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Compound Detail

CHEMBL4447805

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Nc1nc2[nH]c(CCOc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4447805
Phase Preclinical
Structure Type MOL
InChI Key VFYUKZOGWIMWFW-AWEZNQCLSA-N
7
Targets
10
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

443.4
MW (Da)
0.50
ALogP
7
HBA
6
HBD
200.5
PSA (Ų)
0.26
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H21N5O7
MW 443.42
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.12

Activity Summary

IC50 8 meas. best 9.47
Ki 2 meas. best 7.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 9.47 7.81 0.3 2
Folate receptor alpha
CHEMBL2121
 IC50 8.72 8.72 1.9 1
Folate receptor beta
CHEMBL5064
 IC50 8.59 8.59 2.6 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.18 8.18 6.6 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 7.24 7.24 57.5 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 7.21 7.21 61.0 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.19 6.19 640.0 1
Reduced folate transporter
CHEMBL4833
 IC50 6.19 6.19 641.0 1
Unchecked
CHEMBL612545
 IC50 6.03 6.03 940.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 0.34 nM 9.47 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 27458733
Folate receptor alpha IC50 = 1.89 nM 8.72 Inhibition of human FR-alpha receptor expressed in Chinese hamster RT16 cells as... 27458733
Folate receptor beta IC50 = 2.59 nM 8.59 Inhibition of human FR-beta receptor expressed in Chinese hamster D4 cells asses... 27458733
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 6.62 nM 8.18 Inhibition of GARFTase in human KB cells expressing RFC/FR-alpha/PCFT assessed a... 27458733
Proton-coupled folate transporter IC50 = 57.5 nM 7.24 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 27458733
Trifunctional purine biosynthetic protein adenosine-3 Ki = 61.0 nM 7.21 Inhibition of recombinant N-terminal 6His-tagged human GARFTase assessed as form... 27458733
Reduced folate transporter IC50 = 641.0 nM 6.19 Inhibition of human RFC expressed in Chinese hamster PC43-10 cells assessed as a... 27458733
Proton-coupled folate transporter Ki = 640.0 nM 6.19 Inhibition of [3H]MTX uptake at human PCFT expressed in Chinese hamster R2/PCFT4... 27458733
KB IC50 = 704.0 nM 6.15 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 27458733
Unchecked IC50 = 940.0 nM 6.03 Cytotoxicity in RFC-null Chinese hamster R2 cells assessed as reduction in cell ... 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 Folate receptor beta 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

Data from ChEMBL 36 via Core Engine