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Merck

495604

Okadaic acid

from Prorocentrum sp., ≥95% (HPLC), solid (glassy), protein phosphatase 1 inhibitor, Calbiochem

Synonym(s):

Okadaic Acid, Prorocentrum sp., OA

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About This Item

Empirical Formula (Hill Notation):
C44H68O13
CAS Number:
78111-17-8
Molecular Weight:
805.00
UNSPSC Code:
12352106
NACRES:
NA.77
MDL number:
MFCD00083455

Product Name

Okadaic Acid, Prorocentrum sp., Okadaic Acid, CAS 78111-17-8, is a highly potent inhibitor of protein phosphatase 1 (IC50 = 10-15 nM) and 2A (IC50 = 0.1 nM).

SMILES string

O1[C@]7(O[C@@H](CC[C@H]7O)C[C@](O)(C)C(=O)O)C=C(C[C@H]1[C@H](C)\C=C\[C@@H]2O[C@@]3(OC4[C@H](O[C@@H](C(=C)[C@H]4O)[C@@H](O)C[C@@H](C5O[C@]6(OCCCC6)CC[C@H]5C)C)CC3)CC2)C

InChI

1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37?,38+,39?,41-,42+,43-,44-/m1/s1

InChI key

QNDVLZJODHBUFM-AAWJMCDUSA-N

assay

≥95% (HPLC)

form

solid (glassy)

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

colorless

solubility

DMF: soluble
chloroform: soluble
ethanol: soluble
methanol: soluble

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: no
Primary Target
Protein phosphatase
Product does not compete with ATP.
Reversible: no
Target IC50: 10-15 nM and 0.1 nM against protein phosphatase 1 and protein phosphatase 2A, respectively

Disclaimer

Toxicity: Toxic (F)

General description

An ionophore-like polyether derivative of a C38 fatty acid compound isolated from the dinoflagellates that have fed on the marine sponge Halinchrondria okadai. It is a potent non-comepetitive, reversible inhibitor of serine/threonine-specific protein phosphatases 1 (PP1, IC50 = 10-15 nM, rabbit skeletal muscle, catalytic subunit) and 2A (PP2A, IC50 = 0.1 nM, rabbit skeletal muscle, catalytic subunit). It has only a trivial effect on protein phosphatase 2B (IC50 = 5 µM), a Ca2+/calmodulin-dependent enzyme, while PP2C, a Mg2+ dependent enzyme, is unaffected. Okadaic acid has no significant effect on the activities of tyrosine phosphatases, alkaline phosphatase, acid phosphatase, and inositol trisphosphatase. It is also a non-phorbol ester-type tumor promoter on mouse skin. Useful for the study of protein phosphatases and of PP1/PP2A in cell extracts, as well as in intact cells. Induces apoptosis in human breast carcinoma (MB-231 and MCF-7) and in myeloid cells, but inhibits glucocorticoid-induced apoptosis in T-cell hybridomas. Has marked contractile effect on smooth muscles and heart muscles. Implicated as a causative agent of diarrhetic shellfish poisoning.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
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Cohen, P., et al. 1990. Trends Biochem. Sci.15, 98.
Cohen, P. 1989. Annu. Rev. Biochem.58, 453.
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Haystead, T.A., et al. 1989. Nature337, 78.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Skin Irrit. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bence Hajdú et al.
Biomolecules, 12(11) (2022-11-12)
Autophagy-dependent cellular survival is tightly regulated by both kinases and phosphatases. While mTORC1 inhibits autophagy by phosphorylating ULK1, PP2A is able to remove this phosphate group from ULK1 and promotes the key inducer of autophagosome formation. However, ULK1 inhibits mTORC1
Sosuke Yagishita et al.
Neurology international, 16(3), 653-662 (2024-06-26)
The tau protein is a microtubule-associated protein that promotes microtubule stabilization. The phosphorylation of the tau protein has been linked to its dissociation from microtubules. Here, we examined the relationship between neuronal depolarization activity and tau protein phosphorylation by employing
Tan Tan et al.
Molecular biology of the cell, 33(12), ar115-ar115 (2022-08-18)
The term M-phase supershift denotes the phosphorylation-dependent substantial increase in the apparent molecular weight of numerous proteins of varied biological functions during M-phase induction. Although the M-phase supershift of multiple key mitotic regulators has been attributed to the multisite phosphorylation
Viviana Job et al.
iScience, 25(7), 104596-104596 (2022-07-06)
Two-partner secretion (TPS) is widespread in the bacterial world. The pore-forming TPS toxin ExlA of Pseudomonas aeruginosa is conserved in pathogenic and environmental Pseudomonas. While P. chlororaphis and P. entomophila displayed ExlA-dependent killing, P. putida did not cause damage to eukaryotic cells. ExlA
Sierra N Cullati et al.
Molecular cell, 82(11), 2006-2020 (2022-03-31)
CK1s are acidophilic serine/threonine kinases with multiple critical cellular functions; their misregulation contributes to cancer, neurodegenerative diseases, and sleep phase disorders. Here, we describe an evolutionarily conserved mechanism of CK1 activity: autophosphorylation of a threonine (T220 in human CK1δ) located

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