ETHACRYNIC ACID

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Trade Names
Synonyms
Status
Molecule Category Free-form
UNII M5DP350VZV
EPA CompTox DTXSID3025257

Structure

InChI Key AVOLMBLBETYQHX-UHFFFAOYSA-N
Smiles C=C(CC)C(=O)c1ccc(OCC(=O)O)c(Cl)c1Cl
InChI
InChI=1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H12Cl2O4
Molecular Weight 303.14
AlogP 3.61
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 63.6
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 19.0

Bioactivity

Mechanism of Action Action Reference
Sodium-(potassium)-chloride cotransporter 2 inhibitor INHIBITOR DOI
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Isomerase
- 14000 - - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE7 family
- 4500 - - -
Enzyme Transferase
- 3400-4000 - - 24-94
Enzyme
- 3400-4000 - - 24-94
Other cytosolic protein
- 8500 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 112
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 3850 - - -
Unclassified protein
- 4700-5200 - - 66-85
Assay Description Organism Bioactivity Reference
Inhibition of Trypanosoma brucei GalE at 50 uM Trypanosoma brucei 75.0 %
Inhibition of GSTP1-1 activity at 40 umol/L after 30 mins relative to control None 94.4 %
Inhibition of human H-PGDS expressed in Escherichia coli BL21 assessed as rate of glutathione-chloro-dinitro benzene conjugation at 50 uM Homo sapiens 25.3 %
Inhibition of glutathione S-transferase pi in human HL60 cells using CDNB and GSH as substrates at 5 uM by spectrophotometry Homo sapiens 65.1 %
Inhibition of glutathione S-transferase pi in human HL60 cells using CDNB and GSH as substrates at 1 uM by spectrophotometry Homo sapiens 24.2 %
TP_TRANSPORTER: inhibition of PAH uptake (PAH: 2 uM, Ethacrynic acid; 2000 uM) in Xenopus laevis oocytes Xenopus laevis 85.0 %
Inhibition of glutathione S-transferase P1-1 in Homo sapiens (human) HL60 cell lysate using CDNB and GSH as substrate at 20 uM by spectrophotometric analysis Homo sapiens 88.6 %
Inhibition of glutathione S-transferase pi in human Bel7402 cell lysates at 10 uM using CDNB and GSH as substrates by spectrophotometry Homo sapiens 78.34 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 171.77 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 111.8 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 39.53 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 0.95 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 8.53 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 11.3 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 27.96 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 21.12 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -8.91 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 2.72 %
Inhibition of human FBPase expressed in Escherichia coli BL21 (DE3) at 500 uM using FBP as substrate incubated for 5 mins by malachite green dye based spectrophotometry relative to control Homo sapiens 56.0 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured soluble pig heart MDH refolding by measuring MDH enzyme activity using sodium mesoxalate as substrate after 20 to 40 mins by malachite green dye based spectrometric analysis relative to untreated control Escherichia coli 66.0 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured rhodanese refolding by measuring rhodanese enzyme activity after 45 mins by Fe(SCN)3 dye based spectrometric analysis relative to untreated control Escherichia coli 85.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 0.4834 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.95 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.95 %

Cross References

Resources Reference
ChEBI 4876
ChEMBL CHEMBL456
DrugBank DB00903
DrugCentral 1071
FDA SRS M5DP350VZV
Human Metabolome Database HMDB0015039
Guide to Pharmacology 7179
KEGG D00313
PDB EAA
PharmGKB PA449518
PubChem 3278
SureChEMBL SCHEMBL26353
ZINC ZINC000000001382
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