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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:50 UTC
HMDB IDHMDB0015039
Secondary Accession Numbers
  • HMDB15039
Metabolite Identification
Common NameEthacrynic acid
DescriptionEthacrynic acid, also known as ethacrynate or edecrina, 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. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC2.5.1.18) inhibitor. Ethacrynic acid is a drug which is used for the treatment of high blood pressure and edema caused by diseases like congestive heart failure, liver failure, and kidney failure. Ethacrynic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). ethacrynic acid can be converted into ethacrynic acid; which is catalyzed by the enzyme solute carrier family 22 member 6. In humans, ethacrynic acid is involved in ethacrynic acid action pathway. An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4.
Structure
Data?1582753250
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 Weight303.138
Monoisotopic Molecular Weight302.011264286
IUPAC Name2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
Traditional Nameethacrynic acid
CAS Registry Number58-54-8
SMILES
CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1
InChI Identifier
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)
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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point122.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.019 g/LNot Available
LogP3.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+168.99530932474
DeepCCS[M-H]-166.63730932474
DeepCCS[M-2H]-199.52330932474
DeepCCS[M+Na]+175.08830932474
AllCCS[M+H]+163.032859911
AllCCS[M+H-H2O]+159.632859911
AllCCS[M+NH4]+166.032859911
AllCCS[M+Na]+166.932859911
AllCCS[M-H]-161.832859911
AllCCS[M+Na-2H]-161.932859911
AllCCS[M+HCOO]-162.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethacrynic acidCCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C13624.3Standard polar33892256
Ethacrynic acidCCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C12146.8Standard non polar33892256
Ethacrynic acidCCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C12319.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethacrynic acid,1TMS,isomer #1C=C(CC)C(=O)C1=CC=C(OCC(=O)O[Si](C)(C)C)C(Cl)=C1Cl2298.0Semi standard non polar33892256
Ethacrynic acid,1TBDMS,isomer #1C=C(CC)C(=O)C1=CC=C(OCC(=O)O[Si](C)(C)C(C)(C)C)C(Cl)=C1Cl2546.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ethacrynic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-05mo-7090000000-ad262bb070e8e48d2d632017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethacrynic acid GC-MS (1 TMS) - 70eV, Positivesplash10-062i-9012000000-fbc841e49aad01b35c492017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethacrynic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethacrynic acid LC-ESI-qTof , Positive-QTOFsplash10-0a4i-0690000000-f598b8bee69a6b62e8172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethacrynic acid , positive-QTOFsplash10-0a4i-0690000000-f598b8bee69a6b62e8172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethacrynic acid , positive-QTOFsplash10-0fb9-2930000000-143e32f52c12761e81dd2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 10V, Positive-QTOFsplash10-0f89-9036000000-649cbeb1b954b158866f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 20V, Positive-QTOFsplash10-0f8i-9084000000-84c8027d849b76f0fc822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 40V, Positive-QTOFsplash10-0ue9-9000000000-a3a5b075c90ba85c8e902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 10V, Negative-QTOFsplash10-0udi-0029000000-21fb3e922a0d4368b1602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 20V, Negative-QTOFsplash10-0udi-1095000000-7cbed97a8be9a8a9c7dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 40V, Negative-QTOFsplash10-000i-4690000000-87b7486401d3036ea50c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 10V, Positive-QTOFsplash10-0udi-0059000000-51c16f82d9d3dcd362d62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 20V, Positive-QTOFsplash10-0udr-2095000000-984d8aafed69f00c25bf2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 40V, Positive-QTOFsplash10-022c-4950000000-fd4ac1ee6524d20821992021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 10V, Negative-QTOFsplash10-0udi-0039000000-dd7be49fbec8d532bd2d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 20V, Negative-QTOFsplash10-0f89-9086000000-b20750e2d0d1b3645cb12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethacrynic acid 40V, Negative-QTOFsplash10-0543-6490000000-fb32fecaea2c34a668a62021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00903 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00903 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00903
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3163
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtacrynic_acid
METLIN IDNot Available
PubChem Compound3278
PDB IDEAA
ChEBI ID4876
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA2
Uniprot ID:
P09210
Molecular weight:
25663.675
References
  1. Depeille P, Cuq P, Passagne I, Evrard A, Vian L: Combined effects of GSTP1 and MRP1 in melanoma drug resistance. Br J Cancer. 2005 Jul 25;93(2):216-23. [PubMed:15999103 ]
  2. Awasthi S, Srivastava SK, Ahmad F, Ahmad H, Ansari GA: Interactions of glutathione S-transferase-pi with ethacrynic acid and its glutathione conjugate. Biochim Biophys Acta. 1993 Jul 10;1164(2):173-8. [PubMed:8329448 ]
  3. Iersel ML, Ploemen JP, Struik I, van Amersfoort C, Keyzer AE, Schefferlie JG, van Bladeren PJ: Inhibition of glutathione S-transferase activity in human melanoma cells by alpha,beta-unsaturated carbonyl derivatives. Effects of acrolein, cinnamaldehyde, citral, crotonaldehyde, curcumin, ethacrynic acid, and trans-2-hexenal. Chem Biol Interact. 1996 Oct 21;102(2):117-32. [PubMed:8950226 ]
  4. van Iersel ML, Ploemen JP, Lo Bello M, Federici G, van Bladeren PJ: Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1. Chem Biol Interact. 1997 Dec 12;108(1-2):67-78. [PubMed:9463521 ]
  5. Morrow CS, Smitherman PK, Townsend AJ: Combined expression of multidrug resistance protein (MRP) and glutathione S-transferase P1-1 (GSTP1-1) in MCF7 cells and high level resistance to the cytotoxicities of ethacrynic acid but not oxazaphosphorines or cisplatin. Biochem Pharmacol. 1998 Oct 15;56(8):1013-21. [PubMed:9776312 ]
General function:
Involved in ATP binding
Specific function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular weight:
112895.01
References
  1. Ronquist G, Agren GK: A Mg2+- and Ca2+-stimulated adenosine triphosphatase at the outer surface of Ehrlich ascites tumor cells. Cancer Res. 1975 Jun;35(6):1402-6. [PubMed:124205 ]
  2. Proverbio F, Condrescu-Guidi M, Whittembury G: Ouabain-insensitive Na+ stimulation of an Mg-2+ -dependent ATPase in kidney tissue. Biochim Biophys Acta. 1975 Jun 25;394(2):281-92. [PubMed:124600 ]
  3. Valdes RM, Huff MO, El-Masri MA, El-Mallakh RS: Effect of ethacrynic acid on sodium pump alpha isoforms in SH-SY5Y cells. Bipolar Disord. 2003 Apr;5(2):123-8. [PubMed:12680902 ]
  4. Kiil F, Sejersted OM: Analysis of energy metabolism and mechanism of loop diuretics in the thick ascending limb of Henle's loop in dog kidneys. Acta Physiol Scand. 2003 May;178(1):73-82. [PubMed:12713517 ]
  5. Schurek HJ, Aulbert E, Ebel H, Muller-Suur C: Influence of ouabain and ethacrynic acid on sodium transport and NaK-ATPase activity in the isolated perfused rat kidney. Curr Probl Clin Biochem. 1975;4:162-8. [PubMed:127690 ]

Transporters

General function:
Involved in transport
Specific function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume
Gene Name:
SLC12A1
Uniprot ID:
Q13621
Molecular weight:
121449.1
References
  1. Bowes TJ, Gupta RS: Induction of mitochondrial fusion by cysteine-alkylators ethacrynic acid and N-ethylmaleimide. J Cell Physiol. 2005 Mar;202(3):796-804. [PubMed:15389563 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [PubMed:9228014 ]