Oligomycin
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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
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Other names
Oligomycin
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.014.334 |
EC Number |
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MeSH | Oligomycins |
PubChem CID
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RTECS number
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
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).
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Oligomycins are
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.[1]
Oligomycin A is an
UCP1
.
Administering oligomycin to rats can result in very high levels of lactate accumulating in the blood and urine.[3]
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 |