IC50 = 35.3 nM 7.45 Binding affinity to human FR2 expressed in human HeLa R1-11 cells assessed as an... 29701475
IGROV-1 IC50 = 40.7 nM 7.39 Antiproliferative activity against human IGROV1 cells harboring non targeted con... 29701475
R2 IC50 = 41.54 nM 7.38 Growth inhibition of Chinese hamster R2 cells expressing human PCFT incubated fo... 22243528
Proton-coupled folate transporter IC50 = 41.5 nM 7.38 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 29701475
IGROV-1 IC50 = 54.3 nM 7.26 Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ... 29701475
Proton-coupled folate transporter IC50 = 72.6 nM 7.14 Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ... 29701475
Proton-coupled folate transporter Ki = 360.0 nM 6.44 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 29701475
Proton-coupled folate transporter Ki = 390.0 nM 6.41 Inhibition of [3H]MTX transport at human PCFT expressed in Chinese hamster R2 ce... 22243528
Proton-coupled folate transporter Ki = 28100.0 nM 4.55 Inhibition of [3H]MTX transport at human PCFT expressed in Chinese hamster R2 ce... 22243528

Literature References

PubMed DOI Target Context # Activities
22243528 10.1021/jm201688n KB 7
29701475 10.1021/acs.jmedchem.8b00408 Proton-coupled folate transporter 6
22243528 10.1021/jm201688n IGROV-1 5
29701475 10.1021/acs.jmedchem.8b00408 Reduced folate transporter 4
29701475 10.1021/acs.jmedchem.8b00408 IGROV-1 4
22243528 10.1021/jm201688n NON-PROTEIN TARGET 3
22243528 10.1021/jm201688n R2 3
22243528 10.1021/jm201688n Proton-coupled folate transporter 3
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor beta 3
22243528 10.1021/jm201688n Trifunctional purine biosynthetic protein adenosine-3 2
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor alpha 2
22243528 10.1021/jm201688n Folate receptor alpha 1
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