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Compound Detail

CHEMBL3628346

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Nc1nc2[nH]c(CCCc3cc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cs3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3628346
Phase Preclinical
Structure Type MOL
InChI Key RMEHPWHLFJJYTB-ZDUSSCGKSA-N
9
Targets
15
Activities
2
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

447.5
MW (Da)
1.12
ALogP
7
HBA
6
HBD
191.3
PSA (Ų)
0.27
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H21N5O6S
MW 447.47
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.28

Activity Summary

IC50 14 meas. best 10.05
Ki 1 meas. best 8.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 10.05 8.515 0.1 2
Folate receptor beta
CHEMBL5064
 IC50 10.0 8.09 0.1 2
Folate receptor alpha
CHEMBL2121
 IC50 9.21 7.755 0.6 2
IGROV-1
CHEMBL613984
 IC50 9.11 7.835 0.8 2
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.59 8.59 2.6 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 8.19 8.19 6.5 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 8.04 8.04 9.1 1
SK-OV-3
CHEMBL614925
 IC50 7.81 7.465 15.5 2
Reduced folate transporter
CHEMBL4833
 IC50 6.72 6.72 189.0 1
R2
CHEMBL614385
 IC50 6.54 6.54 290.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 0.09 nM 10.05 Antiproliferative activity against human KB cells expressing FRalpha/PCFT/RFC as... 26317331
Folate receptor beta IC50 = 0.1 nM 10.0 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 26317331
Folate receptor alpha IC50 = 0.61 nM 9.21 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 26317331
IGROV-1 IC50 = 0.77 nM 9.11 Antiproliferative activity against human IGROV1 cells after 96 hrs by CellTiter-... 26317331
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 2.6 nM 8.59 Inhibition of GARFTase in human KB cells expressing FRalpha/PCFT/RFC assessed as... 26317331
Proton-coupled folate transporter IC50 = 6.51 nM 8.19 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 26317331
Trifunctional purine biosynthetic protein adenosine-3 Ki = 9.1 nM 8.04 Inhibition of human recombinant His-tagged GARFTase assessed as formation of 5,8... 26317331
SK-OV-3 IC50 = 15.5 nM 7.81 Antiproliferative activity against human SKOV3 cells after 96 hrs by CellTiter-B... 26317331
SK-OV-3 IC50 = 76.0 nM 7.12 Antiproliferative activity against human SKOV3 cells after 96 hrs by CellTiter-B... 26317331
KB IC50 = 105.0 nM 6.98 Antiproliferative activity against human KB cells expressing FRalpha/PCFT/RFC as... 26317331
Reduced folate transporter IC50 = 189.0 nM 6.72 Binding affinity to human RFC expressed in Chinese hamster PC43-10 cells assesse... 26317331
IGROV-1 IC50 = 276.0 nM 6.56 Antiproliferative activity against human IGROV1 cells after 96 hrs by CellTiter-... 26317331
R2 IC50 = 290.0 nM 6.54 Cytotoxicity against PCFT-null Chinese hamster R2 cells assessed as cell growth ... 26317331
Folate receptor alpha IC50 = 506.0 nM 6.3 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 26317331
Folate receptor beta IC50 = 654.0 nM 6.18 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 26317331

Literature References

PubMed DOI Target Context # Activities
26317331 10.1021/acs.jmedchem.5b00801 Proton-coupled folate transporter 8
26317331 10.1021/acs.jmedchem.5b00801 SK-OV-3 6
26317331 10.1021/acs.jmedchem.5b00801 Trifunctional purine biosynthetic protein adenosine-3 6
26317331 10.1021/acs.jmedchem.5b00801 Folate receptor alpha 5
26317331 10.1021/acs.jmedchem.5b00801 Folate receptor beta 5
26317331 10.1021/acs.jmedchem.5b00801 R2 3
26317331 10.1021/acs.jmedchem.5b00801 Unchecked 3
26317331 10.1021/acs.jmedchem.5b00801 KB 3
26317331 10.1021/acs.jmedchem.5b00801 IGROV-1 2
26317331 10.1021/acs.jmedchem.5b00801 Mus musculus 2
26317331 10.1021/acs.jmedchem.5b00801 Reduced folate transporter 1

Data from ChEMBL 36 via Core Engine