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Compound Detail

CHEMBL1834488

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Nc1nc2[nH]c(CCCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)s3)cc2c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1834488
Phase Preclinical
Structure Type MOL
InChI Key WMBYSCVMFMNUQV-LBPRGKRZSA-N
13
Targets
64
Activities
2
Assay Types
0
PK Parameters
20
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 -0.34

Activity Summary

IC50 58 meas. best 9.8
Ki 6 meas. best 7.17

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Folate receptor beta
CHEMBL5064
 IC50 9.8 8.752 0.2 5
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.77 8.558 0.2 5
KB
CHEMBL398
 IC50 9.59 8.7267 0.3 6
Folate receptor alpha
CHEMBL2121
 IC50 9.51 8.8 0.3 4
IGROV-1
CHEMBL613984
 IC50 9.26 7.8591 0.6 11
Unchecked
CHEMBL612545
 IC50 9.16 7.88 0.7 2
R2
CHEMBL614385
 IC50 8.85 7.167 1.4 10
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 IC50 8.74 8.6333 1.8 3
SK-OV-3
CHEMBL614925
 IC50 8.66 7.995 2.2 2
Proton-coupled folate transporter
CHEMBL1795188
 IC50 8.48 8.18 3.3 4
A2780
CHEMBL614004
 IC50 7.56 7.56 27.4 1
Trifunctional purine biosynthetic protein adenosine-3
CHEMBL3972
 Ki 7.17 7.17 68.0 2
Reduced folate transporter
CHEMBL4833
 IC50 7.0 6.83 101.0 4
Proton-coupled folate transporter
CHEMBL1795188
 Ki 6.89 6.49 130.0 4
ADMET
CHEMBL612558
 IC50 6.54 6.54 288.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Folate receptor beta IC50 = 0.16 nM 9.8 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 29701475
Folate receptor beta IC50 = 0.17 nM 9.77 Binding affinity to human FRbeta expressed in Chinese hamster D4 cells assessed ... 26317331
Folate receptor beta IC50 = 0.17 nM 9.77 Inhibition of FRbeta (unknown origin) expressed in Chinese hamster D4 cells asse... 25234128
NON-PROTEIN TARGET IC50 = 0.17 nM 9.77 Antiproliferative activity against chinese hamster D4 cells expressing human FRb... 21879757
KB IC50 = 0.26 nM 9.59 Antiproliferative activity against human KB cells expressing human RFC, FRalpha ... 21879757
KB IC50 = 0.26 nM 9.59 Growth inhibition of human KB cells endogenously expressing RFC/FRalpha/PCFT inc... 22243528
KB IC50 = 0.26 nM 9.59 Cytotoxicity against human KB cells assessed as cell growth inhibition incubated... 25234128
KB IC50 = 0.26 nM 9.59 Antiproliferative activity against human KB cells expressing FRalpha/PCFT/RFC as... 26317331
Folate receptor alpha IC50 = 0.31 nM 9.51 Inhibition of FRalpha (unknown origin) expressed in Chinese hamster RT16 cells a... 25234128
Folate receptor alpha IC50 = 0.31 nM 9.51 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 29701475
NON-PROTEIN TARGET IC50 = 0.31 nM 9.51 Growth inhibition of Chinese hamster RT16 cells expressing human folate receptor... 22243528
NON-PROTEIN TARGET IC50 = 0.31 nM 9.51 Antiproliferative activity against chinese hamster RT16 cells expressing human F... 21879757
Folate receptor alpha IC50 = 0.38 nM 9.42 Binding affinity to human FRalpha expressed in Chinese hamster RT16 cells assess... 26317331
IGROV-1 IC50 = 0.55 nM 9.26 Antiproliferative activity against human IGROV1 cells expressing human RFC, FRal... 21879757
IGROV-1 IC50 = 0.55 nM 9.26 Growth inhibition of human IGROV1 cells endogenously expressing RFC/FRalpha/PCFT... 22243528
Unchecked IC50 = 0.69 nM 9.16 Inhibition of GARFTase in chinese hamster R2 cells expressing human PCFT assesse... 21879757
IGROV-1 IC50 = 0.73 nM 9.14 Antiproliferative activity against human IGROV1 cells after 96 hrs by CellTiter-... 26317331
IGROV-1 IC50 = 0.95 nM 9.02 Antiproliferative activity against human IGROV1 cells expressing human FR-alpha/... 27458733
R2 IC50 = 1.4 nM 8.85 Antiproliferative activity against chinese hamster R2 cells expressing human PCF... 21879757
Trifunctional purine biosynthetic protein adenosine-3 IC50 = 1.8 nM 8.74 Inhibition of GARFTase in human IGROV1 cells assessed as decrease in incorporati... 29701475

Literature References

PubMed DOI Target Context # Activities
29701475 10.1021/acs.jmedchem.8b00408 IGROV-1 9
21879757 10.1021/jm200739e IGROV-1 8
27458733 10.1021/acs.jmedchem.6b00594 IGROV-1 8
21879757 10.1021/jm200739e Mus musculus 7
21879757 10.1021/jm200739e R2 6
21879757 10.1021/jm200739e Proton-coupled folate transporter 6
26317331 10.1021/acs.jmedchem.5b00801 SK-OV-3 6
33773393 10.1016/j.bmc.2021.116093 Unchecked 6
29701475 10.1021/acs.jmedchem.8b00408 Proton-coupled folate transporter 6
25234128 10.1021/jm501113m Proton-coupled folate transporter 6
21879757 10.1021/jm200739e NON-PROTEIN TARGET 5
26317331 10.1021/acs.jmedchem.5b00801 Trifunctional purine biosynthetic protein adenosine-3 5
25234128 10.1021/jm501113m KB 5
29701475 10.1021/acs.jmedchem.8b00408 Reduced folate transporter 4
29701475 10.1021/acs.jmedchem.8b00408 ADMET 4
31679978 10.1016/j.bmc.2019.115125 KB 4
27458733 10.1021/acs.jmedchem.6b00594 ADMET 4
25234128 10.1021/jm501113m Folate receptor beta 3
29701475 10.1021/acs.jmedchem.8b00408 Unchecked 3
37582241 10.1021/acs.jmedchem.3c00763 KB 3

Data from ChEMBL 36 via Core Engine