Oligomycin A

Names

[ CAS No. ]:
579-13-5

[ Name ]:
Oligomycin A

[Synonym ]:
(1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonaMethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonaco
(1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione
Oligomycin A
(1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27S,28R,29S)-22-Ethyl-7,11,14,15-tetrahydroxy-6'-[(2S)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione
Spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-[2H]pyran]-3,9,13-trione, 22-ethyl-3',4',5',6'-tetrahydro-7,11,14,15-tetrahydroxy-6'-[(2S)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-, (1S,4E,5'R,6R,6'R,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,27S,28R,29S)-
MCH 32
MFCD00065705
OLIGOMYCIN,STREPTOMYCES DIASTATOCHROMOGENES
EINECS 209-473-3
OLIGOMYCIN A,STREPTOMYCES DIASTATOCHROMOGENES

Biological Activity

[Description]:

Oligomycin A, created by Streptomyces, acts as a mitochondrial F0F1-ATPase inhibitor, with a Ki of 1 μM; Oligomycin A shows anti-fungal activity.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> ATP Synthase

Research Areas >> Cancer

Research Areas >> Infection

Natural Products >> Others

[Target]

Ki: 1 μM (F0F1-ATPase)[1]

[In Vitro]

Oligomycin A is a mitochondrial F0F1-ATPase inhibitor with a Ki of 1 μM. Oligomycin A shows cytotoxic to the NCI-60 cell lines, with GI50 of 10 nM. Oligomycin A also inhibits the activity of Triton X-100-solubilized ATPase with a Ki of 0.1 μM. Furthermore, Oligomycin A has anti-fungal activity[1]. Oligomycin A (2.4 µM) inhibits the ability of spermatozoa to achieve feasible in vitro capacitation (IVC), and also suppresses progesterone-induced in vitro acrosome exocytosis (IVAE) as well as the concomitant peaks of O2 consumption and ATP levels[2].

[Cell Assay]

Drug (Oligomycin A, etc.) dilutions are added to monolayer or suspension cells in 96 well plates in triplicate for varying times. MTT is then added to the wells at a final concentration of 0.5 mg/mL. Supernatant is removed after pelleting the reduced MTT crystals. The crystals are fully dissolved in 40 mM HCl in isopropanol. Plates are scanned on a microplate reader at 595 nm[1].

[References]

[1]. Salomon AR, et al. Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase. Chem Biol. 2001 Jan;8(1):71-80.

[2]. Ramió-Lluch L, et al. Oligomycin A-induced inhibition of mitochondrial ATP-synthase activity suppresses boar sperm motility and in vitro capacitation achievement without modifying overall sperm energy levels. Reprod Fertil Dev. 2014;26(6):883-97.

[Related Small Molecules]

BTB06584

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
886.3±65.0 °C at 760 mmHg

[ Melting Point ]:
150-151ºC

[ Molecular Formula ]:
C₄₅H₇₄O₁₁

[ Molecular Weight ]:
791.063

[ Flash Point ]:
252.0±27.8 °C

[ Exact Mass ]:
790.523132

[ PSA ]:
180.05000

[ LogP ]:
6.17

[ Appearance of Characters ]:
white to off-white

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.543

[ Storage condition ]:
−20°C

[ Water Solubility ]:
Soluble in DMSO, ethanol or acetone

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RK3328000

CHEMICAL NAME :: Oligomycin A

CAS REGISTRY NUMBER :: 579-13-5

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C45-H74-O11

MOLECULAR WEIGHT :: 791.19

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JACSAT Journal of the American Chemical Society. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1879- Volume(issue)/page/year: 80,6092,1958

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn,T

[ Risk Phrases ]:
22-68/20/21/22-20/21/22

[ Safety Phrases ]:
36/37

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ RTECS ]:
RK3325000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
29419090

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