A potent inhibitor of protein phosphatases
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Okadaic Acid

Item No. 10011490

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6R)-αR,5R-dihydroxy-a,10-dimethyl-8S-[(2E)-1R-methyl-3-[(2R,4'aR,8'aS)-octahydro-8'R-hydroxy-6'S-[1S-hydroxy-3S-[(6S)-3R-methyl-1,7-dioxaspiro[5.5]undec-2S-yl]butyl]-7'-methylenespiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran]-5R-yl]-2S-propen-1-yl]-1,7-dioxaspiro[5.5]undec-10-ene-2S-propanoic acid
CAS Number
78111-17-8
Synonyms
  • Acanthifolicin
  • 35-demethyl DTX1
  • NSC 677083
  • OA
Molecular Formula
C44H68O13
Formula Weight
805.0
Purity
≥95%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
OC([C@](C)(O)C[C@H]1[C@@H](O)CC[C@@]2(OC([C@H](C)/C=C/[C@@H]3O[C@]4(CCC(O[C@H]([C@@H](O)C[C@H](C)[C@H]5O[C@@]6(CCCCO6)CC[C@H]5C)C([C@H]7O)=C)C7O4)CC3)CC(C)=C2)O1)=O
InChi Code
InChI=1S/C44H68O13/c1-25-21-34(54-44(23-25)18-13-31(45)35(55-44)24-41(6,50)40(48)49)26(2)9-10-30-12-17-43(53-30)19-14-33-39(57-43)36(47)29(5)38(52-33)32(46)22-28(4)37-27(3)11-16-42(56-37)15-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2
InChi Key
MXGNSHJYTLIUNO-VZBWRVJUSA-N
Origin
Alga/Prorocentrum lima
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    25 µg

    $66

    Add

    50 µg

    $126

    Add

    100 µg

    $198

    Add
    Cayman Chemical
    Visit Our Environmental Toxicology Resource Center

    Explore additional resources to study natural toxins, pollutants including PFAS and 6-PPD-Q, and their biological effects.

    ENVIRONMENTAL TOXICOLOGY TOOLS & SERVICES
    Product Description

    Okadaic acid is a marine sponge toxin which potently inhibits certain serine/threonine protein phosphatases. This cell permeable inhibitor targets the multiple isoforms of PP1 (IC50 = 10-50 nM), both isoforms of PP2A (IC50 = 0.5 nM) and PP3 (IC50 = 4 nM).1,2,3 It is a very weak inhibitor of PP2B (IC50 > 2 μM) and does not inhibit PP2C or other phosphatases.1,3 Presumably through these actions, okadaic acid is a potent carcinogen and induces tau phosphorylation.4,5 In sponge, okadaic acid plays a role in defense, inducing apoptosis in symbiotic or parasitic annelids.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bialojan, C., and Takai, A. Inhibitory effect of a marine-sponge toxin, okadaic acid, on protein phosphatases. Specificity and kinetics. Biochem. J. 256(1), 283-290 (1988).

    2. Gupta, V., Ogawa, A.K., Du, X., et al. A model for binding of structurally diverse natural product inhibitors of protein phosphatases PP1 and PP2A. J. Med. Chem. 40(2), 3199-3206 (1997).

    3. McCluskey, A., Sim, A.T.R., and Sakoff, J.A. Serine-threonine protein phosphatase inhibitors: Development of potential therapeutic strategies. J. Med. Chem. 45(6), 1151-1175 (2002).

    4. Suganuma, M., Fujiki, H., Suguri, H., et al. Okadaic acid: An additional non-phorbol-12-tetradecanoate-13-acetate-type tumor promoter. Proc. Natl. Acad. Sci. USA 85(6), 1768-1771 (1988).

    5. Zhang, Z., and Simpkins, J.W. Okadaic acid induces tau phosphorylation in SH-SY5Y cells in an estrogen-preventable manner. Brain Res. 1345, 176-181 (2010).

    6. Schröder, H.C., Breter, H.J., Fattorusso, E., et al. Okadaic acid, an apoptogenic toxin for symbiotic/parasitic annelids in the demosponge Suberites domuncula. Appl. Environ. Microbiol. 72(7), 4907-4916 (2006).