Ethacrynic acid (CED0005389)

Record Information
Version1.0
Creation Date2016-05-22 03:54:48 UTC
Update Date2026-08-18 22:52:02 UTC
Accession NumberCHEM017079
Identification
Common NameEthacrynic acid
ClassSmall Molecule
Description
Ethacrynic acid (C13H12Cl2O4) is a compound with an average molecular weight of 303.14 g/mol. Ethacrynic acid belongs to the phenoxyacetic acid derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It functions as a biological inhibitor (PMC5350610). Its recorded protein targets include the Sodium/potassium-transporting ATPase subunit alpha-1 (ATP1A1), Lymphoid enhancer-binding factor 1 (LEF1), Glutathione S-transferase P (GSTP1), and the Solute carrier family 12 member 1 (SLC12A1), which it inhibits. The compound is found in or released from 13 recorded sources. These include healthcare, pharmaceuticals, and veterinary products, where it is used as a diuretic. It is also associated with household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Additionally, it is linked to electrical and electronic equipment, including antennas, conductors or conductive bodies characterised by the conductive materials, electrodes, electric hearing aids, and electrically stimulated smoking devices. Recorded exposure routes for ethacrynic acid include oral and intravenous administration.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acidChEBI
Acide etacryniqueChEBI
Acido etacrinicoChEBI
Acidum etacrynicumChEBI
CrinurylChEBI
EdecrilChEBI
EdecrinaChEBI
EndecrilChEBI
Etacrinic acidChEBI
EthacrynateChEBI
HidromedinChEBI
HydromedinChEBI
Methylenebutyrylphenoxyacetic acidChEBI
MingitChEBI
OtacrilChEBI
ReomaxChEBI
TaladrenChEBI
UregitChEBI
Etacrynic acidKegg
(2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetateGenerator
EtacrinateGenerator
MethylenebutyrylphenoxyacetateGenerator
EtacrynateGenerator
Etakrinic acidHMDB
Ethacryinic acidHMDB
Acid, ethacrinicHMDB
Ethacrinic acidHMDB
Ethacrynate sodiumHMDB
Ethacrynic acid, sodium saltHMDB
Sodium, ethacrynateHMDB
Acid, etacrynicHMDB
Acid, ethacrynicHMDB
EdecrinHMDB
Chemical FormulaC13H12Cl2O4
Average Molecular Mass303.138 g/mol
Monoisotopic Mass302.011 g/mol
CAS Registry Number58-54-8
IUPAC Name2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
Traditional Nameethacrynic acid
SMILESCCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1
InChI IdentifierInChI=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)
InChI KeyAVOLMBLBETYQHX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorophenoxyacetates. Chlorophenoxyacetates are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentChlorophenoxyacetates
Alternative Parents
Substituents
  • Chlorophenoxyacetate
  • Butyrophenone
  • 1,2-dichlorobenzene
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Aryl ketone
  • Halobenzene
  • Chlorobenzene
  • Alkyl aryl ether
  • Aryl halide
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Aryl chloride
  • Alpha,beta-unsaturated ketone
  • Enone
  • Vinylogous halide
  • Acryloyl-group
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Ether
  • Organic oxygen compound
  • Carbonyl group
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.42ALOGPS
logP3.66ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.8ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.22 m³·mol⁻¹ChemAxon
Polarizability28.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05mo-7090000000-ad262bb070e8e48d2d63Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-062i-9012000000-fbc841e49aad01b35c49Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0690000000-f598b8bee69a6b62e817Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0690000000-f598b8bee69a6b62e817Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fb9-2930000000-143e32f52c12761e81ddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-9036000000-649cbeb1b954b158866fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f8i-9084000000-84c8027d849b76f0fc82Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-9000000000-a3a5b075c90ba85c8e90Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0029000000-21fb3e922a0d4368b160Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1095000000-7cbed97a8be9a8a9c7dcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-4690000000-87b7486401d3036ea50cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0059000000-51c16f82d9d3dcd362d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-2095000000-984d8aafed69f00c25bfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-022c-4950000000-fd4ac1ee6524d2082199Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0039000000-dd7be49fbec8d532bd2dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-9086000000-b20750e2d0d1b3645cb1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0543-6490000000-fb32fecaea2c34a668a6Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
881.0Log mg/kg[500:1600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
290DiureticsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAldo-keto reductase family 1 member B1P07943Rattus norvegicusPredicted (SEA)5.99439
Glutathione S-transferase A1 structureClick to view 3D structureGlutathione S-transferase A1P08263HumansPredicted (SEA)0.0778492
Glutathione S-transferase P structureClick to view 3D structureGlutathione S-transferase PP09211HumansPredicted (SEA)0.155698
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)59.1654
Prostaglandin D2 receptor 2 structureClick to view 3D structureProstaglandin D2 receptor 2Q9Y5Y4HumansPredicted (SEA)15.0249
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)496.756
Dual specificity mitogen-activated protein kinase kinase 6 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 6P52564HumansPredicted (SEA)63.2136
Click to view 3D structureProstaglandin D2 receptorQ13258HumansPredicted (SEA)20.0072
ATP-binding cassette sub-family C member 2 structureClick to view 3D structureATP-binding cassette sub-family C member 2Q92887HumansPredicted (SEA)0.155698
Phospholipase A2 structureClick to view 3D structurePhospholipase A2P04054HumansPredicted (SEA)7.00643
Click to view 3D structureGroup IIF secretory phospholipase A2Q9BZM2HumansPredicted (SEA)2.56902
Click to view 3D structureGroup IIF secretory phospholipase A2Q9QZT4Mus musculusPredicted (SEA)2.56902
Click to view 3D structureGroup IID secretory phospholipase A2Q9WVF6Mus musculusPredicted (SEA)2.56902
Phospholipase A2, membrane associated structureClick to view 3D structurePhospholipase A2, membrane associatedP14555HumansPredicted (SEA)10.0426
Click to view 3D structurePhospholipase A2, membrane associatedP31482Mus musculusPredicted (SEA)4.5931
Click to view 3D structurePhospholipase A2 group VP39877HumansPredicted (SEA)5.0602
Group 10 secretory phospholipase A2 structureClick to view 3D structureGroup 10 secretory phospholipase A2O15496HumansPredicted (SEA)5.13805
Click to view 3D structurePhospholipase A2 group VP97391Mus musculusPredicted (SEA)3.42537
Click to view 3D structureGroup 10 secretory phospholipase A2Q9QXX3Mus musculusPredicted (SEA)3.03612
Click to view 3D structureGroup IIE secretory phospholipase A2Q9QUL3Mus musculusPredicted (SEA)2.64687
Click to view 3D structurePhospholipase A2Q9Z0Y2Mus musculusPredicted (SEA)2.64687
Group IIE secretory phospholipase A2 structureClick to view 3D structureGroup IIE secretory phospholipase A2Q9NZK7HumansPredicted (SEA)2.64687
Click to view 3D structureGlutathione-S-transferaseQ26513Schistosoma japonicumPredicted (SEA)0.0778492
Click to view 3D structureGroup IIC secretory phospholipase A2P48076Mus musculusPredicted (SEA)3.65891
Small ubiquitin-related modifier 1 structureClick to view 3D structureSmall ubiquitin-related modifier 1P63165HumansPredicted (SEA)87.8918
Concentrations
Not Available
External Links
DrugBank IDDB00903
HMDB IDHMDB0015039
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDEAA
Wikipedia LinkEtacrynic_acid
Chemspider ID3163
ChEBI ID4876
PubChem Compound ID3278
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=7932170