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Compound Detail

CHEMBL2158682

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Nc1nc2[nH]c(CCCCc3cc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cs3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2158682
Phase Preclinical
Structure Type MOL
InChI Key JBVKQLSCSCXKDY-AWEZNQCLSA-N
6
Targets
8
Activities
2
Assay Types
0
PK Parameters
7
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 -0.27

Activity Summary

IC50 6 meas. best 9.8
Ki 2 meas. best 6.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 9.8 9.685 0.2 2
IGROV-1
CHEMBL613984
 IC50 8.85 8.85 1.4 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.69 8.69 2.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.59 8.59 2.6 1
R2
CHEMBL614385
 IC50 7.2 7.2 63.8 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.38 5.445 420.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 0.16 nM 9.8 Inhibition of colony formation of human KB cells endogenously expressing RFC/FRa... 22243528
KB IC50 = 0.27 nM 9.57 Growth inhibition of human KB cells endogenously expressing RFC/FRalpha/PCFT inc... 22243528
IGROV-1 IC50 = 1.4 nM 8.85 Growth inhibition of human IGROV1 cells endogenously expressing RFC/FRalpha/PCFT... 22243528
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 2.03 nM 8.69 Inhibition of GARFTase in human IGROV1 cells assessed as reduction in [14C]glyci... 22243528
NON-PROTEIN TARGET IC50 = 2.6 nM 8.59 Growth inhibition of Chinese hamster RT16 cells expressing human folate receptor... 22243528
R2 IC50 = 63.82 nM 7.2 Growth inhibition of Chinese hamster R2 cells expressing human PCFT incubated fo... 22243528
Proton-coupled folate transporter Ki = 420.0 nM 6.38 Inhibition of [3H]MTX transport at human PCFT expressed in Chinese hamster R2 ce... 22243528
Proton-coupled folate transporter Ki = 30700.0 nM 4.51 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
22243528 10.1021/jm201688n IGROV-1 5
22243528 10.1021/jm201688n NON-PROTEIN TARGET 3
22243528 10.1021/jm201688n R2 3
22243528 10.1021/jm201688n Proton-coupled folate transporter 3
22243528 10.1021/jm201688n Trifunctional purine biosynthetic protein adenosine-3 2
22243528 10.1021/jm201688n Folate receptor alpha 1

Data from ChEMBL 36 via Core Engine