Oligomycin

Oligomycin A

File:Oligomycin A.png
Names
IUPAC 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-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
Other names Oligomycin
Identifiers
CAS Number	1404-19-9 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28285
ChemSpider	21106358 checkY
ECHA InfoCard
EC Number	215-767-9
E number
MeSH	Oligomycins
PubChem CID	6450197
RTECS number	RK3325000
UNII	14JVM0OHLV checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI 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 checkY Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N checkY 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 Key: QBAMBSAJEFIQBK-GJHUHQBXBC Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N
SMILES C[C@](C)(O)C[C@H]1O[C@@]2(CC[C@H]1C)O[C@H]3CC[C@@H](CC)/C=C\C=C\C[C@H](C)[C@H](O)[C@](C)(O)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@@H](C)[C@H](O)[C@H](C)/C=C/C(=O)O[C@H]([C@H]2C)[C@H]3C
Properties
Chemical formula	C45H74O11
Molar mass	791.062 g/mol
Hazards
Safety data sheet (SDS)	MSDS at Fermentek
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). checkY verify (what is checkY☒N ?) Infobox references

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 (F_O 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.

Oligomycins

File:Oligomycins.png
	R1	R2	R3	R4	R5
Oligomycin A	CH3	H	OH	H,H	CH3
Oligomycin B	CH3	H	OH	O	CH3
Oligomycin C	CH3	H	H	H,H	CH3
Oligomycin D (Rutamycin A)	H	H	OH	H,H	CH3
Oligomycin E	CH3	OH	OH	O	CH3
Oligomycin F	CH3	H	OH	H,H	CH2CH3
Rutamycin B	H	H	H	H,H	CH3
44-Homooligomycin A	CH2CH3	H	OH	H,H	CH3
44-Homooligomycin B	CH2CH3	H	OH	O	CH3