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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:3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid
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Accession:CHEBI:75390 term browser browse the term
Definition:A member of the class of indoles that is 1H-indole substituted by a isopropyl group at position 5, a tert-butylsulfanediyl group at position 3, a 4-chlorobenzyl group at position 1 and a 2-carboxy-2-methylpropyl group at position 2. It acts as an inhibitor of arachidonate 5-lipoxygenase.
Synonyms:related_synonym: 3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid;   3-[3-tert-butylsulfanyl-1-[(4-chlorophenyl)methyl]-5-propan-2-ylindol-2-yl]-2,2-dimethylpropanoic acid;   Formula=C27H34ClNO2S;   InChI=1S/C27H34ClNO2S/c1-17(2)19-10-13-22-21(14-19)24(32-26(3,4)5)23(15-27(6,7)25(30)31)29(22)16-18-8-11-20(28)12-9-18/h8-14,17H,15-16H2,1-7H3,(H,30,31);   InChIKey=QAOAOVKBIIKRNL-UHFFFAOYSA-N;   MK886;   SMILES=CC(C)c1ccc2n(Cc3ccc(Cl)cc3)c(CC(C)(C)C(O)=O)c(SC(C)(C)C)c2c1
 xref: LINCS:LSM-37008
 xref_mesh: MESH:C060893
 xref: PMID:12080072;   PMID:19862483;   PMID:22962275;   PMID:23261452;   PMID:23305233;   Patent:US5081138;   Reaxys:7449132


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3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcd2 ATP binding cassette subfamily D member 2 increases expression ISO MK-886 results in increased expression of ABCD2 mRNA CTD PMID:18292206 NCBI chr 7:132,294,564...132,343,169
Ensembl chr 7:132,294,562...132,343,169
JBrowse link
G Acmsd aminocarboxymuconate semialdehyde decarboxylase multiple interactions EXP MK-886 inhibits the reaction [pirinixic acid results in decreased expression of ACMSD mRNA] CTD PMID:18320257 NCBI chr13:44,424,689...44,468,734
Ensembl chr13:44,424,689...44,468,734
JBrowse link
G Acox1 acyl-CoA oxidase 1 multiple interactions
increases expression
EXP
ISO
MK-886 inhibits the reaction [pirinixic acid results in increased expression of ACOX1 mRNA]
MK-886 results in increased expression of ACOX1 mRNA
CTD PMID:18292206, PMID:18320257 NCBI chr10:104,724,534...104,748,003
Ensembl chr10:104,722,958...104,748,050
JBrowse link
G Acta2 actin alpha 2, smooth muscle multiple interactions ISO MK-886 inhibits the reaction [Arsenic Trioxide results in increased expression of ACTA2 protein] CTD PMID:30677399 NCBI chr 1:252,537,614...252,550,394
Ensembl chr 1:252,537,615...252,550,394
JBrowse link
G Alox5 arachidonate 5-lipoxygenase multiple interactions
decreases activity
ISO
EXP
MK-886 inhibits the reaction [ALOX5 protein results in increased metabolism of Hydroxyeicosatetraenoic Acids metabolite]; MK-886 inhibits the reaction [Nicotine results in increased expression of ALOX5 protein]
MK-886 results in decreased activity of ALOX5 protein
EPHX2 gene mutant form promotes the reaction [MK-886 inhibits the reaction [Lipopolysaccharides results in increased expression of ALOX5 protein]]; MK-886 inhibits the reaction [Lipopolysaccharides results in increased expression of ALOX5 protein]
CTD PMID:9445378, PMID:11861792, PMID:14726295, PMID:19896470, PMID:20061081 NCBI chr 4:148,398,004...148,446,308
Ensembl chr 4:148,398,892...148,446,303
JBrowse link
G Alox5ap arachidonate 5-lipoxygenase activating protein multiple interactions
decreases activity
ISO
EXP
[MK-886 results in decreased activity of ALOX5AP protein] which results in decreased abundance of Leukotriene C4; MK-886 binds to and results in decreased activity of ALOX5AP protein; MK-886 inhibits the reaction [ALOX5AP protein results in increased susceptibility to [Histamine results in increased abundance of Leukotriene B4]] CTD PMID:7990266, PMID:8058773, PMID:8666909, PMID:9113110, PMID:9609743, PMID:9850156, PMID:12629151 NCBI chr12:6,854,930...6,879,112
Ensembl chr12:6,854,920...6,879,154
JBrowse link
G Apoa1 apolipoprotein A1 multiple interactions
decreases expression
ISO MK-886 inhibits the reaction [TNF protein results in decreased expression of APOA1 mRNA]
MK-886 results in decreased expression of APOA1 protein
CTD PMID:19883121 NCBI chr 8:50,525,091...50,526,875
Ensembl chr 8:50,525,091...50,526,875
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in decreased expression of BAX protein] CTD PMID:20061081 NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of BCL2 protein] CTD PMID:20061081 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in decreased expression of CASP3 protein] CTD PMID:20061081 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions EXP [13-hydroperoxy-9,11-octadecadienoic acid co-treated with MK-886] results in increased expression of CCL2 mRNA; [13-hydroperoxy-9,11-octadecadienoic acid co-treated with MK-886] results in increased expression of CCL2 protein CTD PMID:22135674 NCBI chr10:69,412,065...69,413,863
Ensembl chr10:69,412,017...69,413,870
JBrowse link
G Ccnd1 cyclin D1 multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of CCND1 mRNA]; MK-886 inhibits the reaction [Nicotine results in increased expression of CCND1 protein] CTD PMID:20061081 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Ccne1 cyclin E1 multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of CCNE1 protein] CTD PMID:20061081 NCBI chr 1:94,485,830...94,495,112
Ensembl chr 1:94,485,832...94,494,980
JBrowse link
G Cdh1 cadherin 1 multiple interactions ISO [MK-886 binds to and results in decreased activity of PPARA protein] inhibits the reaction [perfluorooctanoic acid results in decreased expression of CDH1 protein]; MK-886 inhibits the reaction [Nicotine results in decreased expression of CDH1 mRNA] CTD PMID:20061081, PMID:23978332 NCBI chr19:38,768,467...38,838,395
Ensembl chr19:38,768,467...38,838,395
JBrowse link
G Ctnnb1 catenin beta 1 multiple interactions ISO [MK-886 binds to and results in decreased activity of PPARA protein] inhibits the reaction [perfluorooctanoic acid results in decreased expression of CTNNB1 protein] CTD PMID:23978332 NCBI chr 8:129,601,511...129,628,378
Ensembl chr 8:129,617,812...129,627,372
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions ISO MK-886 promotes the reaction [Dronabinol results in increased expression of CYP1A1 mRNA] CTD PMID:25291031 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G E2f1 E2F transcription factor 1 multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of E2F1 protein] CTD PMID:20061081 NCBI chr 3:150,062,895...150,073,721
Ensembl chr 3:150,047,826...150,073,721
JBrowse link
G Egr1 early growth response 1 multiple interactions EXP [13-hydroperoxy-9,11-octadecadienoic acid co-treated with MK-886] results in increased expression of EGR1 mRNA; [13-hydroperoxy-9,11-octadecadienoic acid co-treated with MK-886] results in increased expression of EGR1 protein CTD PMID:22135674 NCBI chr18:27,657,903...27,660,101
Ensembl chr18:27,657,628...27,661,429
JBrowse link
G Ephx2 epoxide hydrolase 2 multiple interactions ISO EPHX2 gene mutant form promotes the reaction [[Lipopolysaccharides co-treated with MK-886] results in decreased abundance of 11,12-dihydroxyeicosatrienoic acid]; EPHX2 gene mutant form promotes the reaction [[Lipopolysaccharides co-treated with MK-886] results in decreased abundance of 14,15-dihydroxyeicosatrienoic acid]; EPHX2 gene mutant form promotes the reaction [MK-886 inhibits the reaction [Lipopolysaccharides results in increased abundance of 5-hydroxy-6,8,11,14-eicosatetraenoic acid]]; EPHX2 gene mutant form promotes the reaction [MK-886 inhibits the reaction [Lipopolysaccharides results in increased expression of ALOX5 protein]]; MK-886 promotes the reaction [EPHX2 gene mutant form results in decreased susceptibility to Lipopolysaccharides] CTD PMID:19896470 NCBI chr15:42,757,241...42,794,211
Ensembl chr15:42,757,235...42,794,279
JBrowse link
G F3 coagulation factor III, tissue factor multiple interactions ISO MK-886 inhibits the reaction [3-((O-6-deoxymannopyranosyl-1-2-O-(xylopyranosyl-1-3)arabinopyranosyl)oxy)-21-glucopyranosyloxy-20-hydroxydammar-24-en-19-al inhibits the reaction [Lipopolysaccharides results in increased activity of F3 protein]]; MK-886 inhibits the reaction [pirinixic acid inhibits the reaction [Lipopolysaccharides results in increased activity of F3 protein]] CTD PMID:17141290 NCBI chr 2:225,310,686...225,322,281
Ensembl chr 2:225,310,624...225,322,272
JBrowse link
G Fa2h fatty acid 2-hydroxylase multiple interactions ISO MK-886 inhibits the reaction [Dronabinol results in increased expression of FA2H mRNA]; MK-886 promotes the reaction [Dronabinol results in increased expression of FA2H mRNA] CTD PMID:23535410, PMID:25291031 NCBI chr19:43,545,380...43,596,788
Ensembl chr19:43,545,378...43,596,801
JBrowse link
G Il10 interleukin 10 multiple interactions ISO MK-886 inhibits the reaction [Zymosan results in increased secretion of IL10 protein] CTD PMID:16313356 NCBI chr13:47,738,933...47,743,392
Ensembl chr13:47,739,526...47,743,392
JBrowse link
G Il6 interleukin 6 multiple interactions ISO MK-886 promotes the reaction [Lipopolysaccharides results in increased secretion of IL6 protein] CTD PMID:19896470 NCBI chr 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Lpl lipoprotein lipase multiple interactions ISO MK-886 inhibits the reaction [mangiferin results in increased activity of LPL protein]; MK-886 inhibits the reaction [mangiferin results in increased expression of LPL mRNA]; MK-886 inhibits the reaction [Plant Extracts results in increased activity of LPL protein]; MK-886 inhibits the reaction [Plant Extracts results in increased expression of LPL mRNA] CTD PMID:15975614 NCBI chr16:22,537,687...22,561,487
Ensembl chr16:22,537,056...22,561,496
JBrowse link
G Ltb4r leukotriene B4 receptor multiple interactions EXP MK-886 binds to and results in decreased activity of LTB4R protein; MK-886 inhibits the reaction [LTB4R protein results in increased susceptibility to Formaldehyde] CTD PMID:19835937 NCBI chr15:34,449,299...34,453,352
Ensembl chr15:34,452,116...34,453,171
JBrowse link
G Map1lc3b microtubule-associated protein 1 light chain 3 beta multiple interactions ISO MK-886 inhibits the reaction [Arsenic Trioxide results in increased cleavage of MAP1LC3B protein] CTD PMID:30677399 NCBI chr19:53,635,449...53,643,970
Ensembl chr19:53,629,779...53,646,058
JBrowse link
G Mmp7 matrix metallopeptidase 7 multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of MMP7 mRNA] CTD PMID:20061081 NCBI chr 8:5,893,253...5,900,965
Ensembl chr 8:5,893,249...5,901,049
JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of MMP9 mRNA]
MK-886 inhibits the reaction [4-hydroxy-2-nonenal results in increased expression of MMP9 protein]
CTD PMID:19837106, PMID:20061081 NCBI chr 3:161,413,410...161,421,473
Ensembl chr 3:161,413,298...161,421,520
JBrowse link
G Nos3 nitric oxide synthase 3 multiple interactions ISO [fulvestrant co-treated with MK-886] inhibits the reaction [resveratrol results in increased expression of NOS3 mRNA] CTD PMID:21791144 NCBI chr 4:7,321,908...7,342,404
Ensembl chr 4:7,320,668...7,342,410
JBrowse link
G Pdk4 pyruvate dehydrogenase kinase 4 multiple interactions ISO MK-886 inhibits the reaction [Bezafibrate results in increased expression of PDK4 mRNA]; MK-886 inhibits the reaction [Bezafibrate results in increased expression of PDK4 protein] CTD PMID:19683050 NCBI chr 4:30,546,772...30,556,774
Ensembl chr 4:30,546,664...30,556,814
JBrowse link
G Pla2g4a phospholipase A2 group IVA multiple interactions ISO MK-886 inhibits the reaction [Histamine results in increased expression of PLA2G4A mRNA] CTD PMID:9609743 NCBI chr13:67,062,252...67,206,688
Ensembl chr13:66,988,937...67,206,693
JBrowse link
G Plau plasminogen activator, urokinase multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of PLAU mRNA] CTD PMID:20061081 NCBI chr15:3,644,296...3,650,765
Ensembl chr15:3,644,769...3,650,819
JBrowse link
G Plaur plasminogen activator, urokinase receptor multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of PLAUR mRNA] CTD PMID:20061081 NCBI chr 1:81,328,171...81,344,954
Ensembl chr 1:81,328,183...81,344,708
JBrowse link
G Poli DNA polymerase iota decreases activity ISO MK-886 results in decreased activity of POLI protein CTD PMID:23305233 NCBI chr18:65,749,107...65,768,805
Ensembl chr18:65,748,908...65,768,781
JBrowse link
G Polk DNA polymerase kappa decreases activity ISO MK-886 results in decreased activity of POLK protein CTD PMID:23305233 NCBI chr 2:27,305,718...27,364,906
Ensembl chr 2:27,305,728...27,364,906
JBrowse link
G Polm DNA polymerase mu decreases activity ISO MK-886 results in decreased activity of POLM protein CTD PMID:23305233 NCBI chr14:86,069,378...86,079,327
Ensembl chr14:86,069,016...86,078,954
JBrowse link
G Ppara peroxisome proliferator activated receptor alpha multiple interactions
increases expression
ISO
EXP
[MK-886 binds to and results in decreased activity of PPARA protein] inhibits the reaction [perfluorooctanoic acid results in decreased expression of CDH1 protein]; [MK-886 binds to and results in decreased activity of PPARA protein] inhibits the reaction [perfluorooctanoic acid results in decreased expression of CTNNB1 protein]; [MK-886 binds to and results in decreased activity of PPARA protein] which results in decreased susceptibility to perfluorooctanoic acid; MK-886 binds to and results in decreased activity of PPARA protein; MK-886 inhibits the reaction [Arsenic Trioxide results in increased expression of PPARA protein]; MK-886 inhibits the reaction [Bezafibrate results in increased expression of PPARA mRNA]; MK-886 inhibits the reaction [mangiferin results in increased activity of PPARA protein]; MK-886 inhibits the reaction [perfluorooctane sulfonic acid results in increased activity of PPARA protein]; MK-886 inhibits the reaction [perfluorooctanoic acid results in increased activity of PPARA protein]; MK-886 inhibits the reaction [Plant Extracts results in increased activity of PPARA protein]; MK-886 promotes the reaction [Dronabinol results in increased expression of PPARA mRNA]
[MK-886 binds to and results in decreased activity of PPARA protein] which results in decreased susceptibility to palmidrol analog; MK-886 binds to and results in decreased activity of PPARA protein
MK-886 binds to and results in decreased activity of PPARA protein; MK-886 inhibits the reaction [perfluorooctane sulfonic acid results in increased activity of PPARA protein]; MK-886 inhibits the reaction [perfluorooctanoic acid results in increased activity of PPARA protein]
MK-886 results in increased expression of PPARA mRNA
CTD PMID:15899809, PMID:15975614, PMID:17047030, PMID:17558434, PMID:18292206, PMID:18320257, PMID:19403796, PMID:19683050, PMID:19883121, PMID:23978332, PMID:25291031, PMID:30677399 NCBI chr 7:126,618,872...126,687,282
Ensembl chr 7:126,619,196...126,681,752
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions
increases expression
increases activity
affects localization
ISO [Indomethacin co-treated with MK-886] affects the localization of PPARG protein; Indomethacin promotes the reaction [MK-886 results in increased activity of PPARG protein]
MK-886 results in increased expression of PPARG mRNA
MK-886 affects the localization of PPARG protein
CTD PMID:15899809 NCBI chr 4:147,274,055...147,399,383
Ensembl chr 4:147,274,107...147,399,380
JBrowse link
G Ptges prostaglandin E synthase decreases activity ISO MK-886 results in decreased activity of PTGES protein CTD PMID:20933508, PMID:25451575 NCBI chr 3:9,727,408...9,738,752
Ensembl chr 3:9,727,408...9,738,752
JBrowse link
G Rb1 RB transcriptional corepressor 1 multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of RB1 protein modified form] CTD PMID:20061081 NCBI chr15:55,081,582...55,209,060
Ensembl chr15:55,083,140...55,209,342
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO MK-886 inhibits the reaction [pirinixic acid results in decreased phosphorylation of RELA protein] CTD PMID:17371993 NCBI chr 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
JBrowse link
G Rxra retinoid X receptor alpha increases expression
multiple interactions
ISO MK-886 results in increased expression of RXRA mRNA
[MK-886 co-treated with Indomethacin] results in increased expression of RXRA mRNA
CTD PMID:15899809 NCBI chr 3:6,272,560...6,295,354
Ensembl chr 3:6,211,789...6,295,908
JBrowse link
G S100b S100 calcium binding protein B multiple interactions EXP MK-886 inhibits the reaction [pirinixic acid affects the expression of S100B protein] CTD PMID:16863991 NCBI chr20:13,130,633...13,142,856
Ensembl chr20:13,130,636...13,142,856
JBrowse link
G Selp selectin P multiple interactions ISO MK-886 inhibits the reaction [N-Formylmethionine Leucyl-Phenylalanine results in increased expression of SELP protein] CTD PMID:11116075 NCBI chr13:82,428,914...82,464,629
Ensembl chr13:82,429,063...82,464,628
JBrowse link
G Sod2 superoxide dismutase 2 multiple interactions ISO MK-886 promotes the reaction [SOD2 gene mutant form results in decreased abundance of Adenosine Triphosphate]; MK-886 promotes the reaction [SOD2 gene mutant form results in increased abundance of Lactic Acid] CTD PMID:25362851 NCBI chr 1:47,914,757...47,921,587
Ensembl chr 1:47,914,759...47,921,587
JBrowse link
G Tfdp1 transcription factor Dp-1 multiple interactions ISO MK-886 inhibits the reaction [Nicotine results in increased expression of TFDP1 protein] CTD PMID:20061081 NCBI chr16:81,088,642...81,127,244
Ensembl chr16:81,089,292...81,127,257
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO [Ovalbumin co-treated with MK-886] results in increased expression of TNF protein; MK-886 inhibits the reaction [TNF protein results in decreased expression of APOA1 mRNA]; monascin inhibits the reaction [[Ovalbumin co-treated with MK-886] results in increased expression of TNF protein] CTD PMID:19883121, PMID:22381257 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Ucp2 uncoupling protein 2 multiple interactions EXP MK-886 inhibits the reaction [pirinixic acid results in increased expression of UCP2 mRNA]; MK-886 inhibits the reaction [pirinixic acid results in increased expression of UCP2 protein] CTD PMID:16782780 NCBI chr 1:165,506,375...165,512,744
Ensembl chr 1:165,506,361...165,512,744
JBrowse link

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  CHEBI ontology 19816
    role 19764
      application 19426
        pharmaceutical 19301
          drug 19301
            antineoplastic agent 17001
              3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid 48
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  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic molecule 19522
                              organic cyclic compound 19320
                                organic heterocyclic compound 18432
                                  organic heteropolycyclic compound 17844
                                    organic heterobicyclic compound 16765
                                      benzopyrrole 9530
                                        indoles 9198
                                          3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid 48
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.