An inhibitor of mitochondrial F1FO-ATPase
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Oligomycin D

Item No. 20184

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,2'R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,29R)-22-ethyl-3',4',5',6'-tetrahydro-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,29-octamethyl-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-[2H]pyran]-3,9,13-trione
CAS Number
1404-59-7
Synonyms
  • 26-Demethyloligomycin A
  • RR 32705
  • Rutamycin
Molecular Formula
C44H72O11
Formula Weight
777.0
Purity
≥95%
Formulation
A lyophilisate
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
C[C@H](C[C@H]1[C@@H](C)CC[C@@]2(C[C@@H]([C@@]([H])([C@@H](O2)CC[C@@]([H])(CC)/C=C/C=C/C[C@@H](C)[C@H](O)[C@@](O)(C3=O)C)C)OC(/C=C/[C@H](C)[C@@H](O)[C@H](C)C([C@H](C)[C@@H](O)[C@@H]3C)=O)=O)O1)O
InChi Code
InChI=1S/C44H72O11/c1-11-33-16-14-12-13-15-27(4)41(50)43(10,52)42(51)32(9)40(49)31(8)39(48)30(7)38(47)26(3)17-20-37(46)53-36-24-44(54-34(19-18-33)29(36)6)22-21-25(2)35(55-44)23-28(5)45/h12-14,16-17,20,25-36,38,40-41,45,47,49-50,52H,11,15,18-19,21-24H
InChi Key
LVWVMRBMGDJZLM-BONFEJLISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $369

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    2.5 mg

    $827

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    Cayman Chemical
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    Product Description

    Oligomycin D is a macrolide antibiotic produced by several species of Streptomyces that inhibits the mitochondrial F1FO-ATPase and is used to uncouple oxidative phosphorylation from electron transport.1 Oligomycin D is reported to inhibit K-Ras plasma membrane localization in MDCK cells with an IC50 value of 3.49 nM and is cytotoxic to SW620 colon cancer cells with an IC50 value of 36 µM.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Inoue, S., Mizutani, A., Sugita, R., et al. Purification and characterization of a novel protein activator of Ca2+/calmodulin-dependent protein kinase I. Biochem. Biophys. Res. Commun. 215(3), 861-867 (1995).

    2. Salim, A.A., Tan, L., Huang, X.-C., et al. Oligomycins as inhibitors of K-Ras plasma membrane localisation. Org. Biomol. Chem. 14(2), 711-715 (2016).