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Compound Detail

CHEMBL1474963

BENZARONE
💊 Approved Drug
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💊 Approved Drug
CCc1oc2ccccc2c1C(=O)c1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1474963
Name BENZARONE
Phase Approved
Structure Type MOL
InChI Key RFRXIWQYSOIBDI-UHFFFAOYSA-N

Known Names

Benzarona Benzarone L 2197 L-2197 NSC-82134
5
Targets
11
Activities
1
Assay Types
0
PK Parameters
20
Publications
5
Known Names
1
Mechanisms

Molecular Properties

266.3
MW (Da)
3.93
ALogP
3
HBA
1
HBD
50.4
PSA (Ų)
0.73
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product
USAN Stem -arone

Extended Properties

Molecular Formula C17H14O3
MW 266.30
Aromatic Rings 3
Heavy Atoms 20
NP-Likeness 0.32

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Drug Warnings

Withdrawn
hepatotoxicity
Hepatitis
Country: Germany   Year: 1992
Withdrawn
hepatotoxicity
Hepatitis
Country: Germany   Year: 1992
Withdrawn
hepatotoxicity
Hepatitis
Country: Germany   Year: 1992

Activity Summary

IC50 11 meas. best 5.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Staphylococcus aureus
CHEMBL352
 IC50 5.89 5.89 1294.0 1
Unchecked
CHEMBL612545
 IC50 5.89 5.89 1290.0 1
Solute carrier family 22 member 12
CHEMBL6120
 IC50 5.55 5.55 2800.0 1
Eyes absent homolog 3
CHEMBL4296245
 IC50 4.77 4.76 17000.0 5
Eyes absent homolog 3
CHEMBL4296244
 IC50 4.72 4.72 19200.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Staphylococcus aureus IC50 = 1294.0 nM 5.89 PUBCHEM_BIOASSAY: Inhibitors of Bacterial Quorum Sensing Structure Activity Rela... -
Unchecked IC50 = 1290.0 nM 5.89 Inhibition of Staphylococcus aureus AgrC1 23294220
Solute carrier family 22 member 12 IC50 = 2800.0 nM 5.55 Inhibition of human URAT1 expressed in xenopus oocyte assessed as inhibition of ... 21449597
Eyes absent homolog 3 IC50 = 17000.0 nM 4.77 Inhibition of human Eya3 isoform 2 (127 to 573 residues) incubated for 30 mins b... -
Eyes absent homolog 3 IC50 = 17000.0 nM 4.77 Inhibition of poly-histidine and GST-tagged full length human Eya3 isoform 2 (12... -
Eyes absent homolog 3 IC50 = 17000.0 nM 4.77 Inhibitory Assay: An inhibitory assay was conducted using the previously describ... -
Eyes absent homolog 3 IC50 = 17000.0 nM 4.77 Inhibition Assay: The compounds were then tested using full-length human recombi... -
Eyes absent homolog 3 IC50 = 19200.0 nM 4.72 Inhibition of mouse Eya3 catalytic domain (223 to 510 residues) by p-nitrophenyl... -
Eyes absent homolog 3 IC50 = 19200.0 nM 4.72 Inhibition of mouse Eya3 catalytic domain (223 to 510 residues) using para-nitro... -
Eyes absent homolog 3 IC50 = 19200.0 nM 4.72 Inhibitory Assay: An inhibitory assay was conducted using the previously describ... -
Eyes absent homolog 3 IC50 = 19200.0 nM 4.72 Inhibition Assay: The compounds were then tested using full-length human recombi... -

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20014752 10.1021/tx900326k Hepatotoxicity 3
21449597 10.1021/jm1015022 Solute carrier family 22 member 12 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4513161 Pseudomonas aeruginosa 2
- 10.6019/CHEMBL4513161 HEK293 1
- 10.6019/CHEMBL4513161 Erythrocyte 1
- 10.6019/CHEMBL4513161 Staphylococcus aureus 1
- 10.6019/CHEMBL4513161 Acinetobacter baumannii 1
- 10.6019/CHEMBL4513161 Klebsiella pneumoniae 1
- 10.6019/CHEMBL4513161 Escherichia coli 1
- 10.6019/CHEMBL4513161 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513161 Candida albicans 1
27397500 10.1016/j.bmcl.2016.06.088 Cytochrome P450 2C9 1
27397500 10.1016/j.bmcl.2016.06.088 Cytochrome P450 2D6 1
27397500 10.1016/j.bmcl.2016.06.088 Cytochrome P450 3A4 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
23294220 10.1021/jm3014635 Unchecked 1
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1

Data from ChEMBL 36 via Core Engine