Oligomycin A (MCH 32), the main analogue of the isomer, is an inhibitor of mitochondrial F1FO ATP synthase, inhibiting oxidative phosphorylation and all ATP-dependent processes that occur on mitochondrial coupled membranes. It inhibits ATP synthase by blocking the proton channel (Fo subunit) necessary for oxidative phosphorylation of ADP to ATP. It also induces apoptosis in many cell types.

 

Brand: BCM

 

Target: ATPase; Antibiotic; Antifungal

 

Signaling Pathways: Membrane transporter/Ion channel; Microbiology/Virology

 

In Vitro: Oligomycin A is an inhibitor of ATP synthase, inhibits oxidative phosphorylation and all the ATP-dependent processes occurring on the coupling membrane of mitochondria.Oligomycin A inhibits ATP synthase by blocking its proton channel (Fo subunit), which is necessary for oxidative phosphorylation of ADP to ATP. The inhibition of ATP synthesis by oligomycin A will significantly reduce electron flow through the electron transport chain; however, electron flow is not stopped completely due to a process known as proton leak or mitochondrial uncoupling. In a group of cancer cells, Oligomycin at 100 ng/ml completely inhibits oxidative phosphorylation activity in 1 h and induces various levels of glycolysis gains by 6 h. Oligomycin, inhibitor of the F0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis. Oligomycin inhibits mitochondrial respiration in melanoma, sensitizes melanoma cells to therapy, blocks the emergence of the slow-cycling, long-term tumor-maintaining melanoma cells.

 

Melting Point: 150-151℃

 

Boiling Point: 886.3±65.0 °C(Predicted)

 

pKa: 12.52±0.70(Predicted)

 

Solubility: Soluble in DMSO. Insoluble in Water; Insoluble in Ethanol.

 

GHS: GHS07

 

Isomeric SMILES: CC[C@@H]\1CC[C@H]2[C@H]([C@H]([C@@H]([C@]3(O2)CC[C@@H]([C@@H](O3)C[C@@H](C)O)C)C)OC(=O)/C=C/[C@@H]([C@H]([C@@H](C(=O)[C@@H]([C@H]([C@@H](C(=O)[C@]([C@H]([C@@H](C/C=C/C=C1)C)O)(C)O)C)O)C)C)O)C)C  

 

InChIKey: MNULEGDCPYONBU-AWJDAWNUSA-N  

 

InChI: InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-/m0/s1

 

Attribute
[Chem Name]	(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-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-oxane]-3,9,13-trione
[Synonym]	Oligomycin A
[CAS No.]	579-13-5
[EINECS]	209-437-3
[MDL No.]	MFCD00065705
[Formula]	C45H74O11
[Molecular]	791.06
[Form]	White to off-white powder
[Storage]	Sealed in dry. Store in freezer, under -20°C

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