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Revision as of 17:26, 3 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit		Latest revision as of 02:25, 4 January 2025 edit undoPreimage (talk | contribs)Extended confirmed users1,364 edits removed Category:Triketones; added Category:Diketones using HotCat
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			{{short description|Group of chemical compounds}}
	{{chembox
			{{Chembox
			| 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 = 21106358		| ChemSpiderID = 21106358
	| InChI = 1/C46H76O11/c1-13-34-18-16-14-15-17-28(4)42(51)45(12,54)43(52)32(8)40(50)31(7)39(49)30(6)38(48)27(3)19-22-37(47)55-41-29(5)35(21-20-34)56-46(33(41)9)24-23-26(2)36(57-46)25-44(10,11)53/h14-16,18-19,22,26-36,38,40-42,48,50-51,53-54H,13,17,20-21,23-25H2,1-12H3/b15-14+,18-16-,22-19+/t26-,27-,28+,29+,30+,31-,32-,33-,34+,35?,36-,38-,40+,41+,42+,45+,46-/m1/s1		| InChI = 1S/C46H76O11/c1-13-34-18-16-14-15-17-28(4)42(51)45(12,54)43(52)32(8)40(50)31(7)39(49)30(6)38(48)27(3)19-22-37(47)55-41-29(5)35(21-20-34)56-46(33(41)9)24-23-26(2)36(57-46)25-44(10,11)53/h14-16,18-19,22,26-36,38,40-42,48,50-51,53-54H,13,17,20-21,23-25H2,1-12H3/b15-14+,18-16-,22-19+/t26-,27-,28+,29+,30+,31-,32-,33-,34+,35?,36-,38-,40+,41+,42+,45+,46-/m1/s1
	| InChIKey = QBAMBSAJEFIQBK-GJHUHQBXBC		| InChIKey = QBAMBSAJEFIQBK-GJHUHQBXBC
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C46H76O11/c1-13-34-18-16-14-15-17-28(4)42(51)45(12,54)43(52)32(8)40(50)31(7)39(49)30(6)38(48)27(3)19-22-37(47)55-41-29(5)35(21-20-34)56-46(33(41)9)24-23-26(2)36(57-46)25-44(10,11)53/h14-16,18-19,22,26-36,38,40-42,48,50-51,53-54H,13,17,20-21,23-25H2,1-12H3/b15-14+,18-16-,22-19+/t26-,27-,28+,29+,30+,31-,32-,33-,34+,35?,36-,38-,40+,41+,42+,45+,46-/m1/s1		| StdInChI = 1S/C46H76O11/c1-13-34-18-16-14-15-17-28(4)42(51)45(12,54)43(52)32(8)40(50)31(7)39(49)30(6)38(48)27(3)19-22-37(47)55-41-29(5)35(21-20-34)56-46(33(41)9)24-23-26(2)36(57-46)25-44(10,11)53/h14-16,18-19,22,26-36,38,40-42,48,50-51,53-54H,13,17,20-21,23-25H2,1-12H3/b15-14+,18-16-,22-19+/t26-,27-,28+,29+,30+,31-,32-,33-,34+,35?,36-,38-,40+,41+,42+,45+,46-/m1/s1
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = QBAMBSAJEFIQBK-GJHUHQBXSA-N		| StdInChIKey = 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 = }}
		⚫	| 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 oxidation 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}}
	]		]
			]
			]
			]
	]
	]
	]
	]		]
	]
	]
	]