Etoposide 1μM R00 exp19

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

Compound References

PubChem Name: Etoposide
Synonyms: VP-16; VP-16-213
CAS #: 33419-42-0
PubChem CID: 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

Compound Supplier

Supplier Name: Sigma-Aldrich
Catalog #: E1383
Lot #: N/A

Compound Characterization

HRMS (ESI-TOF) m/z: (M+H)+ Calcd for C29H32O13 589.19157; found 589.19262

Dose Response Curve

Platform ID: Etoposide
Min: -33.3567; Max: 88.0314

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

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	Scores	View	View	View	View	View

Gene	CRANKS Score	FDR
MTCH2	-3.10	<0.01
VPS25	-3.05	0.07
MAP3K7	-3.04	<0.01
UBE4A	-2.93	0.02
FAM208A	-2.90	0.01
TOP1	-2.84	0.06
ZFC3H1	-2.83	0.03
USP5	-2.74	0.05
CNOT2	-2.67	0.03
TAF1	-2.58	0.07
PSMD1	-2.58	0.27
DDX3X	-2.57	0.04
RBM7	-2.54	0.04
ACACA	-2.53	0.05
XIAP	-2.51	0.04
TSG101	-2.50	0.09
KIDINS220	-2.50	0.06
ATP6V0C	-2.49	0.39
SEPHS2	-2.44	0.05
BRD2	-2.44	0.05
ISCU	-2.43	0.32
MUL1	-2.43	0.05
XPR1	-2.40	0.05
RNF113A	-2.40	0.19
SYS1	-2.39	0.05
SKIV2L2	-2.39	0.25
PSMB4	-2.35	0.15
SAP130	-2.34	0.15
SGCB	-2.34	0.06
PSMA2	-2.32	0.27
C4orf3	2.66	<0.01
ALG5	2.68	<0.01
HCCS	2.73	0.02
USP15	2.74	<0.01
MTOR	2.76	0.02
CARS	2.79	0.01
CASP9	2.86	<0.01
HARS	2.88	0.05
VDAC2	3.00	<0.01
NXT1	3.03	<0.01
RAD23B	3.07	<0.01
TRIAP1	3.11	<0.01
MEAF6	3.11	<0.01
AURKB	3.16	<0.01
CCT7	3.16	<0.01
TSR2	3.24	<0.01
HSPD1	3.33	<0.01
TOP2A	3.39	<0.01
EIF4G1	3.43	<0.01
PELO	3.46	<0.01
ENY2	3.58	<0.01
COPS7B	3.60	<0.01
CYCS	3.64	<0.01
UBQLN1	3.70	<0.01
MARCH5	4.02	<0.01
FAF2	4.13	<0.01
DIABLO	4.30	<0.01
BAK1	5.30	<0.01
APAF1	5.65	<0.01
PLAA	6.13	<0.01

Screen	Correlation	Plot
Pimelic-diphenylamide-106 5μM R00 exp28	0.199	View
Rotenone 20μM R00 exp34	0.158	View
MLN-4924 2μM R00 exp22	0.109	View
Mitomycin-C 0.06μM R08 exp503	0.095	View
PU-H71 1μM R08 exp515	0.089	View
RO-3307 4.7μM R02 exp80	0.083	View
THZ1 0.06μM R08 exp531	0.081	View
Rotenone 2μM R00 exp33	0.075	View
Hippuristanol 0.12μM R08 exp489 no dilution day6	0.07	View
Staurosporine 0.02μM R08 exp524	0.07	View
Tanespimycin 14μM R08 exp527	0.068	View
Hippuristanol 0.12μM R08 exp488	0.066	View
MS023 7μM R03 exp135	0.065	View
JQ1 0.8μM R08 exp435	0.064	View
SNS-032 15μM R08 exp443	0.064	View
Nocodazole 0.2μM R00 exp24	0.063	View
GSK461364A 0.1μM R03 exp126	0.062	View
Oligomycin-A 20μM R00 exp26	0.062	View
Olaparib 4μM R08 exp512	0.057	View
UM0129480 7μM R02 exp85	0.055	View
GSK-J4 1.5μM R08 exp441	0.054	View
MS023 2μM R03 exp134	0.052	View
GSK626616 14μM R08 exp485	0.051	View
5-Fluorouracil 20μM R00 exp2	0.181	View
Etoposide 0.3μM R05 exp199	0.177	View
Actinomycin-D 0.001μM R00 exp3	0.165	View
DABN 20μM R00 exp17	0.11	View
Bleomycin 5μM R08 exp459	0.1	View
Benzoate 20000μM R08 exp456	0.1	View
Bortezomib 0.05μM R00 exp7	0.095	View
Doxorubicin 0.02μM R08 exp478	0.087	View
42°C R08 exp539	0.077	View
CI-1040 9.5μM R08 exp472	0.072	View
AICAR 240μM R05 exp211	0.071	View
Aphidicolin 0.4μM R08 exp440	0.071	View
Diepoxybutane 3μM R07 exp354	0.062	View
6-Thio-2-deoxyguanosine 2μM R06 exp259	0.062	View
Deferoxamine 11μM R07 exp350	0.059	View
Centrinone 0.5μM R07 exp343	0.058	View
CR131-b 0.005μM R08 exp474	0.058	View
Actinomycin-D 0.01μM R00 exp4	0.057	View
Atovaquone 15μM R08 exp451	0.055	View
Dinaciclib 0.007μM R07 exp355	0.055	View

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

Etoposide 1μM R00 exp19

Mechanism of Action

Technical Notes

Compound References

Compound Supplier

Compound Characterization

Dose Response Curve

Screen Summary

Screen Results