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Compound Detail

CHEMBL4471269

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Nc1nc2[nH]c(CCN(C=O)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 CHEMBL4471269
Phase Preclinical
Structure Type MOL
InChI Key CYOOKDIMCAPJGV-HNNXBMFYSA-N
6
Targets
8
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

470.4
MW (Da)
0.09
ALogP
7
HBA
6
HBD
211.6
PSA (Ų)
0.21
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H22N6O7
MW 470.44
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness 0.16

Activity Summary

IC50 6 meas. best 9.28
Ki 2 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Folate receptor beta
CHEMBL5064
 IC50 9.28 9.28 0.5 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.68 8.68 2.1 1
KB
CHEMBL398
 IC50 8.68 8.68 2.1 1
Folate receptor alpha
CHEMBL2121
 IC50 8.52 8.52 3.0 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 7.05 7.05 88.5 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 7.0 7.0 99.0 1
Reduced folate transporter
CHEMBL4833
 IC50 6.19 6.19 642.0 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.14 6.14 730.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Folate receptor beta IC50 = 0.53 nM 9.28 Inhibition of human FR-beta receptor expressed in Chinese hamster D4 cells asses... 27458733
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 2.11 nM 8.68 Inhibition of GARFTase in human KB cells expressing RFC/FR-alpha/PCFT assessed a... 27458733
KB IC50 = 2.09 nM 8.68 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 27458733
Folate receptor alpha IC50 = 3.01 nM 8.52 Inhibition of human FR-alpha receptor expressed in Chinese hamster RT16 cells as... 27458733
Proton-coupled folate transporter IC50 = 88.5 nM 7.05 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 27458733
Trifunctional purine biosynthetic protein adenosine-3 Ki = 99.0 nM 7.0 Inhibition of recombinant N-terminal 6His-tagged human GARFTase assessed as form... 27458733
Reduced folate transporter IC50 = 642.0 nM 6.19 Inhibition of human RFC expressed in Chinese hamster PC43-10 cells assessed as a... 27458733
Proton-coupled folate transporter Ki = 730.0 nM 6.14 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