Oligomycin A

SKU
O-1063
  • CAS:579-13-5
  • Formula:C45H74O11
  • MW:791.1 Da
  • Appearance:White Lyophilisate
  • Purity:>95% by HPLC

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Description

Oligomycin A is an inhibitor of ATP synthase. In oxidative phosphorylation research, it is used to prevent state 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 coupling. This process occurs due to the facilitated diffusion of protons into the mitochondrial matrix through an uncoupling protein such as thermogenin, or UCP1.

Oligomycin A stimulates lysosome acidification due to shunting of membrane potential. Induces apoptosis in a variety of cell types. Oligomycin A also induces autophagy in the IPLB-LdFB insect cell line.

Isolated from Streptomyces sp.

Not for human therapeutic use or for medicinal purposes. For research applications only.

More Information
Alternate Name/Synonyms
Oligomycin
SKU
O-1063
CAS #
579-13-5
Chemical Name
(1R,2'R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,28S,29R)-22-ETHYL-7,11,14,15-TETRAHYDROXY-6'-((R)-2-HYDROXYPROPYL)-5',6,8,10,12,14,16,28,29-NONAMETHYL-3',4',5',6'-TETRAHYDRO-2,26-DIOXASPIRO[BICYCLO[23.3.1]NONACOSA[4,18,20]TRIENE-27,2'-
Chemical Formula
C45H74O11
Molecular Weight
791.1 Da
Appearance
White Lyophilisate
Purity
>95% by HPLC
Solubility
Soluble in ethanol, methanol, DMF, or DMSO. Poor water solubility.
Storage Temp
-20°C
THERAPEUTIC AREA
Infectious Diseases
USE
A mitochondrial ATPase inhibitor use as antibiotics, antifungal activities.
Merck Index
13.6902.2001
MDL NUMBER
MFCD00065705
CHEMACX
X1094055-9
INCHI
InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-/m1/s1
SMILES
CC[C@H]1CC[C@@H]2[C@@H]([C@@H]([C@H]([C@@]3(O2)CC[C@H]([C@H](O3)C[C@H](C)O)C)C)OC(=O)/C=C/[C@H]([C@@H]([C@H](C(=O)[C@H]([C@@H]([C@H](C(=O)[C@@]([C@@H]([C@H](C/C=C/C=C1)C)O)(C)O)C)O)C)C)O)C)C
RTECS
RK3328000
Handling
Warning: Toxic. May be Carcinogenic. May be Teratogenic. Protect from light.
Certificate of Analysis 1
Certificate of Analysis 2
Certificate of Analysis 3
GHS PICTOGRAMS
Handling Warning: Toxic. May be Carcinogenic. May be Teratogenic. Protect from light.
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