====== Etoposide 1μM R00 exp19 ====== ==== Mechanism of Action ==== Binds DNA-TopII complex, blocks re-ligation, induces strand breaks, semi-synthetic derivative of podophyllotoxin * **Class / Subclass 1:** DNA Damage, Repair and Replication / Topoisomerase II Inhibitor ==== Technical Notes ==== * **PubChem Name:** %%Etoposide%% * **Synonyms:** VP-16; VP-16-213 * **CAS #:** 33419-42-0 * **PubChem CID:** [[https://pubchem.ncbi.nlm.nih.gov/compound/36462|36462]] * **IUPAC:** %%(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one%% * **INCHI Name:** InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1 * **INCHI Key:** VJJPUSNTGOMMGY-MRVIYFEKSA-N * **Molecular Weight:** 588.6 * **Canonical SMILES:** CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O * **Isomeric SMILES:** C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O * **Molecular Formula:** C29H32O13 {{:chemogenomics:structures:chem-0011.svg?nolink}} * **Supplier Name:** Sigma-Aldrich * **Catalog #:** E1383 * **Lot #:** N/A * **HRMS (ESI-TOF) m/z:** (M+H)+ Calcd for C29H32O13 589.19157; found 589.19262 * **Platform ID:** Etoposide * **Min:** -33.3567; **Max:** 88.0314 {{:chemogenomics:dose_response:dr_265.png?nolink&500 |}} \\ \\ \\ \\ |< 300px 100px 200px >| ^ IC ^ Concentration (µM) ^ | IC10 |N/A | | IC20 |0.1877 | | IC30 |0.2644 | | IC40 |0.3501 | | IC50 |0.4531 | | IC60 |N/A | | IC70 |N/A | | IC80 |N/A | | IC90 |N/A | \\ ==== Screen Summary ==== * **Round**: 00 * **Dose**: 1µM * **Days of incubation**: 8 * **Doublings**: 0.1 * **Numbers of reads**: 11249121 ==== 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^ |13/56|[[https://files.tyerslab.com/files/public/chemogenomics/cranks/Etoposide_1uM_Round-0_exp19.txt|Scores]]|||||| {{:chemogenomics:cranks_plots:exp19.png?nolink}} ^Gene^CRANKS Score^FDR^ |[[:human_genes:M:MTCH2|MTCH2]]|-3.10|<0.01| |[[:human_genes:V:VPS25|VPS25]]|-3.05|0.07| |[[:human_genes:M:MAP3K7|MAP3K7]]|-3.04|<0.01| |[[:human_genes:U:UBE4A|UBE4A]]|-2.93|0.02| |[[:human_genes:F:FAM208A|FAM208A]]|-2.90|0.01| |[[:human_genes:T:TOP1|TOP1]]|-2.84|0.06| |[[:human_genes:Z:ZFC3H1|ZFC3H1]]|-2.83|0.03| |[[:human_genes:U:USP5|USP5]]|-2.74|0.05| |[[:human_genes:C:CNOT2|CNOT2]]|-2.67|0.03| |[[:human_genes:T:TAF1|TAF1]]|-2.58|0.07| |[[:human_genes:P:PSMD1|PSMD1]]|-2.58|0.27| |[[:human_genes:D:DDX3X|DDX3X]]|-2.57|0.04| |[[:human_genes:R:RBM7|RBM7]]|-2.54|0.04| |[[:human_genes:A:ACACA|ACACA]]|-2.53|0.05| |[[:human_genes:X:XIAP|XIAP]]|-2.51|0.04| |[[:human_genes:T:TSG101|TSG101]]|-2.50|0.09| |[[:human_genes:K:KIDINS220|KIDINS220]]|-2.50|0.06| |[[:human_genes:A:ATP6V0C|ATP6V0C]]|-2.49|0.39| |[[:human_genes:S:SEPHS2|SEPHS2]]|-2.44|0.05| |[[:human_genes:B:BRD2|BRD2]]|-2.44|0.05| |[[:human_genes:I:ISCU|ISCU]]|-2.43|0.32| |[[:human_genes:M:MUL1|MUL1]]|-2.43|0.05| |[[:human_genes:X:XPR1|XPR1]]|-2.40|0.05| |[[:human_genes:R:RNF113A|RNF113A]]|-2.40|0.19| |[[:human_genes:S:SYS1|SYS1]]|-2.39|0.05| |[[:human_genes:S:SKIV2L2|SKIV2L2]]|-2.39|0.25| |[[:human_genes:P:PSMB4|PSMB4]]|-2.35|0.15| |[[:human_genes:S:SAP130|SAP130]]|-2.34|0.15| |[[:human_genes:S:SGCB|SGCB]]|-2.34|0.06| |[[:human_genes:P:PSMA2|PSMA2]]|-2.32|0.27| |[[:human_genes:C:C4orf3|C4orf3]]|2.66|<0.01| |[[:human_genes:A:ALG5|ALG5]]|2.68|<0.01| |[[:human_genes:H:HCCS|HCCS]]|2.73|0.02| |[[:human_genes:U:USP15|USP15]]|2.74|<0.01| |[[:human_genes:M:MTOR|MTOR]]|2.76|0.02| |[[:human_genes:C:CARS|CARS]]|2.79|0.01| |[[:human_genes:C:CASP9|CASP9]]|2.86|<0.01| |[[:human_genes:H:HARS|HARS]]|2.88|0.05| |[[:human_genes:V:VDAC2|VDAC2]]|3.00|<0.01| |[[:human_genes:N:NXT1|NXT1]]|3.03|<0.01| |[[:human_genes:R:RAD23B|RAD23B]]|3.07|<0.01| |[[:human_genes:T:TRIAP1|TRIAP1]]|3.11|<0.01| |[[:human_genes:M:MEAF6|MEAF6]]|3.11|<0.01| |[[:human_genes:A:AURKB|AURKB]]|3.16|<0.01| |[[:human_genes:C:CCT7|CCT7]]|3.16|<0.01| |[[:human_genes:T:TSR2|TSR2]]|3.24|<0.01| |[[:human_genes:H:HSPD1|HSPD1]]|3.33|<0.01| |[[:human_genes:T:TOP2A|TOP2A]]|3.39|<0.01| |[[:human_genes:E:EIF4G1|EIF4G1]]|3.43|<0.01| |[[:human_genes:P:PELO|PELO]]|3.46|<0.01| |[[:human_genes:E:ENY2|ENY2]]|3.58|<0.01| |[[:human_genes:C:COPS7B|COPS7B]]|3.60|<0.01| |[[:human_genes:C:CYCS|CYCS]]|3.64|<0.01| |[[:human_genes:U:UBQLN1|UBQLN1]]|3.70|<0.01| |[[:human_genes:M:MARCH5|MARCH5]]|4.02|<0.01| |[[:human_genes:F:FAF2|FAF2]]|4.13|<0.01| |[[:human_genes:D:DIABLO|DIABLO]]|4.30|<0.01| |[[:human_genes:B:BAK1|BAK1]]|5.30|<0.01| |[[:human_genes:A:APAF1|APAF1]]|5.65|<0.01| |[[:human_genes:P:PLAA|PLAA]]|6.13|<0.01| ^Screen^Correlation^Plot^ |[[:results:exp28|Pimelic-diphenylamide-106 5μM R00 exp28]]|0.199|| |[[:results:exp34|Rotenone 20μM R00 exp34]]|0.158|| |[[:results:exp22|MLN-4924 2μM R00 exp22]]|0.109|| |[[:results:exp503|Mitomycin-C 0.06μM R08 exp503]]|0.095|| |[[:results:exp515|PU-H71 1μM R08 exp515]]|0.089|| |[[:results:exp80|RO-3307 4.7μM R02 exp80]]|0.083|| |[[:results:exp531|THZ1 0.06μM R08 exp531]]|0.081|| |[[:results:exp33|Rotenone 2μM R00 exp33]]|0.075|| |[[:results:exp489|Hippuristanol 0.12μM R08 exp489 no dilution day6]]|0.07|| |[[:results:exp524|Staurosporine 0.02μM R08 exp524]]|0.07|| |[[:results:exp527|Tanespimycin 14μM R08 exp527]]|0.068|| |[[:results:exp488|Hippuristanol 0.12μM R08 exp488]]|0.066|| |[[:results:exp135|MS023 7μM R03 exp135]]|0.065|| |[[:results:exp435|JQ1 0.8μM R08 exp435]]|0.064|| |[[:results:exp443|SNS-032 15μM R08 exp443]]|0.064|| |[[:results:exp24|Nocodazole 0.2μM R00 exp24]]|0.063|| |[[:results:exp126|GSK461364A 0.1μM R03 exp126]]|0.062|| |[[:results:exp26|Oligomycin-A 20μM R00 exp26]]|0.062|| |[[:results:exp512|Olaparib 4μM R08 exp512]]|0.057|| |[[:results:exp85|UM0129480 7μM R02 exp85]]|0.055|| |[[:results:exp441|GSK-J4 1.5μM R08 exp441]]|0.054|| |[[:results:exp134|MS023 2μM R03 exp134]]|0.052|| |[[:results:exp485|GSK626616 14μM R08 exp485]]|0.051|| |[[:results:exp2|5-Fluorouracil 20μM R00 exp2]]|0.181|| |[[:results:exp199|Etoposide 0.3μM R05 exp199]]|0.177|| |[[:results:exp3|Actinomycin-D 0.001μM R00 exp3]]|0.165|| |[[:results:exp17|DABN 20μM R00 exp17]]|0.11|| |[[:results:exp459|Bleomycin 5μM R08 exp459]]|0.1|| |[[:results:exp456|Benzoate 20000μM R08 exp456]]|0.1|| |[[:results:exp7|Bortezomib 0.05μM R00 exp7]]|0.095|| |[[:results:exp478|Doxorubicin 0.02μM R08 exp478]]|0.087|| |[[:results:exp539|42°C R08 exp539]]|0.077|| |[[:results:exp472|CI-1040 9.5μM R08 exp472]]|0.072|| |[[:results:exp211|AICAR 240μM R05 exp211]]|0.071|| |[[:results:exp440|Aphidicolin 0.4μM R08 exp440]]|0.071|| |[[:results:exp354|Diepoxybutane 3μM R07 exp354]]|0.062|| |[[:results:exp259|6-Thio-2-deoxyguanosine 2μM R06 exp259]]|0.062|| |[[:results:exp350|Deferoxamine 11μM R07 exp350]]|0.059|| |[[:results:exp343|Centrinone 0.5μM R07 exp343]]|0.058|| |[[:results:exp474|CR131-b 0.005μM R08 exp474]]|0.058|| |[[:results:exp4|Actinomycin-D 0.01μM R00 exp4]]|0.057|| |[[:results:exp451|Atovaquone 15μM R08 exp451]]|0.055|| |[[:results:exp355|Dinaciclib 0.007μM R07 exp355]]|0.055|| {{:chemogenomics:comparison_plots:exp19_vs_exp28.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp34.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp22.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp503.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp515.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp80.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp531.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp33.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp524.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp527.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp488.png?nolink |}} {{:chemogenomics:comparison_plots:exp135_vs_exp19.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp435.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp443.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp24.png?nolink |}} {{:chemogenomics:comparison_plots:exp126_vs_exp19.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp26.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp512.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp85.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp441.png?nolink |}} {{:chemogenomics:comparison_plots:exp134_vs_exp19.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp485.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp2.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp199.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp3.png?nolink |}} {{:chemogenomics:comparison_plots:exp17_vs_exp19.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp459.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp456.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp7.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp478.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp539.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp472.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp211.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp440.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp354.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp259.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp350.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp343.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp474.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp4.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp451.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp355.png?nolink |}} No GO term hits below threshold. (FDR <0.05) ^GO Term^Fold Change^Genes^ |apoptosome|552.73|APAF1,CASP9| |activation of cysteine-type endopeptidase activity involved in apoptotic process by cytochrome c|442.19|APAF1,DIABLO,CYCS,CASP9| |activation of cysteine-type endopeptidase activity involved in apoptotic process|34.01|APAF1,CYCS,HSPD1,CASP9| |cellular response to UV|31.41|BAK1,AURKB,TRIAP1,CASP9,MAPK14| |positive regulation of cysteine-type endopeptidase activity|26.75|APAF1,BAK1,DIABLO,CYCS,HSPD1,CASP9| |cellular response to light stimulus|24.68|BAK1,AURKB,TRIAP1,CASP9,MAPK14| |positive regulation of endopeptidase activity|22.87|APAF1,BAK1,DIABLO,CYCS,HSPD1,CASP9| |regulation of cysteine-type endopeptidase activity involved in apoptotic process|21.26|APAF1,DIABLO,CYCS,HSPD1,TRIAP1,CASP9| |positive regulation of peptidase activity|20.86|APAF1,BAK1,DIABLO,CYCS,HSPD1,CASP9| |regulation of cysteine-type endopeptidase activity|20.58|APAF1,BAK1,DIABLO,CYCS,HSPD1,TRIAP1,CASP9| |response to UV|18.42|BAK1,AURKB,TRIAP1,CASP9,MAPK14| |regulation of endopeptidase activity|14.44|APAF1,BAK1,DIABLO,CYCS,HSPD1,TRIAP1,CASP9| |regulation of peptidase activity|13.30|APAF1,BAK1,DIABLO,CYCS,HSPD1,TRIAP1,CASP9| |positive regulation of proteolysis|11.52|APAF1,BAK1,DIABLO,UBQLN1,CYCS,HSPD1,CASP9| |positive regulation of hydrolase activity|9.21|PLAA,APAF1,BAK1,DIABLO,CYCS,HSPD1,CASP9,MTOR| |regulation of proteolysis|8.43|APAF1,BAK1,DIABLO,UBQLN1,CYCS,HSPD1,TRIAP1,RAD23B,CASP9| |regulation of hydrolase activity|6.76|PLAA,APAF1,BAK1,DIABLO,CYCS,HSPD1,TRIAP1,CASP9,MTOR| |mitochondrial envelope|6.62|BAK1,DIABLO,MARCHF5,CYCS,HSPD1,TRIAP1,VDAC2,MTOR,HCCS| |positive regulation of catalytic activity|6.11|PLAA,APAF1,BAK1,DIABLO,CYCS,HSPD1,AURKB,CASP9,MTOR,MAPK14|