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Compound Detail

CHEMBL365307

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Nc1nc2[nH]c(CCCCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL365307
Phase Preclinical
Structure Type MOL
InChI Key CEPQCJFDTGQKDN-INIZCTEOSA-N
13
Targets
38
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

455.5
MW (Da)
1.45
ALogP
6
HBA
6
HBD
191.3
PSA (Ų)
0.23
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H25N5O6
MW 455.47
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness 0.06

Activity Summary

IC50 32 meas. best 9.0
EC50 4 meas. best 5.96
Ki 2 meas. best 6.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
KB
CHEMBL398
 IC50 9.0 8.8133 1.0 3
IGROV-1
CHEMBL613984
 IC50 8.95 8.494 1.1 5
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.72 8.38 1.9 3
Proton-coupled folate transporter
CHEMBL1795188
 IC50 8.28 7.2067 5.2 3
Folate receptor beta
CHEMBL5064
 IC50 8.25 8.1467 5.6 3
Unchecked
CHEMBL612545
 IC50 8.24 7.7775 5.7 4
Folate receptor alpha
CHEMBL2121
 IC50 8.2 8.2 6.3 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.2 8.1 6.3 2
A2780
CHEMBL614004
 IC50 7.85 7.85 14.2 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3690
 IC50 6.82 6.82 150.0 1
R2
CHEMBL614385
 IC50 6.67 6.67 213.0 2
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.34 6.34 460.0 2
CCRF-CEM
CHEMBL382
 EC50 5.96 5.33 1100.0 4
Dihydrofolate reductase
CHEMBL1809
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
KB IC50 = 1.0 nM 9.0 Antiproliferative activity against human KB cells expressing human RFC/FR-alpha/... 29425443
IGROV-1 IC50 = 1.12 nM 8.95 Antiproliferative activity against human IGROV1 cells expressing human FR-alpha/... 29425443
KB IC50 = 1.9 nM 8.72 Antiproliferative activity against human RFC and FRalpha expressing human KB cel... 18680275
KB IC50 = 1.9 nM 8.72 Growth inhibition of human KB cells expressing RFC, FRalpha and PCFT after 96 hr... 20085328
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.9 nM 8.72 Inhibition of GARFTase in human KB cells expressing RFC/FRalpha/PCFT assessed as... 32503687
IGROV-1 IC50 = 3.6 nM 8.44 Antiproliferative activity against human RFC and FRalpha expressing human IGROV1... 18680275
IGROV-1 IC50 = 3.6 nM 8.44 Growth inhibition of human IGROV1 cells expressing RFC, FRalpha and PCFT after 9... 20085328
IGROV-1 IC50 = 4.37 nM 8.36 Antiproliferative activity against wild type human IGROV1 cells after 96 hrs by ... 29701475
Proton-coupled folate transporter IC50 = 5.21 nM 8.28 Binding affinity to human PCFT4 expressed in human HeLa R1-11 cells assessed as ... 29701475
IGROV-1 IC50 = 5.21 nM 8.28 Antiproliferative activity against human IGROV1 cells harboring non targeted con... 29701475
Folate receptor beta IC50 = 5.6 nM 8.25 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 5.6 nM 8.25 Inhibition of GARFTase in human KB cells assessed as decrease in [14C]formyl GAR... 29425443
Folate receptor beta IC50 = 5.6 nM 8.25 Binding affinity to human FR-beta receptor expressed in Chinese hamster D4 cells... 29425443
Unchecked IC50 = 5.71 nM 8.24 Inhibition of GARFTase in human KB cells assessed as incorporation of [14C]-glyc... 24256410
NON-PROTEIN TARGET IC50 = 6.3 nM 8.2 Antiproliferative activity against human FRalpha expressing Chinese hamster RT16... 18680275
Folate receptor alpha IC50 = 6.3 nM 8.2 Binding affinity to human FR-alpha receptor expressed in Chinese hamster RT16 ce... 29425443
Folate receptor alpha IC50 = 6.3 nM 8.2 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
Unchecked IC50 = 6.3 nM 8.2 Inhibition of GARFTase in Chinese Hamster RT16 cells expressing human FRalpha as... 32503687
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 6.8 nM 8.17 Inhibition of GARFTase in human KB cells assessed as inhibition of [14C]glycine ... 18680275
NON-PROTEIN TARGET IC50 = 10.0 nM 8.0 Antiproliferative activity against human FRbeta expressing Chinese hamster D4 ce... 18680275

Literature References

PubMed DOI Target Context # Activities
24256410 10.1021/jm401328u KB 11
16078850 10.1021/jm058213s CCRF-CEM 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
29425443 10.1021/acs.jmedchem.7b01708 Proton-coupled folate transporter 6
32503687 10.1016/j.bmc.2020.115544 Unchecked 5
29425443 10.1021/acs.jmedchem.7b01708 KB 5
18680275 10.1021/jm8003366 NON-PROTEIN TARGET 5
29701475 10.1021/acs.jmedchem.8b00408 IGROV-1 4
29701475 10.1021/acs.jmedchem.8b00408 Reduced folate transporter 4
16078850 10.1021/jm058213s Thymidylate synthase 3
29701475 10.1021/acs.jmedchem.8b00408 Unchecked 3
18680275 10.1021/jm8003366 KB 3
29425443 10.1021/acs.jmedchem.7b01708 Folate receptor alpha 3
29701475 10.1021/acs.jmedchem.8b00408 Folate receptor beta 3
29425443 10.1021/acs.jmedchem.7b01708 Folate receptor beta 3
16078850 10.1021/jm058213s ADMET 3
16078850 10.1021/jm058213s Dihydrofolate reductase 3
18680275 10.1021/jm8003366 IGROV-1 2
18680275 10.1021/jm8003366 Trifunctional purine biosynthetic protein adenosine-3 2

Data from ChEMBL 36 via Core Engine