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Compound Detail

CHEMBL253777

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COc1cc(O)ccc1C(=O)/C=C/c1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL253777
Phase Preclinical
Structure Type MOL
InChI Key PACBGANPVNHGNP-RUDMXATFSA-N
16
Targets
29
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

270.3
MW (Da)
3.00
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.66
QED
0
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 C16H14O4
MW 270.28
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.59

Activity Summary

IC50 25 meas. best 6.42
EC50 3 meas. best 4.62
Ki 1 meas. best 4.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 6.42 6.42 380.0 1
Poly [ADP-ribose] polymerase 1
CHEMBL3105
 IC50 5.72 5.72 1920.0 1
HepG2
CHEMBL395
 IC50 5.13 5.13 7370.0 1
RAW264.7
CHEMBL612557
 IC50 5.09 5.09 8100.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 5.0 5.0 10110.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.91 4.5367 12300.0 6
Calpain-1 catalytic subunit
CHEMBL3891
 IC50 4.77 4.77 16920.0 1
Unchecked
CHEMBL612545
 Ki 4.7 4.7 20100.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 4.62 4.3867 24000.0 3
Unchecked
CHEMBL612545
 IC50 4.61 4.61 24300.0 1
Neuraminidase
CHEMBL6135
 IC50 4.61 4.61 24300.0 1
HT-1080
CHEMBL614580
 IC50 4.57 4.43 26700.0 2
A549
CHEMBL392
 IC50 4.49 4.2933 32600.0 3
HeLa
CHEMBL399
 IC50 4.48 4.325 33300.0 2
3T3-L1
CHEMBL614510
 IC50 4.38 4.38 41800.0 1
MDA-MB-231
CHEMBL400
 IC50 4.35 4.35 44440.0 1
MCF7
CHEMBL387
 IC50 4.29 4.29 51410.0 1
Ca9-22
CHEMBL1075404
 IC50 4.24 4.24 57560.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amine oxidase [flavin-containing] B IC50 = 380.0 nM 6.42 Inhibition of human MAO-B using kynuramine as substrate incubated for 20 mins by... 32920430
Poly [ADP-ribose] polymerase 1 IC50 = 1920.0 nM 5.72 Inhibition of PARP1 (unknown origin) by ELISA 38516606
HepG2 IC50 = 7370.0 nM 5.13 Cytotoxicity against human HepG2 cells after 3 days by MTT assay 21800859
RAW264.7 IC50 = 8100.0 nM 5.09 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 23127886
Amine oxidase [flavin-containing] A IC50 = 10110.0 nM 5.0 Inhibition of human MAO-A using kynuramine as substrate incubated for 20 mins by... 32920430
NON-PROTEIN TARGET IC50 = 12300.0 nM 4.91 Cytotoxicity against mouse colon 26-L5 cells after 72 hrs by MTT assay 18440233
NON-PROTEIN TARGET IC50 = 14100.0 nM 4.85 Cytotoxicity against mouse Colon 26-L5 cells after 72 hrs by MTT assay 19689125
Calpain-1 catalytic subunit IC50 = 16920.0 nM 4.77 Inhibition of human erythrocytes mu-calpain using Pep2 as substrate incubated fo... 27318120
NON-PROTEIN TARGET IC50 = 17890.0 nM 4.75 Cytotoxicity against human Hep3B cells after 3 days by MTT assay 21800859
Unchecked Ki = 20100.0 nM 4.7 Inhibition of Spanish flu (A/Bervig_Mission/1/18) neuraminidase by noncompetitiv... 20064716
NON-PROTEIN TARGET EC50 = 24000.0 nM 4.62 Antiviral activity against KJ56-1 Porcine rotavirus G5P[7] infected in african g... 20850329
Unchecked IC50 = 24300.0 nM 4.61 Inhibition of Spanish flu (A/Bervig_Mission/1/18) neuraminidase 20064716
Neuraminidase IC50 = 24300.0 nM 4.61 Inhibition of Influenza A virus H1N1 neuraminidase 23664211
HT-1080 IC50 = 26700.0 nM 4.57 Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay 19689125
A549 IC50 = 32600.0 nM 4.49 Cytotoxicity against human A549 cells after 3 days by MTT assay 21800859
HeLa IC50 = 33300.0 nM 4.48 Cytotoxicity against human HeLa cells after 72 hrs by MTT assay 19689125
3T3-L1 IC50 = 41800.0 nM 4.38 Antiadipogenic activity against mouse 3T3L1 cells assessed as inhibition of diff... 19757853
NON-PROTEIN TARGET EC50 = 41800.0 nM 4.38 Antiviral activity against KJ56-1 Bovine rotavirus G8P[7] infected in african gr... 20850329
MDA-MB-231 IC50 = 44440.0 nM 4.35 Cytotoxicity against human MDA-MB-231 cells after 3 days by MTT assay 21800859
NON-PROTEIN TARGET IC50 = 49900.0 nM 4.3 Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay 19689125

Literature References

PubMed DOI Target Context # Activities
20850329 10.1016/j.bmc.2010.07.073 NON-PROTEIN TARGET 7
18440233 10.1016/j.bmc.2008.04.016 NON-PROTEIN TARGET 3
20850329 10.1016/j.bmc.2010.07.073 Unchecked 3
19689125 10.1021/np9003323 NON-PROTEIN TARGET 2
21800859 10.1021/np100920q MCF7 2
23127886 10.1016/j.bmcl.2012.10.055 RAW264.7 2
20064716 10.1016/j.bmcl.2009.12.106 Unchecked 2
18610999 10.1021/jm701501x Fibroblast growth factor receptor 1 1
19689125 10.1021/np9003323 HT-1080 1
19757853 10.1021/np900397f 3T3-L1 1
18610999 10.1021/jm701501x Hepatocyte growth factor receptor 1
18610999 10.1021/jm701501x Fibroblast growth factor receptor 2 1
17883259 10.1021/np070260v Helicobacter pylori 1
38516606 10.1039/d3md00751k Poly [ADP-ribose] polymerase 1 1
18610999 10.1021/jm701501x Mast/stem cell growth factor receptor Kit 1
18610999 10.1021/jm701501x Vascular endothelial growth factor receptor 2 1
18610999 10.1021/jm701501x Proto-oncogene tyrosine-protein kinase Src 1
18440233 10.1016/j.bmc.2008.04.016 HT-1080 1
18440233 10.1016/j.bmc.2008.04.016 HeLa 1
18440233 10.1016/j.bmc.2008.04.016 A549 1

Data from ChEMBL 36 via Core Engine