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Compound Detail

CHEMBL274993

2,6-DIBENZYLIDENECYCLOHEXANONE
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O=C1/C(=C/c2ccccc2)CCC/C1=C\c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL274993
Name 2,6-DIBENZYLIDENECYCLOHEXANONE
Phase Preclinical
Structure Type MOL
InChI Key CTKKGXDAWIAYSA-JSAVKQRWSA-N
12
Targets
16
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

274.4
MW (Da)
4.91
ALogP
1
HBA
0
HBD
17.1
PSA (Ų)
0.71
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H18O
MW 274.36
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.25

Activity Summary

IC50 12 meas. best 9.59
EC50 2 meas. best 5.7
Ki 2 meas. best 6.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tissue factor
CHEMBL4081
 IC50 9.59 9.59 0.3 1
Unchecked
CHEMBL612545
 Ki 6.15 6.15 704.3 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 6.05 6.05 900.0 1
Molecular identity unknown
CHEMBL612546
 EC50 5.7 5.7 2000.0 1
Leishmania amazonensis
CHEMBL612877
 IC50 5.55 5.315 2800.0 2
DLD-1
CHEMBL614285
 IC50 5.52 5.52 3000.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 4.74 4.74 18400.0 1
A549
CHEMBL392
 IC50 4.58 4.58 26310.0 1
HepG2
CHEMBL395
 IC50 4.55 4.55 28460.0 1
HT-1080
CHEMBL614580
 IC50 4.49 4.49 32650.0 1
Trypanothione reductase
CHEMBL5131
 IC50 4.34 4.34 45800.0 1
NCI-H460
CHEMBL396
 IC50 4.3 4.3 50480.0 1
Trypanosoma cruzi
CHEMBL368
 EC50 4.12 4.12 76200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tissue factor IC50 = 0.26 nM 9.59 Inhibition of tissue factor in Homo sapiens (human) THP1-cells using factor 10a ... -
Unchecked Ki = 704.3 nM 6.15 Displacement of [125I]IMPY from amyloid beta (1 to 42) aggregate after 2 hrs by ... 21417461
Cytochrome P450 1A2 IC50 = 900.0 nM 6.05 Inhibition of human recombinant CYP1A2 18249473
Molecular identity unknown EC50 = 2000.0 nM 5.7 Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells after 24 hrs by firef... 24275249
Leishmania amazonensis IC50 = 2800.0 nM 5.55 Antiparasitic activity against promastigote form of Leishmania amazonensis MHOM/... 29920454
DLD-1 IC50 = 3000.0 nM 5.52 Antiproliferative activity against human DLD-1 cells assessed as cell growth inh... 32172081
Leishmania amazonensis IC50 = 8400.0 nM 5.08 Antileishmanial activity against Leishmania amazonensis IFLA/BR/1967/PH-8 promas... 24321832
Trypanosoma cruzi IC50 = 18400.0 nM 4.74 Antiparasitic activity against epimastigote form of Trypanosoma cruzi Y assessed... 29920454
A549 IC50 = 26310.0 nM 4.58 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 36758308
HepG2 IC50 = 28460.0 nM 4.55 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i... 36758308
HT-1080 IC50 = 32650.0 nM 4.49 Cytotoxicity against human HT-1080 cells assessed as reduction in cell viability... 36758308
Trypanothione reductase IC50 = 45800.0 nM 4.34 Inhibition of Trypanosoma cruzi trypanothione reductase expressed in Escherichia... 24321832
NCI-H460 IC50 = 50480.0 nM 4.3 Cytotoxicity against human NCI-H460 cells assessed as reduction in cell viabilit... 36758308
Trypanosoma cruzi EC50 = 76200.0 nM 4.12 Antiparasitic activity against trypomastigote form of Trypanosoma cruzi assessed... 29920454

Literature References

PubMed DOI Target Context # Activities
24275249 10.1016/j.ejmech.2013.10.073 Molecular identity unknown 7
- 10.1007/s00044-013-0780-4 Unchecked 3
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 1A2 3
32172081 10.1016/j.ejmech.2020.112177 Unchecked 3
29920454 10.1016/j.ejmech.2018.06.031 Unchecked 3
12467629 10.1016/s0960-894x(02)00832-6 NON-PROTEIN TARGET 2
- 10.1007/s00044-012-0116-9 NON-PROTEIN TARGET 2
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 3A4 2
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2D6 2
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2B6 2
18952325 10.1016/j.ejmech.2008.09.026 Mycobacterium tuberculosis 2
29920454 10.1016/j.ejmech.2018.06.031 Trypanosoma cruzi 2
24321832 10.1016/j.ejmech.2013.11.011 Cruzipain 2
32172081 10.1016/j.ejmech.2020.112177 DLD-1 2
24321832 10.1016/j.ejmech.2013.11.011 Trypanothione reductase 2
18952325 10.1016/j.ejmech.2008.09.026 Candida albicans 1
18952325 10.1016/j.ejmech.2008.09.026 Candida parapsilosis 1
18952325 10.1016/j.ejmech.2008.09.026 Aspergillus fumigatus 1
18952325 10.1016/j.ejmech.2008.09.026 Cryptococcus neoformans 1
18249473 10.1016/j.ejmech.2007.10.034 No relevant target 1

Data from ChEMBL 36 via Core Engine