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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:etacrynic acid
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Accession:CHEBI:4876 term browser browse the term
Definition: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. 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 (EC 2.5.1.18) inhibitor.
Synonyms:exact_synonym: [2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
 related_synonym: (2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid;   Crinuryl;   Edecril;   Edecrina;   Endecril;   Etacrinic acid;   Ethacrynate;   Formula=C13H12Cl2O4;   Hidromedin;   Hydromedin;   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);   InChIKey=AVOLMBLBETYQHX-UHFFFAOYSA-N;   Methylenebutyrylphenoxyacetic acid;   Mingit;   Otacril;   Reomax;   SMILES=CCC(=C)C(=O)c1ccc(OCC(O)=O)c(Cl)c1Cl;   Taladren;   Uregit;   acide etacrynique;   acido etacrinico;   acidum etacrynicum;   ethacrynic acid
 xref: Beilstein:1915060;   CAS:58-54-8;   DrugBank:DB00903;   Drug_Central:1071;   HMDB:HMDB0015039;   KEGG:D00313;   LINCS:LSM-3420
 xref_mesh: MESH:D004976
 xref: PDBeChem:EAA;   PMID:7932170;   Reaxys:1915060;   Wikipedia:Etacrynic_acid


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etacrynic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcc1 ATP binding cassette subfamily C member 1 multiple interactions
decreases response to substance
ISO GSTP1 protein promotes the reaction [ABCC1 protein results in decreased susceptibility to Ethacrynic Acid] CTD PMID:10900222 NCBI chr10:549,537...672,235
Ensembl chr10:549,883...672,196
JBrowse link
G Abcc2 ATP binding cassette subfamily C member 2 increases transport ISO ABCC2 protein results in increased transport of Ethacrynic Acid CTD PMID:16316932 NCBI chr 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
JBrowse link
G Akr7a2 aldo-keto reductase family 7, member A2 multiple interactions ISO Ethacrynic Acid inhibits the reaction [4-nitrobenzaldehyde affects the reduction of AKR7A5 protein] CTD PMID:12604212 NCBI chr 5:157,759,448...157,768,473
Ensembl chr 5:157,759,416...157,768,471
JBrowse link
G Bcl2l1 Bcl2-like 1 increases expression
multiple interactions
ISO Ethacrynic Acid results in increased expression of BCL2L1 protein
[arsenic trioxide co-treated with Ethacrynic Acid] results in increased expression of BCL2L1 protein
CTD PMID:23082001 NCBI chr 3:148,259,594...148,314,191
Ensembl chr 3:148,259,596...148,313,810
JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 multiple interactions ISO [arsenic trioxide co-treated with Ethacrynic Acid] results in decreased expression of BIRC5 protein CTD PMID:23082001 NCBI chr10:106,856,097...106,864,419
Ensembl chr10:106,856,097...106,864,413
JBrowse link
G Casp3 caspase 3 multiple interactions ISO [arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of CASP3 protein; [MCL1 mutant form results in increased susceptibility to [Ethacrynic Acid co-treated with arsenic trioxide]] which results in increased cleavage of CASP3 protein; GSTP1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of CASP3 protein]; pyrazolanthrone inhibits the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of CASP3 protein] CTD PMID:23082001 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp8 caspase 8 multiple interactions
increases cleavage
ISO [arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of CASP8 protein
Ethacrynic Acid results in increased cleavage of CASP8 protein
CTD PMID:23082001 NCBI chr 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
JBrowse link
G Casp9 caspase 9 increases cleavage
multiple interactions
ISO Ethacrynic Acid results in increased cleavage of CASP9 protein
arsenic trioxide promotes the reaction [Ethacrynic Acid results in increased cleavage of CASP9 protein]; GSTP1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of CASP9 protein]; MCL1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of CASP9 protein]
CTD PMID:23082001 NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
JBrowse link
G Cat catalase multiple interactions ISO CAT mutant form promotes the reaction [arsenic trioxide promotes the reaction [Ethacrynic Acid results in decreased expression of MCL1 protein]] CTD PMID:23082001 NCBI chr 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
JBrowse link
G Cbr1 carbonyl reductase 1 multiple interactions ISO Ethacrynic Acid inhibits the reaction [CBR1 protein results in increased metabolism of 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone] CTD PMID:11306090 NCBI chr11:33,813,041...33,815,418
Ensembl chr11:33,845,463...33,847,793
JBrowse link
G Ccnd1 cyclin D1 decreases expression ISO Ethacrynic Acid results in decreased expression of CCND1 mRNA CTD PMID:20011538 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression ISO Ethacrynic Acid results in increased expression of CDKN1A mRNA CTD PMID:25817893 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
JBrowse link
G Cflar CASP8 and FADD-like apoptosis regulator multiple interactions
decreases expression
ISO arsenic trioxide promotes the reaction [Ethacrynic Acid results in decreased expression of CFLAR protein] CTD PMID:23082001 NCBI chr 9:65,534,608...65,586,395
Ensembl chr 9:65,534,704...65,587,251
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases expression
multiple interactions
ISO
EXP
Ethacrynic Acid results in increased expression of CYP1A1 mRNA
Ethacrynic Acid inhibits the reaction [Tetrachlorodibenzodioxin results in increased activity of CYP1A1 protein]
CTD PMID:9973208 PMID:18493746 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 multiple interactions
increases expression
ISO Acetylcysteine inhibits the reaction [Ethacrynic Acid results in increased expression of DDIT3 mRNA]; Glutathione inhibits the reaction [Ethacrynic Acid results in increased expression of DDIT3 mRNA] CTD PMID:17171638 PMID:25817893 NCBI chr 7:70,578,564...70,585,074
Ensembl chr 7:70,580,198...70,585,084
JBrowse link
G Fn1 fibronectin 1 decreases expression ISO Ethacrynic Acid results in decreased expression of FN1 mRNA CTD PMID:20011538 NCBI chr 9:78,900,111...78,969,018
Ensembl chr 9:78,900,103...78,969,078
JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit increases expression ISO Ethacrynic Acid results in increased expression of FOS mRNA CTD PMID:10407097 PMID:12946577 NCBI chr 6:109,300,433...109,303,299
Ensembl chr 6:109,300,433...109,303,299
JBrowse link
G Fzd5 frizzled class receptor 5 increases expression ISO Ethacrynic Acid results in increased expression of FZD5 mRNA CTD PMID:20011538 NCBI chr 9:71,443,784...71,445,541
Ensembl chr 9:71,443,588...71,445,739
JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit multiple interactions ISO [GCLC protein co-treated with GCLM protein] results in decreased susceptibility to Ethacrynic Acid CTD PMID:10900222 NCBI chr 8:85,059,051...85,097,471
Ensembl chr 8:85,059,051...85,097,468
JBrowse link
G Gclm glutamate cysteine ligase, modifier subunit multiple interactions ISO [GCLC protein co-treated with GCLM protein] results in decreased susceptibility to Ethacrynic Acid CTD PMID:10900222 NCBI chr 2:225,827,504...225,847,876
Ensembl chr 2:225,827,504...225,847,874
JBrowse link
G Gsta1 glutathione S-transferase alpha 1 decreases response to substance
increases expression
multiple interactions
affects metabolic processing
ISO
EXP
GSTA1 protein results in decreased susceptibility to Ethacrynic Acid
Ethacrynic Acid results in increased expression of GSTA1 mRNA
[GSTA1 protein binds to GSTA2 protein] which affects the metabolism of Ethacrynic Acid
GSTA1 protein affects the metabolism of Ethacrynic Acid analog
CTD PMID:1985777 PMID:9799558 PMID:9877184 PMID:12781783 NCBI chr 9:27,366,404...27,381,004
Ensembl chr 9:27,368,272...27,452,902
JBrowse link
G Gsta2 glutathione S-transferase alpha 2 affects metabolic processing
multiple interactions
EXP GSTA2 protein affects the metabolism of Ethacrynic Acid
[GSTA1 protein binds to GSTA2 protein] which affects the metabolism of Ethacrynic Acid
CTD PMID:9877184 NCBI chr 8:85,640,081...85,645,621 JBrowse link
G Gsta3 glutathione S-transferase alpha 3 increases glutathionylation ISO GSTA3 protein results in increased glutathionylation of Ethacrynic Acid CTD PMID:21876218 NCBI chr 9:27,357,490...27,417,023
Ensembl chr 9:27,402,381...27,417,023
JBrowse link
G Gsta4 glutathione S-transferase alpha 4 increases expression
affects metabolic processing
EXP Ethacrynic Acid results in increased expression of GSTA4 mRNA; Ethacrynic Acid results in increased expression of GSTA4 protein
GSTA4 protein affects the metabolism of Ethacrynic Acid
CTD PMID:2619714 PMID:9799558 NCBI chr 8:85,497,557...85,514,732
Ensembl chr 8:85,497,557...85,518,879
JBrowse link
G Gstm1 glutathione S-transferase mu 1 affects metabolic processing ISO GSTM1 protein affects the metabolism of Ethacrynic Acid CTD PMID:12069689 NCBI chr 2:210,803,869...210,809,461
Ensembl chr 2:210,803,869...210,809,306
JBrowse link
G Gstm7 glutathione S-transferase, mu 7 affects metabolic processing ISO GSTM7 protein affects the metabolism of Ethacrynic Acid CTD PMID:12069689 NCBI chr 2:210,720,719...210,726,179
Ensembl chr 2:210,720,704...210,782,856
JBrowse link
G Gstp1 glutathione S-transferase pi 1 decreases activity
affects metabolic processing
decreases response to substance
increases expression
multiple interactions
ISO
EXP
Ethacrynic Acid analog results in decreased activity of GSTP1 protein; Ethacrynic Acid results in decreased activity of GSTP1 protein
GSTP1 protein affects the metabolism of Ethacrynic Acid
GSTP1 protein results in decreased susceptibility to Ethacrynic Acid
GSTP1 protein affects the metabolism of Ethacrynic Acid analog
Ethacrynic Acid results in increased expression of GSTP1 protein
Ethacrynic Acid binds to and results in decreased activity of GSTP1 protein; Ethacrynic Acid inhibits the reaction [Chlorophyllides inhibits the reaction [GSTP1 protein results in increased metabolism of 1-chloro-2,4-dinitrobenzene-glutathione conjugate]]; Ethacrynic Acid inhibits the reaction [GSTP1 protein affects the metabolism of Isotretinoin]; Ethacrynic Acid inhibits the reaction [GSTP1 protein results in decreased susceptibility to Etoposide]; Ethacrynic Acid inhibits the reaction [GSTP1 protein results in increased metabolism of 1-chloro-2,4-dinitrobenzene-glutathione conjugate]; GSTP1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of CASP3 protein]; GSTP1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of CASP9 protein]; GSTP1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of PARP1 protein]; GSTP1 protein promotes the reaction [ABCC1 protein results in decreased susceptibility to Ethacrynic Acid]; GSTP1 protein results in decreased susceptibility to [arsenic trioxide co-treated with Ethacrynic Acid]; Pyrimethamine inhibits the reaction [GSTP1 protein affects the metabolism of and results in decreased activity of Ethacrynic Acid]; Quinidine inhibits the reaction [GSTP1 protein affects the metabolism of and results in decreased activity of Ethacrynic Acid]; Quinine inhibits the reaction [GSTP1 protein affects the metabolism of and results in decreased activity of Ethacrynic Acid]; Tetracycline inhibits the reaction [GSTP1 protein affects the metabolism of and results in decreased activity of Ethacrynic Acid]
CTD PMID:2619714 PMID:2747627 PMID:9463521 PMID:9806904 PMID:9877184 PMID:10900222 PMID:11807801 PMID:12781783 PMID:14556662 PMID:15911318 PMID:15999103 PMID:23082001 PMID:23769903 NCBI chr 1:219,291,679...219,294,147
Ensembl chr 1:219,291,679...219,294,147
JBrowse link
G Gstt2 glutathione S-transferase, theta 2 affects metabolic processing EXP GSTT2 protein affects the metabolism of Ethacrynic Acid CTD PMID:2114406 NCBI chr20:13,760,810...13,764,481
Ensembl chr20:13,760,810...13,764,475
JBrowse link
G Gstz1 glutathione S-transferase zeta 1 affects metabolic processing ISO GSTZ1 protein affects the metabolism of Ethacrynic Acid CTD PMID:9396740 NCBI chr 6:111,176,798...111,187,246
Ensembl chr 6:111,176,798...111,187,244
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions
increases expression
ISO Acetylcysteine inhibits the reaction [Ethacrynic Acid results in increased expression of HMOX1 mRNA]; Acetylcysteine inhibits the reaction [Ethacrynic Acid results in increased expression of HMOX1 protein]; Deferoxamine inhibits the reaction [Ethacrynic Acid affects the localization of HMOX1 protein]; Deferoxamine inhibits the reaction [Ethacrynic Acid results in increased expression of HMOX1 mRNA]; Glutathione inhibits the reaction [Ethacrynic Acid results in increased expression of HMOX1 mRNA]; Glutathione inhibits the reaction [Ethacrynic Acid results in increased expression of HMOX1 protein]
Ethacrynic Acid results in increased expression of HMOX1 mRNA; Ethacrynic Acid results in increased expression of HMOX1 protein
CTD PMID:20934533 PMID:25817893 PMID:26945724 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit multiple interactions ISO [Ethacrynic Acid co-treated with arsenic trioxide] results in increased phosphorylation of JUN protein; pyrazolanthrone inhibits the reaction [[Ethacrynic Acid co-treated with arsenic trioxide] results in increased phosphorylation of JUN protein] CTD PMID:23082001 NCBI chr 5:114,011,184...114,014,277
Ensembl chr 5:114,011,189...114,014,277
JBrowse link
G Lef1 lymphoid enhancer binding factor 1 decreases expression
affects binding
ISO Ethacrynic Acid results in decreased expression of LEF1 mRNA
Ethacrynic Acid binds to LEF1 protein
CTD PMID:20011538 NCBI chr 2:236,232,115...236,345,061
Ensembl chr 2:236,233,239...236,345,056
JBrowse link
G Map2k1 mitogen activated protein kinase kinase 1 increases expression ISO Ethacrynic Acid results in increased expression of MAP2K1 protein CTD PMID:14556662 NCBI chr 8:69,134,218...69,722,573
Ensembl chr 8:69,134,223...69,164,758
JBrowse link
G Mapk14 mitogen activated protein kinase 14 decreases expression ISO Ethacrynic Acid results in decreased expression of MAPK14 protein CTD PMID:14556662 NCBI chr20:5,933,290...5,995,137
Ensembl chr20:5,933,303...5,995,137
JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases expression ISO Ethacrynic Acid results in increased expression of MAPK3 protein CTD PMID:14556662 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mapk8 mitogen-activated protein kinase 8 decreases expression ISO Ethacrynic Acid results in decreased expression of MAPK8 protein CTD PMID:14556662 NCBI chr16:9,620,854...9,709,342
Ensembl chr16:9,625,177...9,709,347
JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member multiple interactions
decreases expression
ISO [MCL1 mutant form results in increased susceptibility to [Ethacrynic Acid co-treated with arsenic trioxide]] which results in increased cleavage of CASP3 protein; Acetylcysteine inhibits the reaction [arsenic trioxide promotes the reaction [Ethacrynic Acid results in decreased expression of MCL1 protein]]; arsenic trioxide promotes the reaction [Ethacrynic Acid results in decreased expression of MCL1 protein]; benzyloxycarbonylleucyl-leucyl-leucine aldehyde inhibits the reaction [arsenic trioxide promotes the reaction [Ethacrynic Acid results in decreased expression of MCL1 protein]]; CAT mutant form promotes the reaction [arsenic trioxide promotes the reaction [Ethacrynic Acid results in decreased expression of MCL1 protein]]; MCL1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of CASP9 protein]; MCL1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of PARP1 protein]; MCL1 mutant form results in increased susceptibility to [Ethacrynic Acid co-treated with arsenic trioxide]; pyrazolanthrone inhibits the reaction [arsenic trioxide promotes the reaction [Ethacrynic Acid results in decreased expression of MCL1 protein]] CTD PMID:23082001 NCBI chr 2:197,786,212...197,788,992 JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 multiple interactions
affects localization
affects response to substance
increases expression
ISO NFE2L2 protein promotes the reaction [sulforaphane results in decreased susceptibility to Ethacrynic Acid]
ferrous sulfate inhibits the reaction [Deferoxamine inhibits the reaction [Ethacrynic Acid affects the localization of NFE2L2 protein]]
[NFE2L2 affects the susceptibility to sulforaphane] which affects the susceptibility to Ethacrynic Acid
Ethacrynic Acid results in increased expression of NFE2L2 protein
CTD PMID:19303893 PMID:20932822 PMID:20934533 PMID:25817893 PMID:26945724 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
JBrowse link
G Ngf nerve growth factor increases expression ISO Ethacrynic Acid results in increased expression of NGF mRNA CTD PMID:10407097 NCBI chr 2:204,886,158...204,939,523
Ensembl chr 2:204,886,202...204,940,453
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions EXP Ethacrynic Acid promotes the reaction [Potassium Cyanide results in increased expression of NOS2 protein] CTD PMID:16933320 NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO [arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of PARP1 protein; Acetylcysteine inhibits the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of PARP1 protein]; benzyloxycarbonyl-valyl-alanyl-aspartic acid analog inhibits the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of PARP1 protein]; GSTP1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of PARP1 protein]; MCL1 mutant form promotes the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of PARP1 protein]; pyrazolanthrone inhibits the reaction [[arsenic trioxide co-treated with Ethacrynic Acid] results in increased cleavage of PARP1 protein] CTD PMID:23082001 NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
JBrowse link
G Slc12a2 solute carrier family 12 member 2 decreases activity
multiple interactions
ISO Ethacrynic Acid results in decreased activity of SLC12A2 protein
Ethacrynic Acid inhibits the reaction [SLC12A2 protein results in increased uptake of Rubidium]
CTD PMID:29959396 NCBI chr18:52,917,124...52,985,281
Ensembl chr18:52,917,124...52,985,261
JBrowse link
G Tp53 tumor protein p53 affects localization ISO Ethacrynic Acid affects the localization of TP53 protein CTD PMID:25817893 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link
G Xiap X-linked inhibitor of apoptosis multiple interactions ISO [arsenic trioxide co-treated with Ethacrynic Acid] results in decreased expression of XIAP protein CTD PMID:23082001 NCBI chr  X:128,409,425...128,455,786
Ensembl chr  X:128,409,472...128,453,000
JBrowse link

Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 19781
    role 19726
      application 19412
        food additive 14953
          food acidity regulator 11719
            acetic acid 10855
              etacrynic acid 44
Path 2
Term Annotations click to browse term
  CHEBI ontology 19781
    subatomic particle 19779
      composite particle 19779
        hadron 19779
          baryon 19779
            nucleon 19779
              atomic nucleus 19779
                atom 19779
                  main group element atom 19669
                    p-block element atom 19669
                      carbon group element atom 19588
                        carbon atom 19578
                          organic molecular entity 19578
                            organic group 18620
                              organic divalent group 18611
                                organodiyl group 18611
                                  carbonyl group 18526
                                    carbonyl compound 18526
                                      carboxylic acid 18202
                                        monocarboxylic acid 17606
                                          acetic acid 10855
                                            etacrynic acid 44
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