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Compound Detail

CHEMBL4467936

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Nc1nc2[nH]c(CCSc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4467936
Phase Preclinical
Structure Type MOL
InChI Key HPAURQDCTYKMTE-AWEZNQCLSA-N
5
Targets
7
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

459.5
MW (Da)
1.22
ALogP
7
HBA
6
HBD
191.3
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 C20H21N5O6S
MW 459.48
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.35

Activity Summary

IC50 5 meas. best 9.47
Ki 2 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Folate receptor beta
CHEMBL5064
 IC50 9.47 9.47 0.3 1
Folate receptor alpha
CHEMBL2121
 IC50 9.29 9.29 0.5 1
KB
CHEMBL398
 IC50 8.78 8.78 1.7 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.28 8.28 5.2 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 6.7 6.7 201.0 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 6.57 6.57 267.0 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 5.83 5.83 1480.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Folate receptor beta IC50 = 0.34 nM 9.47 Inhibition of human FR-beta receptor expressed in Chinese hamster D4 cells asses... 27458733
Folate receptor alpha IC50 = 0.51 nM 9.29 Inhibition of human FR-alpha receptor expressed in Chinese hamster RT16 cells as... 27458733
KB IC50 = 1.66 nM 8.78 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 27458733
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 5.25 nM 8.28 Inhibition of GARFTase in human KB cells expressing RFC/FR-alpha/PCFT assessed a... 27458733
Trifunctional purine biosynthetic protein adenosine-3 Ki = 201.0 nM 6.7 Inhibition of recombinant N-terminal 6His-tagged human GARFTase assessed as form... 27458733
Proton-coupled folate transporter IC50 = 267.0 nM 6.57 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 27458733
Proton-coupled folate transporter Ki = 1480.0 nM 5.83 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 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 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