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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 7:122,263,034...122,311,642
Ensembl chr 7:122,263,032...122,311,642
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 chr13:39,200,486...39,244,337
Ensembl chr13:39,200,314...39,245,209
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 chr10:101,406,197...101,431,242
Ensembl chr10:101,406,197...101,431,232
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 1:231,746,527...231,759,307
Ensembl chr 1:231,746,548...231,759,554
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 4:149,531,329...149,578,696
Ensembl chr 4:149,531,515...149,578,743
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 More... NCBI chr12:5,748,941...5,772,986
Ensembl chr12:5,748,944...5,772,986
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 8:46,527,251...46,529,035
Ensembl chr 8:46,527,144...46,529,035
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 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
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 chr13:22,689,783...22,853,920 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 chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
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 chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226
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 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602
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 1:90,781,947...90,791,188
Ensembl chr 1:90,781,949...90,791,101
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 chr19:34,492,371...34,561,775
Ensembl chr19:34,492,371...34,561,775
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 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111
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 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125
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 3:143,064,535...143,075,362 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 chr18:26,463,333...26,465,531
Ensembl chr18:26,462,981...26,466,766
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 chr15:40,289,901...40,327,632
Ensembl chr15:40,289,902...40,327,615
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 2:209,827,061...209,838,666
Ensembl chr 2:209,826,959...209,838,668
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 chr19:39,312,904...39,364,153
Ensembl chr19:39,312,906...39,364,153
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 chr13:42,472,625...42,477,308
Ensembl chr13:42,472,839...42,477,313
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 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
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 chr16:20,830,055...20,853,855
Ensembl chr16:20,829,465...20,855,249
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 chr15:29,263,126...29,265,716 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 chr19:49,665,795...49,673,655
Ensembl chr19:49,665,791...49,677,690
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 8:4,848,186...4,855,908
Ensembl chr 8:4,848,186...4,855,902
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 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
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 4:10,793,834...10,814,170
Ensembl chr 4:10,793,834...10,814,166
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 4:33,591,796...33,601,798
Ensembl chr 4:33,589,799...33,601,850
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 chr13:61,877,818...62,022,261
Ensembl chr13:61,877,813...62,022,266
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 chr15:3,456,230...3,462,732
Ensembl chr15:3,456,232...3,462,775
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 1:80,053,441...80,068,384
Ensembl chr 1:80,050,324...80,068,595
JBrowse link
G Poli DNA polymerase iota decreases activity ISO MK-886 results in decreased activity of POLI protein CTD PMID:23305233 NCBI chr18:64,116,774...64,134,373
Ensembl chr18:64,116,774...64,163,418
JBrowse link
G Polk DNA polymerase kappa decreases activity ISO MK-886 results in decreased activity of POLK protein CTD PMID:23305233 NCBI chr 2:27,822,228...27,882,331
Ensembl chr 2:27,822,679...27,882,313
JBrowse link
G Polm DNA polymerase mu decreases activity ISO MK-886 results in decreased activity of POLM protein CTD PMID:23305233 NCBI chr14:80,707,075...80,716,677
Ensembl chr14:80,706,345...80,717,086
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 More... NCBI chr 7:116,832,405...116,900,878
Ensembl chr 7:116,832,756...116,895,346
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 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468
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 3:14,177,892...14,189,236 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 chr15:48,371,295...48,502,473
Ensembl chr15:48,371,296...48,502,302
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 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
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 3:10,989,832...11,076,366
Ensembl chr 3:10,989,832...11,073,712
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 chr20:12,372,866...12,381,619
Ensembl chr20:12,372,881...12,394,743
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 chr13:76,476,229...76,511,846
Ensembl chr13:76,476,295...76,511,845
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 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189
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 chr16:76,162,040...76,200,871
Ensembl chr16:76,162,043...76,200,817
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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
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 1:154,839,242...154,845,612
Ensembl chr 1:154,839,209...154,845,611
JBrowse link

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  CHEBI ontology 19821
    role 19769
      application 19481
        pharmaceutical 19329
          drug 19329
            antineoplastic agent 17317
              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 19821
    subatomic particle 19819
      composite particle 19819
        hadron 19819
          baryon 19819
            nucleon 19819
              atomic nucleus 19819
                atom 19819
                  main group element atom 19716
                    p-block element atom 19716
                      carbon group element atom 19640
                        carbon atom 19630
                          organic molecular entity 19630
                            organic molecule 19569
                              organic cyclic compound 19360
                                organic heterocyclic compound 18591
                                  organic heteropolycyclic compound 18064
                                    organic heterobicyclic compound 16868
                                      benzopyrrole 9559
                                        indoles 9231
                                          3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid 48
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