O9381

Okadaic acid

Name: Okadaic acid
Brand: SIGMA

from Prorocentrum concavum, 92-100% (HPLC), powder, protein phosphatase 1 inhibitor

Synonym(s):

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About This Item

Empirical Formula (Hill Notation):

C₄₄H₆₈O₁₃

CAS Number:

78111-17-8

Molecular Weight:

805.00

UNSPSC Code:

12352106

PubChem Substance ID:

24898069

NACRES:

NA.77

MDL number:

MFCD00083455

Product Name

Okadaic acid from Prorocentrum concavum, 92-100% (HPLC)

SMILES string

O[C@@H](C[C@@H]([C@@]1([H])O[C@@]2(CCCCO2)CC[C@H]1C)C)[C@]3([H])C([C@@H](O)[C@]4([H])O[C@]5(CC[C@@](/C=C/[C@@H](C)[C@@]6([H])O[C@]7(O[C@H](C[C@@](C)(O)C(O)=O)CC[C@H]7O)C=C(C)C6)([H])O5)CC[C@@]4([H])O3)=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-WFXQOWMNSA-N

assay

92-100% (HPLC)

form

powder

solubility

DMSO: ≥1 mg/mL
ethanol: ≥1 mg/mL
methanol: ≥1 mg/mL
H₂O: insoluble

storage temp.

−20°C

Quality Level

200

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Okadaic acid from Prorocentrum concavum has been used as a phosphatase inhibitor:

to inhibit protein phosphatase 2 in spermatocytes culture
to treat SH-SY5Y cells to prevent dephosphorylation to maintain tau
to treat human embryonic kidney 293T cells (HEK293T) or H4 cells to analyse its effect on fused in sarcoma (FUS) protein

Biochem/physiol Actions

Dinoflagellate toxin and an ionophore-like polyether derivative of a 38 carbon, fatty acid. Readily enters cells. Inhibitor of type 1 and type 2A protein phosphatases. Does not inhibit tyrosine phosphatases, alkaline phosphatases or acid phosphatase. Known tumor promotor. Used to study various cellular processes including cell cycle, apoptosis, nitric oxide metabolism and calcium signaling.

Okadaic acid is a dinoflagellate toxin and an ionophore-like polyether derivative of a 38 carbon, fatty acid.

Features and Benefits

This compound is featured on the Phosphoprotein Phosphatases (Serine/Threonine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

General description

Okadaic acid is a polyether fatty acid. It is a marine toxin produced by the genera of Prorocentrum and Dinophysis.

Preparation Note

Isolated from unialgal cultures of dinoflagellates.

pictograms

GHS06

signalword

Danger

hcodes

H301 + H311 + H331,H315

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Identification of okadaic acid production in the marine dinoflagellate Prorocentrum rhathymum from Florida Bay

An T, et al.

Toxicon, 55(2-3), 653-657 (2010)

Cohesin removal along the chromosome arms during the first meiotic division depends on a NEK1-PP1gamma-WAPL axis in the mouse

Brieno-Enriquez MA, et al.

Testing, 17(4), 977-986 (2016)

Okadaic acid, an inhibitor of protein phosphatase 1 and 2A, induces premature separation of sister chromatids during meiosis I and aneuploidy in mouse oocytes in vitro

Mailhes JB, et al.

Chromosome Research, 11(6), 619-631 (2003)

Pseudo-phosphorylation at AT8 epitopes regulates the tau truncation at aspartate 421

Cao L, et al.

Experimental Cell Research, 370(1), 103-115 (2018)

The prionlike domain of FUS is multiphosphorylated following DNA damage without altering nuclear localization

Rhoads SN, et al.

Molecular Biology of the Cell, 29(15), 1786-1797 (2018)

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