Rotenone 2μM R00 exp33

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

Compound References

PubChem Name: Rotenone
Synonyms: N/A
CAS #: 83-79-4
PubChem CID: 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

Compound Supplier

Supplier Name: Sigma-Aldrich
Catalog #: R8875
Lot #: SLBG7568V

Compound Characterization

HRMS (ESI-TOF) m/z: (M+H)+ Calcd for C23H22O6 395.14891; found 395.15075

Dose Response Curve

Platform ID: Rotenone
Min: 11.0154; Max: 87.2842

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: 2µM
Days of incubation: 8
Doublings: 0.3
Numbers of reads: 11335210

Sensitive/Resistant hits (FDR<0.05)	CRANKS	Score Plot	Top 30 Genes	Screen Similarity	Top 30 Sensitive GO terms	Top 30 Resistant GO terms
7/173	Scores	View	View	View	View	View

Gene	CRANKS Score	FDR
SEPHS2	-3.26	<0.01
ATP6AP1	-3.17	0.28
DDX3X	-3.05	<0.01
PSTK	-2.92	0.02
COX7A2L	-2.89	0.01
ATP6V0C	-2.61	0.48
BRD2	-2.57	0.05
HNRNPA0	-2.54	0.05
ATP6V1A	-2.53	0.09
YPEL5	-2.53	0.05
ATP6V1B2	-2.48	0.09
RAB43	-2.45	0.10
GZF1	-2.43	0.17
TSC2	-2.39	0.09
MTCH2	-2.35	0.09
POLE	-2.34	0.48
MRS2	-2.34	0.09
SLC6A12	-2.33	0.14
AATF	-2.32	0.28
EEFSEC	-2.29	0.10
PCGF1	-2.28	0.10
SLC6A17	-2.25	0.11
CLSPN	-2.24	0.29
BIRC5	-2.24	0.28
TAF1	-2.23	0.28
UIMC1	-2.21	0.20
ANKRD13C	-2.18	0.32
FBXL14	-2.15	0.17
YY1	-2.11	0.28
SCGB1C1	-2.10	0.20
DPY19L1	3.46	<0.01
NOD1	3.49	<0.01
HOXA7	3.50	<0.01
PLEKHA8	3.54	<0.01
ELMO1	3.56	<0.01
COL28A1	3.57	<0.01
GPR141	3.59	<0.01
HIBADH	3.62	<0.01
DFNA5	3.63	<0.01
HOXA3	3.65	<0.01
CENPE	3.68	<0.01
CYTH3	3.70	<0.01
ZDHHC4	3.71	<0.01
TNRC18	3.73	<0.01
USP42	3.80	<0.01
PDE1C	3.82	<0.01
HOXA5	3.83	<0.01
C7orf41	4.11	<0.01
MAD2L1	5.07	<0.01
ZWILCH	5.08	<0.01
RBM14-RBM4	5.72	<0.01
MAD2L1BP	5.91	<0.01
MAD1L1	6.31	<0.01
RBM14	6.36	<0.01
CDC20	6.44	<0.01
BUB1B	6.80	<0.01
BUB3	6.90	<0.01
TRIP13	7.30	<0.01
ZW10	8.24	<0.01
KNTC1	8.27	<0.01

Screen	Correlation	Plot
SB743921 0.001μM R05 exp244	0.338	View
Vinblastine 0.015μM R05 exp208	0.225	View
Vinblastine 0.2μM R03 exp108	0.052	View
Nocodazole 0.2μM R00 exp24	0.387	View
Nocodazole 0.1μM R03 exp94	0.343	View
DABN racemic mixture R03 exp93	0.274	View
R-DABN 8μM R03 exp111	0.256	View
HMS-I1 10μM R06 exp256	0.211	View
Nocodazole 0.2μM R02 exp64	0.197	View
DABN 20μM R00 exp17	0.094	View
BI-6727 0.04μM R03 exp98	0.092	View
Etoposide 1μM R00 exp19	0.075	View
Rotenone 20μM R00 exp34	0.069	View
5-Fluorouracil 20μM R00 exp2	0.061	View
Pimelic-diphenylamide-106 5μM R00 exp28	0.06	View
Actinomycin-D 0.001μM R00 exp3	0.056	View

GO Term	Fold Change	Genes
Golgi lumen acidification	190.60	ATP6AP1,ATP6V0C,ATP6V1A
endosomal lumen acidification	131.95	ATP6AP1,ATP6V0C,ATP6V1A
synaptic vesicle lumen acidification	114.36	ATP6AP1,ATP6V1A,ATP6V1B2
proton-transporting V-type ATPase complex	84.71	ATP6AP1,ATP6V0C,ATP6V1A,ATP6V1B2
lysosomal lumen acidification	81.68	ATP6AP1,ATP6V0C,ATP6V1A
ATPase activity, coupled to transmembrane movement of ions, rotational mechanism	74.58	ATP6V0C,ATP6V1A,ATP6V1B2
proton-transporting ATPase activity, rotational mechanism	74.58	ATP6V0C,ATP6V1A,ATP6V1B2
ATPase-coupled ion transmembrane transporter activity	74.58	ATP6V0C,ATP6V1A,ATP6V1B2
vacuolar proton-transporting V-type ATPase complex	71.47	ATP6V0C,ATP6V1A,ATP6V1B2
regulation of lysosomal lumen pH	61.26	ATP6AP1,ATP6V0C,ATP6V1A
proton-transporting two-sector ATPase complex	50.83	ATP6AP1,ATP6V0C,ATP6V1A,ATP6V1B2
intracellular pH reduction	44.85	ATP6AP1,ATP6V0C,ATP6V1A,ATP6V1B2
regulation of intracellular pH	26.29	ATP6AP1,ATP6V0C,ATP6V1A,ATP6V1B2
regulation of cellular pH	24.86	ATP6AP1,ATP6V0C,ATP6V1A,ATP6V1B2
exocytic vesicle membrane	23.43	ATP6AP1,ATP6V0C,ATP6V1A,ATP6V1B2,SLC6A17
synaptic vesicle membrane	23.43	ATP6AP1,ATP6V0C,ATP6V1A,ATP6V1B2,SLC6A17
proton transmembrane transport	21.66	ATP6AP1,COX7A2L,ATP6V0C,ATP6V1A,ATP6V1B2
ATPase complex	20.42	ATP6AP1,ATP6V0C,ATP6V1A,ATP6V1B2,YY1
monoatomic cation transmembrane transport	7.22	ATP6AP1,COX7A2L,ATP6V0C,ATP6V1A,ATP6V1B2,MRS2,SLC6A12,SLC6A17

GO Term	Fold Change	Genes
mitotic spindle assembly checkpoint signaling	177.66	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
spindle assembly checkpoint signaling	177.66	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
mitotic spindle checkpoint signaling	177.66	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
negative regulation of mitotic sister chromatid separation	160.47	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
negative regulation of mitotic sister chromatid segregation	160.47	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
spindle checkpoint signaling	152.48	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH
negative regulation of chromosome separation	150.75	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
negative regulation of metaphase/anaphase transition of cell cycle	150.75	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
negative regulation of chromosome segregation	150.75	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
negative regulation of mitotic metaphase/anaphase transition	142.64	KNTC1,ZW10,TRIP13,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
negative regulation of sister chromatid segregation	142.64	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH
negative regulation of nuclear division	108.14	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,ZWILCH,MAD2L1
regulation of mitotic sister chromatid segregation	93.86	KNTC1,ZW10,TRIP13,BUB3,BUB1B,MAD1L1,MAD2L1BP,ZWILCH,MAD2L1
regulation of mitotic sister chromatid separation	85.77	ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,MAD2L1BP,ZWILCH,MAD2L1
regulation of chromosome separation	75.72	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,MAD2L1BP,ZWILCH,MAD2L1
regulation of mitotic metaphase/anaphase transition	68.32	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,MAD2L1BP,ZWILCH,MAD2L1,CENPE
regulation of metaphase/anaphase transition of cell cycle	66.09	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,MAD2L1BP,ZWILCH,MAD2L1,CENPE
regulation of sister chromatid segregation	59.03	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,MAD2L1BP,ZWILCH,MAD2L1,CENPE
regulation of chromosome segregation	48.25	KNTC1,ZW10,TRIP13,BUB3,BUB1B,CDC20,MAD1L1,MAD2L1BP,ZWILCH,MAD2L1,CENPE

Rotenone 2μM R00 exp33

Mechanism of Action

Technical Notes

Compound References

Compound Supplier

Compound Characterization

Dose Response Curve

Screen Summary

Screen Results