O4511

Sigma-Aldrich

Okadaic acid from Prorocentrum concavum

≥90% (HPLC), translucent film

Synonym(s):
OA
Empirical Formula (Hill Notation):
C44H68O13
CAS Number:
Molecular Weight:
805.00
MDL number:
PubChem Substance ID:

biological source

plant (Prorocentrum concavum)

assay

≥90% (HPLC)

form

translucent film

solubility

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

storage temp.

−20°C

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

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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.

Certificate of Analysis

Certificate of Origin

M Mourtada-Maarabouni et al.
Oncogene, 28(2), 195-208 (2008-10-07)
Effective control of both cell survival and cell proliferation is critical to the prevention of oncogenesis and to successful cancer therapy. Using functional expression cloning, we have identified GAS5 (growth arrest-specific transcript 5) as critical to the control of mammalian...
Keiichi Konoki et al.
Bioorganic & medicinal chemistry, 18(21), 7607-7610 (2010-09-25)
Okadaic acid (OA) and dinophysistoxin-1 (DTX1) cause diarrheic shellfish poisoning. This article examines the biochemical interactions of the two toxins with novel okadaic acid binding proteins (OABPs) 2.1 and 2.3, originally isolated from the marine sponge Halichondria okadai. First, recombinant...
Michelle M Gehringer
FEBS letters, 557(1-3), 1-8 (2004-01-27)
Microcystins, potent heptapeptide hepatotoxins produced by certain bloom-forming cyanobacteria, are strong protein phosphatase inhibitors. They covalently bind the serine/threonine protein phosphatases 1 and 2A (PP1 and PP2A), thereby influencing regulation of cellular protein phosphorylation. The paralytic shellfish poison, okadaic acid...
Rodrigo González-Romero et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 155(2), 175-181 (2011-09-29)
Marine biotoxins synthesized by Harmful Algal Blooms (HABs) represent one of the most important sources of contamination in marine environments as well as a serious threat to fisheries and aquaculture-based industries in coastal areas. Among these biotoxins Okadaic Acid (OA)...
M A Battistone et al.
Molecular human reproduction, 19(9), 570-580 (2013-05-01)
In all mammalian species studied so far, sperm capacitation correlates with an increase in protein tyrosine (Tyr) phosphorylation mediated by a bicarbonate-dependent cAMP/protein kinase A (PKA) pathway. Recent studies in mice revealed, however, that a Src family kinase (SFK)-induced inactivation...

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