====== Hippuristanol 0.12μM R08 exp489 no dilution day6 ====== ==== Mechanism of Action ==== Inhibits translation by trapping EIF4A on mRNA at poly-purine sites * **Class / Subclass 1:** Proteostasis / Translation Inhibitor ==== Technical Notes ==== * **PubChem Name:** %%Hippuristanol%% * **Synonyms:** N/A * **CAS #:** 80442-78-0 * **PubChem CID:** [[https://pubchem.ncbi.nlm.nih.gov/compound/9981822|9981822]] * **IUPAC:** %%(1S,2S,3'S,4S,6R,7R,8R,9S,11S,12S,13S,16R,18S)-2',2',3',7,9,13-hexamethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,5'-oxolane]-7,11,16-triol%% * **INCHI Name:** InChI=1S/C28H46O5/c1-15-13-28(33-24(15,2)3)27(6,31)23-21(32-28)12-19-18-8-7-16-11-17(29)9-10-25(16,4)22(18)20(30)14-26(19,23)5/h15-23,29-31H,7-14H2,1-6H3/t15-,16-,17+,18-,19-,20-,21-,22+,23-,25-,26-,27+,28+/m0/s1 * **INCHI Key:** HPHXKNOXVBFETI-SHCCRYCOSA-N * **Molecular Weight:** 462.7 * **Canonical SMILES:** CC1CC2(C(C3C(O2)CC4C3(CC(C5C4CCC6C5(CCC(C6)O)C)O)C)(C)O)OC1(C)C * **Isomeric SMILES:** C[C@H]1C[C@]2([C@]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(C[C@@H]([C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@H](C6)O)C)O)C)(C)O)OC1(C)C * **Molecular Formula:** C28H46O5 {{:chemogenomics:structures:chem-0297.svg?nolink}} * **Supplier Name:** In house - McGill University - Jerry Pelletier group * **Catalog #:** N/A * **Lot #:** N/A * **HRMS (ESI-TOF) m/z:** (M+Na)+ Calcd for C28H46O5 485.32375; found 485.31999 * **Platform ID:** Hippuristanol * **Min:** -26.3565; **Max:** 90.5289 {{:chemogenomics:dose_response:dr_544.png?nolink&500 |}} \\ \\ \\ \\ |< 300px 100px 200px >| ^ IC ^ Concentration (µM) ^ | IC10 |0.0839 | | IC20 |0.1055 | | IC30 |0.1229 | | IC40 |0.1392 | | IC50 |0.1561 | | IC60 |0.1751 | | IC70 |0.1984 | | IC80 |0.2310 | | IC90 |0.2906 | \\ ==== Screen Summary ==== * **Round**: 08 * **Dose**: 120nM * **Days of incubation**: 8 * **Doublings**: 2.0 * **Numbers of reads**: 15925511 ==== 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^ |6/124|[[https://files.tyerslab.com/files/public/chemogenomics/cranks/Hippuristanol_0.12uM_Round-8_exp489.txt|Scores]]|||||| {{:chemogenomics:cranks_plots:exp489.png?nolink}} ^Gene^CRANKS Score^FDR^ |[[:human_genes:D:DDX3X|DDX3X]]|-3.78|<0.01| |[[:human_genes:S:SF3B3|SF3B3]]|-3.18|0.06| |[[:human_genes:K:KIDINS220|KIDINS220]]|-3.04|<0.01| |[[:human_genes:T:TSSC1|TSSC1]]|-2.95|<0.01| |[[:human_genes:F:FZR1|FZR1]]|-2.87|0.02| |[[:human_genes:C:CHMP2A|CHMP2A]]|-2.82|0.07| |[[:human_genes:S:SMG5|SMG5]]|-2.77|0.28| |[[:human_genes:R:RANBP1|RANBP1]]|-2.69|0.02| |[[:human_genes:A:ARL1|ARL1]]|-2.66|0.02| |[[:human_genes:M:MTF2|MTF2]]|-2.58|0.06| |[[:human_genes:S:SPI1|SPI1]]|-2.56|0.06| |[[:human_genes:R:RSRC2|RSRC2]]|-2.51|0.36| |[[:human_genes:P:PKN1|PKN1]]|-2.49|0.06| |[[:human_genes:P:PHACTR4|PHACTR4]]|-2.44|0.06| |[[:human_genes:Z:ZFAND5|ZFAND5]]|-2.41|0.06| |[[:human_genes:N:NUDT2|NUDT2]]|-2.39|0.06| |[[:human_genes:T:TP53BP1|TP53BP1]]|-2.37|0.09| |[[:human_genes:P:PTPN11|PTPN11]]|-2.34|0.10| |[[:human_genes:P:PPP2R2A|PPP2R2A]]|-2.34|0.07| |[[:human_genes:R:RHOA|RHOA]]|-2.33|0.07| |[[:human_genes:C:COPA|COPA]]|-2.26|0.36| |[[:human_genes:B:BIRC6|BIRC6]]|-2.26|0.09| |[[:human_genes:Z:ZBTB10|ZBTB10]]|-2.25|0.09| |[[:human_genes:E:EIF4G2|EIF4G2]]|-2.24|0.09| |[[:human_genes:T:TIMELESS|TIMELESS]]|-2.22|0.32| |[[:human_genes:U:UPF3B|UPF3B]]|-2.21|0.10| |[[:human_genes:A:ANAPC11|ANAPC11]]|-2.21|0.33| |[[:human_genes:Y:YY1|YY1]]|-2.20|0.25| |[[:human_genes:S:SCEL|SCEL]]|-2.19|0.11| |[[:human_genes:S:STYX|STYX]]|-2.16|0.19| |[[:human_genes:I:IKZF1|IKZF1]]|3.22|0.00| |[[:human_genes:T:TSC1|TSC1]]|3.24|0.00| |[[:human_genes:G:GNAS|GNAS]]|3.24|0.00| |[[:human_genes:H:HNRNPF|HNRNPF]]|3.28|0.00| |[[:human_genes:P:PLAA|PLAA]]|3.32|0.00| |[[:human_genes:S:SYK|SYK]]|3.33|0.00| |[[:human_genes:R:ROMO1|ROMO1]]|3.33|0.00| |[[:human_genes:E:EIF4ENIF1|EIF4ENIF1]]|3.36|0.00| |[[:human_genes:T:TKT|TKT]]|3.36|0.00| |[[:human_genes:C:CD19|CD19]]|3.49|0.00| |[[:human_genes:S:SUV420H1|SUV420H1]]|3.55|0.00| |[[:human_genes:B:BCL2L11|BCL2L11]]|3.57|0.00| |[[:human_genes:T:TAZ|TAZ]]|3.63|<0.01| |[[:human_genes:H:HDAC3|HDAC3]]|3.70|0.00| |[[:human_genes:T:TSC2|TSC2]]|3.81|0.00| |[[:human_genes:V:VDAC2|VDAC2]]|3.83|0.00| |[[:human_genes:A:APAF1|APAF1]]|3.84|0.00| |[[:human_genes:R:RICTOR|RICTOR]]|3.84|0.00| |[[:human_genes:A:ALAS1|ALAS1]]|3.86|0.00| |[[:human_genes:M:MARCH5|MARCH5]]|4.07|0.00| |[[:human_genes:P:PIK3CD|PIK3CD]]|4.09|0.00| |[[:human_genes:N:NPRL3|NPRL3]]|4.20|0.00| |[[:human_genes:L:LPAR5|LPAR5]]|4.22|0.00| |[[:human_genes:C:CASP9|CASP9]]|4.25|0.00| |[[:human_genes:E:ELP6|ELP6]]|4.37|0.00| |[[:human_genes:K:KLF16|KLF16]]|4.53|0.00| |[[:human_genes:M:MAPKAP1|MAPKAP1]]|4.63|0.00| |[[:human_genes:E:ELP3|ELP3]]|4.67|0.00| |[[:human_genes:B:BAK1|BAK1]]|6.40|0.00| |[[:human_genes:E:EIF4A1|EIF4A1]]|7.64|0.00| ^Screen^Correlation^Plot^ |[[:results:exp134|MS023 2μM R03 exp134]]|0.185|| |[[:results:exp135|MS023 7μM R03 exp135]]|0.153|| |[[:results:exp524|Staurosporine 0.02μM R08 exp524]]|0.12|| |[[:results:exp512|Olaparib 4μM R08 exp512]]|0.117|| |[[:results:exp525|Sulforaphane 9μM R08 exp525]]|0.098|| |[[:results:exp503|Mitomycin-C 0.06μM R08 exp503]]|0.092|| |[[:results:exp531|THZ1 0.06μM R08 exp531]]|0.091|| |[[:results:exp526|Sulforaphane 9μM R08 exp526 no dilution day6]]|0.085|| |[[:results:exp529|Thimerosal 0.85μM R08 exp529]]|0.084|| |[[:results:exp515|PU-H71 1μM R08 exp515]]|0.083|| |[[:results:exp28|Pimelic-diphenylamide-106 5μM R00 exp28]]|0.08|| |[[:results:exp374|Latrunculin-B 10μM R07 exp374]]|0.076|| |[[:results:exp527|Tanespimycin 14μM R08 exp527]]|0.075|| |[[:results:exp21|MLN-4924 0.2μM R00 exp21]]|0.074|| |[[:results:exp535|Trimetrexate 0.03μM R08 exp535]]|0.074|| |[[:results:exp502|Milciclib 2μM R08 exp502]]|0.073|| |[[:results:exp443|SNS-032 15μM R08 exp443]]|0.071|| |[[:results:exp500|LY2090314 0.003μM R08 exp500 no dilution day6]]|0.068|| |[[:results:exp80|RO-3307 4.7μM R02 exp80]]|0.067|| |[[:results:exp497|Lead acetate 2000μM R08 exp497]]|0.065|| |[[:results:exp414|Tozasertib 0.1μM R07 exp414]]|0.064|| |[[:results:exp435|JQ1 0.8μM R08 exp435]]|0.064|| |[[:results:exp498|Lead acetate 2000μM R08 exp498 no dilution day6]]|0.061|| |[[:results:exp85|UM0129480 7μM R02 exp85]]|0.06|| |[[:results:exp499|LY2090314 0.003μM R08 exp499]]|0.059|| |[[:results:exp407|Thapsigargin 0.005μM R07 exp407]]|0.059|| |[[:results:exp30|Rapamycin 10μM R00 exp30]]|0.054|| |[[:results:exp102|Nifuroxazide 5μM R03 exp102]]|0.053|| |[[:results:exp439|QNZ 0.01μM R08 exp439]]|0.052|| |[[:results:exp492|iCRT14 30μM R08 exp492]]|0.052|| |[[:results:exp34|Rotenone 20μM R00 exp34]]|0.052|| |[[:results:exp504|MK2206 4μM R08 exp504]]|0.051|| |[[:results:exp416|Tubacin 1.6μM R07 exp416]]|0.051|| |[[:results:exp488|Hippuristanol 0.12μM R08 exp488]]|0.49|| |[[:results:exp456|Benzoate 20000μM R08 exp456]]|0.149|| |[[:results:exp440|Aphidicolin 0.4μM R08 exp440]]|0.138|| |[[:results:exp485|GSK626616 14μM R08 exp485]]|0.104|| |[[:results:exp234|Ethanol 0.01 R05 exp234]]|0.104|| |[[:results:exp459|Bleomycin 5μM R08 exp459]]|0.092|| |[[:results:exp474|CR131-b 0.005μM R08 exp474]]|0.088|| |[[:results:exp3|Actinomycin-D 0.001μM R00 exp3]]|0.088|| |[[:results:exp116|AICAR 240μM R03 exp116]]|0.083|| |[[:results:exp478|Doxorubicin 0.02μM R08 exp478]]|0.081|| |[[:results:exp472|CI-1040 9.5μM R08 exp472]]|0.079|| |[[:results:exp450|Artemisinin 50μM R08 exp450]]|0.078|| |[[:results:exp357|Dorsomorphin 5μM R07 exp357]]|0.077|| |[[:results:exp259|6-Thio-2-deoxyguanosine 2μM R06 exp259]]|0.074|| |[[:results:exp2|5-Fluorouracil 20μM R00 exp2]]|0.074|| |[[:results:exp199|Etoposide 0.3μM R05 exp199]]|0.072|| |[[:results:exp468|CB-5083 0.4μM R08 exp468]]|0.07|| |[[:results:exp19|Etoposide 1μM R00 exp19]]|0.07|| |[[:results:exp264|Arsenate 40μM R06 exp264]]|0.07|| |[[:results:exp275|Citral 75μM R06 exp275]]|0.069|| |[[:results:exp211|AICAR 240μM R05 exp211]]|0.068|| |[[:results:exp216|Erlotinib 10μM R05 exp216]]|0.067|| |[[:results:exp451|Atovaquone 15μM R08 exp451]]|0.063|| |[[:results:exp355|Dinaciclib 0.007μM R07 exp355]]|0.061|| |[[:results:exp447|Amiloride 100μM R08 exp447]]|0.06|| |[[:results:exp445|∆-9-Tetrahydrocannabinol 30μM R08 exp445]]|0.06|| |[[:results:exp539|42°C R08 exp539]]|0.057|| |[[:results:exp214|2-Deoxy-D-glucose 800μM R05 exp214]]|0.054|| |[[:results:exp448|Ammonium tetrathiomolybdate 10μM R08 exp448]]|0.052|| |[[:results:exp441|GSK-J4 1.5μM R08 exp441]]|0.052|| {{:chemogenomics:comparison_plots:exp134_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp135_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp524.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp512.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp525.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp503.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp531.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp526.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp529.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp515.png?nolink |}} {{:chemogenomics:comparison_plots:exp28_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp374_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp527.png?nolink |}} {{:chemogenomics:comparison_plots:exp21_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp535.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp502.png?nolink |}} {{:chemogenomics:comparison_plots:exp443_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp500.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp80.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp497.png?nolink |}} {{:chemogenomics:comparison_plots:exp414_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp435_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp498.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp85.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp499.png?nolink |}} {{:chemogenomics:comparison_plots:exp407_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp30_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp102_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp439_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp492.png?nolink |}} {{:chemogenomics:comparison_plots:exp34_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp504.png?nolink |}} {{:chemogenomics:comparison_plots:exp416_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp488_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp456_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp440_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp485_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp234_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp459_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp474_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp3_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp116_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp478_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp472_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp450_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp357_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp259_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp2_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp199_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp468_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp19_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp264_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp275_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp211_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp216_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp451_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp355_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp447_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp445_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp489_vs_exp539.png?nolink |}} {{:chemogenomics:comparison_plots:exp214_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp448_vs_exp489.png?nolink |}} {{:chemogenomics:comparison_plots:exp441_vs_exp489.png?nolink |}} ^GO Term^Fold Change^Genes^ |regulation of cell cycle process|8.54|DDX3X,FZR1,CHMP2A,RANBP1,TP53BP1,PTPN11,RHOA,BIRC6,TIMELESS,ANAPC11| ^GO Term^Fold Change^Genes^ |apoptosome|552.30|CASP9,APAF1| |activation of cysteine-type endopeptidase activity involved in apoptotic process by cytochrome c|220.92|CASP9,APAF1| |porin activity|220.92|BAK1,VDAC2| |elongator holoenzyme complex|220.92|ELP3,ELP6| |positive regulation of IRE1-mediated unfolded protein response|184.10|BAK1,BCL2L11| |TORC2 signaling|184.10|MAPKAP1,RICTOR| |tRNA wobble uridine modification|103.56|ELP3,ELP6,KTI12| |tRNA wobble base modification|87.21|ELP3,ELP6,KTI12| |positive regulation of mitochondrial membrane permeability|59.18|BAK1,VDAC2,BCL2L11| |positive regulation of membrane permeability|53.45|BAK1,VDAC2,BCL2L11| |TOR signaling|47.34|MAPKAP1,NPRL3,RICTOR| |regulation of TORC1 signaling|25.69|NPRL3,TSC2,SYK,TSC1| |regulation of TOR signaling|24.55|NPRL3,RICTOR,TSC2,HDAC3,SYK,TSC1| |mitochondrial membrane organization|21.04|BAK1,VDAC2,BCL2L11,ROMO1| |lymphocyte differentiation|11.67|BAK1,PIK3CD,CD19,SYK,TSC1,IKZF1| |mononuclear cell differentiation|10.13|BAK1,PIK3CD,CD19,SYK,TSC1,IKZF1| |cellular response to external stimulus|10.13|BAK1,MAPKAP1,NPRL3,RICTOR,TSC2,TSC1| |enzyme activator activity|6.82|CASP9,NPRL3,RICTOR,APAF1,TSC2,PLAA,GNAS| |hemopoiesis|6.65|BAK1,CASP9,PIK3CD,ALAS1,CD19,SYK,TSC1,IKZF1|