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Compound Detail

CHEMBL314360

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CC(=O)N(O)C/C=C/c1cccc(Oc2ccccc2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL314360
Phase Preclinical
Structure Type MOL
InChI Key CEUDWZXMLMKPNN-SOFGYWHQSA-N
5
Targets
37
Activities
1
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

283.3
MW (Da)
3.73
ALogP
3
HBA
1
HBD
49.8
PSA (Ų)
0.67
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H17NO3
MW 283.33
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.09

Activity Summary

IC50 37 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 7.89 7.0475 13.0 32
Homo sapiens
CHEMBL372
 IC50 7.4 7.2 40.0 2
RBL-1
CHEMBL614772
 IC50 7.0 7.0 100.0 1
Arachidonate 5-lipoxygenase-activating protein
CHEMBL4550
 IC50 6.96 6.96 110.0 1
Cyclooxygenase
CHEMBL2094253
 IC50 5.5 5.5 3200.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 2.0 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 13.0 nM 7.89 Inhibition of 5-LO-mediated 5-HETE formation in LPS-stimulated human monocytes p... 24920381
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 13.0 nM 7.89 Inhibition of 5-LO-mediated LTB4 formation in LPS-stimulated human monocytes pre... 24920381
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 13.0 nM 7.89 Inhibition of 5-LO-mediated 5,12-DiHETE formation in LPS-stimulated human monocy... 24920381
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 20.0 nM 7.7 Inhibition of human recombinant 5-LO expressed in Escherichia coli Bl21 (DE3) us... 24920381
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 38.0 nM 7.42 Inhibition of recombinant human 5-Lipoxygenase expressed in Escherichia coli lys... 21868137
Homo sapiens IC50 = 40.0 nM 7.4 Compound was tested for in vitro inhibition on human PMNL. 8709092
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 50.0 nM 7.3 Inhibition of 5-LO in human neutrophils using arachidonic acid as substrate prei... 24920381
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 50.0 nM 7.3 Inhibition of 5-lipoxygenase in cell free S100 freshly isolated human PMNL cells... 22551629
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 50.0 nM 7.3 Inhibition of 5-lipoxygenase in S100 cell free fraction of human polymorphonucle... 22326163
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 50.0 nM 7.3 Inhibition of 5-lipoxygenase in S100 supernatant assessed as inhibition of (5(S)... 21341744
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 50.0 nM 7.3 Inhibition of 5-lipoxygenase in S100 supernatant assessed as inhibition of LTB4 ... 21341744
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 60.0 nM 7.22 Inhibition of 5-Lipoxygenase in arachidonic acid-stimulated human neutrophils af... 21868137
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 80.0 nM 7.1 Inhibition of 5-lipoxygenase in human polymorphonuclear leukocytes assessed as i... 21341744
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 80.0 nM 7.1 Inhibition of 5-lipoxygenase in human polymorphonuclear leukocytes assessed as i... 21341744
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 80.0 nM 7.1 Inhibition of 5-lipoxygenase in A23187-stimulated human PMNL assessed as enzyme ... 21570310
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 80.0 nM 7.1 Inhibition of 5-lipoxygenase in human polymorphonuclear leukocytes assessed as r... 22326163
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 80.0 nM 7.1 Inhibition of 5-lipoxygenase-mediated 5(S)-H(p)ETE formation in fMLP-stimulated ... 21591611
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 100.0 nM 7.0 Inhibition of 5-LO in human leucocytes by measuring FLAP-dependent 5-LOproduct L... 35152061
Homo sapiens IC50 = 100.0 nM 7.0 Compound was tested for in vitro inhibition on rat whole blood. 8709092
RBL-1 IC50 = 100.0 nM 7.0 Compound was tested for in vitro inhibition on broken human PMNL 8709092

Literature References

PubMed DOI Target Context # Activities
21591611 10.1021/jm200092b Polyunsaturated fatty acid 5-lipoxygenase 6
24920381 10.1021/jm500308c Polyunsaturated fatty acid 5-lipoxygenase 5
21868137 10.1016/j.ejmech.2011.08.009 Polyunsaturated fatty acid 5-lipoxygenase 4
22551629 10.1016/j.bmc.2012.04.003 Polyunsaturated fatty acid 5-lipoxygenase 4
21466167 10.1021/jm101309g Polyunsaturated fatty acid 5-lipoxygenase 4
21341744 10.1021/jm101165z Polyunsaturated fatty acid 5-lipoxygenase 4
22607880 10.1016/j.bmc.2012.04.048 Arachidonate 5-lipoxygenase-activating protein 3
18710209 10.1021/jm800588x Polyunsaturated fatty acid 5-lipoxygenase 3
19053751 10.1021/jm801085s Polyunsaturated fatty acid 5-lipoxygenase 3
8709092 10.1021/jm960088k Homo sapiens 2
22326163 10.1016/j.bmcl.2012.01.038 Polyunsaturated fatty acid 5-lipoxygenase 2
21570310 10.1016/j.bmc.2011.04.034 Polyunsaturated fatty acid 5-lipoxygenase 2
22551629 10.1016/j.bmc.2012.04.003 U-937 2
25036790 10.1016/j.ejmech.2014.07.025 Polyunsaturated fatty acid 5-lipoxygenase 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
16821792 10.1021/jm050801i Polyunsaturated fatty acid 5-lipoxygenase 2
23871907 10.1016/j.ejmech.2013.06.039 Polyunsaturated fatty acid 5-lipoxygenase 2
29597170 10.1016/j.ejmech.2018.03.045 Polyunsaturated fatty acid 5-lipoxygenase 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine