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Substance Name: Oligomycin
RN: 1404-19-9
InChIKey: MNULEGDCPYONBU-DJRUDOHVSA-N

Note

  • A closely related group of toxic substances elaborated by various strains of Streptomyces. They are 26-membered macrolides with lactone moieties and double bonds and inhibit various ATPases, causing uncoupling of phosphorylation from mitochondrial respiration. Used as tools in cytochemistry. Some specific oligomycins are RUTAMYCIN, peliomycin, and botrycidin (formerly venturicidin X).

Molecular Weight

  • 791.0686
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Uncoupling Agents
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Names and Synonyms

MeSH Heading

  • Oligomycins

Synonyms

  • EINECS 215-767-9
  • Oligomycin

Systematic Name

  • Oligomycin

Registry Numbers

CAS Registry Number

  • 1404-19-9

System Generated Number

  • 0001404199

Structure Descriptors

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

InChIKey

MNULEGDCPYONBU-DJRUDOHVSA-N

Smiles

CC[C@@H]/1CC[C@H]2C(C([C@H]([C@@]3(O2)CC[C@H]([C@H](O3)CC(C)O)C)C)OC(=O)/C=C/[C@@H]([C@H]([C@H](C(=O)C([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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 2500ug/kg (2.5mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS
Antibiotics and Chemotherapy Vol. 4, Pg. 962, 1954.
mouse LDLo intravenous 2500ug/kg (2.5mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Antibiotics and Chemotherapy Vol. 4, Pg. 962, 1954.
rat LDLo intraperitoneal 500ug/kg (0.5mg/kg)   Agents and Actions, A Swiss Journal of Pharmacology. Vol. 15, Pg. 660, 1984.