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Compound Detail

CHEMBL301226

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COc1ccc(-c2c3c4cc(OC)c(O)cc4oc(=O)c3n3ccc4cc(O)c(OC)cc4c23)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL301226
Phase Preclinical
Structure Type MOL
InChI Key POCZBHBFCIWCCV-UHFFFAOYSA-N
17
Targets
23
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

499.5
MW (Da)
5.16
ALogP
9
HBA
3
HBD
123.0
PSA (Ų)
0.28
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H21NO8
MW 499.48
Aromatic Rings 6
Heavy Atoms 37
NP-Likeness 0.91

Activity Summary

IC50 23 meas. best 9.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
T47D
CHEMBL614361
 IC50 9.22 9.22 0.6 1
Glycogen synthase kinase-3
CHEMBL2366565
 IC50 8.3 8.3 5.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.1 7.0467 8.0 3
IMR-32
CHEMBL614585
 IC50 7.72 7.72 19.0 1
HepG2
CHEMBL395
 IC50 7.7 7.7 20.0 1
Cyclin-dependent kinase 5/CDK5 activator 1
CHEMBL1907600
 IC50 7.6 7.6 25.0 1
HeLa
CHEMBL399
 IC50 7.5 7.45 32.0 2
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
 IC50 7.46 7.46 35.0 1
A549
CHEMBL392
 IC50 7.4 7.4 40.0 1
HL-60
CHEMBL383
 IC50 7.4 7.4 40.0 1
Serine/threonine-protein kinase pim-1
CHEMBL2147
 IC50 7.26 7.26 55.0 1
KB
CHEMBL398
 IC50 7.22 7.22 60.0 1
H69AR
CHEMBL5209893
 IC50 7.22 7.22 60.0 1
Unchecked
CHEMBL612545
 IC50 7.16 6.13 70.0 2
P388
CHEMBL389
 IC50 7.1 7.1 80.0 1
MDA-MB-231
CHEMBL400
 IC50 6.22 6.22 600.0 1
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 6.0 5.1567 1000.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
T47D IC50 = 0.6 nM 9.22 Cytotoxicity against human T47D cells after 48 hrs by XTT assay -
Glycogen synthase kinase-3 IC50 = 5.0 nM 8.3 Inhibition of porcine brain GSK-3alpha/beta using GS-1 peptide and [gamma-33P]AT... 23981088
NON-PROTEIN TARGET IC50 = 8.0 nM 8.1 Cytotoxicity against human HuCCa1 cells after 48 hrs by XTT assay -
IMR-32 IC50 = 19.0 nM 7.72 Cytotoxicity against human IMR32 cells after 72 hrs by MTS assay 23981088
HepG2 IC50 = 20.0 nM 7.7 Cytotoxicity against human HepG2 cells after 48 hrs by XTT assay -
Cyclin-dependent kinase 5/CDK5 activator 1 IC50 = 25.0 nM 7.6 Inhibition of recombinant CDK5/p25 (unknown origin) expressed in Escherichia col... 23981088
HeLa IC50 = 32.0 nM 7.5 Cytotoxicity against human HeLa cells after 72 hrs by colony formation assay 23981088
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 35.0 nM 7.46 Inhibition of human recombinant DYRK1A expressed in Escherichia coli using [gamm... 23981088
HL-60 IC50 = 40.0 nM 7.4 Cytotoxicity against human HL60 cells after 48 hrs by XTT assay -
HeLa IC50 = 40.0 nM 7.4 Cytotoxicity against human HeLa cells after 48 hrs by XTT assay -
A549 IC50 = 40.0 nM 7.4 Cytotoxicity against human A549 cells after 48 hrs by XTT assay -
NON-PROTEIN TARGET IC50 = 40.0 nM 7.4 Cytotoxicity against human SH-SY5Y cells after 72 hrs by MTS assay 23981088
Serine/threonine-protein kinase pim-1 IC50 = 55.0 nM 7.26 Inhibition of PIM1 (unknown origin) expressed in Escherichia coli using [gamma-3... 23981088
KB IC50 = 60.0 nM 7.22 Cytotoxicity against human KB cells after 48 hrs by XTT assay -
H69AR IC50 = 60.0 nM 7.22 Cytotoxicity against human H69AR cells after 48 hrs by XTT assay -
Unchecked IC50 = 70.0 nM 7.16 Inhibition of M-phase starfish oocytes CDK1/cyclin B using [gamma-33P]ATP after ... 23981088
P388 IC50 = 80.0 nM 7.1 Cytotoxicity against mouse P388 cells after 48 hrs by XTT assay -
MDA-MB-231 IC50 = 600.0 nM 6.22 Cytotoxicity against human MDA-MB-231 cells after 48 hrs by XTT assay -
Human immunodeficiency virus type 1 integrase IC50 = 1000.0 nM 6.0 The compound was tested in vitro for inhibition of HIV-1 replication 10354398
NON-PROTEIN TARGET IC50 = 2300.0 nM 5.64 Cytotoxicity against human HCC-S102 cells after 48 hrs by XTT assay -

Literature References

PubMed DOI Target Context # Activities
23981088 10.1021/jm400719y Unchecked 3
10354398 10.1021/jm9806650 Human immunodeficiency virus type 1 integrase 3
29133033 10.1016/j.bmc.2017.10.030 Epidermal growth factor receptor 2
- 10.1039/C1MD00003A NON-PROTEIN TARGET 2
23981088 10.1021/jm400719y Glycogen synthase kinase-3 1
33276991 10.1016/j.ejmech.2020.113034 Unchecked 1
- 10.1039/C1MD00003A KB 1
- 10.1039/C1MD00003A HL-60 1
- 10.1039/C1MD00003A HeLa 1
- 10.1039/C1MD00003A A549 1
- 10.1039/C1MD00003A HepG2 1
- 10.1039/C1MD00003A T47D 1
23981088 10.1021/jm400719y Cyclin-dependent kinase 5/CDK5 activator 1 1
23981088 10.1021/jm400719y Serine/threonine-protein kinase pim-1 1
23981088 10.1021/jm400719y Dual specificity tyrosine-phosphorylation-regulated kinase 1A 1
23981088 10.1021/jm400719y HeLa 1
23981088 10.1021/jm400719y NON-PROTEIN TARGET 1
23981088 10.1021/jm400719y IMR-32 1
10354398 10.1021/jm9806650 Molluscum contagiosum virus 1
10354398 10.1021/jm9806650 HeLa 1

Data from ChEMBL 36 via Core Engine