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Compound Detail

CHEMBL3628344

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Nc1nc2[nH]c(CCCc3csc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3628344
Phase Preclinical
Structure Type MOL
InChI Key UNSSSMUKJOLMJV-LBPRGKRZSA-N
10
Targets
26
Activities
2
Assay Types
0
PK Parameters
16
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 -0.15

Activity Summary

IC50 24 meas. best 9.77
Ki 2 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 9.77 8.12 0.2 2
Folate receptor alpha
CHEMBL2121
 IC50 9.48 8.4233 0.3 3
Folate receptor beta
CHEMBL5064
 IC50 9.47 8.3275 0.3 4
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 9.0 8.81 1.0 2
Proton-coupled folate transporter
CHEMBL1795188
 IC50 8.27 7.98 5.4 3
IGROV-1
CHEMBL613984
 IC50 7.92 7.605 12.1 4
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 7.89 7.89 13.0 1
A2780
CHEMBL614004
 IC50 7.66 7.66 21.7 1
Reduced folate transporter
CHEMBL4833
 IC50 7.2 6.8733 62.9 3
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.55 6.55 280.0 1
Unchecked
CHEMBL612545
 IC50 6.45 6.45 355.0 1
R2
CHEMBL614385
 IC50 6.45 6.45 355.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 0.17 nM 9.77 Antiproliferative activity against human KB cells expressing FRalpha/PCFT/RFC as... 26317331
Folate receptor alpha IC50 = 0.33 nM 9.48 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 26317331
Folate receptor alpha IC50 = 0.33 nM 9.48 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
Folate receptor beta IC50 = 0.34 nM 9.47 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 26317331
Folate receptor beta IC50 = 0.34 nM 9.47 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.0 nM 9.0 Inhibition of GARFTase in human IGROV1 cells assessed as decrease in incorporati... 29701475
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 2.4 nM 8.62 Inhibition of GARFTase in human KB cells expressing FRalpha/PCFT/RFC assessed as... 26317331
Proton-coupled folate transporter IC50 = 5.39 nM 8.27 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 26317331
Proton-coupled folate transporter IC50 = 5.4 nM 8.27 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 29701475
Folate receptor beta IC50 = 7.57 nM 8.12 Binding affinity to human FR2 expressed in human HeLa R1-11 cells assessed as an... 29701475
IGROV-1 IC50 = 12.1 nM 7.92 Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ... 29701475
IGROV-1 IC50 = 12.8 nM 7.89 Antiproliferative activity against human IGROV1 cells harboring non targeted con... 29701475
Trifunctional purine biosynthetic protein adenosine-3 Ki = 13.0 nM 7.89 Inhibition of human recombinant His-tagged GARFTase assessed as formation of 5,8... 26317331
A2780 IC50 = 21.7 nM 7.66 Antiproliferative activity against human A2780 cells after 96 hrs by Cell-Titer ... 29701475
IGROV-1 IC50 = 30.3 nM 7.52 Antiproliferative activity against FRalpha knockout human IGROV1 KD10 cells afte... 29701475
Proton-coupled folate transporter IC50 = 40.0 nM 7.4 Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ... 29701475
Reduced folate transporter IC50 = 62.9 nM 7.2 Binding affinity to human RFC2 expressed in human HeLa R1-11 cells assessed as a... 29701475
IGROV-1 IC50 = 80.5 nM 7.09 Antiproliferative activity against FRalpha knockout human IGROV1 KD4 cells after... 29701475
Reduced folate transporter IC50 = 197.0 nM 6.71 Binding affinity to human RFC expressed in Chinese hamster PC43-10 cells assesse... 26317331
Reduced folate transporter IC50 = 197.0 nM 6.71 Binding affinity to human RFC expressed in Chinese hamster PC43-10 cells assesse... 29701475

Literature References

PubMed DOI Target Context # Activities
26317331 10.1021/acs.jmedchem.5b00801 Trifunctional purine biosynthetic protein adenosine-3 6
29701475 10.1021/acs.jmedchem.8b00408 Proton-coupled folate transporter 6
26317331 10.1021/acs.jmedchem.5b00801 Folate receptor alpha 4
26317331 10.1021/acs.jmedchem.5b00801 Folate receptor beta 4
29701475 10.1021/acs.jmedchem.8b00408 Reduced folate transporter 4
29701475 10.1021/acs.jmedchem.8b00408 IGROV-1 4
26317331 10.1021/acs.jmedchem.5b00801 Unchecked 3
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor beta 3
26317331 10.1021/acs.jmedchem.5b00801 R2 2
26317331 10.1021/acs.jmedchem.5b00801 Proton-coupled folate transporter 2
26317331 10.1021/acs.jmedchem.5b00801 KB 2
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor alpha 2
26317331 10.1021/acs.jmedchem.5b00801 Reduced folate transporter 1
29701475 10.1021/acs.jmedchem.8b00408 Unchecked 1
29701475 10.1021/acs.jmedchem.8b00408 A2780 1
29701475 10.1021/acs.jmedchem.8b00408 Trifunctional purine biosynthetic protein adenosine-3 1

Data from ChEMBL 36 via Core Engine