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579-13-5

579-13-5 structure

579-13-5 structure

Name: Oligomycin A
Chemical Name: Oligomycin A
CAS Number: 579-13-5
Molecular Formula: C₄₅H₇₄O₁₁
Molecular Weight: 791.063
Catalog: API Antibiotics Other antibiotics
Create Date: 2018-07-09 06:40:16
Modify Date: 2024-01-02 17:27:32
Oligomycin A, created by Streptomyces, acts as a mitochondrial F0F1-ATPase inhibitor, with a Ki of 1 μM; Oligomycin A shows anti-fungal activity.

Name	Oligomycin A
Synonyms	(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

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.

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	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

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

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