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Ask your administrator if you think this is wrong. ====== Rotenone 0.07μM R08 exp431 ====== ==== Mechanism of Action ==== Inhibits complex I, blocks electron transfer from iron-sulfur centers to ubiquinone, generates ROS, also inhibits microtubule assembly * **<color #00a2e8>Class / Subclass 1:</color>** Organelle Function / Mitochondrial Inhibitor * **<color #00a2e8>Class / Subclass 2:</color>** Cell Cycle / Microtubule Poison ==== Technical Notes ==== <accordion collapsed='true'> <panel title='Compound References' collapsed='true'> * **<color #00a2e8>PubChem Name:</color>** %%Rotenone%% * **<color #00a2e8>Synonyms:</color>** N/A * **<color #00a2e8>CAS #:</color>** 83-79-4 * **<color #00a2e8>PubChem CID:</color>** [[https://pubchem.ncbi.nlm.nih.gov/compound/6758|6758]] * **<color #00a2e8>IUPAC:</color>** %%(1S,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one%% * **<color #00a2e8>INCHI Name:</color>** InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1 * **<color #00a2e8>INCHI Key:</color>** JUVIOZPCNVVQFO-HBGVWJBISA-N * **<color #00a2e8>Molecular Weight:</color>** 394.4 * **<color #00a2e8>Canonical SMILES:</color>** CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC * **<color #00a2e8>Isomeric SMILES:</color>** CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC * **<color #00a2e8>Molecular Formula:</color>** C23H22O6 {{:chemogenomics:structures:chem-0018.svg?nolink}} </panel> <panel title='Compound Supplier' collapsed='true'> * **<color #00a2e8>Supplier Name:</color>** Sigma-Aldrich * **<color #00a2e8>Catalog #:</color>** R8875 * **<color #00a2e8>Lot #:</color>** SLBG7568V </panel> <panel title='Compound Characterization' collapsed='true'> * **<color #00a2e8>HRMS (ESI-TOF) m/z:</color>** (M+H)+ Calcd for C23H22O6 395.14891; found 395.15075 </panel> <panel title='Dose Response Curve' collapsed='true'> * **<color #00a2e8>Platform ID:</color>** Rotenone * **<color #00a2e8>Min:</color>** 27.6098; **<color #00a2e8>Max:</color>** 94.6238 {{:chemogenomics:dose_response:dr_577.png?nolink&500 |}} \\ \\ \\ \\ |< 300px 100px 200px >| ^ IC ^ Concentration (µM) ^ | IC10 |0.0001 | | IC20 |0.0013 | | IC30 |0.0061 | | IC40 |0.0217 | | IC50 |0.0692 | | IC60 |0.2208 | | IC70 |0.7819 | | IC80 |3.6570 | | IC90 |37.2500 | \\ </panel> </accordion> ==== Screen Summary ==== * **<color #00a2e8>Round</color>**: 08 * **<color #00a2e8>Dose</color>**: 70nM * **<color #00a2e8>Days of incubation</color>**: 8 * **<color #00a2e8>Doublings</color>**: 2.9 * **<color #00a2e8>Numbers of reads</color>**: 16548653 ==== Screen Results ==== ^Sensitive/Resistant hits (FDR<0.05)^CRANKS^Score Plot^Top 30 Genes^Screen Similarity^Top 30 Sensitive GO terms^Top 30 Resistant GO terms^ |5/22|<color #e85500>[[https://files.tyerslab.com/files/public/chemogenomics/cranks/Rotenone_0.07uM_Round-8_exp431.txt|Scores]]</color>|<button type="primary" size="sm" modal="ScorePlot">View</button>|<button type="primary" size="sm" modal="modal_hits">View</button>|<button type="primary" size="sm" modal="modal_screen_similarity">View</button>|<button type="primary" size="sm" modal="modal_go_sensitive">View</button>|<button type="primary" size="sm" modal="modal_go_resistant">View</button>| <modal id='ScorePlot' size='lg' title='Rotenone 0.07μM R08 exp431'> {{:chemogenomics:cranks_plots:exp431.png?nolink}} </modal> <modal id="modal_hits" size="sm" title="Top 30 S/R Genes"> ^Gene^CRANKS Score^FDR^ |[[:human_genes:G:GOT1|GOT1]]|-4.52|<0.01| |[[:human_genes:S:SUCLG1|SUCLG1]]|-3.28|<0.01| |[[:human_genes:C:CHMP7|CHMP7]]|-2.93|<0.01| |[[:human_genes:A:ADSS|ADSS]]|-2.75|0.14| |[[:human_genes:A:ACAT1|ACAT1]]|-2.74|0.02| |[[:human_genes:M:MECR|MECR]]|-2.61|0.04| |[[:human_genes:T:TMEM161B|TMEM161B]]|-2.53|0.05| |[[:human_genes:T:TSC1|TSC1]]|-2.51|0.10| |[[:human_genes:N:NUDT5|NUDT5]]|-2.50|0.10| |[[:human_genes:H:HK1|HK1]]|-2.49|0.06| |[[:human_genes:E:ESPL1|ESPL1]]|-2.33|0.35| |[[:human_genes:G:GRPEL1|GRPEL1]]|-2.32|0.47| |[[:human_genes:M:MAN2C1|MAN2C1]]|-2.31|0.12| |[[:human_genes:A:AHCYL1|AHCYL1]]|-2.29|0.17| |[[:human_genes:S:SUCLA2|SUCLA2]]|-2.29|0.12| |[[:human_genes:C:CTR9|CTR9]]|-2.26|0.17| |[[:human_genes:E:EDF1|EDF1]]|-2.24|0.17| |[[:human_genes:P:PFKP|PFKP]]|-2.23|0.15| |[[:human_genes:S:SLC16A1|SLC16A1]]|-2.19|0.35| |[[:human_genes:G:GCDH|GCDH]]|-2.19|0.16| |[[:human_genes:D:DOPEY1|DOPEY1]]|-2.19|0.16| |[[:human_genes:A:ACACA|ACACA]]|-2.18|0.22| |[[:human_genes:C:CNOT2|CNOT2]]|-2.17|0.17| |[[:human_genes:P:PGP|PGP]]|-2.16|0.23| |[[:human_genes:L:LIPT1|LIPT1]]|-2.14|0.17| |[[:human_genes:E:EXOG|EXOG]]|-2.14|0.37| |[[:human_genes:D:DEPTOR|DEPTOR]]|-2.13|0.17| |[[:human_genes:S:SEPHS2|SEPHS2]]|-2.11|0.17| |[[:human_genes:S:SWI5|SWI5]]|-2.08|0.31| |[[:human_genes:R:RIC8A|RIC8A]]|-2.06|0.22| |[[:human_genes:R:RBM7|RBM7]]|2.27|0.11| |[[:human_genes:U:UGP2|UGP2]]|2.28|0.06| |[[:human_genes:P:PDHB|PDHB]]|2.29|0.06| |[[:human_genes:A:ACSL3|ACSL3]]|2.30|0.08| |[[:human_genes:S:SKIV2L|SKIV2L]]|2.31|0.10| |[[:human_genes:A:ATP5D|ATP5D]]|2.36|0.07| |[[:human_genes:B:BAK1|BAK1]]|2.36|0.04| |[[:human_genes:P:PMAIP1|PMAIP1]]|2.41|0.04| |[[:human_genes:C:CEPT1|CEPT1]]|2.44|0.03| |[[:human_genes:K:KMT2D|KMT2D]]|2.48|0.03| |[[:human_genes:P:PTDSS1|PTDSS1]]|2.50|0.03| |[[:human_genes:F:FDPS|FDPS]]|2.51|0.04| |[[:human_genes:E:ENY2|ENY2]]|2.52|0.04| |[[:human_genes:A:ASUN|ASUN]]|2.54|0.02| |[[:human_genes:G:GATC|GATC]]|2.54|0.02| |[[:human_genes:G:G6PD|G6PD]]|2.55|0.02| |[[:human_genes:R:RHOBTB1|RHOBTB1]]|2.55|0.02| |[[:human_genes:I:IKZF1|IKZF1]]|2.56|0.02| |[[:human_genes:M:METTL14|METTL14]]|2.57|0.10| |[[:human_genes:S:SHMT2|SHMT2]]|2.64|0.05| |[[:human_genes:P:PTPMT1|PTPMT1]]|2.66|0.07| |[[:human_genes:I:IPMK|IPMK]]|2.72|0.01| |[[:human_genes:M:MOCS3|MOCS3]]|2.78|0.03| |[[:human_genes:A:AGPAT1|AGPAT1]]|2.80|0.03| |[[:human_genes:P:PGM3|PGM3]]|3.01|<0.01| |[[:human_genes:H:HSD17B12|HSD17B12]]|3.05|0.02| |[[:human_genes:F:FASTKD5|FASTKD5]]|3.10|<0.01| |[[:human_genes:A:ATP5A1|ATP5A1]]|3.48|<0.01| |[[:human_genes:I:ITPK1|ITPK1]]|3.70|<0.01| |[[:human_genes:S:SLC25A51|SLC25A51]]|4.34|<0.01| </modal> <modal id="modal_screen_similarity" size="lg" title="Correlated Screens"> ^Screen^Correlation^Plot^ |[[:results:exp492|iCRT14 30μM R08 exp492]]|0.071|<button type="primary" size="small" modal="1">View</button>| |[[:results:exp532|TIC10 10μM R08 exp532]]|0.066|<button type="primary" size="small" modal="2">View</button>| |[[:results:exp439|QNZ 0.01μM R08 exp439]]|0.212|<button type="primary" size="small" modal="3">View</button>| |[[:results:exp48|Mubritinib 0.2μM R01 exp48]]|0.13|<button type="primary" size="small" modal="4">View</button>| |[[:results:exp65|Mubritinib 0.2μM R02 exp65]]|0.114|<button type="primary" size="small" modal="5">View</button>| |[[:results:exp241|QNZ 0.01μM R05 exp241]]|0.108|<button type="primary" size="small" modal="6">View</button>| |[[:results:exp380|NMS-873 0.07μM R07 exp380]]|0.104|<button type="primary" size="small" modal="7">View</button>| |[[:results:exp212|Phenformin 20μM R05 exp212]]|0.102|<button type="primary" size="small" modal="8">View</button>| |[[:results:exp447|Amiloride 100μM R08 exp447]]|0.085|<button type="primary" size="small" modal="9">View</button>| |[[:results:exp13|Chloramphenicol 20μM R00 exp13]]|0.076|<button type="primary" size="small" modal="10">View</button>| |[[:results:exp445|∆-9-Tetrahydrocannabinol 30μM R08 exp445]]|0.065|<button type="primary" size="small" modal="11">View</button>| |[[:results:exp143|Phenformin 20μM R03 exp143]]|0.057|<button type="primary" size="small" modal="12">View</button>| |[[:results:exp474|CR131-b 0.005μM R08 exp474]]|0.057|<button type="primary" size="small" modal="13">View</button>| |[[:results:exp451|Atovaquone 15μM R08 exp451]]|0.054|<button type="primary" size="small" modal="14">View</button>| |[[:results:exp102|Nifuroxazide 5μM R03 exp102]]|0.054|<button type="primary" size="small" modal="15">View</button>| |[[:results:exp135|MS023 7μM R03 exp135]]|0.054|<button type="primary" size="small" modal="16">View</button>| |[[:results:exp275|Citral 75μM R06 exp275]]|0.053|<button type="primary" size="small" modal="17">View</button>| |[[:results:exp488|Hippuristanol 0.12μM R08 exp488]]|0.052|<button type="primary" size="small" modal="18">View</button>| |[[:results:exp274|Citral 50μM R06 exp274]]|0.051|<button type="primary" size="small" modal="19">View</button>| |[[:results:exp211|AICAR 240μM R05 exp211]]|0.051|<button type="primary" size="small" modal="20">View</button>| </modal> <modal id="1" size="lg" title="Rotenone 0.07μM R08 exp431 vs iCRT14 30μM R08 exp492"> {{:chemogenomics:comparison_plots:exp431_vs_exp492.png?nolink |}} </modal> <modal id="2" size="lg" title="Rotenone 0.07μM R08 exp431 vs TIC10 10μM R08 exp532"> {{:chemogenomics:comparison_plots:exp431_vs_exp532.png?nolink |}} </modal> <modal id="3" size="lg" title="QNZ 0.01μM R08 exp439 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp431_vs_exp439.png?nolink |}} </modal> <modal id="4" size="lg" title="Mubritinib 0.2μM R01 exp48 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp431_vs_exp48.png?nolink |}} </modal> <modal id="5" size="lg" title="Mubritinib 0.2μM R02 exp65 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp431_vs_exp65.png?nolink |}} </modal> <modal id="6" size="lg" title="QNZ 0.01μM R05 exp241 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp241_vs_exp431.png?nolink |}} </modal> <modal id="7" size="lg" title="NMS-873 0.07μM R07 exp380 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp380_vs_exp431.png?nolink |}} </modal> <modal id="8" size="lg" title="Phenformin 20μM R05 exp212 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp212_vs_exp431.png?nolink |}} </modal> <modal id="9" size="lg" title="Amiloride 100μM R08 exp447 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp431_vs_exp447.png?nolink |}} </modal> <modal id="10" size="lg" title="Chloramphenicol 20μM R00 exp13 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp13_vs_exp431.png?nolink |}} </modal> <modal id="11" size="lg" title="∆-9-Tetrahydrocannabinol 30μM R08 exp445 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp431_vs_exp445.png?nolink |}} </modal> <modal id="12" size="lg" title="Phenformin 20μM R03 exp143 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp143_vs_exp431.png?nolink |}} </modal> <modal id="13" size="lg" title="CR131-b 0.005μM R08 exp474 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp431_vs_exp474.png?nolink |}} </modal> <modal id="14" size="lg" title="Atovaquone 15μM R08 exp451 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp431_vs_exp451.png?nolink |}} </modal> <modal id="15" size="lg" title="Nifuroxazide 5μM R03 exp102 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp102_vs_exp431.png?nolink |}} </modal> <modal id="16" size="lg" title="MS023 7μM R03 exp135 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp135_vs_exp431.png?nolink |}} </modal> <modal id="17" size="lg" title="Citral 75μM R06 exp275 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp275_vs_exp431.png?nolink |}} </modal> <modal id="18" size="lg" title="Hippuristanol 0.12μM R08 exp488 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp431_vs_exp488.png?nolink |}} </modal> <modal id="19" size="lg" title="Citral 50μM R06 exp274 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp274_vs_exp431.png?nolink |}} </modal> <modal id="20" size="lg" title="AICAR 240μM R05 exp211 vs Rotenone 0.07μM R08 exp431"> {{:chemogenomics:comparison_plots:exp211_vs_exp431.png?nolink |}} </modal> <modal id="modal_go_sensitive" size="lg" title="Top 30 sensitive GO terms"> ^GO Term^Fold Change^Genes^ |succinate-CoA ligase activity|571.34|SUCLG1,SUCLA2| |nucleoside bisphosphate catabolic process|155.82|SUCLG1,ACAT1,SUCLA2| |purine nucleoside bisphosphate catabolic process|155.82|SUCLG1,ACAT1,SUCLA2| |acyl-CoA metabolic process|32.84|SUCLG1,ACAT1,SUCLA2,GCDH,ACACA| |nucleoside bisphosphate metabolic process|24.84|SUCLG1,ACAT1,SUCLA2,GCDH,ACACA| |purine nucleoside bisphosphate metabolic process|24.84|SUCLG1,ACAT1,SUCLA2,GCDH,ACACA| |ribonucleoside bisphosphate metabolic process|24.84|SUCLG1,ACAT1,SUCLA2,GCDH,ACACA| |purine ribonucleotide metabolic process|12.58|SUCLG1,ADSS2,ACAT1,NUDT5,SUCLA2,GCDH,ACACA| |nucleobase-containing compound catabolic process|12.16|SUCLG1,ACAT1,NUDT5,SUCLA2,CNOT2,EXOG| |ribonucleotide metabolic process|11.87|SUCLG1,ADSS2,ACAT1,NUDT5,SUCLA2,GCDH,ACACA| |sulfur compound metabolic process|11.70|SUCLG1,ACAT1,AHCYL1,SUCLA2,GCDH,ACACA| |ribose phosphate metabolic process|11.59|SUCLG1,ADSS2,ACAT1,NUDT5,SUCLA2,GCDH,ACACA| |small molecule catabolic process|11.39|GOT1,ACAT1,NUDT5,HK1,PFKP,SLC16A1,GCDH| |purine nucleotide metabolic process|10.07|SUCLG1,ADSS2,ACAT1,NUDT5,SUCLA2,GCDH,ACACA| |purine-containing compound metabolic process|9.41|SUCLG1,ADSS2,ACAT1,NUDT5,SUCLA2,GCDH,ACACA| |carboxylic acid metabolic process|8.52|GOT1,ADSS2,ACAT1,MECR,HK1,SUCLA2,PFKP,SLC16A1,GCDH,ACACA,LIPT1,SEPHS2| |oxoacid metabolic process|8.29|GOT1,ADSS2,ACAT1,MECR,HK1,SUCLA2,PFKP,SLC16A1,GCDH,ACACA,LIPT1,SEPHS2| |organic acid metabolic process|8.22|GOT1,ADSS2,ACAT1,MECR,HK1,SUCLA2,PFKP,SLC16A1,GCDH,ACACA,LIPT1,SEPHS2| |organophosphate metabolic process|6.64|SUCLG1,ADSS2,ACAT1,NUDT5,HK1,SUCLA2,PFKP,GCDH,ACACA,PGP| </modal> <modal id="modal_go_resistant" size="lg" title="Top 30 resistant GO terms"> ^GO Term^Fold Change^Genes^ |inositol trisphosphate kinase activity|276.15|ITPK1,IPMK| |inositol tetrakisphosphate kinase activity|276.15|ITPK1,IPMK| |thioester biosynthetic process|41.42|HSD17B12,ACSL3,PDHB| |ligase activity|21.11|ATP5F1A,MOCS3,GATC,ATP5F1D,ACSL3,LARS2| |ribose phosphate biosynthetic process|17.08|ATP5F1A,HSD17B12,G6PD,ATP5F1D,ACSL3,PDHB| |purine ribonucleotide biosynthetic process|15.96|ATP5F1A,HSD17B12,ATP5F1D,ACSL3,PDHB| |purine-containing compound biosynthetic process|15.13|ATP5F1A,HSD17B12,SHMT2,ATP5F1D,ACSL3,PDHB| |ribonucleotide biosynthetic process|14.77|ATP5F1A,HSD17B12,ATP5F1D,ACSL3,PDHB| |organophosphate biosynthetic process|13.91|ATP5F1A,HSD17B12,AGPAT1,MOCS3,IPMK,PTPMT1,G6PD,FDPS,PTDSS1,CEPT1,ATP5F1D,ACSL3,PDHB| |purine nucleotide biosynthetic process|13.15|ATP5F1A,HSD17B12,ATP5F1D,ACSL3,PDHB| |organophosphate metabolic process|9.62|ITPK1,ATP5F1A,HSD17B12,AGPAT1,MOCS3,IPMK,PTPMT1,G6PD,FDPS,PTDSS1,CEPT1,ATP5F1D,ACSL3,PDHB,UGP2| |ribose phosphate metabolic process|9.61|ATP5F1A,HSD17B12,G6PD,ATP5F1D,ACSL3,PDHB| |phospholipid metabolic process|9.58|AGPAT1,IPMK,PTPMT1,FDPS,PTDSS1,CEPT1| |nucleobase-containing small molecule metabolic process|9.33|ATP5F1A,HSD17B12,PGM3,SHMT2,G6PD,ATP5F1D,ACSL3,PDHB,UGP2| |purine-containing compound metabolic process|9.10|ATP5F1A,HSD17B12,SHMT2,G6PD,ATP5F1D,ACSL3,PDHB| |generation of precursor metabolites and energy|8.84|SLC25A51,ATP5F1A,G6PD,ATP5F1D,PDHB,UGP2| |mitochondrial membrane|6.27|SLC25A51,ATP5F1A,PTPMT1,SHMT2,PMAIP1,BAK1,ATP5F1D,ACSL3| |mitochondrial envelope|5.88|SLC25A51,ATP5F1A,PTPMT1,SHMT2,PMAIP1,BAK1,ATP5F1D,ACSL3| |heterocycle biosynthetic process|5.52|ATP5F1A,HSD17B12,PGM3,MOCS3,SHMT2,ENY2,ATP5F1D,ACSL3,PDHB| </modal> Last modified: 2026/01/15 21:36by 127.0.0.1