====== Rotenone 20μM R00 exp34 ====== ==== Mechanism of Action ==== Inhibits complex I, blocks electron transfer from iron-sulfur centers to ubiquinone, generates ROS, also inhibits microtubule assembly * **Class / Subclass 1:** Organelle Function / Mitochondrial Inhibitor * **Class / Subclass 2:** Cell Cycle / Microtubule Poison ==== Technical Notes ==== * **PubChem Name:** %%Rotenone%% * **Synonyms:** N/A * **CAS #:** 83-79-4 * **PubChem CID:** [[https://pubchem.ncbi.nlm.nih.gov/compound/6758|6758]] * **IUPAC:** %%(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%% * **INCHI Name:** 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 * **INCHI Key:** JUVIOZPCNVVQFO-HBGVWJBISA-N * **Molecular Weight:** 394.4 * **Canonical SMILES:** CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC * **Isomeric SMILES:** CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC * **Molecular Formula:** C23H22O6 {{:chemogenomics:structures:chem-0018.svg?nolink}} * **Supplier Name:** Sigma-Aldrich * **Catalog #:** R8875 * **Lot #:** SLBG7568V * **HRMS (ESI-TOF) m/z:** (M+H)+ Calcd for C23H22O6 395.14891; found 395.15075 * **Platform ID:** Rotenone * **Min:** 11.0154; **Max:** 87.2842 {{:chemogenomics:dose_response:dr_275.png?nolink&500 |}} \\ \\ \\ \\ |< 300px 100px 200px >| ^ IC ^ Concentration (µM) ^ | IC10 |N/A | | IC20 |0.0123 | | IC30 |0.0322 | | IC40 |0.0711 | | IC50 |0.1468 | | IC60 |N/A | | IC70 |N/A | | IC80 |N/A | | IC90 |N/A | \\ ==== Screen Summary ==== * **Round**: 00 * **Dose**: 20µM * **Days of incubation**: 8 * **Doublings**: 0.1 * **Numbers of reads**: 9667752 ==== 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^ |15/52|[[https://files.tyerslab.com/files/public/chemogenomics/cranks/Rotenone_20uM_Round-0_exp34.txt|Scores]]|||||| {{:chemogenomics:cranks_plots:exp34.png?nolink}} ^Gene^CRANKS Score^FDR^ |[[:human_genes:G:GOLGA6L1|GOLGA6L1]]|-3.57|0.05| |[[:human_genes:D:DDX3X|DDX3X]]|-3.35|<0.01| |[[:human_genes:M:MPHOSPH10|MPHOSPH10]]|-3.07|0.03| |[[:human_genes:C:COX7A2L|COX7A2L]]|-3.06|<0.01| |[[:human_genes:C:C6orf118|C6orf118]]|-2.99|0.02| |[[:human_genes:P:POLR2J3|POLR2J3]]|-2.88|0.10| |[[:human_genes:T:TAF1|TAF1]]|-2.83|0.03| |[[:human_genes:P:PSMA3|PSMA3]]|-2.77|0.12| |[[:human_genes:P:POLR2I|POLR2I]]|-2.69|0.03| |[[:human_genes:S:SIN3A|SIN3A]]|-2.63|0.03| |[[:human_genes:B:BRD2|BRD2]]|-2.62|0.03| |[[:human_genes:E:EIF5B|EIF5B]]|-2.60|0.10| |[[:human_genes:A:ATP6V1A|ATP6V1A]]|-2.58|0.04| |[[:human_genes:S:SYS1|SYS1]]|-2.57|0.03| |[[:human_genes:T:TFPT|TFPT]]|-2.53|0.05| |[[:human_genes:P:PCYT1A|PCYT1A]]|-2.51|0.03| |[[:human_genes:P:PLEKHJ1|PLEKHJ1]]|-2.50|0.03| |[[:human_genes:H:HK1|HK1]]|-2.48|0.06| |[[:human_genes:R:RAD54L2|RAD54L2]]|-2.47|0.03| |[[:human_genes:M:MSI2|MSI2]]|-2.47|0.03| |[[:human_genes:R:RPL34|RPL34]]|-2.46|0.27| |[[:human_genes:R:RPL35|RPL35]]|-2.44|0.07| |[[:human_genes:C:CANX|CANX]]|-2.44|0.10| |[[:human_genes:E:EGR2|EGR2]]|-2.40|0.16| |[[:human_genes:E:ERCC2|ERCC2]]|-2.39|0.11| |[[:human_genes:T:TAF7|TAF7]]|-2.38|0.08| |[[:human_genes:C:CDK7|CDK7]]|-2.37|0.08| |[[:human_genes:A:ARID4B|ARID4B]]|-2.35|0.08| |[[:human_genes:Z:ZBTB7A|ZBTB7A]]|-2.33|0.06| |[[:human_genes:W:WDR75|WDR75]]|-2.33|0.22| |[[:human_genes:T:TIMM23B|TIMM23B]]|2.64|0.09| |[[:human_genes:I:ID3|ID3]]|2.66|<0.01| |[[:human_genes:K:KCTD5|KCTD5]]|2.68|<0.01| |[[:human_genes:S:SEC63|SEC63]]|2.69|0.01| |[[:human_genes:E:EPC1|EPC1]]|2.76|<0.01| |[[:human_genes:N:NSD1|NSD1]]|2.79|0.03| |[[:human_genes:C:CASP9|CASP9]]|2.87|<0.01| |[[:human_genes:C:CRLS1|CRLS1]]|2.89|<0.01| |[[:human_genes:N:NUDT21|NUDT21]]|2.92|<0.01| |[[:human_genes:T:TRIAP1|TRIAP1]]|2.96|<0.01| |[[:human_genes:H:HMGB2|HMGB2]]|2.97|<0.01| |[[:human_genes:H:HARS|HARS]]|3.05|0.03| |[[:human_genes:P:PMPCB|PMPCB]]|3.11|<0.01| |[[:human_genes:Z:ZNF608|ZNF608]]|3.15|<0.01| |[[:human_genes:U:UBQLN1|UBQLN1]]|3.19|<0.01| |[[:human_genes:M:MTOR|MTOR]]|3.25|<0.01| |[[:human_genes:M:MARCH5|MARCH5]]|3.29|<0.01| |[[:human_genes:M:MEAF6|MEAF6]]|3.38|<0.01| |[[:human_genes:A:ATP2B1|ATP2B1]]|3.40|<0.01| |[[:human_genes:R:RPTOR|RPTOR]]|3.53|<0.01| |[[:human_genes:C:CSNK2B|CSNK2B]]|3.63|<0.01| |[[:human_genes:F:FAF2|FAF2]]|3.95|<0.01| |[[:human_genes:N:NXT1|NXT1]]|4.12|<0.01| |[[:human_genes:P:PLAA|PLAA]]|4.12|<0.01| |[[:human_genes:H:HCCS|HCCS]]|4.32|<0.01| |[[:human_genes:T:TLE4|TLE4]]|4.52|<0.01| |[[:human_genes:C:CYCS|CYCS]]|4.57|<0.01| |[[:human_genes:E:ENY2|ENY2]]|4.72|<0.01| |[[:human_genes:B:BAK1|BAK1]]|4.86|<0.01| |[[:human_genes:A:APAF1|APAF1]]|5.96|<0.01| ^Screen^Correlation^Plot^ |[[:results:exp531|THZ1 0.06μM R08 exp531]]|0.093|| |[[:results:exp106|UM131593 0.2μM R03 exp106]]|0.091|| |[[:results:exp443|SNS-032 15μM R08 exp443]]|0.083|| |[[:results:exp524|Staurosporine 0.02μM R08 exp524]]|0.07|| |[[:results:exp33|Rotenone 2μM R00 exp33]]|0.069|| |[[:results:exp527|Tanespimycin 14μM R08 exp527]]|0.061|| |[[:results:exp85|UM0129480 7μM R02 exp85]]|0.056|| |[[:results:exp2|5-Fluorouracil 20μM R00 exp2]]|0.193|| |[[:results:exp3|Actinomycin-D 0.001μM R00 exp3]]|0.158|| |[[:results:exp19|Etoposide 1μM R00 exp19]]|0.158|| |[[:results:exp28|Pimelic-diphenylamide-106 5μM R00 exp28]]|0.151|| |[[:results:exp199|Etoposide 0.3μM R05 exp199]]|0.116|| |[[:results:exp456|Benzoate 20000μM R08 exp456]]|0.107|| |[[:results:exp503|Mitomycin-C 0.06μM R08 exp503]]|0.107|| |[[:results:exp472|CI-1040 9.5μM R08 exp472]]|0.101|| |[[:results:exp80|RO-3307 4.7μM R02 exp80]]|0.099|| |[[:results:exp459|Bleomycin 5μM R08 exp459]]|0.099|| |[[:results:exp478|Doxorubicin 0.02μM R08 exp478]]|0.098|| |[[:results:exp22|MLN-4924 2μM R00 exp22]]|0.087|| |[[:results:exp7|Bortezomib 0.05μM R00 exp7]]|0.086|| |[[:results:exp17|DABN 20μM R00 exp17]]|0.079|| |[[:results:exp211|AICAR 240μM R05 exp211]]|0.078|| |[[:results:exp435|JQ1 0.8μM R08 exp435]]|0.072|| |[[:results:exp26|Oligomycin-A 20μM R00 exp26]]|0.072|| |[[:results:exp259|6-Thio-2-deoxyguanosine 2μM R06 exp259]]|0.071|| |[[:results:exp515|PU-H71 1μM R08 exp515]]|0.066|| |[[:results:exp135|MS023 7μM R03 exp135]]|0.062|| |[[:results:exp440|Aphidicolin 0.4μM R08 exp440]]|0.062|| |[[:results:exp20|Etoposide 10μM R00 exp20]]|0.061|| |[[:results:exp488|Hippuristanol 0.12μM R08 exp488]]|0.061|| |[[:results:exp512|Olaparib 4μM R08 exp512]]|0.055|| |[[:results:exp357|Dorsomorphin 5μM R07 exp357]]|0.055|| |[[:results:exp539|42°C R08 exp539]]|0.054|| |[[:results:exp489|Hippuristanol 0.12μM R08 exp489 no dilution day6]]|0.052|| {{:chemogenomics:comparison_plots:exp34_vs_exp531.png?nolink |}} {{:chemogenomics:comparison_plots:exp106_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp443.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp524.png?nolink |}} {{:chemogenomics:comparison_plots:exp33_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp527.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp85.png?nolink |}} {{:chemogenomics:comparison_plots:exp2_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp3_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp28_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp199_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp456.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp503.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp472.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp80.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp459.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp478.png?nolink |}} {{:chemogenomics:comparison_plots:exp22_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp7.png?nolink |}} {{:chemogenomics:comparison_plots:exp17_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp211_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp435.png?nolink |}} {{:chemogenomics:comparison_plots:exp26_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp259_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp515.png?nolink |}} {{:chemogenomics:comparison_plots:exp135_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp440.png?nolink |}} {{:chemogenomics:comparison_plots:exp20_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp488.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp512.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp357.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp539.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp489.png?nolink |}} ^GO Term^Fold Change^Genes^ |CAK-ERCC2 complex|409.41|ERCC2,CDK7| |transcription factor TFIID complex|54.19|TAF1,ERCC2,TAF7| |RNA polymerase II, holoenzyme|51.18|POLR2J3,TAF1,POLR2I,ERCC2,TAF7,CDK7| |nuclear DNA-directed RNA polymerase complex|39.20|POLR2J3,TAF1,POLR2I,ERCC2,TAF7,CDK7| |DNA-directed RNA polymerase complex|37.99|POLR2J3,TAF1,POLR2I,ERCC2,TAF7,CDK7| |RNA polymerase complex|37.22|POLR2J3,TAF1,POLR2I,ERCC2,TAF7,CDK7| |transcription initiation at RNA polymerase II promoter|35.09|TAF1,POLR2I,TAF7,CDK7| |DNA-templated transcription initiation|24.08|TAF1,POLR2I,TAF7,CDK7| |ATP-dependent activity, acting on DNA|21.36|DDX3X,RAD54L2,ERCC2,CDK7| |transferase complex, transferring phosphorus-containing groups|15.19|POLR2J3,TAF1,POLR2I,ERCC2,TAF7,CDK7,ZBTB7A| |transcription by RNA polymerase II|12.68|POLR2J3,TAF1,POLR2I,ERCC2,TAF7,CDK7,ARID4B| |DNA-templated transcription|10.32|POLR2J3,TAF1,POLR2I,ERCC2,TAF7,CDK7,ARID4B,ZBTB7A| |RNA biosynthetic process|10.07|POLR2J3,TAF1,POLR2I,ERCC2,TAF7,CDK7,ARID4B,ZBTB7A| |chromatin remodeling|7.62|TAF1,SIN3A,BRD2,TFPT,RAD54L2,ARID4B,ZBTB7A| |nucleobase-containing compound biosynthetic process|6.64|POLR2J3,TAF1,POLR2I,ATP6V1A,ERCC2,TAF7,CDK7,ARID4B,ZBTB7A| |protein-DNA complex organization|6.27|TAF1,SIN3A,BRD2,TFPT,RAD54L2,TAF7,ARID4B,ZBTB7A| |heterocycle biosynthetic process|6.09|POLR2J3,TAF1,POLR2I,ATP6V1A,ERCC2,TAF7,CDK7,ARID4B,ZBTB7A| |aromatic compound biosynthetic process|6.04|POLR2J3,TAF1,POLR2I,ATP6V1A,ERCC2,TAF7,CDK7,ARID4B,ZBTB7A| ^GO Term^Fold Change^Genes^ |apoptosome|552.70|APAF1,CASP9| |5S rDNA binding|368.47|RPTOR,MTOR| |RNA polymerase III type 2 promoter sequence-specific DNA binding|368.47|RPTOR,MTOR| |RNA polymerase III general transcription initiation factor binding|368.47|RPTOR,MTOR| |activation of cysteine-type endopeptidase activity involved in apoptotic process by cytochrome c|331.62|APAF1,CYCS,CASP9| |regulation of cysteine-type endopeptidase activity|14.70|APAF1,BAK1,CYCS,TRIAP1,CASP9| |positive regulation of hydrolase activity|8.06|APAF1,BAK1,CYCS,PLAA,MTOR,HMGB2,CASP9| |mitochondrial envelope|6.61|BAK1,CYCS,HCCS,MARCHF5,MTOR,PMPCB,TRIAP1,CRLS1,TIMM23B| |mitochondrial membrane|6.26|BAK1,CYCS,HCCS,MARCHF5,MTOR,PMPCB,CRLS1,TIMM23B|