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Compound Detail

CHEMBL4553188

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Nc1nc2[nH]c(CCN(C(=O)C(F)(F)F)c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4553188
Phase Preclinical
Structure Type MOL
InChI Key FTSMBZFBGMYYIT-AWEZNQCLSA-N
6
Targets
9
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

538.4
MW (Da)
1.02
ALogP
7
HBA
6
HBD
211.6
PSA (Ų)
0.22
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H21F3N6O7
MW 538.44
Aromatic Rings 3
Heavy Atoms 38
NP-Likeness -0.41

Activity Summary

IC50 7 meas. best 9.35
Ki 2 meas. best 6.91

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Folate receptor beta
CHEMBL5064
 IC50 9.35 9.35 0.5 1
KB
CHEMBL398
 IC50 9.25 7.64 0.6 2
Folate receptor alpha
CHEMBL2121
 IC50 8.97 8.97 1.1 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.3 8.3 5.0 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 6.96 6.96 109.0 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 6.91 6.91 122.0 1
Reduced folate transporter
CHEMBL4833
 IC50 6.11 6.11 783.0 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.1 6.1 800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Folate receptor beta IC50 = 0.45 nM 9.35 Inhibition of human FR-beta receptor expressed in Chinese hamster D4 cells asses... 27458733
KB IC50 = 0.56 nM 9.25 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 27458733
Folate receptor alpha IC50 = 1.08 nM 8.97 Inhibition of human FR-alpha receptor expressed in Chinese hamster RT16 cells as... 27458733
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 4.95 nM 8.3 Inhibition of GARFTase in human KB cells expressing RFC/FR-alpha/PCFT assessed a... 27458733
Proton-coupled folate transporter IC50 = 109.0 nM 6.96 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 27458733
Trifunctional purine biosynthetic protein adenosine-3 Ki = 122.0 nM 6.91 Inhibition of recombinant N-terminal 6His-tagged human GARFTase assessed as form... 27458733
Reduced folate transporter IC50 = 783.0 nM 6.11 Inhibition of human RFC expressed in Chinese hamster PC43-10 cells assessed as a... 27458733
Proton-coupled folate transporter Ki = 800.0 nM 6.1 Inhibition of [3H]MTX uptake at human PCFT expressed in Chinese hamster R2/PCFT4... 27458733
KB IC50 = 924.0 nM 6.03 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 27458733

Literature References

PubMed DOI Target Context # Activities
27458733 10.1021/acs.jmedchem.6b00594 Proton-coupled folate transporter 5
27458733 10.1021/acs.jmedchem.6b00594 Trifunctional purine biosynthetic protein adenosine-3 3
27458733 10.1021/acs.jmedchem.6b00594 Unchecked 2
27458733 10.1021/acs.jmedchem.6b00594 Folate receptor alpha 2
27458733 10.1021/acs.jmedchem.6b00594 GAR transformylase/AICAR transformylase 2
27458733 10.1021/acs.jmedchem.6b00594 KB 2
27458733 10.1021/acs.jmedchem.6b00594 Reduced folate transporter 1
27458733 10.1021/acs.jmedchem.6b00594 Bifunctional purine biosynthesis protein ATIC 1
27458733 10.1021/acs.jmedchem.6b00594 Folate receptor beta 1

Data from ChEMBL 36 via Core Engine