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Compound Detail

CHEMBL5584045

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C[n+]1c(/C=C/c2c[nH]c3ccccc23)cc(/C=C2\Sc3ccccc3N2CCCN2CCC(C(F)(F)F)CC2)c2ccccc21.[I-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5584045
Phase Preclinical
Structure Type MOL
InChI Key GMHFXZCPVQSFHC-PCARWJJXSA-N
Parent Compound CHEMBL6069596
Active Moiety CHEMBL6069596
11
Targets
18
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

625.8
MW (Da)
8.89
ALogP
3
HBA
1
HBD
26.1
PSA (Ų)
0.18
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C37H36F3IN4S
MW 752.69
Aromatic Rings 5
Heavy Atoms 45
NP-Likeness -0.66

Activity Summary

IC50 11 meas. best 6.17
Kd 7 meas. best 5.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MDA-MB-231
CHEMBL400
 IC50 6.17 5.8925 670.0 4
quadruplex DNA
CHEMBL3832742
 Kd 5.94 5.372 1140.0 5
A549
CHEMBL392
 IC50 5.68 5.68 2100.0 1
PC-3
CHEMBL390
 IC50 5.6 5.6 2500.0 1
HeLa
CHEMBL399
 IC50 5.58 5.58 2600.0 1
Unchecked
CHEMBL612545
 Kd 5.55 5.55 2790.0 1
HepG2
CHEMBL395
 IC50 5.54 5.54 2900.0 1
U2OS
CHEMBL615023
 IC50 5.41 5.41 3900.0 1
HUVEC
CHEMBL613979
 IC50 5.06 5.06 8700.0 1
HK-2
CHEMBL4296428
 IC50 5.03 5.03 9400.0 1
DNA
CHEMBL4649922
 Kd 4.72 4.72 18900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MDA-MB-231 IC50 = 670.0 nM 6.17 Cytotoxicity against human MDA-MB-231 cells assessed as inhibition of cell growt... 38987863
MDA-MB-231 IC50 = 1000.0 nM 6.0 Cytotoxicity against telomerase-positive human MDA-MB-231 cells assessed as inhi... 38987863
quadruplex DNA Kd = 1140.0 nM 5.94 Binding affinity to hTERT G4 DNA assessed as dissociation constant by ITC analys... 38987863
MDA-MB-231 IC50 = 1200.0 nM 5.92 Cytotoxicity against human MDA-MB-231 cells without hTERT overexpression assesse... 38987863
A549 IC50 = 2100.0 nM 5.68 Cytotoxicity against telomerase-positive human A549 cells assessed as inhibition... 38987863
PC-3 IC50 = 2500.0 nM 5.6 Cytotoxicity against telomerase-positive human PC-3 cells assessed as inhibition... 38987863
HeLa IC50 = 2600.0 nM 5.58 Cytotoxicity against telomerase-positive human HeLa cells assessed as inhibition... 38987863
Unchecked Kd = 2790.0 nM 5.55 Binding affinity to antisense i-hTERT DNA assessed as dissociation constant by I... 38987863
HepG2 IC50 = 2900.0 nM 5.54 Cytotoxicity against telomerase-positive human HepG2 cells assessed as inhibitio... 38987863
MDA-MB-231 IC50 = 3300.0 nM 5.48 Cytotoxicity against human MDA-MB-231 cells transfected with hTERT-pcDNA3.1(+)-C... 38987863
quadruplex DNA Kd = 3280.0 nM 5.48 Binding affinity to Telo21 G4 DNA (unknown origin) assessed as dissociation cons... 38987863
quadruplex DNA Kd = 3610.0 nM 5.44 Binding affinity to Bcl-2 G4 DNA (unknown origin) assessed as dissociation const... 38987863
U2OS IC50 = 3900.0 nM 5.41 Cytotoxicity against alternative lengthening of telomere-positive human U2OS cel... 38987863
quadruplex DNA Kd = 6800.0 nM 5.17 Binding affinity to CKIT-2 G4 DNA (unknown origin) assessed as dissociation cons... 38987863
HUVEC IC50 = 8700.0 nM 5.06 Cytotoxicity against HUVEC cells assessed as inhibition of cell growth incubated... 38987863
HK-2 IC50 = 9400.0 nM 5.03 Cytotoxicity against human HK-2 cells assessed as inhibition of cell growth incu... 38987863
quadruplex DNA Kd = 14700.0 nM 4.83 Binding affinity to c-MYC Pu27 G4 DNA (unknown origin) assessed as dissociation ... 38987863
DNA Kd = 18900.0 nM 4.72 Binding affinity to Ds26 duplex DNA (unknown origin) assessed as dissociation co... 38987863

Literature References

PubMed DOI Target Context # Activities
38987863 10.1021/acs.jmedchem.4c01255 Unchecked 67
38987863 10.1021/acs.jmedchem.4c01255 MDA-MB-231 40
38987863 10.1021/acs.jmedchem.4c01255 quadruplex DNA 32
38987863 10.1021/acs.jmedchem.4c01255 ADMET 27
38987863 10.1021/acs.jmedchem.4c01255 DNA 10
38987863 10.1021/acs.jmedchem.4c01255 dsDNA 4
38987863 10.1021/acs.jmedchem.4c01255 HepG2 1
38987863 10.1021/acs.jmedchem.4c01255 PC-3 1
38987863 10.1021/acs.jmedchem.4c01255 HeLa 1
38987863 10.1021/acs.jmedchem.4c01255 A549 1
38987863 10.1021/acs.jmedchem.4c01255 U2OS 1
38987863 10.1021/acs.jmedchem.4c01255 HK-2 1
38987863 10.1021/acs.jmedchem.4c01255 HUVEC 1
38987863 10.1021/acs.jmedchem.4c01255 Telomerase reverse transcriptase 1

Data from ChEMBL 36 via Core Engine