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O7760

Sigma-Aldrich

Okadaic acid sodium salt from Prorocentrum concavum

≥90% (HPLC), film

Synonyme(s) :

OA

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About This Item

Formule empirique (notation de Hill):
C44H67NaO13
Numéro CAS:
209266-80-8
Poids moléculaire :
826.98
Numéro MDL:
MFCD00210208
Code UNSPSC :
12352106
ID de substance PubChem :
329818921
Nomenclature NACRES :
NA.77

Source biologique

plant (Prorocentrum concavum)

Niveau de qualité

200

Pureté

≥90% (HPLC)

Forme

film

Couleur

translucent

Solubilité

0.1% acetic acid in CH3CN: H2O (1:1): 250 μg/mL, clear, colorless

Température de stockage

−20°C

Chaîne SMILES 

[Na+].C[C@@H]1CC[C@]2(CCCCO2)O[C@@H]1[C@@H](C)C[C@H](O)[C@H]3O[C@@H]4CC[C@@]5(CC[C@@H](O5)\C=C\[C@@H](C)[C@@H]6CC(C)=C[C@@]7(O[C@@H](CC[C@H]7O)C[C@@](C)(O)C([O-])=O)O6)O[C@H]4[C@H](O)C3=C

InChI

1S/C44H68O13.Na/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);/q;+1/p-1/b10-9+;/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-;/m1./s1

Clé InChI

BYHIFOCTDVNQQT-GHIYGBLASA-M

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301 + H311 + H331,H315

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

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Diego Figueroa et al.
Journal of toxicology and environmental health. Part A, 83(15-16), 573-588 (2020-07-21)
Okadaic acid-group (OA-group) is a set of lipophilic toxins produced only in seawater by species of the Dinophysis and Prorocentrum genera, and characterized globally by being associated with harmful algal blooms (HABs). The diarrhetic shellfish poisoning toxins okadaic acid (OA)
Ning Zhang et al.
Autophagy, 6(8), 1157-1167 (2010-10-12)
FTY720, a sphingosine analog, is a novel immunosuppressant currently undergoing multiple clinical trials for the prevention of organ transplant rejection and treatment of various autoimmune diseases. Recent studies indicate an additional cytotoxic effect of FTY720 and its preclinical efficacy in
Zhiyuan Fang et al.
Autophagy, 19(8), 2240-2256 (2023-02-14)
Acetaminophen (APAP) overdose is the predominant cause of drug-induced liver injury worldwide. The macroautophagy/autophagy-lysosomal pathway (ALP) is involved in the APAP hepatotoxicity. TFEB (transcription factor EB) promotes the expression of genes related to autophagy and lysosomal biogenesis, thus, pharmacological activation
Abira Rajah et al.
Scientific reports, 9(1), 11430-11430 (2019-08-09)
Cell migration is an important biological phenomenon involved in many homeostatic and aberrant physiological processes. Phosphorylation of the focal adhesion adaptor protein, paxillin, on serine 273 (S273) has been implicated as a key regulator of cell migration. Here, it is
Yunzhong Zhang et al.
Journal of cellular physiology, 236(2), 1345-1361 (2020-07-14)
Fibroblast growth factor 21 (FGF21) as a metabolic stress hormone, is mainly secreted by the liver. In addition to its well-defined roles in energy homeostasis, FGF21 has been shown to promote remyelination after injury in the central nervous system. In
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