Potent inhibitor of PP1 and PP2A
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Calyculin A

Item No. 19246

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S)-3-[4-[(1E)-3-[(2R,3R,5R,7S,8S,9R)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraen-1-yl]-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propen-1-yl]-2-oxazolyl]butyl]-4-deoxy-4-(dimethylamino)-5-O-methyl-L-ribonamide
CAS Number
101932-71-2
Synonyms
  • (−)-Calyculin A
Molecular Formula
C50H81N4O15P
Formula Weight
1009.2
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: Soluble
SMILES
C[C@H]1[C@H](O)C[C@@]2(C(C)(C)[C@@H](OP(O)(O)=O)[C@]([C@@H](OC)C[C@H](O)[C@H](C)[C@H](O)[C@H](C)/C=C(C)/C(C)=C/C=C/C(C)=C\C#N)([H])O2)O[C@H]1C/C=C/C3=COC([C@H](CCNC([C@@H](O)[C@@H](O)[C@@H](N(C)C)COC)=O)C)=N3
InChi Code
InChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,3
InChi Key
FKAWLXNLHHIHLA-YCBIHMBMSA-N
Origin
Animal/Discodermia calyx
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Calyculin A is a natural, cell-permeable inhibitor of the serine-threonine protein phosphatases (PP) PP1 and PP2A (IC50s = 0.3-0.7 and 0.5-1 nM, respectively).1,2,3 It is without significant effect against PP2B, PP2C, and PP4.2 Through its effects on PP1 and PP2A, calyculin A has been shown to either promote or inhibit cancer cell growth in tumor cell lines and animal models.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ishihara, H., Martin, B.L., Brautigan, D.L., et al. Calyculin A and okadaic acid: Inhibitors of protein phosphatase activity. Biochem. Biophys. Res. Commun. 159(3), 871-877 (1989).

    2. 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).

    3. Lindvall, M.K., Pihko, P.M., and Kosikinen, A.M.P. The binding mode of calyculin A to protein phosphatase-1. A novel spiroketal vector model. The Journal of Biological Chemisty 272(37), (1997).

    4. Fujiki, H., Suganuma, M., Yoshizawa, S., et al. Mechanisms of action of okadaic acid class tumor promoters on mouse skin. Environ. Health Perspect. 93, 211-214 (1991).

    5. Zheng, Y.G., Wu, J., Chen, Z., et al. Chemical regulation of epigenetic modifications: Opportunities for new cancer therapy. Med. Res. Rev. 28(5), 645-687 (2008).

    Product Citations

    Li, T., Huang, T., Du, M., et al. Phosphorylation and chromatin tethering prevent cGAS activation during mitosis. Science (2021).