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Compound Detail

CHEMBL5438255

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O=C(/C=C/c1ccccc1)Nc1cc(-c2ccnc(N3CCC(CO)CC3)c2)ccn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5438255
Phase Preclinical
Structure Type MOL
InChI Key KEIAPUMYBMYMQR-VOTSOKGWSA-N
12
Targets
15
Activities
2
Assay Types
4
PK Parameters
16
Publications
0
Known Names

Molecular Properties

414.5
MW (Da)
4.00
ALogP
5
HBA
2
HBD
78.3
PSA (Ų)
0.60
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H26N4O2
MW 414.51
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.84

Activity Summary

IC50 13 meas. best 7.8
Kd 2 meas. best 7.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MDA-MB-231
CHEMBL400
 IC50 7.8 7.8 16.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
 Kd 7.41 7.12 39.4 2
HaCaT
CHEMBL614392
 IC50 7.29 7.29 51.0 1
L02
CHEMBL4296457
 IC50 7.19 7.19 64.0 1
HeLa
CHEMBL399
 IC50 7.11 7.11 77.0 1
HepG2
CHEMBL395
 IC50 6.89 6.89 128.0 1
A549
CHEMBL392
 IC50 6.71 6.2933 196.0 3
NCI-H460
CHEMBL396
 IC50 6.6 6.6 253.0 1
HK-2
CHEMBL4296428
 IC50 6.43 6.43 372.0 1
HCC1937
CHEMBL1075458
 IC50 6.25 6.25 561.0 1
MCF7
CHEMBL387
 IC50 5.63 5.63 2344.0 1
MCF-10A
CHEMBL614321
 IC50 4.73 4.73 18580.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 14615.65 ng.hr.mL-1 Rattus norvegicus
Cmax 19500.13 nM Rattus norvegicus
T1/2 2.23 hr Rattus norvegicus
Tmax 0.14 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MDA-MB-231 IC50 = 16.0 nM 7.8 Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition... 37058970
Retinoic acid receptor RXR-alpha Kd = 39.39 nM 7.41 Binding affinity to RXRalpha LBD (unknown origin) assessed as increase in respon... 37058970
HaCaT IC50 = 51.0 nM 7.29 Cytotoxicity against human HaCaT cells assessed as inhibition of cell proliferat... 37058970
L02 IC50 = 64.0 nM 7.19 Cytotoxicity against human L02 cells assessed as inhibition of cell proliferatio... 37058970
HeLa IC50 = 77.0 nM 7.11 Antiproliferative activity against human HeLa cells assessed as inhibition of ce... 37058970
HepG2 IC50 = 128.0 nM 6.89 Antiproliferative activity against human HepG2 cells assessed as inhibition of c... 37058970
Retinoic acid receptor RXR-alpha Kd = 146.93 nM 6.83 Binding affinity to RXRalpha LBD (unknown origin) assessed as dissociation const... 37058970
A549 IC50 = 196.0 nM 6.71 Antiproliferative activity against wild type human A549 cells assessed as inhibi... 37058970
A549 IC50 = 201.0 nM 6.7 Antiproliferative activity against human A549 cells assessed as inhibition of ce... 37058970
NCI-H460 IC50 = 253.0 nM 6.6 Antiproliferative activity against human NCI-H460 cells assessed as inhibition o... 37058970
HK-2 IC50 = 372.0 nM 6.43 Cytotoxicity against HK-2 cells assessed as inhibition of cell proliferation inc... 37058970
HCC1937 IC50 = 561.0 nM 6.25 Antiproliferative activity against human HCC1937 cells assessed as inhibition of... 37058970
MCF7 IC50 = 2344.0 nM 5.63 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 37058970
A549 IC50 = 3362.0 nM 5.47 Antiproliferative activity against RXRalpha knockout human A549 cells assessed a... 37058970
MCF-10A IC50 = 18580.0 nM 4.73 Cytotoxicity against human MCF-10A cells assessed as inhibition of cell prolifer... 37058970

Literature References

PubMed DOI Target Context # Activities
37058970 10.1016/j.ejmech.2023.115341 MDA-MB-231 46
37058970 10.1016/j.ejmech.2023.115341 A549 38
37058970 10.1016/j.ejmech.2023.115341 ADMET 18
37058970 10.1016/j.ejmech.2023.115341 Unchecked 12
37058970 10.1016/j.ejmech.2023.115341 Retinoic acid receptor RXR-alpha 5
37058970 10.1016/j.ejmech.2023.115341 HepG2 2
37058970 10.1016/j.ejmech.2023.115341 HCC1937 1
37058970 10.1016/j.ejmech.2023.115341 MCF7 1
37058970 10.1016/j.ejmech.2023.115341 NCI-H460 1
37058970 10.1016/j.ejmech.2023.115341 HeLa 1
37058970 10.1016/j.ejmech.2023.115341 MCF-10A 1
37058970 10.1016/j.ejmech.2023.115341 HaCaT 1
37058970 10.1016/j.ejmech.2023.115341 L02 1
37058970 10.1016/j.ejmech.2023.115341 HK-2 1
37058970 10.1016/j.ejmech.2023.115341 Retinoic acid receptor RXR-gamma 1
37058970 10.1016/j.ejmech.2023.115341 Nuclear receptor subfamily 4immunitygroup A member 1 1

Data from ChEMBL 36 via Core Engine