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Compound Detail

CHEMBL58150

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NC1=CC(=O)c2ccc(-c3cccc(C(=O)O)n3)nc2C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL58150
Phase Preclinical
Structure Type MOL
InChI Key HAEQQPWTMBVMLJ-UHFFFAOYSA-N
7
Targets
7
Activities
2
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

295.2
MW (Da)
1.06
ALogP
6
HBA
2
HBD
123.2
PSA (Ų)
0.85
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H9N3O4
MW 295.25
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 0.53

Activity Summary

IC50 5 meas. best 7.16
EC50 2 meas. best 4.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protein-arginine deiminase type-1
CHEMBL1909486
 IC50 7.16 7.16 70.0 1
Protein-arginine deiminase type-2
CHEMBL1909487
 IC50 6.7 6.7 200.0 1
Phosphodiesterase 4
CHEMBL2093863
 IC50 6.62 6.62 240.0 1
Protein-arginine deiminase type-4
CHEMBL6111
 IC50 6.62 6.62 240.0 1
Protein-arginine deiminase type-3
CHEMBL1909488
 IC50 6.15 6.15 710.0 1
U2OS
CHEMBL615023
 EC50 4.23 4.23 58300.0 1
NIH3T3
CHEMBL614822
 EC50 4.21 4.21 61700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protein-arginine deiminase type-1 IC50 = 70.0 nM 7.16 Inhibition of recombinant wild-type PAD1 (unknown origin) using N-alpha-Benzoyl-... 24440480
Protein-arginine deiminase type-2 IC50 = 200.0 nM 6.7 Inhibition of recombinant wild-type PAD2 (unknown origin) using N-alpha-Benzoyl-... 24440480
Protein-arginine deiminase type-4 IC50 = 240.0 nM 6.62 Inhibition of recombinant wild-type PAD4 (unknown origin) using N-alpha-Benzoyl-... 24440480
Phosphodiesterase 4 IC50 = 240.0 nM 6.62 Inhibition of PDE4 (unknown origin) by Fluopol-ABPP HTS assay 34520958
Protein-arginine deiminase type-3 IC50 = 710.0 nM 6.15 Inhibition of recombinant wild-type PAD3 (unknown origin) using N-alpha-Benzoyl-... 24440480
U2OS EC50 = 58300.0 nM 4.23 Cytotoxicity against human U2OS cells after 3 days by XTT-PMS assay 24440480
NIH3T3 EC50 = 61700.0 nM 4.21 Cytotoxicity against mouse NIH/3T3 cells after 3 days by XTT-PMS assay 24440480

Literature References

PubMed DOI Target Context # Activities
24440480 10.1016/j.bmc.2013.12.064 Protein-arginine deiminase type-4 12
24440480 10.1016/j.bmc.2013.12.064 Protein-arginine deiminase type-2 7
24440480 10.1016/j.bmc.2013.12.064 Protein-arginine deiminase type-1 4
24440480 10.1016/j.bmc.2013.12.064 Protein-arginine deiminase type-3 4
24440480 10.1016/j.bmc.2013.12.064 U2OS 2
24440480 10.1016/j.bmc.2013.12.064 NIH3T3 2
3656364 10.1021/jm00393a040 B16 1
34520958 10.1016/j.ejmech.2021.113840 Phosphodiesterase 4 1
3656364 10.1021/jm00393a040 Epidermoid carcinoma cell line 1
3656364 10.1021/jm00393a040 P388 1
3656364 10.1021/jm00393a040 Staphylococcus aureus 1
3656364 10.1021/jm00393a040 L1210 1
3656364 10.1021/jm00393a040 CCRF-CEM 1
3656364 10.1021/jm00393a040 Pseudomonas aeruginosa 1
3656364 10.1021/jm00393a040 Candida albicans 1
3656364 10.1021/jm00393a040 Mycolicibacterium smegmatis 1
3656364 10.1021/jm00393a040 Klebsiella pneumoniae 1
3656364 10.1021/jm00393a040 Salmonella enterica subsp. enterica serovar Gallinarum 1
3656364 10.1021/jm00393a040 Escherichia coli 1

Data from ChEMBL 36 via Core Engine