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Compound Detail

CHEMBL1242095

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CC(=O)c1c(O)cc(O)c(C/C=C(\C)CCC=C(C)C)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1242095
Phase Preclinical
Structure Type MOL
InChI Key RCOXTTLIGHDQHU-XYOKQWHBSA-N
13
Targets
15
Activities
1
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

304.4
MW (Da)
4.24
ALogP
4
HBA
3
HBD
77.8
PSA (Ų)
0.54
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H24O4
MW 304.39
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness 2.25

Activity Summary

IC50 15 meas. best 6.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 6.4 6.4 400.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 6.38 6.0767 420.0 3
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL5211
 IC50 5.75 5.75 1800.0 1
Prostaglandin E synthase
CHEMBL5658
 IC50 5.46 5.46 3500.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.18 5.18 6600.0 1
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 5.16 5.16 6900.0 1
HL-60
CHEMBL383
 IC50 4.72 4.72 19000.0 1
HT-29
CHEMBL384
 IC50 4.72 4.72 19000.0 1
A549
CHEMBL392
 IC50 4.7 4.7 20000.0 1
Unchecked
CHEMBL612545
 IC50 4.69 4.69 20390.0 1
HeLa
CHEMBL399
 IC50 4.68 4.68 21000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.65 4.65 22500.0 1
Radical scavenging activity
CHEMBL613712
 IC50 4.34 4.34 46000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 400.0 nM 6.4 Inhibition of human recombinant COX2 expressed in insect Sf21 cells assessed as ... 21958738
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 420.0 nM 6.38 Inhibition of human 5-LOX in human peripheral blood mononuclear leukocytes asses... 21958738
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 1000.0 nM 6.0 Inhibition of human recombinant 5-LO expressed in Escherichia coli MV1190 using ... 28240894
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 1400.0 nM 5.85 Inhibition of 5-LO in human peripheral blood neutrophils using arachidonic acid ... 28240894
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 1800.0 nM 5.75 Inhibition of 5-LOX in calcium ionophore A23187-stimulated NMRI mouse macrophage... 21958738
Prostaglandin E synthase IC50 = 3500.0 nM 5.46 Inhibition of human A549 cell microsomal membrane-derived mPGES-1 assessed as re... 28240894
Plasmodium falciparum IC50 = 6600.0 nM 5.18 Antiplasmodial activity against intraerythrocytic stage of Plasmodium falciparum... 27228055
Prostaglandin G/H synthase 1 IC50 = 6900.0 nM 5.16 Inhibition of COX1 in human platelets assessed as inhibition of conversion of ar... 21958738
HT-29 IC50 = 19000.0 nM 4.72 Cytotoxicity against human HT-29 cells after 72 hrs by XTT assay 20619940
HL-60 IC50 = 19000.0 nM 4.72 Cytotoxicity against human HL60 cells after 72 hrs by XTT assay 20619940
A549 IC50 = 20000.0 nM 4.7 Cytotoxicity against human A549 cells after 72 hrs by XTT assay 20619940
Unchecked IC50 = 20390.0 nM 4.69 Inhibition of soybean 15-LOX type 1-B assessed as inhibition of conversion of li... 21958738
HeLa IC50 = 21000.0 nM 4.68 Cytotoxicity against human HeLa cells after 72 hrs by XTT assay 20619940
NON-PROTEIN TARGET IC50 = 22500.0 nM 4.65 Antiproliferative activity against human HMEC1 cells after 72 hrs 25128665
Radical scavenging activity IC50 = 46000.0 nM 4.34 Antioxidant activity assessed as DPPH radical scavenging activity 21958738

Literature References

PubMed DOI Target Context # Activities
21958738 10.1016/j.bmc.2011.09.001 Polyunsaturated fatty acid 5-lipoxygenase 7
28240894 10.1021/acs.jnatprod.6b01008 Mus musculus 5
28240894 10.1021/acs.jnatprod.6b01008 Polyunsaturated fatty acid 5-lipoxygenase 5
21958738 10.1016/j.bmc.2011.09.001 Prostaglandin G/H synthase 1 5
21958738 10.1016/j.bmc.2011.09.001 Prostaglandin G/H synthase 2 5
21958738 10.1016/j.bmc.2011.09.001 No relevant target 3
28240894 10.1021/acs.jnatprod.6b01008 Prostaglandin E synthase 1
20619940 10.1016/j.ejmech.2010.06.025 HeLa 1
28240894 10.1021/acs.jnatprod.6b01008 Neutrophil 1
27228055 10.1021/acs.jnatprod.6b00347 Plasmodium falciparum 1
25128665 10.1016/j.ejmech.2014.08.017 NON-PROTEIN TARGET 1
25128665 10.1016/j.ejmech.2014.08.017 No relevant target 1
21958738 10.1016/j.bmc.2011.09.001 Radical scavenging activity 1
21958738 10.1016/j.bmc.2011.09.001 ADMET 1
21958738 10.1016/j.bmc.2011.09.001 Unchecked 1
20619940 10.1016/j.ejmech.2010.06.025 HL-60 1
20619940 10.1016/j.ejmech.2010.06.025 HT-29 1
20619940 10.1016/j.ejmech.2010.06.025 A549 1

Data from ChEMBL 36 via Core Engine