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Compound Detail

CHEMBL4445651

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Nc1nc2[nH]c(CCCc3csc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c3F)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4445651
Phase Preclinical
Structure Type MOL
InChI Key WMTFSFGBNBUALY-NSHDSACASA-N
8
Targets
15
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

465.5
MW (Da)
1.26
ALogP
7
HBA
6
HBD
191.3
PSA (Ų)
0.26
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 C19H20FN5O6S
MW 465.46
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.26

Activity Summary

IC50 14 meas. best 9.85
Ki 1 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Folate receptor alpha
CHEMBL2121
 IC50 9.85 9.85 0.1 1
Folate receptor beta
CHEMBL5064
 IC50 9.72 9.115 0.2 2
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.92 8.92 1.2 1
Proton-coupled folate transporter
CHEMBL1795188
 IC50 8.82 8.255 1.5 2
IGROV-1
CHEMBL613984
 IC50 8.25 7.715 5.6 4
A2780
CHEMBL614004
 IC50 8.12 8.12 7.6 1
Reduced folate transporter
CHEMBL4833
 IC50 7.7 7.44 20.1 2
Unchecked
CHEMBL612545
 IC50 7.69 7.69 20.5 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 7.16 7.16 70.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Folate receptor alpha IC50 = 0.14 nM 9.85 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
Folate receptor beta IC50 = 0.19 nM 9.72 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.2 nM 8.92 Inhibition of GARFTase in human IGROV1 cells assessed as decrease in incorporati... 29701475
Proton-coupled folate transporter IC50 = 1.5 nM 8.82 Binding affinity to human PCFT expressed in Chinese hamster R2/PCFT4 cells asses... 29701475
Folate receptor beta IC50 = 3.11 nM 8.51 Binding affinity to human FR2 expressed in human HeLa R1-11 cells assessed as an... 29701475
IGROV-1 IC50 = 5.61 nM 8.25 Antiproliferative activity against human IGROV1 cells harboring non targeted con... 29701475
IGROV-1 IC50 = 6.92 nM 8.16 Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ... 29701475
A2780 IC50 = 7.6 nM 8.12 Antiproliferative activity against human A2780 cells after 96 hrs by Cell-Titer ... 29701475
Reduced folate transporter IC50 = 20.1 nM 7.7 Binding affinity to human RFC expressed in Chinese hamster PC43-10 cells assesse... 29701475
Unchecked IC50 = 20.5 nM 7.69 Antiproliferative activity in Chinese hamster R2 cells deficient in RFC, PCFT, a... 29701475
Proton-coupled folate transporter IC50 = 20.4 nM 7.69 Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ... 29701475
IGROV-1 IC50 = 42.2 nM 7.38 Antiproliferative activity against FRalpha knockout human IGROV1 KD10 cells afte... 29701475
Reduced folate transporter IC50 = 66.2 nM 7.18 Binding affinity to human RFC2 expressed in human HeLa R1-11 cells assessed as a... 29701475
Proton-coupled folate transporter Ki = 70.0 nM 7.16 Inhibition of human PCFT expressed in Chinese hamster R2/PCFT4 cells assessed as... 29701475
IGROV-1 IC50 = 85.6 nM 7.07 Antiproliferative activity against FRalpha knockout human IGROV1 KD4 cells after... 29701475

Literature References

PubMed DOI Target Context # Activities
29701475 10.1021/acs.jmedchem.8b00408 Proton-coupled folate transporter 6
29701475 10.1021/acs.jmedchem.8b00408 Reduced folate transporter 4
29701475 10.1021/acs.jmedchem.8b00408 IGROV-1 4
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor beta 3
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor alpha 2
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