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Compound Detail

CHEMBL467389

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O=C(O)/C(O)=C/C(=O)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL467389
Phase Preclinical
Structure Type MOL
InChI Key MNQJVITWJHOBFE-TWGQIWQCSA-N
10
Targets
16
Activities
3
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

192.2
MW (Da)
1.40
ALogP
3
HBA
2
HBD
74.6
PSA (Ų)
0.43
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C10H8O4
MW 192.17
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness 0.24

Activity Summary

IC50 8 meas. best 5.7
Ki 7 meas. best 6.32
EC50 1 meas. best 5.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polymerase acidic protein
CHEMBL1169598
 Ki 6.32 6.32 480.0 1
Carbonic anhydrase 2
CHEMBL1697676
 Ki 6.05 6.05 890.0 1
Unchecked
CHEMBL612545
 IC50 5.7 4.9275 2000.0 4
Polymerase acidic protein
CHEMBL1169598
 EC50 5.68 5.68 2070.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 5.47 5.47 3350.0 1
Carbonic anhydrase 2
CHEMBL205
 Ki 5.37 5.37 4300.0 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 5.17 5.17 6790.0 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 5.11 5.11 7750.0 1
Unchecked
CHEMBL612545
 Ki 5.06 5.06 8760.0 1
Polymerase acidic protein
CHEMBL1169598
 IC50 4.67 4.67 21300.0 1
Influenza A virus
CHEMBL613740
 IC50 4.67 4.67 21300.0 1
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 4.62 4.62 24200.0 1
Human immunodeficiency virus 1
CHEMBL378
 IC50 4.6 4.6 25000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polymerase acidic protein Ki = 480.0 nM 6.32 Binding affinity to PA N-terminal domain (Competitive) 22211528
Carbonic anhydrase 2 Ki = 890.0 nM 6.05 Inhibition of Cryptococcus neoformans beta carbonic anhydrase Can2 using CO2 as ... 22901388
Unchecked IC50 = 2000.0 nM 5.7 Inhibition of N-terminal His-tagged Mycobacterium tuberculosis malate synthase e... 38128237
Polymerase acidic protein EC50 = 2070.0 nM 5.68 Plaque growth inhibition 22211528
Carbonic anhydrase 1 Ki = 3350.0 nM 5.47 Inhibition of human CA1 using CO2 as substrate incubated for 6 hrs prior to subs... 22901388
Carbonic anhydrase 2 Ki = 4300.0 nM 5.37 Inhibition of human CA2 using CO2 as substrate incubated for 6 hrs prior to subs... 22901388
Carbonic anhydrase 9 Ki = 6790.0 nM 5.17 Inhibition of human CA9 using CO2 as substrate incubated for 6 hrs prior to subs... 22901388
Carbonic anhydrase 12 Ki = 7750.0 nM 5.11 Inhibition of human CA12 using CO2 as substrate incubated for 6 hrs prior to sub... 22901388
Unchecked Ki = 8760.0 nM 5.06 Inhibition of Candida albicans beta carbonic anhydrase NCE103 using CO2 as subst... 22901388
Polymerase acidic protein IC50 = 21300.0 nM 4.67 Inhibition of cap 1 ALMV primed Influenza transcriptase 7695269
Unchecked IC50 = 21379.62 nM 4.67 Inhibition of influenza A virus RNA-dependent RNA polymerase subunit PA endonucl... 24365156
Unchecked IC50 = 21300.0 nM 4.67 Inhibition of influenza B virus PA endonuclease using 880 nucleotide ALMV capped... 28118010
Unchecked IC50 = 21300.0 nM 4.67 Inhibition of influenza A virus PA endonuclease using 880 nucleotide ALMV capped... 28118010
Influenza A virus IC50 = 21300.0 nM 4.67 Antiviral activity against Influenza A virus A/PR/8/34 (PR8) strain infected in ... 34591488
Human immunodeficiency virus type 1 integrase IC50 = 24200.0 nM 4.62 Inhibition of wild-type HIV1 integrase strand transfer activity using [32P]-labe... 18644730
Human immunodeficiency virus 1 IC50 = 25000.0 nM 4.6 Antiviral activity against HIV1 19112024

Literature References

PubMed DOI Target Context # Activities
29133041 10.1016/j.ejmech.2017.10.045 Staphylococcus aureus 6
22211528 10.1021/cb200439z Polymerase acidic protein 2
22901388 10.1016/j.bmcl.2012.07.094 Carbonic anhydrase 2 2
18644730 10.1016/j.bmc.2008.07.008 Human immunodeficiency virus type 1 integrase 2
28118010 10.1021/acs.jmedchem.6b01227 Unchecked 2
22901388 10.1016/j.bmcl.2012.07.094 Unchecked 1
38128237 10.1016/j.ejmech.2023.116058 Unchecked 1
34591488 10.1021/acs.jmedchem.1c01215 Influenza A virus 1
29133041 10.1016/j.ejmech.2017.10.045 Escherichia coli 1
29133041 10.1016/j.ejmech.2017.10.045 Bacillus subtilis 1
29133041 10.1016/j.ejmech.2017.10.045 Enterococcus faecalis 1
24365156 10.1016/j.bmcl.2013.12.026 Unchecked 1
22901388 10.1016/j.bmcl.2012.07.094 Carbonic anhydrase 12 1
22901388 10.1016/j.bmcl.2012.07.094 Carbonic anhydrase 9 1
22901388 10.1016/j.bmcl.2012.07.094 Carbonic anhydrase 1 1
7695269 10.1128/aac.38.12.2827 Polymerase acidic protein 1
19112024 10.1016/j.bmc.2008.11.075 Human immunodeficiency virus 1 1

Data from ChEMBL 36 via Core Engine