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Compound Detail

CHEMBL17347

ETHYL CAFFEATE
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CCOC(=O)/C=C/c1ccc(O)c(O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL17347
Name ETHYL CAFFEATE
Phase Preclinical
Structure Type MOL
InChI Key WDKYDMULARNCIS-GQCTYLIASA-N
21
Targets
34
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

208.2
MW (Da)
1.67
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.45
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H12O4
MW 208.21
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness 0.81

Activity Summary

IC50 29 meas. best 5.94
EC50 5 meas. best 5.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL312
 IC50 5.94 5.94 1150.0 1
HT-22
CHEMBL614316
 EC50 5.72 5.72 1900.0 1
HeLa
CHEMBL399
 IC50 5.71 5.17 1960.0 2
RAW264.7
CHEMBL612557
 IC50 5.7 5.7 2000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.6 5.0813 2500.0 8
RAW264.7
CHEMBL612557
 EC50 5.5 5.5 3183.0 1
NCI-H1299
CHEMBL612255
 IC50 5.31 5.31 4930.0 1
BeWo
CHEMBL614525
 IC50 5.21 5.21 6200.0 1
LOX IMVI
CHEMBL614096
 IC50 5.21 5.21 6210.0 1
A549
CHEMBL392
 IC50 5.14 5.14 7220.0 1
NCI-H157
CHEMBL614783
 IC50 5.12 5.12 7620.0 1
M14
CHEMBL614317
 IC50 5.01 5.01 9820.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 4.94 4.94 11600.0 1
HOP-62
CHEMBL614643
 IC50 4.9 4.9 12500.0 1
NCI-H460
CHEMBL396
 IC50 4.88 4.88 13100.0 1
Radical scavenging activity
CHEMBL613712
 IC50 4.88 4.73 13300.0 2
Calu-1
CHEMBL613505
 IC50 4.76 4.76 17200.0 1
NCI-H1792
CHEMBL1075525
 IC50 4.74 4.74 18400.0 1
Transthyretin
CHEMBL3194
 EC50 4.64 4.64 23000.0 1
SiHa
CHEMBL612542
 IC50 4.47 4.47 34090.0 1
HepG2
CHEMBL395
 IC50 4.19 4.19 63950.0 1
Dipeptidyl peptidase 4
CHEMBL284
 IC50 4.06 4.06 87720.0 1
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 1150.0 nM 5.94 Inhibition of 5-lipoxygenase of rat basophilic leukemia (RBL) cell cytosolic enz... -
HT-22 EC50 = 1900.0 nM 5.72 Neuroprotective activity against glutamate-induced cell death in mouse HT-22 cel... 32991171
HeLa IC50 = 1960.0 nM 5.71 Cytotoxicity against human HeLa cells after 72 hrs by alamar blue assay 22954735
RAW264.7 IC50 = 2000.0 nM 5.7 Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed a... 31747281
NON-PROTEIN TARGET IC50 = 2500.0 nM 5.6 Antiinflammatory activity in C57BL6/J mouse BV2 cells assessed as inhibition of ... 26110443
RAW264.7 EC50 = 3183.0 nM 5.5 Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells assess... 18667320
NON-PROTEIN TARGET IC50 = 3700.0 nM 5.43 Antiviral activity against Influenza A virus (A/FM/1/47(H1N1)) infected in MDCK ... 26110443
NON-PROTEIN TARGET IC50 = 4160.0 nM 5.38 Cytotoxicity against human SKBR cells after 72 hrs by alamar blue assay 22954735
NCI-H1299 IC50 = 4930.0 nM 5.31 Cytotoxicity against human NCI-H1299 cells after 72 hrs by alamar blue assay 22954735
NON-PROTEIN TARGET IC50 = 5250.0 nM 5.28 Cytotoxicity against human 292G cells after 72 hrs by alamar blue assay 22954735
LOX IMVI IC50 = 6210.0 nM 5.21 Cytotoxicity against human LOXIMVI cells after 72 hrs by alamar blue assay 22954735
BeWo IC50 = 6200.0 nM 5.21 Antitumor activity against human Bewo cells assessed as inhibition of cell growt... 25160837
A549 IC50 = 7220.0 nM 5.14 Cytotoxicity against human A549 cells after 72 hrs by alamar blue assay 22954735
NCI-H157 IC50 = 7620.0 nM 5.12 Cytotoxicity against human NCI-H157 cells after 72 hrs by alamar blue assay 22954735
NON-PROTEIN TARGET IC50 = 8940.0 nM 5.05 Antitumor activity against human HL60 cells assessed as inhibition of cell growt... 25160837
M14 IC50 = 9820.0 nM 5.01 Cytotoxicity against human M14 cells after 72 hrs by alamar blue assay 22954735
NON-PROTEIN TARGET IC50 = 11200.0 nM 4.95 Cytotoxicity against human M4E cells after 72 hrs by alamar blue assay 22954735
NON-PROTEIN TARGET EC50 = 11600.0 nM 4.94 Cytoprotective activity against H2O2-induced cytotoxicity in human EAhy926 cells... -
HOP-62 IC50 = 12500.0 nM 4.9 Cytotoxicity against human HOP62 cells after 72 hrs by alamar blue assay 22954735
NCI-H460 IC50 = 13100.0 nM 4.88 Cytotoxicity against human H460 cells after 72 hrs by alamar blue assay 22954735

Literature References

PubMed DOI Target Context # Activities
- 10.1039/C4MD00022F NON-PROTEIN TARGET 5
25314129 10.1021/jm500997m Transthyretin 4
22954735 10.1016/j.bmcl.2012.08.038 NON-PROTEIN TARGET 4
24582984 10.1016/j.bmcl.2014.02.005 Candida albicans 4
24928402 10.1016/j.bmcl.2014.05.065 No relevant target 3
28051863 10.1021/acs.jmedchem.6b01285 Mus musculus 3
18667320 10.1016/j.bmc.2008.07.006 RAW264.7 3
19058883 10.1016/j.ejmech.2008.10.027 No relevant target 3
24080105 10.1016/j.bmc.2013.08.057 LNCaP 3
23682762 10.1021/jm400374q Unchecked 2
24928402 10.1016/j.bmcl.2014.05.065 Unchecked 2
25160837 10.1016/j.bmcl.2014.08.024 NON-PROTEIN TARGET 2
25025240 10.1021/np500233t No relevant target 2
23357310 10.1016/j.ejmech.2012.12.049 Radical scavenging activity 2
26110443 10.1021/np500951s NON-PROTEIN TARGET 2
23357310 10.1016/j.ejmech.2012.12.049 NON-PROTEIN TARGET 2
32991171 10.1021/acs.jnatprod.0c00756 HT-22 1
19628311 10.1016/j.ejmech.2009.06.029 No relevant target 1
11831895 10.1021/jm010399h Human immunodeficiency virus type 1 integrase 1
11354370 10.1016/s0960-894x(01)00165-2 A-431 1

Data from ChEMBL 36 via Core Engine