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Compound Detail

CHEMBL590740

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Nc1nc2[nH]c(CCCCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)s3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL590740
Phase Preclinical
Structure Type MOL
InChI Key ADFLVKAWSSGDBU-ZDUSSCGKSA-N
9
Targets
29
Activities
2
Assay Types
0
PK Parameters
20
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 -0.33

Activity Summary

IC50 25 meas. best 9.7
Ki 4 meas. best 6.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 9.7 9.2333 0.2 6
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.24 8.94 0.6 5
IGROV-1
CHEMBL613984
 IC50 9.01 9.01 1.0 3
Folate receptor alpha
CHEMBL2121
 IC50 8.74 8.74 1.8 1
Unchecked
CHEMBL612545
 IC50 8.71 8.71 2.0 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.5 7.72 3.1 3
R2
CHEMBL614385
 IC50 7.57 7.4125 27.2 4
Proton-coupled folate transporter
CHEMBL1795188
 IC50 7.36 7.36 43.4 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3690
 IC50 7.22 7.22 60.0 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.89 6.095 130.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 0.2 nM 9.7 Inhibition of colony formation of human KB cells endogenously expressing RFC/FRa... 22243528
KB IC50 = 0.55 nM 9.26 Growth inhibition of human KB cells expressing RFC, FRalpha and PCFT after 96 hr... 20085328
KB IC50 = 0.55 nM 9.26 Antiproliferative activity against human KB cells expressing human RFC, FRalpha ... 21879757
KB IC50 = 0.55 nM 9.26 Growth inhibition of human KB cells endogenously expressing RFC/FRalpha/PCFT inc... 22243528
KB IC50 = 0.55 nM 9.26 Antiproliferative activity against human KB cells expressing RFC/FRalpha/PCFT af... 25602637
NON-PROTEIN TARGET IC50 = 0.57 nM 9.24 Growth inhibition of Chinese hamster D4 cells expressing human FRbeta after 96 h... 20085328
NON-PROTEIN TARGET IC50 = 0.57 nM 9.24 Antiproliferative activity against chinese hamster D4 cells expressing human FRb... 21879757
IGROV-1 IC50 = 0.97 nM 9.01 Growth inhibition of human IGROV1 cells expressing RFC, FRalpha and PCFT after 9... 20085328
IGROV-1 IC50 = 0.97 nM 9.01 Antiproliferative activity against human IGROV1 cells expressing human RFC, FRal... 21879757
IGROV-1 IC50 = 0.97 nM 9.01 Growth inhibition of human IGROV1 cells endogenously expressing RFC/FRalpha/PCFT... 22243528
NON-PROTEIN TARGET IC50 = 1.82 nM 8.74 Growth inhibition of Chinese hamster RT16 cells expressing human FRalpha after 9... 20085328
NON-PROTEIN TARGET IC50 = 1.82 nM 8.74 Antiproliferative activity against chinese hamster RT16 cells expressing human F... 21879757
NON-PROTEIN TARGET IC50 = 1.82 nM 8.74 Growth inhibition of Chinese hamster RT16 cells expressing human folate receptor... 22243528
Folate receptor alpha IC50 = 1.82 nM 8.74 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 25602637
Unchecked IC50 = 1.96 nM 8.71 Inhibition of GARFTase in chinese hamster R2 cells expressing human PCFT assesse... 21879757
KB IC50 = 2.2 nM 8.66 Growth inhibition of human KB cells endogenously expressing RFC/FRalpha/PCFT in ... 22243528
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 3.13 nM 8.5 Inhibition of GARFTase in human KB cells expressing RFC/FRalpha/PCFT assessed as... 25602637
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 3.46 nM 8.46 Inhibition of GARFTase in human IGROV1 cells assessed as reduction in [14C]glyci... 22243528
R2 IC50 = 27.2 nM 7.57 Antiproliferative activity against chinese hamster R2 cells expressing human PCF... 21879757
R2 IC50 = 43.4 nM 7.36 Growth inhibition of Chinese hamster R2 cells expressing human RFC and human PCF... 20085328

Literature References

PubMed DOI Target Context # Activities
20085328 10.1021/jm9015729 KB 12
20085328 10.1021/jm9015729 NON-PROTEIN TARGET 6
21879757 10.1021/jm200739e IGROV-1 6
20085328 10.1021/jm9015729 R2 5
21879757 10.1021/jm200739e NON-PROTEIN TARGET 5
22243528 10.1021/jm201688n KB 4
20085328 10.1021/jm9015729 Mus musculus 4
21879757 10.1021/jm200739e R2 4
21879757 10.1021/jm200739e Proton-coupled folate transporter 4
25602637 10.1021/jm501787c GAR transformylase/AICAR transformylase 3
22243528 10.1021/jm201688n Proton-coupled folate transporter 3
21879757 10.1021/jm200739e Mus musculus 3
22243528 10.1021/jm201688n R2 3
22243528 10.1021/jm201688n NON-PROTEIN TARGET 3
20085328 10.1021/jm9015729 Trifunctional purine biosynthetic protein adenosine-3 2
22243528 10.1021/jm201688n IGROV-1 2
20085328 10.1021/jm9015729 Proton-coupled folate transporter 2
21879757 10.1021/jm200739e KB 2
20085328 10.1021/jm9015729 IGROV-1 2
21879757 10.1021/jm200739e Unchecked 2

Data from ChEMBL 36 via Core Engine