Ethacrynic acid

Details

• Internal ID: 2b5cc77d-f567-4bc1-8b1f-bd478950d9f1
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenoxyacetic acid derivatives > Chlorophenoxyacetates
• IUPAC Name: 2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
• SMILES (Canonical): CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl
• SMILES (Isomeric): CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl
• 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)
• InChI Key: AVOLMBLBETYQHX-UHFFFAOYSA-N
• Popularity: 3,026 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂Cl₂O₄
• Molecular Weight: 303.13 g/mol
• Exact Mass: 302.0112642 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.61
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Etacrynic Acid
• 58-54-8
• ethacrynate
• Edecrin
• Etacrinic acid
• Hydromedin
• Taladren
• Crinuryl
• Edecril
• Edecrina
• Endecril
• Hidromedin
• Otacril
• Mingit
• Reomax
• Uregit
• Etakrinic acid
• Methylenebutyrylphenoxyacetic acid
• MK-595
• Ethacrinique (acide)
• Acido etacrinico
• Acide etacrynique
• Acidum etacrynicum
• Kyselina ethakrynova
• Ethacrinic acid
• Kyselina ethakrynova [Czech]
• Ethacryinic Acid
• 2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
• [2,3-Dichloro-4-(2-methylenebutyryl)phenoxy]acetic acid
• Acide etacrynique [INN-French]
• Acido etacrinico [INN-Spanish]
• Acidum etacrynicum [INN-Latin]
• (2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid
• Methylenebutyryl phenoxyacetic acid
• Ethacrynic acid [USAN:BAN]
• 2,3-Dichloro-4-(2-methylenebutyl)phenoxyacetic acid
• C13H12Cl2O4
• MK 595
• NSC 85791
• Ethacrynic Acid, Sodium Salt
• NSC 624008
• BRN 1915060
• CCRIS 4638
• Acetic acid, (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)-
• HSDB 2136
• Etacrynic acid [INN]
• Ethacrynic acid (USP)
• 2,3-Dichloro-4-(2-methylenebutyryl)phenoxy acetic acid
• (2,3-Dichloro-4-(2-methylenebutyryl)phenoxy)acetic acid
• (4-(2-Methylenebutyryl)-2,3-dichlorophenoxy)acetic acid
• EINECS 200-384-1
• 2-(2,3-Dichloro-4-(2-methylenebutanoyl)phenoxy)acetic acid
• NSC-85791
• CHEMBL456
• UNII-M5DP350VZV
• NSC-624008
• Acetic acid, [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]-
• Kyselina 4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova [Czech]
• M5DP350VZV
• 58-54-8 (free acid)
• Ethacrynic acid [USAN:USP]
• MLS000069535
• MLS002701928
• CHEBI:4876
• Kyselina 4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova
• DTXSID3025257
• Acetic acid, (2,3-dichloro-4-(2-methylenebutyryl)phenoxy)-
• NSC85791
• NSC624008
• CAS-58-54-8
• [4-(2-Methylenebutyryl)-2,3-dichlorophenoxy]acetic acid
• NCGC00016260-05
• [2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
• 2-[2,3-dichloro-4-(2-methylenebutanoyl)phenoxy]acetic acid
• SMR000058600
• [2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid
• E0526
• 2,3-Dichloro-4-(2-methylenebutyryl)phenoxyacetic acid
• DTXCID205257
• [2,3-dichloro-4-(2-methylenebutanoyl)phenoxy]acetic acid
• SR-01000003010
• (2,3-Dichloro-4-[2-methylenebutyryl]phenoxy)acetic acid
• etacrynicacid
• Etacrynsaure
• Crinuril
• Acetic acid, [2,3-dichloro-4-(2-methylenebutyryl)phenoxy]-
• etacrynic-acid
• etacrynsyre-
• 2-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid
• 2-(2,3-DICHLORO-4-(2-METHYLENE-1-OXOBUTYL)PHENOXY)ACETIC ACID
• 1gsf
• 2gss
• Prestwick_671
• Edecrin (TN)
• Opera_ID_61
• Spectrum_000813
• Prestwick0_000259
• Prestwick1_000259
• Prestwick2_000259
• Prestwick3_000259
• Spectrum2_000097
• Spectrum3_000425
• Spectrum4_000544
• Spectrum5_000680
• bmse000134
• D06TNL
• SCHEMBL26353
• BSPBio_000078
• BSPBio_002010
• ETACRYNIC ACID [JAN]
• ETHACRYNIC ACID [MI]
• KBioGR_001207
• KBioSS_001293
• MLS002548854
• DivK1c_000900
• Etacrynic acid (JP15/INN)
• Etacrynic acid (JP17/INN)
• SPECTRUM1500287
• SPBio_000054
• SPBio_002297
• ETHACRYNIC ACID [HSDB]
• ETHACRYNIC ACID [USAN]
• BPBio1_000086
• GTPL7179
• ETACRYNIC ACID [MART.]
• ETHACRYNIC ACID [VANDF]
• ETACRYNIC ACID [WHO-DD]
• HMS502M22
• KBio1_000900
• KBio2_001293
• KBio2_003861
• KBio2_006429
• KBio3_001230
• 2,3-Dichloro-4(2-methylene-butyryl)phenoxy] acetic acid
• NINDS_000900
• HMS1568D20
• HMS1920M16
• HMS2089N17
• HMS2091D17
• HMS2095D20
• HMS3259G03
• HMS3712D20
• Pharmakon1600-01500287
• HY-B1640
• Ethacrynic acid, >=97% (HPLC)
• Tox21_110335
• Tox21_201102
• BDBM50186231
• CCG-38915
• ETACRYNIC ACID [EP IMPURITY]
• LS-240
• MFCD00056693
• NSC757026
• s5561
• WLN: QV1OR BG CG DVY2&U1
• ETACRYNIC ACID [EP MONOGRAPH]
• ETHACRYNIC ACID [ORANGE BOOK]
• GST Inhibitor-2 (Ethacrynic acid))
• AKOS003404732
• Tox21_110335_1
• DB00903
• ETHACRYNIC ACID [USP MONOGRAPH]
• KS-1453
• NC00450
• NSC-757026
• IDI1_000900
• NCGC00016260-01
• NCGC00016260-02
• NCGC00016260-03
• NCGC00016260-04
• NCGC00016260-06
• NCGC00016260-07
• NCGC00016260-08
• NCGC00016260-09
• NCGC00016260-10
• NCGC00016260-11
• NCGC00016260-13
• NCGC00022601-03
• NCGC00022601-04
• NCGC00022601-05
• NCGC00258654-01
• NCI60_041898
• SBI-0051374.P003
• AB00051988
• CS-0013591
• A51097
• D00313
• AB00051988-19
• AB00051988_20
• A831918
• Q418571
• SR-01000003010-2
• SR-01000003010-3
• BRD-K63630713-001-05-0
• BRD-K63630713-001-15-9
• [2,3-Dichloro-4-(2-ethylacryloyl)phenoxy]acetic acid #
• Acetic acid,3-dichloro-4-(2-methylenebutyryl)phenoxy]-
• Z1590781983
• 2,3-DICHLORO-4-(2-METHYLENEBUTYRYL)PHENOXY)ACETATE
• 4-(METHYLENEBUTYRYL)-2,3-DICHLOROPHENOXY)ACETIC ACID
• Acetic acid,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]-
• Ethacrynic acid, European Pharmacopoeia (EP) Reference Standard
• Ethacrynic acid, United States Pharmacopeia (USP) Reference Standard
• Etacrynic acid for system suitability, European Pharmacopoeia (EP) Reference Standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.7213	72.13%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.9714	97.14%
Subcellular localzation	Mitochondria	0.8836	88.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6656	66.56%
P-glycoprotein inhibitior	-	0.9394	93.94%
P-glycoprotein substrate	-	0.8787	87.87%
CYP3A4 substrate	-	0.5770	57.70%
CYP2C9 substrate	-	0.5799	57.99%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.4912	49.12%
CYP inhibitory promiscuity	-	0.8384	83.84%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6787	67.87%
Carcinogenicity (trinary)	Non-required	0.6878	68.78%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.5403	54.03%
Skin irritation	-	0.5630	56.30%
Skin corrosion	-	0.9018	90.18%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6872	68.72%
Micronuclear	+	0.5734	57.34%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	+	0.6665	66.65%
Respiratory toxicity	-	0.8222	82.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.7153	71.53%
Acute Oral Toxicity (c)	III	0.7998	79.98%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	-	0.5850	58.50%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.5593	55.93%
PPAR gamma	+	0.8707	87.07%
Honey bee toxicity	-	0.9538	95.38%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6474	64.74%
Fish aquatic toxicity	+	0.9963	99.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	35481.3 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	39810.7 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	630.96 nM	AC50	via CMAUP
CHEMBL3409	P08263	Glutathione S-transferase A1	5000 nM	IC50	PMID: 16675217
CHEMBL3902	P09211	Glutathione S-transferase Pi	4000 nM; 3400 nM	IC50; IC50	PMID: 16675217; PMID: 20055416
CHEMBL5514	P42858	Huntingtin	5623.4 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	8912.5 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	12589.3 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	3981.1 nM; 4466.8 nM; 3162.3 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	39810.7 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.57%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.59%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.24%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	89.20%	94.73%
CHEMBL4208	P20618	Proteasome component C5	88.66%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.14%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.58%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.07%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.55%	96.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.73%	83.57%

Plants that contains it

• Centella asiatica

Cross-Links

• PubChem: 3278
• NPASS: NPC282294
• ChEMBL: CHEMBL456