Oligomycin A, Streptomyces diastatochromogenes

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Oligomycin A, Streptomyces diastatochromogenes

O-1063
  • CAS: 579-13-5
  • Formula: C45H74O11
  • MW: 791.1
  • Appearance: White to Off-white powder (Lyophilisate).
  • Purity: >95%

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Oligomycin A is a component of the oligomycin complex (O-1060). It 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.

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Additional Information

Product #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'-
FormulaC45H74O11
MW791.1
AppearanceWhite to Off-white powder (Lyophilisate).
Purity>95%
SolubilitySoluble in ethanol, methanol, DMF, or DMSO. Poor water solubility.
Melting Point140-141°C
Storage TempStore Desiccated at -20°C. Protect from light.
Therapeutic AreaInfectious Diseases
UseA mitochondrial ATPase inhibitor use as antibiotics, antifungal activities.

Additional Information

Merck Index13.6902.2001
MDL NumberMFCD00065705
ChemACXX1094055-9
InChIInChI=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
SMILESCC[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

Additional Information

GHS Pictograms
RTECSRK3328000
HandlingWarning.Toxic. May be Carcinogenic. May be Teratogenic. Protect from Light

Additional Information

msds 1O-1063, Oligomycin A, SDS, diamond format.pdf
Certificate of Analysis 1O-1063, J1125.pdf
Certificate of Analysis 2O-1063, F1247.pdf
Certificate of Analysis 3O-1063, F1124.pdf
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