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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 chr12:39,531,025...39,619,803
Ensembl chr12:39,550,033...39,619,803
JBrowse link
G ACMSD aminocarboxymuconate semialdehyde decarboxylase multiple interactions ISO MK-886 inhibits the reaction [pirinixic acid results in decreased expression of ACMSD mRNA] CTD PMID:18320257 NCBI chr 2:134,838,616...134,902,034
Ensembl chr 2:134,838,616...134,902,034
JBrowse link
G ACOX1 acyl-CoA oxidase 1 multiple interactions
increases expression
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 chr17:75,941,507...75,979,166
Ensembl chr17:75,941,507...75,979,177
JBrowse link
G ACTA2 actin alpha 2, smooth muscle multiple interactions EXP MK-886 inhibits the reaction [Arsenic Trioxide results in increased expression of ACTA2 protein] CTD PMID:30677399 NCBI chr10:88,935,074...88,991,337
Ensembl chr10:88,934,822...88,991,339
JBrowse link
G ALOX5 arachidonate 5-lipoxygenase multiple interactions
decreases activity
EXP
ISO
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 chr10:45,374,216...45,446,117
Ensembl chr10:45,374,176...45,446,119
JBrowse link
G ALOX5AP arachidonate 5-lipoxygenase activating protein multiple interactions
decreases activity
EXP
ISO
[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 chr13:30,713,485...30,764,426
Ensembl chr13:30,713,478...30,764,426
JBrowse link
G APOA1 apolipoprotein A1 multiple interactions
decreases expression
EXP 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 chr11:116,835,751...116,837,950
Ensembl chr11:116,835,751...116,837,622
JBrowse link
G BAX BCL2 associated X, apoptosis regulator multiple interactions EXP MK-886 inhibits the reaction [Nicotine results in decreased expression of BAX protein] CTD PMID:20061081 NCBI chr19:48,954,875...48,961,798
Ensembl chr19:48,954,815...48,961,798
JBrowse link
G BCL2 BCL2 apoptosis regulator multiple interactions EXP MK-886 inhibits the reaction [Nicotine results in increased expression of BCL2 protein] CTD PMID:20061081 NCBI chr18:63,123,346...63,320,090
Ensembl chr18:63,123,346...63,320,128
JBrowse link
G CASP3 caspase 3 multiple interactions
increases activity
EXP MK-886 inhibits the reaction [Nicotine results in decreased expression of CASP3 protein]
MK-886 results in increased activity of CASP3 protein
CTD PMID:20061081 PMID:22308955 NCBI chr 4:184,627,696...184,649,447
Ensembl chr 4:184,627,696...184,650,062
JBrowse link
G CCL2 C-C motif chemokine ligand 2 multiple interactions ISO [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 chr17:34,255,285...34,257,203
Ensembl chr17:34,255,274...34,257,208
JBrowse link
G CCND1 cyclin D1 multiple interactions EXP 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 chr11:69,641,156...69,654,474
Ensembl chr11:69,641,156...69,654,474
JBrowse link
G CCNE1 cyclin E1 multiple interactions EXP MK-886 inhibits the reaction [Nicotine results in increased expression of CCNE1 protein] CTD PMID:20061081 NCBI chr19:29,811,991...29,824,312
Ensembl chr19:29,811,991...29,824,312
JBrowse link
G CDH1 cadherin 1 multiple interactions 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 inhibits the reaction [Nicotine results in decreased expression of CDH1 mRNA] CTD PMID:20061081 PMID:23978332 NCBI chr16:68,737,292...68,835,537
Ensembl chr16:68,737,292...68,835,537
JBrowse link
G CTNNB1 catenin beta 1 multiple interactions EXP [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 3:41,199,505...41,240,443
Ensembl chr 3:41,194,741...41,260,096
JBrowse link
G CXCL8 C-X-C motif chemokine ligand 8 multiple interactions EXP MK-886 inhibits the reaction [Histamine results in increased expression of CXCL8 mRNA]; MK-886 inhibits the reaction [Histamine results in increased expression of CXCL8 protein] CTD PMID:9609743 NCBI chr 4:73,740,569...73,743,716
Ensembl chr 4:73,740,519...73,743,716
JBrowse link
G CYP1A1 cytochrome P450 family 1 subfamily A member 1 multiple interactions EXP MK-886 promotes the reaction [Dronabinol results in increased expression of CYP1A1 mRNA] CTD PMID:25291031 NCBI chr15:74,719,542...74,725,528
Ensembl chr15:74,719,542...74,725,536
JBrowse link
G E2F1 E2F transcription factor 1 multiple interactions EXP MK-886 inhibits the reaction [Nicotine results in increased expression of E2F1 protein] CTD PMID:20061081 NCBI chr20:33,675,477...33,686,385
Ensembl chr20:33,675,477...33,686,385
JBrowse link
G EGR1 early growth response 1 multiple interactions ISO [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 chr 5:138,465,479...138,469,303
Ensembl chr 5:138,465,479...138,469,303
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 chr 8:27,491,143...27,548,626
Ensembl chr 8:27,490,781...27,545,564
JBrowse link
G F3 coagulation factor III, tissue factor multiple interactions EXP 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 1:94,529,173...94,541,759
Ensembl chr 1:94,529,173...94,541,759
JBrowse link
G FA2H fatty acid 2-hydroxylase multiple interactions EXP 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 chr16:74,712,969...74,774,820
Ensembl chr16:74,712,955...74,774,831
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 chr 1:206,767,602...206,772,494
Ensembl chr 1:206,767,602...206,774,541
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 7:22,727,200...22,731,998
Ensembl chr 7:22,725,884...22,732,002
JBrowse link
G LPL lipoprotein lipase multiple interactions EXP 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 chr 8:19,939,253...19,967,259
Ensembl chr 8:19,901,717...19,967,259
JBrowse link
G LTB4R leukotriene B4 receptor multiple interactions ISO 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 chr14:24,311,502...24,318,036
Ensembl chr14:24,311,450...24,318,036
JBrowse link
G MAP1LC3B microtubule associated protein 1 light chain 3 beta multiple interactions EXP MK-886 inhibits the reaction [Arsenic Trioxide results in increased cleavage of MAP1LC3B protein] CTD PMID:30677399 NCBI chr16:87,392,336...87,404,774
Ensembl chr16:87,383,953...87,404,779
JBrowse link
G MMP7 matrix metallopeptidase 7 multiple interactions EXP MK-886 inhibits the reaction [Nicotine results in increased expression of MMP7 mRNA] CTD PMID:20061081 NCBI chr11:102,520,508...102,530,747
Ensembl chr11:102,520,508...102,530,750
JBrowse link
G MMP9 matrix metallopeptidase 9 multiple interactions EXP
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 chr20:46,008,908...46,016,561
Ensembl chr20:46,008,908...46,016,561
JBrowse link
G NOS3 nitric oxide synthase 3 multiple interactions EXP [fulvestrant co-treated with MK-886] inhibits the reaction [resveratrol results in increased expression of NOS3 mRNA] CTD PMID:21791144 NCBI chr 7:150,991,017...151,014,588
Ensembl chr 7:150,991,017...151,014,588
JBrowse link
G PDK4 pyruvate dehydrogenase kinase 4 multiple interactions EXP 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 7:95,583,499...95,596,516
Ensembl chr 7:95,583,499...95,596,516
JBrowse link
G PLA2G4A phospholipase A2 group IVA multiple interactions EXP MK-886 inhibits the reaction [Histamine results in increased expression of PLA2G4A mRNA] CTD PMID:9609743 NCBI chr 1:186,828,949...186,988,981
Ensembl chr 1:186,828,949...186,988,981
JBrowse link
G PLAU plasminogen activator, urokinase multiple interactions EXP MK-886 inhibits the reaction [Nicotine results in increased expression of PLAU mRNA] CTD PMID:20061081 NCBI chr10:73,909,164...73,917,494
Ensembl chr10:73,909,177...73,917,496
JBrowse link
G PLAUR plasminogen activator, urokinase receptor multiple interactions EXP MK-886 inhibits the reaction [Nicotine results in increased expression of PLAUR mRNA] CTD PMID:20061081 NCBI chr19:43,646,095...43,670,169
Ensembl chr19:43,646,095...43,670,547
JBrowse link
G POLI DNA polymerase iota decreases activity EXP MK-886 results in decreased activity of POLI protein CTD PMID:23305233 NCBI chr18:54,269,479...54,321,266
Ensembl chr18:54,269,517...54,321,266
JBrowse link
G POLK DNA polymerase kappa decreases activity EXP MK-886 results in decreased activity of POLK protein CTD PMID:23305233 NCBI chr 5:75,510,774...75,609,991
Ensembl chr 5:75,511,845...75,609,991
JBrowse link
G POLM DNA polymerase mu decreases activity EXP MK-886 results in decreased activity of POLM protein CTD PMID:23305233 NCBI chr 7:44,072,062...44,082,530
Ensembl chr 7:44,072,062...44,082,530
JBrowse link
G PPARA peroxisome proliferator activated receptor alpha multiple interactions
increases expression
EXP
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 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 chr22:46,150,526...46,243,756
Ensembl chr22:46,150,521...46,243,755
JBrowse link
G PPARG peroxisome proliferator activated receptor gamma multiple interactions
increases expression
increases activity
affects localization
EXP [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 3:12,287,368...12,434,344
Ensembl chr 3:12,287,368...12,434,356
JBrowse link
G PTGES prostaglandin E synthase decreases activity EXP MK-886 results in decreased activity of PTGES protein CTD PMID:20933508 PMID:25451575 NCBI chr 9:129,738,349...129,753,042
Ensembl chr 9:129,738,331...129,753,042
JBrowse link
G RB1 RB transcriptional corepressor 1 multiple interactions EXP MK-886 inhibits the reaction [Nicotine results in increased expression of RB1 protein modified form] CTD PMID:20061081 NCBI chr13:48,303,751...48,481,890
Ensembl chr13:48,303,744...48,599,436
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 chr11:65,653,601...65,663,857
Ensembl chr11:65,653,599...65,663,090
JBrowse link
G RXRA retinoid X receptor alpha increases expression
multiple interactions
EXP 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 9:134,326,455...134,440,585
Ensembl chr 9:134,317,098...134,440,585
JBrowse link
G S100B S100 calcium binding protein B multiple interactions ISO MK-886 inhibits the reaction [pirinixic acid affects the expression of S100B protein] CTD PMID:16863991 NCBI chr21:46,598,604...46,605,082
Ensembl chr21:46,598,604...46,605,208
JBrowse link
G SELP selectin P multiple interactions EXP MK-886 inhibits the reaction [N-Formylmethionine Leucyl-Phenylalanine results in increased expression of SELP protein] CTD PMID:11116075 NCBI chr 1:169,588,849...169,630,124
Ensembl chr 1:169,588,849...169,630,193
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 6:159,669,069...159,762,281
Ensembl chr 6:159,669,069...159,762,529
JBrowse link
G TFDP1 transcription factor Dp-1 multiple interactions EXP MK-886 inhibits the reaction [Nicotine results in increased expression of TFDP1 protein] CTD PMID:20061081 NCBI chr13:113,584,688...113,641,473
Ensembl chr13:113,584,721...113,641,473
JBrowse link
G TNF tumor necrosis factor multiple interactions EXP [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 chr 6:31,575,565...31,578,336
Ensembl chr 6:31,575,565...31,578,336
JBrowse link
G UCP2 uncoupling protein 2 multiple interactions ISO 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 chr11:73,974,672...73,983,202
Ensembl chr11:73,974,672...73,982,843
JBrowse link

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  CHEBI ontology 26050
    role 25966
      application 25188
        pharmaceutical 24562
          drug 24559
            antineoplastic agent 20861
              3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid 49
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  CHEBI ontology 26050
    subatomic particle 26025
      composite particle 26025
        hadron 26025
          baryon 26025
            nucleon 26025
              atomic nucleus 26025
                atom 26025
                  main group element atom 25850
                    p-block element atom 25850
                      carbon group element atom 25447
                        carbon atom 25405
                          organic molecular entity 25405
                            organic molecule 25233
                              organic cyclic compound 24287
                                organic heterocyclic compound 22334
                                  organic heteropolycyclic compound 21328
                                    organic heterobicyclic compound 18570
                                      benzopyrrole 10285
                                        indoles 9962
                                          3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid 49
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