Atovaquone 15μM R08 exp451

Ubiquinone analog, inhibits mitochondrial complex III, induces DNA strand breaks

Class / Subclass 1: Infectious Disease / Antimalarial
Class / Subclass 2: Organelle Function / Mitochondrial Inhibitor
Class / Subclass 3: DNA Damage, Repair and Replication / DNA Damaging Agent

Compound References

PubChem Name: Atovaquone
Synonyms: Atavaquone
CAS #: 95233-18-4
PubChem CID: 74989
IUPAC: 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
INCHI Name: InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,24H,5-8H2
INCHI Key: BSJMWHQBCZFXBR-UHFFFAOYSA-N
Molecular Weight: 366.8
Canonical SMILES: C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
Isomeric SMILES: N/A
Molecular Formula: C22H19ClO3

Compound Supplier

Supplier Name: Tocris Bioscience
Catalog #: 6358
Lot #: 1A/207968

Compound Characterization

HRMS (ESI-TOF) m/z: (M-H)- Calcd for C22 H19 Cl O3 365.095; found 365.0967

Dose Response Curve

Dose response curve not available.

Screen Summary

Round: 08
Dose: 15µM
Days of incubation: 8
Doublings: 0.3
Numbers of reads: 15492810

Sensitive/Resistant hits (FDR<0.05)	CRANKS	Score Plot	Top 30 Genes	Screen Similarity	Top 30 Sensitive GO terms	Top 30 Resistant GO terms
5/74	Scores	View	View	View	View	View

Gene	CRANKS Score	FDR
NEFM	-2.85	0.03
PANX1	-2.82	0.03
CIT	-2.71	0.03
EIF4B	-2.68	0.03
SLC29A1	-2.64	0.03
MDM2	-2.59	0.13
PRKAA1	-2.50	0.06
PRC1	-2.49	0.12
EIF3H	-2.44	0.13
RNF113A	-2.43	0.13
MCM7	-2.40	0.21
CNOT2	-2.37	0.12
ATP6V1A	-2.37	0.22
ORC1	-2.30	0.19
CDK8	-2.29	0.19
RPS2	-2.25	0.15
SLC17A5	-2.21	0.17
ERN1	-2.20	0.17
ATP6V0B	-2.18	0.50
NDC80	-2.17	0.46
ESPL1	-2.17	0.43
IGBP1	-2.16	0.43
IKZF2	-2.14	0.19
PSMC3	-2.10	0.60
SCEL	-2.10	0.22
LRR1	-2.09	0.47
RPH3A	-2.08	0.22
COPE	-2.07	0.55
USP37	-2.06	0.33
RNF225	-2.03	0.28
ASUN	2.70	<0.01
NDUFA6	2.73	<0.01
C17orf89	2.74	<0.01
CBFB	2.75	<0.01
CSNK2B	2.76	<0.01
BAP1	2.77	<0.01
NDUFA13	2.79	0.01
NDUFS3	2.80	<0.01
PDSS1	2.81	<0.01
NSD1	2.85	<0.01
COX5A	2.85	<0.01
DOHH	2.89	<0.01
NDUFAF3	2.92	<0.01
TP53	2.94	<0.01
ATP5C1	3.00	<0.01
FNDC3B	3.01	<0.01
NDUFB9	3.06	<0.01
NDUFB11	3.11	<0.01
NDUFA2	3.13	<0.01
ATP5B	3.17	<0.01
ATP5D	3.17	<0.01
TAZ	3.24	0.01
ATP5A1	3.35	<0.01
RPTOR	3.38	<0.01
NDUFB6	3.42	<0.01
MARCH5	3.46	<0.01
MBTPS2	3.50	<0.01
NDUFA1	3.68	<0.01
BAK1	3.86	<0.01
IBA57	3.89	<0.01

Screen	Correlation	Plot
Mitomycin-C 0.06μM R08 exp503	0.135	View
CI-1040 9.5μM R08 exp472	0.133	View
Bleomycin 5μM R08 exp459	0.11	View
Tanespimycin 14μM R08 exp527	0.107	View
Doxorubicin 0.02μM R08 exp478	0.103	View
SNS-032 15μM R08 exp443	0.103	View
Etoposide 0.3μM R05 exp199	0.101	View
THZ1 0.06μM R08 exp531	0.099	View
GSK-J4 1.5μM R08 exp441	0.098	View
HMS-I2 10μM R06 exp288	0.098	View
Benzoate 20000μM R08 exp456	0.096	View
Oligomycin-A 2μM R00 exp25	0.09	View
Hinokiflavone 12μM R08 exp487	0.087	View
JQ1 0.8μM R08 exp435	0.086	View
PU-H71 1μM R08 exp515	0.081	View
Pimelic-diphenylamide-106 5μM R00 exp28	0.078	View
UM131593 0.2μM R03 exp106	0.076	View
ONC212 0.15μM R08 exp513	0.076	View
UM0129480 7μM R02 exp85	0.075	View
TIC10 10μM R08 exp532	0.074	View
Hydroxyurea 100μM R07 exp329	0.074	View
BI-2536 0.02μM R03 exp96	0.074	View
MS023 7μM R03 exp135	0.073	View
GSK461364A 0.1μM R03 exp126	0.07	View
CR131-b 0.005μM R08 exp474	0.069	View
Thimerosal 0.85μM R08 exp529	0.069	View
Hippuristanol 0.12μM R08 exp489 no dilution day6	0.063	View
Hippuristanol 0.12μM R08 exp488	0.059	View
RO-3307 4.7μM R02 exp80	0.058	View
Genistein 15μM R07 exp360	0.058	View
UM0125461 0.74μM R02 exp84	0.057	View
Calcium Ionophore 0.4μM R07 exp342	0.056	View
MLN-4924 2μM R00 exp22	0.056	View
Etoposide 1μM R00 exp19	0.055	View
Quercetin 20μM R08 exp517	0.055	View
Rotenone 0.07μM R08 exp431	0.054	View
Nutlin-3A 1.6μM R06 exp294	0.054	View
LY2090314 0.003μM R08 exp500 no dilution day6	0.054	View
QNZ 0.01μM R08 exp439	0.053	View
Staurosporine 0.02μM R08 exp524	0.052	View
Artemisinin 50μM R08 exp450	0.137	View
Ammonium tetrathiomolybdate 10μM R08 exp448	0.136	View
Aphidicolin 0.4μM R08 exp440	0.13	View
AICAR 240μM R05 exp211	0.097	View
5-Fluorouracil 20μM R00 exp2	0.086	View
Actinomycin-D 0.001μM R00 exp3	0.07	View
42°C R08 exp539	0.063	View
6-Thio-2-deoxyguanosine 2μM R06 exp259	0.062	View
AICAR 240μM R03 exp116	0.06	View

GO Term	Fold Change	Genes
proton motive force-driven mitochondrial ATP synthesis	125.05	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
proton motive force-driven ATP synthesis	119.67	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
mitochondrial respiratory chain complex I assembly	106.21	NDUFA1,NDUFB6,NDUFA2,NDUFB11,NDUFB9,NDUFAF3,NDUFS3,NDUFA13,NDUFA6,NDUFA3
NADH dehydrogenase complex assembly	106.21	NDUFA1,NDUFB6,NDUFA2,NDUFB11,NDUFB9,NDUFAF3,NDUFS3,NDUFA13,NDUFA6,NDUFA3
ATP biosynthetic process	104.06	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
purine ribonucleoside triphosphate biosynthetic process	89.75	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
purine nucleoside triphosphate biosynthetic process	88.64	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
ribonucleoside triphosphate biosynthetic process	84.47	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
oxidative phosphorylation	78.10	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,COX5A,NDUFS3,NDUFA13,NDUFA6,NDUFA3
ATP metabolic process	71.80	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
nucleoside triphosphate biosynthetic process	71.26	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
inner mitochondrial membrane protein complex	58.58	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,COX5A,NDUFS3,NDUFA13,NDUFA6,NDUFA3
purine ribonucleoside triphosphate metabolic process	57.90	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
purine nucleoside triphosphate metabolic process	55.66	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
ribonucleoside triphosphate metabolic process	55.23	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
aerobic respiration	54.84	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,COX5A,NDUFS3,NDUFA13,NDUFA6,NDUFA3
nucleoside triphosphate metabolic process	49.52	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,NDUFS3,NDUFA13,NDUFA6,NDUFA3
cellular respiration	45.75	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,COX5A,NDUFS3,NDUFA13,NDUFA6,NDUFA3
energy derivation by oxidation of organic compounds	35.40	NDUFA1,NDUFB6,ATP5F1A,ATP5F1D,ATP5F1B,NDUFA2,NDUFB11,NDUFB9,ATP5F1C,TP53,COX5A,NDUFS3,NDUFA13,NDUFA6,NDUFA3

Atovaquone 15μM R08 exp451

Mechanism of Action

Technical Notes

Compound References

Compound Supplier

Compound Characterization

Dose Response Curve

Screen Summary

Screen Results