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Compound Detail

CHEMBL4437824

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Nc1nc2[nH]c(CCNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4437824
Phase Preclinical
Structure Type MOL
InChI Key UFNWIIALSMNORN-AWEZNQCLSA-N
8
Targets
17
Activities
2
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

442.4
MW (Da)
0.54
ALogP
7
HBA
7
HBD
203.3
PSA (Ų)
0.23
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 C20H22N6O6
MW 442.43
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.24

Activity Summary

IC50 15 meas. best 9.49
Ki 2 meas. best 7.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 9.49 8.0833 0.3 3
KB
CHEMBL398
 IC50 9.49 7.835 0.3 2
Folate receptor beta
CHEMBL5064
 IC50 9.21 9.21 0.6 1
Unchecked
CHEMBL612545
 IC50 9.21 7.77 0.6 4
IGROV-1
CHEMBL613984
 IC50 8.57 7.315 2.7 2
Folate receptor alpha
CHEMBL2121
 IC50 8.52 8.52 3.0 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 7.23 7.23 59.0 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 7.06 7.06 87.4 1
Reduced folate transporter
CHEMBL4833
 IC50 6.29 6.29 510.0 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.07 6.07 850.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 0.32 nM 9.49 Inhibition of GARFTase in human KB cells expressing RFC/FRalpha/PCFT assessed as... 32503687
KB IC50 = 0.32 nM 9.49 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 27458733
Folate receptor beta IC50 = 0.62 nM 9.21 Inhibition of human FR-beta receptor expressed in Chinese hamster D4 cells asses... 27458733
Unchecked IC50 = 0.62 nM 9.21 Inhibition of GARFTase in Chinese Hamster D4 cells expressing human FRbeta asses... 32503687
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 2.64 nM 8.58 Inhibition of GARFTase in human KB cells expressing RFC/FR-alpha/PCFT assessed a... 27458733
IGROV-1 IC50 = 2.7 nM 8.57 Antiproliferative activity against human IGROV1 cells expressing human FR-alpha/... 27458733
Folate receptor alpha IC50 = 3.04 nM 8.52 Inhibition of human FR-alpha receptor expressed in Chinese hamster RT16 cells as... 27458733
Unchecked IC50 = 3.04 nM 8.52 Inhibition of GARFTase in Chinese Hamster RT16 cells expressing human FRalpha as... 32503687
Trifunctional purine biosynthetic protein adenosine-3 Ki = 59.0 nM 7.23 Inhibition of recombinant N-terminal 6His-tagged human GARFTase assessed as form... 27458733
Proton-coupled folate transporter IC50 = 87.4 nM 7.06 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 27458733
Unchecked IC50 = 87.4 nM 7.06 Inhibition of GARFTase in Chinese Hamster MTXRII-OuaR2-4 R2 cells expressing hum... 32503687
Reduced folate transporter IC50 = 510.0 nM 6.29 Inhibition of human RFC expressed in Chinese hamster PC43-10 cells assessed as a... 27458733
Unchecked IC50 = 510.0 nM 6.29 Inhibition of GARFTase in Chinese Hamster PC43-10 cells expressing human RFC ass... 32503687
KB IC50 = 666.0 nM 6.18 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 27458733
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 666.0 nM 6.18 Inhibition of GARFTase in human KB cells expressing RFC/FRalpha/PCFT assessed as... 32503687
Proton-coupled folate transporter Ki = 850.0 nM 6.07 Inhibition of [3H]MTX uptake at human PCFT expressed in Chinese hamster R2/PCFT4... 27458733
IGROV-1 IC50 = 872.0 nM 6.06 Antiproliferative activity against human IGROV1 cells expressing human FR-alpha/... 27458733

Literature References

PubMed DOI Target Context # Activities
27458733 10.1021/acs.jmedchem.6b00594 IGROV-1 7
32503687 10.1016/j.bmc.2020.115544 Trifunctional purine biosynthetic protein adenosine-3 6
27458733 10.1021/acs.jmedchem.6b00594 Proton-coupled folate transporter 5
32503687 10.1016/j.bmc.2020.115544 Unchecked 5
27458733 10.1021/acs.jmedchem.6b00594 ADMET 4
27458733 10.1021/acs.jmedchem.6b00594 Trifunctional purine biosynthetic protein adenosine-3 3
27458733 10.1021/acs.jmedchem.6b00594 Folate receptor beta 2
27458733 10.1021/acs.jmedchem.6b00594 Folate receptor alpha 2
27458733 10.1021/acs.jmedchem.6b00594 Unchecked 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

Data from ChEMBL 36 via Core Engine