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Compound Detail

CHEMBL154716

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O=C1/C(=C/c2ccccc2)CNC/C1=C\c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL154716
Phase Preclinical
Structure Type MOL
InChI Key KPVTZSGWKGUMLH-JYFOCSDGSA-N
21
Targets
36
Activities
1
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

275.4
MW (Da)
3.33
ALogP
2
HBA
1
HBD
29.1
PSA (Ų)
0.85
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H17NO
MW 275.35
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.09

Activity Summary

IC50 36 meas. best 6.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 6.74 6.1 182.0 2
SR
CHEMBL614300
 IC50 6.68 6.68 209.0 1
ADMET
CHEMBL612558
 IC50 6.56 6.2633 275.0 3
K562
CHEMBL385
 IC50 6.31 6.31 490.0 1
SW-620
CHEMBL612262
 IC50 6.24 6.24 575.0 1
HCT-15
CHEMBL612263
 IC50 6.2 6.2 631.0 1
P388
CHEMBL389
 IC50 6.11 6.1 770.0 2
KM12
CHEMBL614709
 IC50 6.1 6.1 794.0 1
Unchecked
CHEMBL612545
 IC50 6.09 6.09 810.0 1
L1210
CHEMBL386
 IC50 6.09 5.31 810.0 5
CCRF-CEM
CHEMBL382
 IC50 6.09 5.89 810.0 5
HepG2
CHEMBL395
 IC50 5.86 5.86 1380.0 1
COLO 205
CHEMBL614561
 IC50 5.81 5.81 1550.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.78 5.565 1670.0 4
HCC 2998
CHEMBL613855
 IC50 5.7 5.7 2000.0 1
NCI-H460
CHEMBL396
 IC50 5.63 5.63 2340.0 1
HeLa
CHEMBL399
 IC50 5.58 5.58 2600.0 1
MRC5
CHEMBL614181
 IC50 5.31 5.31 4850.0 1
HT-1080
CHEMBL614580
 IC50 5.27 5.27 5410.0 1
A549
CHEMBL392
 IC50 5.13 5.13 7360.0 1
CCD-841CoN
CHEMBL4296406
 IC50 5.03 5.03 9450.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.325 hr Mus musculus
T1/2 0.1967 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 182.0 nM 6.74 Cytotoxicity against human HCT116 cells 16996657
SR IC50 = 209.0 nM 6.68 Cytotoxicity against human SR cells 16996657
ADMET IC50 = 275.0 nM 6.56 Cytotoxicity against human RPMI8226 cells 16996657
ADMET IC50 = 363.0 nM 6.44 Cytotoxicity against human HL60 (TB) cells 16996657
K562 IC50 = 490.0 nM 6.31 Cytotoxicity against human K562 cells 16996657
SW-620 IC50 = 575.0 nM 6.24 Cytotoxicity against human SW620 cells 16996657
HCT-15 IC50 = 631.0 nM 6.2 Cytotoxicity against human HCT15 cells 16996657
P388 IC50 = 770.0 nM 6.11 Cytotoxicity against murine P388 cells. 11170648
KM12 IC50 = 794.0 nM 6.1 Cytotoxicity against human KM12 cells 16996657
L1210 IC50 = 810.0 nM 6.09 Antiproliferative activity against mouse L1210 cells assessed as cell growth inh... 32172081
CCRF-CEM IC50 = 810.0 nM 6.09 Antiproliferative activity against human CEM cells assessed as cell growth inhib... 32172081
Unchecked IC50 = 810.0 nM 6.09 Antiproliferative activity against human Molt 4/C8 cells assessed as cell growth... 32172081
P388 IC50 = 810.0 nM 6.09 Antiproliferative activity against mouse P388 cells assessed as cell growth inhi... 32172081
CCRF-CEM IC50 = 900.0 nM 6.05 Cytostatic activity against human CEM cells 25577711
HepG2 IC50 = 1380.0 nM 5.86 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i... 36758308
COLO 205 IC50 = 1550.0 nM 5.81 Cytotoxicity against human COLO205 cells 16996657
ADMET IC50 = 1620.0 nM 5.79 Cytotoxicity against human NCI49 cell lines 16996657
NON-PROTEIN TARGET IC50 = 1670.0 nM 5.78 Antiproliferative activity against human Molt4/C8 cells assessed as cell surviva... 26727215
NON-PROTEIN TARGET IC50 = 1670.0 nM 5.78 Cytotoxicity against human Molt4/C8 cells 19819135
NON-PROTEIN TARGET IC50 = 1670.0 nM 5.78 Cytotoxicity against human Molt 4/C8 cells. 11170648

Literature References

PubMed DOI Target Context # Activities
21514701 10.1016/j.ejmech.2011.03.060 MCF7 3
24139941 10.1016/j.bmc.2013.09.065 Plasmodium berghei 3
17499885 10.1016/j.ejmech.2007.03.010 ADMET 3
21514701 10.1016/j.ejmech.2011.03.060 NCI-H460 3
24139941 10.1016/j.bmc.2013.09.065 Plasmodium falciparum 3
24139941 10.1016/j.bmc.2013.09.065 MDCK 3
25577711 10.1016/j.bmc.2014.12.042 No relevant target 3
21514701 10.1016/j.ejmech.2011.03.060 SF-268 3
21514701 10.1016/j.ejmech.2011.03.060 ADMET 3
36758308 10.1016/j.ejmech.2023.115191 NCI-H460 3
16996657 10.1016/j.ejmech.2006.08.002 ADMET 3
25577711 10.1016/j.bmc.2014.12.042 ADMET 2
18513966 10.1016/j.bmcl.2008.05.034 ATP-dependent translocase ABCB1 2
26727215 10.1021/acs.jmedchem.5b01706 NON-PROTEIN TARGET 2
24139941 10.1016/j.bmc.2013.09.065 Plasma 2
26727215 10.1021/acs.jmedchem.5b01706 CCRF-CEM 2
21514701 10.1016/j.ejmech.2011.03.060 Rattus norvegicus 2
16996657 10.1016/j.ejmech.2006.08.002 HCC 2998 1
36758308 10.1016/j.ejmech.2023.115191 Thioredoxin reductase 1
11170648 10.1021/jm0002580 Unchecked 1

Data from ChEMBL 36 via Core Engine