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Compound Detail

CHEMBL387599

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COc1cc(/C=C2\CCC/C(=C\c3cc(OC)c(OC)c(OC)c3)C2=O)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL387599
Phase Preclinical
Structure Type MOL
InChI Key OXIWSGTZUCVQPH-XOBNHNQQSA-N
9
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

454.5
MW (Da)
4.96
ALogP
7
HBA
0
HBD
72.5
PSA (Ų)
0.52
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C26H30O7
MW 454.52
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness -0.01

Activity Summary

IC50 11 meas. best 7.0
EC50 1 meas. best 4.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
17-beta-hydroxysteroid dehydrogenase type 3
CHEMBL4234
 IC50 7.0 7.0 100.0 1
17-beta-hydroxysteroid dehydrogenase type 3
CHEMBL1075158
 IC50 5.75 5.75 1800.0 1
HT-29
CHEMBL384
 IC50 5.37 5.37 4230.0 1
PC-3
CHEMBL390
 IC50 5.21 4.925 6170.0 2
Trypanosoma cruzi
CHEMBL368
 IC50 5.02 5.02 9500.0 1
PANC-1
CHEMBL614139
 IC50 5.01 5.01 9660.0 1
Leishmania amazonensis
CHEMBL612877
 IC50 4.77 4.77 17000.0 1
HeLa
CHEMBL399
 IC50 4.56 4.56 27500.0 1
KB
CHEMBL398
 IC50 4.53 4.53 29300.0 1
Trypanosoma cruzi
CHEMBL368
 EC50 4.16 4.16 69500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
17-beta-hydroxysteroid dehydrogenase type 3 IC50 = 100.0 nM 7.0 Inhibition of 17beta-HSD3 in human testis microsomes 20346654
17-beta-hydroxysteroid dehydrogenase type 3 IC50 = 1800.0 nM 5.75 Inhibition of 17beta-HSD3 in Sprague-Dawley rat testis microsomes 20346654
HT-29 IC50 = 4230.0 nM 5.37 Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay 22551677
PC-3 IC50 = 6170.0 nM 5.21 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 22551677
Trypanosoma cruzi IC50 = 9500.0 nM 5.02 Antiparasitic activity against epimastigote form of Trypanosoma cruzi Y assessed... 29920454
PANC-1 IC50 = 9660.0 nM 5.01 Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay 22551677
Leishmania amazonensis IC50 = 17000.0 nM 4.77 Antiparasitic activity against promastigote form of Leishmania amazonensis MHOM/... 29920454
PC-3 IC50 = 22700.0 nM 4.64 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 19243951
HeLa IC50 = 27500.0 nM 4.56 Cytotoxicity against human HeLa cells after 72 hrs by MTT assay 19243951
KB IC50 = 29300.0 nM 4.53 Cytotoxicity against human KB cells after 72 hrs by MTT assay 19243951
Trypanosoma cruzi EC50 = 69500.0 nM 4.16 Antiparasitic activity against trypomastigote form of Trypanosoma cruzi assessed... 29920454

Literature References

PubMed DOI Target Context # Activities
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase 1 4
20346654 10.1016/j.bmcl.2010.02.089 17-beta-hydroxysteroid dehydrogenase type 3 3
17383883 10.1016/j.bmc.2007.03.022 ADMET 3
29920454 10.1016/j.ejmech.2018.06.031 Unchecked 3
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase type 2 2
18952325 10.1016/j.ejmech.2008.09.026 Mycobacterium tuberculosis 2
29920454 10.1016/j.ejmech.2018.06.031 Trypanosoma cruzi 2
18952325 10.1016/j.ejmech.2008.09.026 Escherichia coli 1
19243951 10.1016/j.bmc.2008.10.044 HeLa 1
19243951 10.1016/j.bmc.2008.10.044 HL-60 1
19243951 10.1016/j.bmc.2008.10.044 KB 1
18952325 10.1016/j.ejmech.2008.09.026 Klebsiella pneumoniae 1
18952325 10.1016/j.ejmech.2008.09.026 Staphylococcus aureus 1
18952325 10.1016/j.ejmech.2008.09.026 Pseudomonas aeruginosa 1
35447343 10.1016/j.bmcl.2022.128743 Enterobacter cloacae 1
18952325 10.1016/j.ejmech.2008.09.026 Aspergillus fumigatus 1
18952325 10.1016/j.ejmech.2008.09.026 Cryptococcus neoformans 1
18952325 10.1016/j.ejmech.2008.09.026 Candida albicans 1
17383883 10.1016/j.bmc.2007.03.022 HL-60 1
17383883 10.1016/j.bmc.2007.03.022 HSC-3 1

Data from ChEMBL 36 via Core Engine