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Compound Detail

CHEMBL242550

DIOSPYRIN
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Cc1cc(O)c2c(c1)C(=O)C(c1c(C)cc3c(c1O)C(=O)C=CC3=O)=CC2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL242550
Name DIOSPYRIN
Phase Preclinical
Structure Type MOL
InChI Key WRFTYMHHWSAKSK-UHFFFAOYSA-N
10
Targets
21
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

374.4
MW (Da)
3.11
ALogP
6
HBA
2
HBD
108.7
PSA (Ų)
0.79
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H14O6
MW 374.35
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 1.60

Activity Summary

IC50 21 meas. best 6.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.52 5.588 300.0 5
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.1 6.09 800.0 2
A-375
CHEMBL613859
 IC50 6.1 6.0933 800.0 3
Ehrlich
CHEMBL614641
 IC50 6.08 6.08 840.0 1
HEp-2
CHEMBL614735
 IC50 5.45 5.4467 3580.0 3
NFF
CHEMBL614198
 IC50 5.24 5.24 5800.0 1
DNA gyrase subunit A/DNA gyrase subunit B
CHEMBL3430898
 IC50 4.82 4.82 15000.0 1
A-431
CHEMBL614069
 IC50 4.18 4.18 65320.0 1
MCF7
CHEMBL387
 IC50 4.13 4.13 74780.0 1
PBMC
CHEMBL613107
 IC50 4.11 4.11 78300.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 300.0 nM 6.52 Inhibition of human recombinant Glutathione S-transferase 20615584
A-375 IC50 = 800.0 nM 6.1 Cytotoxicity against human A375 cells 20615584
NON-PROTEIN TARGET IC50 = 800.0 nM 6.1 Cytotoxicity against mouse EAC cells 20615584
Unchecked IC50 = 800.0 nM 6.1 Antiproliferative activity against mouse NS-1 cells assessed as reduction in cel... 33314932
A-375 IC50 = 820.0 nM 6.09 Cytotoxicity against human A375 cells after 24 hrs by MTT assay 17400463
A-375 IC50 = 820.0 nM 6.09 Cytotoxicity against human A375 cells after 24 hrs by MTT assay 18281125
NON-PROTEIN TARGET IC50 = 840.0 nM 6.08 Cytotoxicity against mouse EAC cells after 24 hrs by MTT assay 17400463
Ehrlich IC50 = 840.0 nM 6.08 Cytotoxicity against mouse Ehrlich ascites carcinoma cells after 24 hrs by MTT a... 18281125
HEp-2 IC50 = 3580.0 nM 5.45 Cytotoxicity against human Hep2 cells after 24 hrs by MTT assay 17400463
HEp-2 IC50 = 3580.0 nM 5.45 Cytotoxicity against human Hep2 cells after 24 hrs by MTT assay 18281125
HEp-2 IC50 = 3600.0 nM 5.44 Cytotoxicity against human Hep2 cells 20615584
Unchecked IC50 = 4000.0 nM 5.4 Inhibition of Escherichia coli DNA gyrase assessed as inhibition of DNA supercoi... 27569197
NFF IC50 = 5800.0 nM 5.24 Cytotoxicity against human NFF cells assessed as reduction in cell viability aft... 33314932
Unchecked IC50 = 8000.0 nM 5.1 Inhibition of Staphylococcus aureus WCUH29 DNA gyrase expressed in Escherichia c... 27569197
DNA gyrase subunit A/DNA gyrase subunit B IC50 = 15000.0 nM 4.82 Inhibition of Mycobacterium tuberculosis DNA gyrase assessed as inhibition of DN... 27569197
Unchecked IC50 = 15000.0 nM 4.82 Inhibition of Mycobacterium tuberculosis DNA gyrase assessed as reduction in DNA... 33314932
A-431 IC50 = 65320.0 nM 4.18 Cytotoxicity against human A431 cells by MTT assay 18281125
MCF7 IC50 = 74780.0 nM 4.13 Cytotoxicity against human MCF7 cells by MTT assay 18281125
PBMC IC50 = 78320.0 nM 4.11 Cytotoxicity against human PBMCs after 24 hrs by MTT assay 17400463
PBMC IC50 = 78320.0 nM 4.11 Cytotoxicity against human PBMC cells after 24 hrs by MTT assay 18281125

Literature References

PubMed DOI Target Context # Activities
17888665 10.1016/j.bmc.2007.08.064 Unchecked 4
18281125 10.1016/j.ejmech.2007.11.028 Ehrlich 4
33314932 10.1021/acs.jnatprod.0c00800 Unchecked 3
18281125 10.1016/j.ejmech.2007.11.028 Mus musculus 3
27569197 10.1016/j.ejmech.2016.08.034 Unchecked 2
18281125 10.1016/j.ejmech.2007.11.028 HEp-2 1
20615584 10.1016/j.ejmech.2010.06.021 A-375 1
20615584 10.1016/j.ejmech.2010.06.021 K562 1
33333397 10.1016/j.ejmech.2020.113084 Plasmodium falciparum 1
18281125 10.1016/j.ejmech.2007.11.028 A-431 1
18281125 10.1016/j.ejmech.2007.11.028 MCF7 1
18281125 10.1016/j.ejmech.2007.11.028 K562 1
18281125 10.1016/j.ejmech.2007.11.028 HL-60 1
18281125 10.1016/j.ejmech.2007.11.028 PBMC 1
17400463 10.1016/j.bmc.2007.03.050 NON-PROTEIN TARGET 1
18281125 10.1016/j.ejmech.2007.11.028 A-375 1
17888665 10.1016/j.bmc.2007.08.064 Vero 1
17888665 10.1016/j.bmc.2007.08.064 Mycobacterium tuberculosis 1
17400463 10.1016/j.bmc.2007.03.050 A-375 1
17400463 10.1016/j.bmc.2007.03.050 HEp-2 1

Data from ChEMBL 36 via Core Engine