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Compound Detail

CHEMBL414890

PROTOAPIGENONE
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O=C1C=CC(O)(c2cc(=O)c3c(O)cc(O)cc3o2)C=C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL414890
Name PROTOAPIGENONE
Phase Preclinical
Structure Type MOL
InChI Key DLMOVPAUHQQYHA-UHFFFAOYSA-N
17
Targets
23
Activities
2
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

286.2
MW (Da)
1.09
ALogP
6
HBA
3
HBD
108.0
PSA (Ų)
0.72
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 C15H10O6
MW 286.24
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 2.16

Activity Summary

IC50 22 meas. best 6.15
EC50 1 meas. best 5.37

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SK-OV-3
CHEMBL614925
 IC50 6.15 6.15 710.0 1
MDA-MB-231
CHEMBL400
 IC50 5.84 5.805 1430.0 2
Glutathione S-transferase omega-1
CHEMBL3174
 IC50 5.8 5.8 1600.0 1
Unchecked
CHEMBL612545
 IC50 5.79 5.3875 1620.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.64 5.64 2270.0 1
DNA damage-inducible transcript 3 protein
CHEMBL2146304
 IC50 5.59 5.59 2580.0 1
MCF7
CHEMBL387
 IC50 5.43 5.345 3740.0 2
X-box-binding protein 1
CHEMBL1741176
 IC50 5.42 5.42 3840.0 1
RPMI-8226
CHEMBL614882
 IC50 5.41 5.41 3930.0 1
Heat shock factor protein 1
CHEMBL5313
 EC50 5.37 5.37 4281.0 1
PC-3
CHEMBL390
 IC50 5.21 5.21 6130.0 1
HEK293
CHEMBL614818
 IC50 5.17 5.17 6790.0 1
U-266
CHEMBL2366315
 IC50 5.12 5.12 7660.0 1
HepG2
CHEMBL395
 IC50 5.11 5.1 7770.0 2
PBMC
CHEMBL613107
 IC50 5.09 5.09 8110.0 1
A549
CHEMBL392
 IC50 4.86 4.86 13850.0 1
PANC-1
CHEMBL614139
 IC50 4.66 4.66 22090.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SK-OV-3 IC50 = 710.0 nM 6.15 Antitumor activity against human SKOV3 cells assessed as cell proliferation afte... 21515048
MDA-MB-231 IC50 = 1430.0 nM 5.84 Cytotoxicity against human MDA-MB-231 cells after 72 hrs by MTT colorimetric met... 17622129
Glutathione S-transferase omega-1 IC50 = 1600.0 nM 5.8 Inhibition of GSTO1-1 (unknown origin) by 4-NPG substrate based assay 29652143
Unchecked IC50 = 1620.0 nM 5.79 PUBCHEM_BIOASSAY: Dose Response selectivity of uHTS chemical inhibitors of T-cel... -
MDA-MB-231 IC50 = 1700.0 nM 5.77 Antitumor activity against human MDA-MB-231 cells assessed as cell proliferation... 21515048
Unchecked IC50 = 2210.0 nM 5.66 PUBCHEM_BIOASSAY: Dose response confirmation of uHTS chemical inhibitors of T-ce... -
NON-PROTEIN TARGET IC50 = 2270.0 nM 5.64 Cytotoxicity against human Hep3B cells after 72 hrs by MTT colorimetric method 17622129
DNA damage-inducible transcript 3 protein IC50 = 2580.0 nM 5.59 PUBCHEM_BIOASSAY: CHOP dose-response primary assay. (Class of assay: confirmator... -
MCF7 IC50 = 3740.0 nM 5.43 Cytotoxicity against human MCF7 cells after 72 hrs by MTT colorimetric method 17622129
X-box-binding protein 1 IC50 = 3840.0 nM 5.42 PUBCHEM_BIOASSAY: XBP1 DR counterscreen for CHOP. (Class of assay: confirmatory)... -
Unchecked IC50 = 3874.0 nM 5.41 PUBCHEM_BIOASSAY: High Throughput Screen to Identify Inhibitors of Mycobacterium... -
RPMI-8226 IC50 = 3930.0 nM 5.41 Antitumor activity against human RPMI8226 cells assessed as cell proliferation a... 21515048
Heat shock factor protein 1 EC50 = 4281.0 nM 5.37 PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Confirmation HTS to Identify Inhi... -
MCF7 IC50 = 5500.0 nM 5.26 Antitumor activity against human MCF7 cells assessed as cell proliferation after... 21515048
PC-3 IC50 = 6130.0 nM 5.21 Antitumor activity against human PC3 cells assessed as cell proliferation after ... 21515048
HEK293 IC50 = 6790.0 nM 5.17 Cytotoxicity against human HEK293 cells assessed as cell proliferation after 24 ... 21515048
U-266 IC50 = 7660.0 nM 5.12 Antitumor activity against human U266 cells assessed as cell proliferation after... 21515048
HepG2 IC50 = 7770.0 nM 5.11 Antitumor activity against human HepG2 cells assessed as cell proliferation afte... 21515048
HepG2 IC50 = 8110.0 nM 5.09 Cytotoxicity against human HepG2 cells after 72 hrs by MTT colorimetric method 17622129
PBMC IC50 = 8110.0 nM 5.09 Cytotoxicity against human PBMC assessed as cell proliferation after 24 hrs by M... 21515048

Literature References

PubMed DOI Target Context # Activities
21515048 10.1016/j.bmcl.2011.03.108 Mus musculus 6
21515048 10.1016/j.bmcl.2011.03.108 PC-3 1
29652143 10.1021/acs.jmedchem.8b00318 Glutathione S-transferase omega-1 1
21515048 10.1016/j.bmcl.2011.03.108 H22 1
21515048 10.1016/j.bmcl.2011.03.108 PBMC 1
21515048 10.1016/j.bmcl.2011.03.108 HEK293 1
21515048 10.1016/j.bmcl.2011.03.108 U-266 1
21515048 10.1016/j.bmcl.2011.03.108 RPMI-8226 1
21515048 10.1016/j.bmcl.2011.03.108 PANC-1 1
21515048 10.1016/j.bmcl.2011.03.108 HepG2 1
17622129 10.1021/jm070363a HepG2 1
21515048 10.1016/j.bmcl.2011.03.108 SK-OV-3 1
21515048 10.1016/j.bmcl.2011.03.108 MDA-MB-231 1
21515048 10.1016/j.bmcl.2011.03.108 MCF7 1
16038533 10.1021/np050121i Estrogen receptor 1
17622129 10.1021/jm070363a A549 1
17622129 10.1021/jm070363a MCF7 1
17622129 10.1021/jm070363a MDA-MB-231 1
17622129 10.1021/jm070363a NON-PROTEIN TARGET 1

Data from ChEMBL 36 via Core Engine