Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL192632

Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
Nc1nc2[nH]c(CCCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL192632
Phase Preclinical
Structure Type MOL
InChI Key QLSVPQAGJDLITE-HNNXBMFYSA-N
14
Targets
38
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

441.4
MW (Da)
1.06
ALogP
6
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 C21H23N5O6
MW 441.44
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness 0.07

Activity Summary

IC50 31 meas. best 9.0
EC50 4 meas. best 6.34
Ki 3 meas. best 6.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 9.0 8.56 1.0 4
KB
CHEMBL398
 IC50 8.77 8.77 1.7 1
IGROV-1
CHEMBL613984
 IC50 8.71 7.92 2.0 6
A2780
CHEMBL614004
 IC50 8.56 8.56 2.7 1
Folate receptor alpha
CHEMBL2121
 IC50 8.39 8.39 4.1 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.39 7.3375 4.1 4
Unchecked
CHEMBL612545
 IC50 8.39 7.6175 4.1 4
Folate receptor beta
CHEMBL5064
 IC50 8.25 8.08 5.6 2
Proton-coupled folate transporter
CHEMBL1795188
 IC50 8.01 7.825 9.7 2
R2
CHEMBL614385
 IC50 7.64 7.21 23.0 3
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 6.8 6.8 160.0 1
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.66 6.43 220.0 2
Reduced folate transporter
CHEMBL4833
 IC50 6.52 6.52 304.0 1
CCRF-CEM
CHEMBL382
 EC50 6.34 6.025 460.0 4
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3690
 IC50 5.61 5.61 2440.0 1
Dihydrofolate reductase
CHEMBL1809
 IC50 4.66 4.66 22000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
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
KB IC50 = 1.7 nM 8.77 Antiproliferative activity against human RFC and FRalpha expressing human KB cel... 18680275
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.7 nM 8.77 Inhibition of GARFTase in human KB cells expressing RFC/FRalpha/PCFT assessed as... 32503687
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.92 nM 8.72 Inhibition of GARFTase in human KB cells expressing RFC/FR-alpha/PCFT assessed a... 27458733
IGROV-1 IC50 = 1.97 nM 8.71 Antiproliferative activity against human IGROV1 cells harboring non targeted con... 29701475
IGROV-1 IC50 = 2.01 nM 8.7 Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ... 29701475
IGROV-1 IC50 = 2.2 nM 8.66 Antiproliferative activity against human RFC and FRalpha expressing human IGROV1... 18680275
A2780 IC50 = 2.72 nM 8.56 Antiproliferative activity against human A2780 cells after 96 hrs by Cell-Titer ... 29701475
NON-PROTEIN TARGET IC50 = 4.1 nM 8.39 Antiproliferative activity against human FRalpha expressing Chinese hamster RT16... 18680275
Folate receptor alpha IC50 = 4.1 nM 8.39 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
IGROV-1 IC50 = 4.1 nM 8.39 Antiproliferative activity against human IGROV1 cells expressing human FR-alpha/... 27458733
Unchecked IC50 = 4.1 nM 8.39 Inhibition of GARFTase in Chinese Hamster RT16 cells expressing human FRalpha as... 32503687
Unchecked IC50 = 5.6 nM 8.25 Inhibition of GARFTase in Chinese Hamster D4 cells expressing human FRbeta asses... 32503687
Folate receptor beta IC50 = 5.6 nM 8.25 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
NON-PROTEIN TARGET IC50 = 5.6 nM 8.25 Antiproliferative activity against human FRbeta expressing Chinese hamster D4 ce... 18680275
Proton-coupled folate transporter IC50 = 9.71 nM 8.01 Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ... 29701475
Folate receptor beta IC50 = 12.2 nM 7.91 Binding affinity to human FR2 expressed in human HeLa R1-11 cells assessed as an... 29701475
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 18.0 nM 7.75 Inhibition of GARFTase in human KB cells assessed as inhibition of [14C]glycine ... 18680275
R2 IC50 = 23.0 nM 7.64 Growth inhibition of Chinese hamster R2 cells expressing human PCFT4 after 96 hr... 24111942
R2 IC50 = 23.0 nM 7.64 Cytotoxicity against chinese hamster R2 cells expressing human PCFT4 after 96 hr... 24256410

Literature References

PubMed DOI Target Context # Activities
29701475 10.1021/acs.jmedchem.8b00408 IGROV-1 7
32503687 10.1016/j.bmc.2020.115544 Trifunctional purine biosynthetic protein adenosine-3 6
29701475 10.1021/acs.jmedchem.8b00408 Proton-coupled folate transporter 6
18680275 10.1021/jm8003366 NON-PROTEIN TARGET 5
32503687 10.1016/j.bmc.2020.115544 Unchecked 5
18680275 10.1021/jm8003366 KB 4
27458733 10.1021/acs.jmedchem.6b00594 Proton-coupled folate transporter 4
29701475 10.1021/acs.jmedchem.8b00408 Reduced folate transporter 4
31679978 10.1016/j.bmc.2019.115125 KB 4
16078850 10.1021/jm058213s CCRF-CEM 4
27458733 10.1021/acs.jmedchem.6b00594 Trifunctional purine biosynthetic protein adenosine-3 3
16078850 10.1021/jm058213s Dihydrofolate reductase 3
16078850 10.1021/jm058213s Thymidylate synthase 3
16078850 10.1021/jm058213s ADMET 3
27458733 10.1021/acs.jmedchem.6b00594 IGROV-1 2
18680275 10.1021/jm8003366 IGROV-1 2
18680275 10.1021/jm8003366 Trifunctional purine biosynthetic protein adenosine-3 2
24256410 10.1021/jm401328u NON-PROTEIN TARGET 2
24256410 10.1021/jm401328u R2 2
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor beta 2

Data from ChEMBL 36 via Core Engine