Oligomycin

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Group of chemical compounds

title: "Oligomycin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["macrolide-antibiotics", "spiro-compounds", "diketones", "atp-synthase-inhibitors"] description: "Group of chemical compounds" topic_path: "general/macrolide-antibiotics" source: "https://en.wikipedia.org/wiki/Oligomycin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Group of chemical compounds ::

| Watchedfields = changed | verifiedrevid = 432936619 | Name = Oligomycin A | ImageFile = Oligomycin A.png | IUPACName = (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 | OtherNames = Oligomycin |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = | ChemSpiderID = 21106358 | 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 | StdInChI_Ref = | 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 = | StdInChIKey = QBAMBSAJEFIQBK-GJHUHQBXSA-N | InChIKey1 = QBAMBSAJEFIQBK-GJHUHQBXSA-N | CASNo_Ref = | CASNo = 1404-19-9 | UNII_Ref = | UNII = 14JVM0OHLV | EINECS = 215-767-9 | PubChem = 6450197 | SMILES = CC@(O)C[C@H]1O[C@@]2(CC[C@H]1C)O[C@H]3CCC@@H/C=C\C=C\CC@HC@HC@(O)C(=O)C@HC@@HC@HC(=O)C@@HC@HC@H/C=C/C(=O)OC@H[C@H]3C | RTECS = RK3325000 | ChEBI = 28285 | MeSHName = Oligomycins | KEGG_Ref = | KEGG = |Section2={{Chembox Properties | C=45 | H=74 | O=11 | MolarMass = 791.062 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = | IsoelectricPt = | SpecRotation = | RefractIndex = | Viscosity = |Section3={{Chembox Structure | CrystalStruct = | Coordination = | MolShape = | Dipole = |Section4={{Chembox Thermochemistry | DeltaHf = | DeltaHc = | Entropy = | HeatCapacity = |Section5={{Chembox Pharmacology | ATCCode = | Bioavail = | Metabolism = | HalfLife = | Excretion = | PregCat = | AdminRoutes = |Section6={{Chembox Explosive | ShockSens = | FrictionSens = | ExplosiveV = | REFactor = |Section7={{Chembox Hazards | ExternalSDS = MSDS at Fermentek | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = |Section9={{Chembox Related | OtherAnions = | OtherCations = | OtherFunctn = | Function = | OtherCpds =

Oligomycins are macrolides created by Streptomyces that are strong antibacterial agents but are often poisonous to other organisms, including humans.

Function

Oligomycins have use as antibiotics. However, in humans, they have limited or no clinical use due to their toxic effects on mitochondria and ATP synthase.

Oligomycin A is an inhibitor of ATP synthase. In oxidative phosphorylation research, it is used to prevent stage 3 (phosphorylating) respiration. Oligomycin A inhibits ATP synthase by blocking its proton channel (FO subunit), which is necessary for oxidative phosphorylation of ADP to ATP (energy production). 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. This process is due to facilitated diffusion of protons into the mitochondrial matrix through an uncoupling protein such as thermogenin, or UCP1.

Administering oligomycin to rats can result in very high levels of lactate accumulating in the blood and urine.

::data[format=table title="'''Oligomycins'''{{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}}"] | [[Image:Oligomycins.png|200px]] | |---| | | | Oligomycin A | | Oligomycin B | | Oligomycin C | | Oligomycin D (Rutamycin A) | | Oligomycin E | | Oligomycin F | | Rutamycin B | | 44-Homooligomycin A | | 44-Homooligomycin B | ::

References

it:Fosforilazione ossidativa#Inibitori

References

  1. (March 2023). "Inhibitors of ATP Synthase as New Antibacterial Candidates". Antibiotics.
  2. (2010). "Mitochondrial proton and electron leaks". Essays in Biochemistry.
  3. (December 1984). "Oligomycin toxicity in intact rats". Agents and Actions.
  4. (1995). "Synthetic studies on oligomycins. Synthesis of the oligomycin B spiroketal and polypropionate portions". Bulletin of the Chemical Society of Japan.

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macrolide-antibioticsspiro-compoundsdiketonesatp-synthase-inhibitors