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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 chr10:528,961...655,179
Ensembl chr10:531,812...655,114 		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 1:242,664,657...242,723,239
Ensembl chr 1:242,664,657...242,723,238 		JBrowse link
G Akr1c1 aldo-keto reductase family 1, member C1 increases expression ISO Ethacrynic Acid results in increased expression of AKR1C1 mRNA CTD PMID:9973208 NCBI chr17:65,810,474...65,837,385
Ensembl chr17:65,810,475...65,837,326 		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 5:151,552,375...151,560,914
Ensembl chr 5:151,552,343...151,560,909 		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 3:141,253,508...141,304,582
Ensembl chr 3:141,253,523...141,303,479 		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 chr10:103,072,530...103,081,382
Ensembl chr10:103,073,408...103,081,380 		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 chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		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 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542 		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 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		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 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Ccnd1 cyclin D1 decreases expression ISO Ethacrynic Acid results in decreased expression of CCND1 mRNA CTD PMID:20011538 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		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 chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		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 9:60,185,338...60,236,173
Ensembl chr 9:60,185,452...60,237,034 		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 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		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 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201 		JBrowse link
G Fn1 fibronectin 1 decreases expression ISO Ethacrynic Acid results in decreased expression of FN1 mRNA CTD PMID:20011538 NCBI chr 9:73,196,044...73,264,695
Ensembl chr 9:73,196,044...73,264,678 		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 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036 		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 9:66,117,370...66,119,127
Ensembl chr 9:66,113,112...66,121,457 		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 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544 		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 2:210,347,482...210,367,537
Ensembl chr 2:210,347,482...210,367,535 		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 9:23,703,476...23,720,121
Ensembl chr 9:23,703,477...23,720,121 		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 8:79,184,535...79,196,827
Ensembl chr 8:79,184,322...79,196,798 		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 9:23,658,574...23,684,240
Ensembl chr 9:23,658,574...23,684,240 		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 8:79,066,967...79,084,193
Ensembl chr 8:79,066,934...79,084,182 		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 2:195,649,845...195,655,402
Ensembl chr 2:195,649,845...195,655,411 		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 2:195,566,701...195,572,149
Ensembl chr 2:195,566,701...195,572,203 		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 More... NCBI chr 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226 		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 chr20:12,819,617...12,823,288
Ensembl chr20:12,819,170...12,823,288 		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 6:106,794,594...106,805,284
Ensembl chr 6:106,794,074...106,805,284 		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 chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Hsf1 heat shock transcription factor 1 increases activity ISO Ethacrynic Acid results in increased activity of HSF1 protein CTD PMID:34170685 NCBI chr 7:108,196,040...108,223,011
Ensembl chr 7:108,196,056...108,223,011 		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 5:109,894,175...109,897,268
Ensembl chr 5:109,893,145...109,897,656 		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 2:219,666,549...219,779,815
Ensembl chr 2:219,666,592...219,779,794 		JBrowse link
G LOC102556347 carbonyl reductase [NADPH] 1-like 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 chr11:32,892,640...32,895,277
Ensembl chr11:32,857,991...32,895,275 		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 8:64,683,449...64,754,900
Ensembl chr 8:64,683,449...64,755,147 		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 chr20:6,749,646...6,810,590
Ensembl chr20:6,749,670...6,810,589 		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 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		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 chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		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 2:183,219,137...183,235,676
Ensembl chr 2:183,219,220...183,222,303 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 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 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Ngf nerve growth factor increases expression ISO Ethacrynic Acid results in increased expression of NGF mRNA CTD PMID:10407097 NCBI chr 2:189,901,058...189,954,452
Ensembl chr 2:189,901,058...189,954,452 		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 chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210 		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 chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		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 chr18:51,348,282...51,416,448
Ensembl chr18:51,348,302...51,416,440 		JBrowse link
G Tp53 tumor protein p53 affects localization ISO Ethacrynic Acid affects the localization of TP53 protein CTD PMID:25817893 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		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:120,890,537...120,938,413
Ensembl chr  X:120,897,907...120,934,700 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20056
    role 20008
      application 19745
        food additive 15212
          food acidity regulator 11793
            acetic acid 10876
              etacrynic acid 46
Path 2
Term Annotations click to browse term
  CHEBI ontology 20056
    subatomic particle 20054
      composite particle 20054
        hadron 20054
          baryon 20054
            nucleon 20054
              atomic nucleus 20054
                atom 20054
                  main group element atom 19956
                    p-block element atom 19956
                      carbon group element atom 19882
                        carbon atom 19875
                          organic molecular entity 19875
                            organic group 18961
                              organic divalent group 18947
                                organodiyl group 18947
                                  carbonyl group 18900
                                    carbonyl compound 18900
                                      carboxylic acid 18594
                                        monocarboxylic acid 17840
                                          acetic acid 10876
                                            etacrynic acid 46
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