A mitochondrial F1FO ATP synthase inhibitor
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Oligomycin A

Item No. 11342

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,2'R,4E,5'R,6R,6'S,7S,8R,10S,11S,12R,14S,15R,16S,18E,20E,22S,25R,28R,29S)-22-ethyl-3',4',5',6'-tetrahydro-7,11,14,15-tetrahydroxy-6'-[(1Z)-2-hydroxy-1-propen-1-yl]-5',6,8,10,12,14,16,28,29-nonamethyl-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-[2H]pyran]-3,9,13-trione
CAS Number
579-13-5
Synonyms
  • MCH 32
Molecular Formula
C45H74O11
Formula Weight
791.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
λmax
225 nm
SMILES
O=C([C@H](C)[C@@H](O)[C@H](C)/C=C/1)[C@@H](C)[C@H](O)[C@@H](C)C([C@](O)(C)[C@H](O)[C@@H](C)C/C=C/C=C/[C@](CC)([H])CC[C@]2([H])[C@H](C)[C@]([C@@H](C)[C@]3(CC[C@@H](C)[C@](C[C@@H](O)C)([H])O3)O2)([H])OC1=O)=O
InChi Code
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-
InChi Key
MNULEGDCPYONBU-WMBHJXFZSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $62

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    5 mg

    $154

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    10 mg

    $278

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    25 mg

    $462

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    Cayman Chemical
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    Product Description

    Oligomycin A, a dominant analog of the isomers, is an inhibitor of mitochondrial F1FO ATP synthase that induces apoptosis in a variety of cell types (average GI50 = 270 nM).1,2,3 Oligomycin A exhibits antifungal, antitumor, and nematocidal activities, but has poor solubility in water and other biocompatible solvents, which limits its clinical application.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Salomon, A.R., Voehringer, D.W., Herzenberg, L.A., et al. Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase. Chem. Biol. 8, 71-80 (2001).

    2. Shin, Y.K., Yoo, B.C., Chang, H.J., et al. Down-regulation of mitochondrial F1F0-ATP synthase in human colon cancer cells with induced 5-fluorouracil resistance. Cancer Res. 65(8), 3162-3170 (2005).

    3. Laatsch, H., Kellner, M., Wolf, G., et al. Oligomycin F, a new immunosuppressive homologue of oligomycin A. J. Antibiot. (Tokyo) 46(9), 1334-1341 (1993).

    4. Zu, Y., Zhao, Q., Zhao, X., et al. Process optimization of the preparation of oligomycin-loaded folate-conjugated chitosan nanoparticles as a tumor-targeted drug delivery system using a two-level factorial design method. Int. J. Nanomedicine 6, 3429-3441 (2011).

    Product Citations

    Tagi, H., Qiu, C., Zeng, Y., et al. Serine supplementation suppresses hypoxia-induced pathological retinal angiogenesis. Theranostics 15(1), 5087-5105 (2025).

    Kremer, D.M., Nelson, B.S., Lin, L., et al. GOT1 inhibition primes pancreatic cancer for ferroptosis through the autophagic release of labile iron. bioRxiv (2020).