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Compound Detail

CHEMBL4444011

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CC(=O)N(CCc1cc2c(=O)[nH]c(N)nc2[nH]1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4444011
Phase Preclinical
Structure Type MOL
InChI Key UPENPAQNDNZZTP-INIZCTEOSA-N
6
Targets
8
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

484.5
MW (Da)
0.48
ALogP
7
HBA
6
HBD
211.6
PSA (Ų)
0.24
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 C22H24N6O7
MW 484.47
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -0.31

Activity Summary

IC50 6 meas. best 8.8
Ki 2 meas. best 7.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Folate receptor beta
CHEMBL5064
 IC50 8.8 8.8 1.6 1
KB
CHEMBL398
 IC50 8.59 8.59 2.6 1
Folate receptor alpha
CHEMBL2121
 IC50 8.31 8.31 4.9 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.25 8.25 5.6 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 7.21 7.21 62.0 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 7.09 7.09 81.7 1
Reduced folate transporter
CHEMBL4833
 IC50 6.09 6.09 808.0 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 5.78 5.78 1680.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Folate receptor beta IC50 = 1.57 nM 8.8 Inhibition of human FR-beta receptor expressed in Chinese hamster D4 cells asses... 27458733
KB IC50 = 2.57 nM 8.59 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 27458733
Folate receptor alpha IC50 = 4.87 nM 8.31 Inhibition of human FR-alpha receptor expressed in Chinese hamster RT16 cells as... 27458733
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 5.58 nM 8.25 Inhibition of GARFTase in human KB cells expressing RFC/FR-alpha/PCFT assessed a... 27458733
Trifunctional purine biosynthetic protein adenosine-3 Ki = 62.0 nM 7.21 Inhibition of recombinant N-terminal 6His-tagged human GARFTase assessed as form... 27458733
Proton-coupled folate transporter IC50 = 81.7 nM 7.09 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 27458733
Reduced folate transporter IC50 = 808.0 nM 6.09 Inhibition of human RFC expressed in Chinese hamster PC43-10 cells assessed as a... 27458733
Proton-coupled folate transporter Ki = 1680.0 nM 5.78 Inhibition of [3H]MTX uptake at human PCFT expressed in Chinese hamster R2/PCFT4... 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 Folate receptor beta 1
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