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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:zileuton
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Accession:CHEBI:10112 term browser browse the term
Definition:A member of the class of 1-benzothiophenes that is 1-benzothiophene in which the hydrogen at position 2 is replaced by a 1-[carbamoyl(hydroxy)amino]ethyl group. A selective 5-lipoxygenase inhibitor, it inhibits the formation of leukotrienes LTB4, LTC4, LDT4, and LTE4. It is used for the management of chronic asthma.
Synonyms:exact_synonym: 1-[1-(1-benzothien-2-yl)ethyl]-1-hydroxyurea
 related_synonym: (+-)-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea;   Formula=C11H12N2O2S;   InChI=1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14);   InChIKey=MWLSOWXNZPKENC-UHFFFAOYSA-N;   Leutrol;   N-(1-Benzo(b)thien-2-ylethyl)-N-hydroxyurea;   N-[1-(benzo[b]thiophen-2-yl)ethyl]-N-hydroxyurea;   SMILES=CC(N(O)C(N)=O)c1cc2ccccc2s1;   Zyflo;   zileutonum
 xref: CAS:111406-87-2;   DrugBank:DB00744;   Drug_Central:2862;   KEGG:D00414;   LINCS:LSM-5084
 xref_mesh: MESH:C063449
 xref: PMID:19309543;   PMID:19645854;   PMID:20204486;   PMID:20436887;   Reaxys:4869674;   Wikipedia:Zileuton


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zileuton 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 affects response to substance ISO ABCC1 gene SNP affects the susceptibility to zileuton CTD PMID:19214143 NCBI chr10:528,961...655,179
Ensembl chr10:531,812...655,114 		JBrowse link
G Acta2 actin alpha 2, smooth muscle multiple interactions ISO zileuton inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of ACTA2 protein] CTD PMID:27697457 NCBI chr 1:231,746,527...231,759,307
Ensembl chr 1:231,746,548...231,759,554 		JBrowse link
G Alb albumin multiple interactions ISO zileuton metabolite binds to and results in increased alkylation of ALB protein CTD PMID:17944539 NCBI chr14:17,607,397...17,622,814
Ensembl chr14:17,607,381...17,622,836 		JBrowse link
G Alox5 arachidonate 5-lipoxygenase affects response to substance
decreases expression
multiple interactions
decreases activity		 ISO
EXP		 ALOX5 gene SNP affects the susceptibility to zileuton
zileuton results in decreased expression of ALOX5 mRNA
[[zileuton co-treated with Calcimycin] results in decreased activity of ALOX5 protein] which results in decreased abundance of Leukotriene B4; [zileuton results in decreased activity of ALOX5 protein] inhibits the reaction [Calcimycin results in increased abundance of Leukotriene B4]; [zileuton results in decreased activity of ALOX5 protein] inhibits the reaction [Indomethacin results in increased abundance of Leukotriene B4]; [zileuton results in decreased activity of ALOX5 protein] which results in decreased abundance of Leukotriene B4; zileuton binds to and results in decreased activity of ALOX5 protein; zileuton inhibits the reaction [ALOX5 protein affects the abundance of lipoxin A4]; zileuton inhibits the reaction [IL13 protein results in increased expression of ALOX5 mRNA]; zileuton inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in decreased activity of ALOX5 protein]; zileuton inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in decreased expression of ALOX5 protein]; zileuton inhibits the reaction [Peroxynitrous Acid results in increased nitrosation of ALOX5 protein]
[zileuton results in decreased activity of ALOX5 protein] which results in decreased abundance of Leukotriene B4; [zileuton results in decreased activity of ALOX5 protein] which results in decreased expression of NOS1; zileuton inhibits the reaction [ALOX5 protein promotes the reaction [Ovalbumin results in increased abundance of Leukotriene B4]]; zileuton inhibits the reaction [ALOX5 protein promotes the reaction [Ovalbumin results in increased abundance of Leukotriene C4]]; zileuton inhibits the reaction [ALOX5 protein promotes the reaction [Ovalbumin results in increased abundance of Leukotriene D4]]; zileuton inhibits the reaction [ALOX5 protein promotes the reaction [Ovalbumin results in increased abundance of Leukotriene E4]]; zileuton inhibits the reaction [Ovalbumin results in increased expression of ALOX5 mRNA]
[zileuton results in decreased activity of ALOX5 protein] inhibits the reaction [Calcimycin results in increased abundance of Platelet Activating Factor]; [zileuton results in decreased activity of ALOX5 protein] inhibits the reaction [N-Formylmethionine Leucyl-Phenylalanine results in increased abundance of Leukotriene C4]; [zileuton results in decreased activity of ALOX5 protein] which affects the abundance of Arachidonic Acid; [zileuton results in decreased activity of ALOX5 protein] which results in decreased abundance of Leukotriene B4; [zileuton results in decreased activity of ALOX5 protein] which results in decreased abundance of Leukotriene C4; [zileuton results in decreased activity of ALOX5 protein] which results in decreased abundance of Leukotriene D4; [zileuton results in decreased activity of ALOX5 protein] which results in decreased abundance of Leukotriene E4; [zileuton results in decreased activity of ALOX5 protein] which results in decreased susceptibility to Arachidonic Acid; zileuton inhibits the reaction [ALOX5 protein promotes the reaction [lipopolysaccharide, E. coli O26-B6 results in increased abundance of Leukotriene B4]]; zileuton inhibits the reaction [ALOX5 protein promotes the reaction [lysophosphatidic acid results in increased abundance of Hydrogen Peroxide]]; zileuton inhibits the reaction [ALOX5 protein results in increased metabolism of Arachidonic Acid]; zileuton inhibits the reaction [ALOX5 protein results in increased susceptibility to [Histamine results in increased abundance of Leukotriene B4]]; zileuton inhibits the reaction [L 708714 binds to ALOX5 protein]		 CTD PMID:1781415 PMID:7577949 PMID:7592874 PMID:7665580 PMID:7812673 More... NCBI chr 4:149,531,329...149,578,696
Ensembl chr 4:149,531,515...149,578,743 		JBrowse link
G Casp3 caspase 3 multiple interactions
increases activity		 ISO Palmitic Acid promotes the reaction [zileuton results in increased activity of CASP3 protein] CTD PMID:22700542 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp7 caspase 7 multiple interactions
increases activity		 ISO Palmitic Acid promotes the reaction [zileuton results in increased activity of CASP7 protein] CTD PMID:22700542 NCBI chr 1:255,437,438...255,476,737
Ensembl chr 1:255,437,172...255,476,729 		JBrowse link
G Ccl11 C-C motif chemokine ligand 11 multiple interactions ISO zileuton inhibits the reaction [Ovalbumin results in increased expression of CCL11 mRNA] CTD PMID:12794006 NCBI chr10:67,028,328...67,032,929
Ensembl chr10:67,028,328...67,032,926 		JBrowse link
G Ccl12 C-C motif chemokine ligand 12 multiple interactions ISO zileuton inhibits the reaction [CCL12 protein results in increased abundance of Leukotriene B4]; zileuton inhibits the reaction [Ovalbumin results in increased expression of CCL12 mRNA] CTD PMID:12388339 PMID:12794006 NCBI chr10:67,070,230...67,071,780
Ensembl chr10:67,070,230...67,071,780 		JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions ISO zileuton inhibits the reaction [CCL2 protein results in increased abundance of Leukotriene B4]; zileuton inhibits the reaction [Ovalbumin results in increased expression of CCL2 mRNA] CTD PMID:12388339 PMID:12794006 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226 		JBrowse link
G Col10a1 collagen type X alpha 1 chain increases expression ISO zileuton results in increased expression of COL10A1 mRNA CTD PMID:19544365 NCBI chr20:38,183,103...38,189,488
Ensembl chr20:38,182,494...38,189,494 		JBrowse link
G Col2a1 collagen type II alpha 1 chain increases expression ISO zileuton results in increased expression of COL2A1 mRNA CTD PMID:19544365 NCBI chr 7:129,098,489...129,127,560
Ensembl chr 7:129,098,786...129,127,546 		JBrowse link
G Cxcl3 C-X-C motif chemokine ligand 3 multiple interactions ISO zileuton inhibits the reaction [CXCL1 protein results in increased abundance of Leukotriene B4] CTD PMID:12388339 NCBI chr14:17,287,727...17,289,451
Ensembl chr14:17,270,146...17,289,511 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases activity EXP zileuton results in increased activity of CYP1A1 protein CTD PMID:11509739 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 multiple interactions
decreases activity		 ISO zileuton inhibits the reaction [CYP1A2 protein results in increased metabolism of Phenacetin]
zileuton results in decreased activity of CYP1A2 protein		 CTD PMID:14570767 NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312 		JBrowse link
G Cyp2b2 cytochrome P450, family 2, subfamily b, polypeptide 2 increases expression EXP zileuton results in increased expression of CYP2B2 mRNA CTD PMID:12883083 NCBI chr 1:81,594,534...81,608,567
Ensembl chr 1:81,594,555...81,608,566 		JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 decreases activity ISO zileuton results in decreased activity of CYP3A4 protein CTD PMID:15482930 NCBI chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008 		JBrowse link
G Ddit3 DNA-damage inducible transcript 3 decreases expression EXP zileuton results in decreased expression of DDIT3 mRNA CTD PMID:12883083 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201 		JBrowse link
G Epx eosinophil peroxidase multiple interactions ISO zileuton inhibits the reaction [Ovalbumin results in increased expression of EPX protein] CTD PMID:12794006 NCBI chr10:72,666,865...72,677,952
Ensembl chr10:72,666,865...72,677,952 		JBrowse link
G Fth1 ferritin heavy chain 1 decreases expression EXP zileuton results in decreased expression of FTH1 mRNA CTD PMID:12883083 NCBI chr 1:206,627,142...206,629,430
Ensembl chr 1:206,627,103...206,725,424 		JBrowse link
G Hdac1 histone deacetylase 1 decreases expression EXP zileuton results in decreased expression of HDAC1 mRNA CTD PMID:12883083 NCBI chr 5:141,853,992...141,881,057
Ensembl chr 5:141,853,989...141,881,111 		JBrowse link
G Hmgcs1 3-hydroxy-3-methylglutaryl-CoA synthase 1 decreases expression EXP zileuton results in decreased expression of HMGCS1 mRNA CTD PMID:12883083 NCBI chr 2:51,649,368...51,667,100
Ensembl chr 2:51,649,497...51,667,100 		JBrowse link
G Hsd11b2 hydroxysteroid 11-beta dehydrogenase 2 increases activity ISO zileuton results in increased activity of HSD11B2 protein CTD PMID:10377029 NCBI chr19:33,397,656...33,402,899
Ensembl chr19:33,397,656...33,402,899 		JBrowse link
G Icam1 intercellular adhesion molecule 1 affects expression
multiple interactions		 ISO zileuton affects the expression of ICAM1 protein
zileuton inhibits the reaction [dinitrobenzenesulfonic acid results in increased expression of ICAM1 protein]		 CTD PMID:15266012 PMID:15821759 NCBI chr 8:19,553,063...19,565,438
Ensembl chr 8:19,553,645...19,565,438 		JBrowse link
G Il12a interleukin 12A multiple interactions ISO zileuton inhibits the reaction [Leukotriene D4 results in increased secretion of [IL12A protein binds to IL12B protein]] CTD PMID:19118273 NCBI chr 2:152,965,769...152,973,035
Ensembl chr 2:152,965,769...152,972,734 		JBrowse link
G Il12b interleukin 12B multiple interactions ISO zileuton inhibits the reaction [Leukotriene D4 results in increased secretion of [IL12A protein binds to IL12B protein]] CTD PMID:19118273 NCBI chr10:28,888,832...28,903,802
Ensembl chr10:28,893,008...28,902,903 		JBrowse link
G Il13 interleukin 13 affects expression
multiple interactions		 ISO
EXP		 zileuton affects the expression of IL13 protein
zileuton inhibits the reaction [Ovalbumin results in increased expression of IL13 mRNA]
zileuton inhibits the reaction [IL13 protein results in increased abundance of Leukotriene B4]; zileuton inhibits the reaction [IL13 protein results in increased expression of ALOX5 mRNA]; zileuton inhibits the reaction [IL13 protein results in increased expression of MUC5AC mRNA]; zileuton inhibits the reaction [IL13 protein results in increased expression of MUC5AC protein]		 CTD PMID:12654629 PMID:12794006 PMID:15927844 NCBI chr10:37,790,130...37,792,687
Ensembl chr10:37,790,130...37,792,737 		JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO zileuton inhibits the reaction [Bleomycin results in increased expression of IL1B protein] CTD PMID:17118201 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il4 interleukin 4 multiple interactions ISO zileuton inhibits the reaction [Ovalbumin results in increased expression of IL4 mRNA] CTD PMID:12794006 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750 		JBrowse link
G Il6 interleukin 6 multiple interactions
decreases secretion		 ISO zileuton inhibits the reaction [Endotoxins results in increased expression of IL6 protein]; zileuton inhibits the reaction [Leukotriene D4 results in increased secretion of IL6 protein]
zileuton results in decreased secretion of IL6 protein		 CTD PMID:7496871 PMID:19118273 PMID:20436887 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Itgam integrin subunit alpha M multiple interactions ISO zileuton inhibits the reaction [Lipopolysaccharides results in increased expression of ITGAM protein] CTD PMID:15328337 NCBI chr 1:182,659,047...182,709,501
Ensembl chr 1:182,659,000...182,709,503 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 affects expression ISO zileuton affects the expression of MAPK1 protein modified form CTD PMID:18059327 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 affects expression
decreases expression		 ISO
EXP		 zileuton affects the expression of MAPK3 protein modified form
zileuton results in decreased expression of MAPK3 mRNA		 CTD PMID:12883083 PMID:18059327 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mgst1 microsomal glutathione S-transferase 1 decreases activity EXP zileuton results in decreased activity of MGST1 protein CTD PMID:9890956 NCBI chr 4:171,029,666...171,044,893
Ensembl chr 4:171,029,630...171,044,892 		JBrowse link
G Mmp9 matrix metallopeptidase 9 decreases activity
decreases expression		 EXP zileuton results in decreased activity of MMP9 protein
zileuton results in decreased expression of MMP9 mRNA		 CTD PMID:19309543 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120 		JBrowse link
G Mpo myeloperoxidase multiple interactions
decreases activity		 ISO
EXP		 zileuton inhibits the reaction [Bleomycin results in increased activity of MPO protein]; zileuton inhibits the reaction [dinitrobenzenesulfonic acid results in increased activity of MPO protein]; zileuton inhibits the reaction [Ovalbumin results in increased expression of MPO protein]; zileuton inhibits the reaction [Tetradecanoylphorbol Acetate results in increased activity of MPO protein]
zileuton inhibits the reaction [Dextran Sulfate results in increased activity of MPO protein]; zileuton inhibits the reaction [Trinitrobenzenesulfonic Acid results in increased activity of MPO protein]
zileuton results in decreased activity of MPO protein		 CTD PMID:7812673 PMID:11698051 PMID:12794006 PMID:15339030 PMID:15821759 More... NCBI chr10:72,594,883...72,608,862
Ensembl chr10:72,594,661...72,604,819 		JBrowse link
G Muc5ac mucin 5AC, oligomeric mucus/gel-forming multiple interactions ISO
EXP		 zileuton inhibits the reaction [Ovalbumin results in increased expression of MUC5AC mRNA]; zileuton inhibits the reaction [Ovalbumin results in increased expression of MUC5AC protein]
zileuton inhibits the reaction [IL13 protein results in increased expression of MUC5AC mRNA]; zileuton inhibits the reaction [IL13 protein results in increased expression of MUC5AC protein]		 CTD PMID:12654629 PMID:12794006 NCBI chr 1:196,864,336...196,896,475
Ensembl chr 1:196,864,336...196,896,475 		JBrowse link
G Nos1 nitric oxide synthase 1 multiple interactions ISO [zileuton results in decreased activity of ALOX5 protein] which results in decreased expression of NOS1 CTD PMID:11694324 NCBI chr12:38,615,111...38,795,492
Ensembl chr12:38,626,714...38,710,945 		JBrowse link
G Ocln occludin multiple interactions ISO zileuton inhibits the reaction [dinitrobenzenesulfonic acid affects the localization of OCLN protein] CTD PMID:16670640 NCBI chr 2:31,657,217...31,707,466
Ensembl chr 2:31,657,220...31,764,150 		JBrowse link
G Ptafr platelet-activating factor receptor multiple interactions ISO zileuton binds to and results in decreased activity of PTAFR protein; zileuton inhibits the reaction [Platelet Activating Factor binds to PTAFR protein] CTD PMID:11529688 NCBI chr 5:144,765,770...144,795,057
Ensembl chr 5:144,765,976...144,795,251 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 affects expression
multiple interactions		 ISO zileuton affects the expression of PTGS2 protein
zileuton inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of PTGS2 mRNA]		 CTD PMID:18059327 PMID:28487374 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Rplp0 ribosomal protein lateral stalk subunit P0 decreases expression EXP zileuton results in decreased expression of RPLP0 mRNA CTD PMID:12883083 NCBI chr12:41,054,363...41,057,632
Ensembl chr12:41,054,179...41,057,632 		JBrowse link
G Sele selectin E multiple interactions ISO zileuton inhibits the reaction [dinitrobenzenesulfonic acid results in increased expression of SELE protein] CTD PMID:15821759 NCBI chr13:76,402,841...76,412,741
Ensembl chr13:76,403,304...76,412,741 		JBrowse link
G Selp selectin P multiple interactions ISO zileuton inhibits the reaction [dinitrobenzenesulfonic acid results in increased expression of SELP protein]
zileuton inhibits the reaction [N-Formylmethionine Leucyl-Phenylalanine results in increased expression of SELP protein]		 CTD PMID:11116075 PMID:15821759 NCBI chr13:76,476,229...76,511,846
Ensembl chr13:76,476,295...76,511,845 		JBrowse link
G Sox9 SRY-box transcription factor 9 increases expression ISO zileuton results in increased expression of SOX9 mRNA CTD PMID:19544365 NCBI chr10:97,806,485...97,811,994
Ensembl chr10:97,806,485...97,811,994 		JBrowse link
G Tjp1 tight junction protein 1 multiple interactions ISO zileuton inhibits the reaction [dinitrobenzenesulfonic acid affects the localization of TJP1 protein] CTD PMID:16670640 NCBI chr 1:118,849,838...119,094,492
Ensembl chr 1:118,849,838...119,094,432 		JBrowse link
G Tnf tumor necrosis factor affects expression
multiple interactions		 ISO zileuton affects the expression of TNF protein
zileuton inhibits the reaction [Bleomycin results in increased expression of TNF protein]
zileuton inhibits the reaction [Endotoxins results in increased expression of TNF protein]; zileuton inhibits the reaction [Leukotriene D4 results in increased secretion of TNF protein]		 CTD PMID:7496871 PMID:17118201 PMID:18059327 PMID:19118273 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Vcam1 vascular cell adhesion molecule 1 multiple interactions ISO zileuton inhibits the reaction [dinitrobenzenesulfonic acid results in increased expression of VCAM1 protein] CTD PMID:15821759 NCBI chr 2:204,038,120...204,057,852
Ensembl chr 2:204,038,114...204,057,958 		JBrowse link
Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 19921
    role 19896
      biological role 19894
        inhibitor 18933
          ferroptosis inhibitor 8051
            zileuton 47
Path 2
Term Annotations click to browse term
  CHEBI ontology 19921
    subatomic particle 19919
      composite particle 19919
        hadron 19919
          baryon 19919
            nucleon 19919
              atomic nucleus 19919
                atom 19919
                  main group element atom 19867
                    p-block element atom 19867
                      carbon group element atom 19812
                        carbon atom 19807
                          organic molecular entity 19807
                            organic group 18971
                              organic divalent group 18952
                                organodiyl group 18952
                                  carbonyl group 18905
                                    carbonyl compound 18905
                                      carboxylic acid 18622
                                        carboacyl group 17704
                                          univalent carboacyl group 17704
                                            carbamoyl group 17550
                                              carboxamide 17550
                                                monocarboxylic acid amide 15653
                                                  urea 5564
                                                    ureas 5562
                                                      zileuton 47
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