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Compound Detail

CHEMBL27323

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C/C(=C\C(=O)Nc1ccccc1C(=O)O)c1ccc2ccccc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL27323
Phase Preclinical
Structure Type MOL
InChI Key PGFQXGLPJUCTOI-WYMLVPIESA-N
11
Targets
26
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

331.4
MW (Da)
4.58
ALogP
2
HBA
2
HBD
66.4
PSA (Ų)
0.69
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H17NO3
MW 331.37
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -0.52

Activity Summary

IC50 26 meas. best 7.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HeLa
CHEMBL399
 IC50 7.92 7.92 12.0 1
Telomerase reverse transcriptase
CHEMBL2916
 IC50 7.04 6.3273 91.0 15
MDA-MB-231
CHEMBL400
 IC50 6.77 6.77 170.0 1
Calu-3
CHEMBL614534
 IC50 6.68 6.68 210.0 1
NCI-H460
CHEMBL396
 IC50 6.41 6.41 390.0 1
NCI-H1650
CHEMBL1075518
 IC50 6.28 6.28 520.0 1
MCF7
CHEMBL387
 IC50 6.28 6.28 520.0 1
A549
CHEMBL392
 IC50 6.14 6.14 730.0 1
CT26
CHEMBL613866
 IC50 4.37 4.37 42905.0 1
HL-60
CHEMBL383
 IC50 4.32 4.32 47824.0 1
L02
CHEMBL4296457
 IC50 4.09 4.09 80450.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HeLa IC50 = 12.0 nM 7.92 Antiproliferative activity against human HeLa cells by CCK8 assay 34922028
Telomerase reverse transcriptase IC50 = 91.0 nM 7.04 Inhibition of telomerase activity in human HL-60 cells incubated for 96 hrs by T... 39140071
Telomerase reverse transcriptase IC50 = 93.0 nM 7.03 Inhibition of telomerase in human HeLa cells after 2 hrs by [alpha-32P]dGTP inco... 22413845
Telomerase reverse transcriptase IC50 = 93.0 nM 7.03 Inhibition of human telomerase isolated from human HeLa cells nuclear extracts e... 24053596
Telomerase reverse transcriptase IC50 = 93.0 nM 7.03 Inhibition of human telomerase 26900656
Telomerase reverse transcriptase IC50 = 93.0 nM 7.03 Inhibition of recombinant His-tagged human telomerase expressed in insect cells ... 36669398
Telomerase reverse transcriptase IC50 = 93.0 nM 7.03 Inhibition of human TERT 38117230
Telomerase reverse transcriptase IC50 = 170.0 nM 6.77 Inhibition of telomerase in human MDA-MB-231 cells after 24 hrs by TRAP-PCR-ELIS... 25965778
MDA-MB-231 IC50 = 170.0 nM 6.77 Antiproliferative activity against human MDA-MB-231 cells by CCK8 assay 34922028
Calu-3 IC50 = 210.0 nM 6.68 Antiproliferative activity against human Calu-3 cells by CCK8 assay 34922028
Telomerase reverse transcriptase IC50 = 280.0 nM 6.55 Inhibition of telomerase in human MGC803 cell extracts after 24 hrs by TRAP-PCR-... 24119869
Telomerase reverse transcriptase IC50 = 280.0 nM 6.55 Inhibition of telomerase in human MGC803 cells after 24 hrs by TRAP-PCR-ELISA 25554922
NCI-H460 IC50 = 390.0 nM 6.41 Antiproliferative activity against human H460 cells by CCK8 assay 34922028
Telomerase reverse transcriptase IC50 = 410.0 nM 6.39 Inhibition of telomerase in human MGC803 cell extracts after 24 hrs by TRAP-PCR-... 25812966
MCF7 IC50 = 520.0 nM 6.28 Antiproliferative activity against human MCF7 cells by CCK8 assay 34922028
NCI-H1650 IC50 = 520.0 nM 6.28 Antiproliferative activity against human H1650 cells by CCK8 assay 34922028
A549 IC50 = 730.0 nM 6.14 Antiproliferative activity against human A549 cells by CCK8 assay 34922028
Telomerase reverse transcriptase IC50 = 3600.0 nM 5.44 Inhibition of telomerase in human HeLa cells using 5'-AAT CCG TCG AGC AGA GTT-3'... 22413845
Telomerase reverse transcriptase IC50 = 3600.0 nM 5.44 Inhibition of human telomerase activity isolated from HEK293 cells assessed as r... 27657809
Telomerase reverse transcriptase IC50 = 4600.0 nM 5.34 Inhibition of telomerase in human HeLa cells using 5'-AAT CCG TCG AGC AGA GTT-3'... 22413845

Literature References

PubMed DOI Target Context # Activities
22413845 10.1021/jm201191d Telomerase reverse transcriptase 6
34922028 10.1016/j.bmcl.2021.128503 A549 5
38117230 10.1021/acs.jmedchem.3c01708 Telomerase reverse transcriptase 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
27657809 10.1016/j.ejmech.2016.09.028 Telomerase reverse transcriptase 2
22413845 10.1021/jm201191d Unchecked 2
25554922 10.1016/j.ejmech.2014.12.013 Telomerase reverse transcriptase 1
25812966 10.1016/j.ejmech.2015.03.039 Telomerase reverse transcriptase 1
25965778 10.1016/j.ejmech.2015.04.063 Telomerase reverse transcriptase 1
26900656 10.1016/j.ejmech.2016.02.009 Telomerase reverse transcriptase 1
24119869 10.1016/j.ejmech.2013.06.014 Telomerase reverse transcriptase 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
31071547 10.1016/j.ejmech.2019.04.041 Telomerase reverse transcriptase 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
24053596 10.1021/jm400528t Telomerase reverse transcriptase 1
34922028 10.1016/j.bmcl.2021.128503 HeLa 1
34922028 10.1016/j.bmcl.2021.128503 MDA-MB-231 1
39140071 10.1021/acsmedchemlett.4c00310 GES1 1
22413845 10.1021/jm201191d Nucleic Acid 1

Data from ChEMBL 36 via Core Engine