ContaminantDB: Ethacrynic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:54:48 UTC

Update Date

2016-11-09 01:15:31 UTC

Accession Number

CHEM017079

Identification

Common Name

Ethacrynic acid

Class

Small Molecule

Description

A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid	ChEBI
Acide etacrynique	ChEBI
Acido etacrinico	ChEBI
Acidum etacrynicum	ChEBI
Crinuryl	ChEBI
Edecril	ChEBI
Edecrina	ChEBI
Endecril	ChEBI
Etacrinic acid	ChEBI
Ethacrynate	ChEBI
Hidromedin	ChEBI
Hydromedin	ChEBI
Methylenebutyrylphenoxyacetic acid	ChEBI
Mingit	ChEBI
Otacril	ChEBI
Reomax	ChEBI
Taladren	ChEBI
Uregit	ChEBI
Etacrynic acid	Kegg
(2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetate	Generator
Etacrinate	Generator
Methylenebutyrylphenoxyacetate	Generator
Etacrynate	Generator
Etakrinic acid	HMDB
Ethacryinic acid	HMDB
Acid, ethacrinic	HMDB
Ethacrinic acid	HMDB
Ethacrynate sodium	HMDB
Ethacrynic acid, sodium salt	HMDB
Sodium, ethacrynate	HMDB
Acid, etacrynic	HMDB
Acid, ethacrynic	HMDB
Edecrin	HMDB

Chemical Formula

C₁₃H₁₂Cl₂O₄

Average Molecular Mass

303.138 g/mol

Monoisotopic Mass

302.011 g/mol

CAS Registry Number

58-54-8

IUPAC Name

2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid

Traditional Name

ethacrynic acid

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 Key

AVOLMBLBETYQHX-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Chlorophenoxyacetates

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:4876 )
monocarboxylic acid (CHEBI:4876 )
dichlorobenzene (CHEBI:4876 )
aromatic ketone (CHEBI:4876 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	3.42	ALOGPS
logP	3.66	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.8	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.22 m³·mol⁻¹	ChemAxon
Polarizability	28.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05mo-7090000000-ad262bb070e8e48d2d63	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-062i-9012000000-fbc841e49aad01b35c49	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4i-0690000000-f598b8bee69a6b62e817	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-0690000000-f598b8bee69a6b62e817	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0fb9-2930000000-143e32f52c12761e81dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-9036000000-649cbeb1b954b158866f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f8i-9084000000-84c8027d849b76f0fc82	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9000000000-a3a5b075c90ba85c8e90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-21fb3e922a0d4368b160	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1095000000-7cbed97a8be9a8a9c7dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-4690000000-87b7486401d3036ea50c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0059000000-51c16f82d9d3dcd362d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-2095000000-984d8aafed69f00c25bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-022c-4950000000-fd4ac1ee6524d2082199	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0039000000-dd7be49fbec8d532bd2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f89-9086000000-b20750e2d0d1b3645cb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0543-6490000000-fb32fecaea2c34a668a6	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00903

HMDB ID

HMDB0015039

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=7932170

Ethacrynic acid (CHEM017079)

Structure for CHEM017079: Ethacrynic acid