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			{{short description|Group of chemical compounds}}
	{{chembox
			{{Chembox
⚫	| verifiedrevid = 400341109
			| Watchedfields = changed
		⚫	| verifiedrevid = 432936619
	| Name = Oligomycin A		| Name = Oligomycin A
	| ImageFile = Oligomycin.png		| ImageFile = Oligomycin A.png
	| IUPACName = (1''R'',4''E'',5<nowiki>'</nowiki>''S'',6''S'',6<nowiki>'</nowiki>''S'',7''R'',8''S'',10''R'',11''R'',12''S'',14''R'',15''S'',16''R'',18''E'',20''E'',22''R'',25''S'',27''R'',28''S'',29''R'')-22-ethyl-7,11,14,15-tetrahydroxy-6'--5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3''H'',9''H'',13''H''-spirononacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione		| IUPACName = (1''R'',4''E'',5<nowiki>'</nowiki>''S'',6''S'',6<nowiki>'</nowiki>''S'',7''R'',8''S'',10''R'',11''R'',12''S'',14''R'',15''S'',16''R'',18''E'',20''E'',22''R'',25''S'',27''R'',28''S'',29''R'')-22-ethyl-7,11,14,15-tetrahydroxy-6'--5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3''H'',9''H'',13''H''-spirononacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione
	| IUPACName_hidden = yes
	| OtherNames = Oligomycin		| OtherNames = Oligomycin
		⚫	|Section1={{Chembox Identifiers
⚫	|C=45|H=74|O=11
⚫	| Section1 = {{Chembox Identifiers
	| Abbreviations =		| Abbreviations =
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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	| StdInChIKey = QBAMBSAJEFIQBK-GJHUHQBXSA-N		| StdInChIKey = QBAMBSAJEFIQBK-GJHUHQBXSA-N
	| InChIKey1 = QBAMBSAJEFIQBK-GJHUHQBXSA-N		| InChIKey1 = QBAMBSAJEFIQBK-GJHUHQBXSA-N
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 1404-19-9		| CASNo = 1404-19-9
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 14JVM0OHLV
	| EINECS = 215-767-9		| EINECS = 215-767-9
	| PubChem = 6450197		| PubChem = 6450197
	| SMILES = C(C)(O)C1O2(CC1C)O3CC(CC)/C=C\C=C\C(C)(O)(C)(O)C(=O)(C)(O)(C)C(=O)(C)(O)(C)/C=C/C(=O)O(2C)3C		| SMILES = C(C)(O)C1O2(CC1C)O3CC(CC)/C=C\C=C\C(C)(O)(C)(O)C(=O)(C)(O)(C)C(=O)(C)(O)(C)/C=C/C(=O)O(2C)3C
	| InChI =
	| RTECS = RK3325000		| RTECS = RK3325000
	| ChEBI =		| ChEBI = 28285
	| MeSHName = Oligomycins		| MeSHName = Oligomycins
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = }}		| KEGG =
			}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
		⚫	| C=45 | H=74 | O=11
	| MolarMass = 791.062 g/mol		| MolarMass = 791.062 g/mol
	| Appearance =		| Appearance =
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	| RefractIndex =		| RefractIndex =
	| Viscosity =		| Viscosity =
			}}
	| Dipole = }}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| CrystalStruct =		| CrystalStruct =
	| Coordination =		| Coordination =
	| MolShape =		| MolShape =
	| Dipole = }}		| Dipole =
			}}
	| Section4 = {{Chembox Thermochemistry		|Section4={{Chembox Thermochemistry
	| DeltaHf =		| DeltaHf =
	| DeltaHc =		| DeltaHc =
	| Entropy =		| Entropy =
	| HeatCapacity = }}		| HeatCapacity =
			}}
	| Section5 = {{Chembox Pharmacology		|Section5={{Chembox Pharmacology
	| ATCCode =		| ATCCode =
	| Bioavail =		| Bioavail =
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	| Excretion =		| Excretion =
	| PregCat =		| PregCat =
	| AdminRoutes = }}		| AdminRoutes =
			}}
	| Section6 = {{Chembox Explosive		|Section6={{Chembox Explosive
	| ShockSens =		| ShockSens =
	| FrictionSens =		| FrictionSens =
	| ExplosiveV =		| ExplosiveV =
	| REFactor = }}		| REFactor =
			}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| EUClass =
	| MainHazards =		| MainHazards =
	| NFPA-H =		| NFPA-H =
	| NFPA-F =		| NFPA-F =
	| NFPA-R =		| NFPA-R =
	| NFPA-O =		| NFPA-S =
	| RPhrases =
	| SPhrases =
	| RSPhrases =
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	| ExploLimits =		| ExploLimits =
	| PEL = }}		| PEL =
			}}
	| Section8 = {{Chembox Supplement}}		|Section9={{Chembox Related
	| Section9 = {{Chembox Related
	| OtherAnions =		| OtherAnions =
	| OtherCations =		| OtherCations =
	| OtherFunctn =		| OtherFunctn =
	| Function =		| Function =
	| OtherCpds = }}		| OtherCpds =
			}}
	}}		}}
	'''Oligomycins''' are ]s created by '']'' that can be ] to other organisms.		'''Oligomycins''' are ]s created by '']'' that are strong antibacterial agents but are often ] to other organisms, including humans.
	==Function==		== Function ==
			Oligomycins have use as ]. However, in humans, they have limited or no clinical use due to their toxic effects on ] and ].<ref name=":0">{{cite journal | vauthors = Mackieh R, Al-Bakkar N, Kfoury M, Roufayel R, Sabatier JM, Fajloun Z | title = Inhibitors of ATP Synthase as New Antibacterial Candidates | journal = Antibiotics | volume = 12 | issue = 4 | pages = 650 | date = March 2023 | pmid = 37107012 | pmc = 10135114 | doi = 10.3390/antibiotics12040650 | doi-access = free }}</ref>
	They have use as ].
	In addition, oligomycin <!-- oligomycin A? --> inhibits ] by blocking its proton channel (Fo subunit), which is necessary for ] of ] to ] (energy production). The inhibition of ATP synthesis would also stop electron transport chain. Because the high proton concentration build up is not dissipated, the free energy released by biological ] of substrates is not enough to pump any more protons against the steep gradient.		Oligomycin A is an ] of ATP synthase.<ref name=":0" /> In oxidative phosphorylation research, it is used to prevent stage 3 (phosphorylating) respiration. Oligomycin A inhibits ATP synthase by blocking its proton channel (F<sub>O</sub> subunit), which is necessary for ] of ] to ] (energy production). The inhibition of ATP synthesis by oligomycin A will significantly reduce electron flow through the ]; however, electron flow is not stopped completely due to a process known as ''proton leak'' or '']''.<ref>{{cite journal | vauthors = Jastroch M, Divakaruni AS, Mookerjee S, Treberg JR, Brand MD | title = Mitochondrial proton and electron leaks | journal = Essays in Biochemistry | volume = 47 | issue = 1 | pages = 53–67 | year = 2010 | pmid = 20533900 | pmc = 3122475 | doi = 10.1042/bse0470053 }}</ref> This process is due to ] of protons into the ] through an ] such as ], or ].
	Administering oligomycin <!-- oligomycin A? --> to an individual can result in very high levels of lactate accumulating in the blood and urine.{{Fact|date=December 2007}}		Administering oligomycin <!-- oligomycin A? --> to rats can result in very high levels of lactate accumulating in the blood and urine.<ref>{{cite journal | vauthors = Kramar R, Hohenegger M, Srour AN, Khanakah G | title = Oligomycin toxicity in intact rats | journal = Agents and Actions | volume = 15 | issue = 5–6 | pages = 660–663 | date = December 1984 | pmid = 6532186 | doi = 10.1007/BF01966788 | s2cid = 7837164 }}</ref>
	Oligomycin <!-- oligomycin A? --> is an inhibitor of ATP synthase. In oxidative phosphorylation research, it is used to prevent state 3 (phosphorylating) respiration.
	{| border="1" cellpadding="5" cellspacing="0"		{| border="1" cellpadding="5" cellspacing="0"
	|+'''Oligomycins'''<ref>{{cite journal|author=Nakata, Masaya; Ishiyama, Takashi; Akamatsu, Shinichi; Hirose, Youichi; Maruoka, Hiroshi; Suzuki, Rika; Tatsuta, Kuniaki |title=Synthetic studies on oligomycins. Synthesis of the oligomycin B spiroketal and polypropionate portions| journal=Bulletin of the Chemical Society of Japan |year=1995 |volume=68 |issue=3 |pages=967–89|doi=10.1246/bcsj.68.967}}</ref>		|+'''Oligomycins'''<ref>{{cite journal| vauthors = Nakata M, Ishiyama T, Akamatsu S, Hirose Y, Maruoka H, Suzuki R, Tatsuta K |title=Synthetic studies on oligomycins. Synthesis of the oligomycin B spiroketal and polypropionate portions| journal=Bulletin of the Chemical Society of Japan |year=1995 |volume=68 |issue=3 |pages=967–89|doi=10.1246/bcsj.68.967}}</ref>
	|-		|-
	! colspan="6" | ]		! colspan="6" | ]
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	| CH<sub>3</sub>		| CH<sub>3</sub>
	|}		|}
	{{-}}		{{Clear}}
	==References==		== References ==
	{{reflist}}		{{reflist}}
	]		]
			]
			]
			]
	]
	]
	]
	]		]
	]
	]
	]