| Stereochemistry | ABSOLUTE |
| Molecular Formula | C44H68O13 |
| Molecular Weight | 805.0029 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 17 / 17 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(CC(C)=C[C@@]2(O[C@H](C[C@@](C)(O)C(O)=O)CC[C@H]2O)O1)[C@H](C)\C=C\[C@H]3CC[C@@]4(CC[C@@]5([H])O[C@]([H])([C@@H](O)C[C@H](C)[C@@]6([H])O[C@@]7(CCCCO7)CC[C@H]6C)C(=C)[C@@H](O)[C@]5([H])O4)O3
InChI
InChIKey=QNDVLZJODHBUFM-WFXQOWMNSA-N
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
Okadaic acid (OA) is a naturally occurring polyether toxin that was originally derived from marine dinoflagellates, Prorocentrium spp.. It is a reversible, potent and selective inhibitor of two serine threonine protein phosphatases: PP2A-C (PP2A) which is inhibited completely at 1 nM and PP1 which is inhibited at higher concentrations (IC50= 10-15 nM). PP2B is much less sensitive to okadaic acid than PP1, while PP2C is not inhibited. This selectivity is the basis for an improved identification and quantification procedure for these enzymes. The hydrophobic backbone of okadaic acid enables it to enter cells where it stimulates intracellular protein phosphorylation. It mimics the effects of insulin, enhances transmitter release at neuromuscular junctions, causes vasodilation and is a very potent tumor promoter. Okadaic acid is an extremely useful tool for studying cellular processes that are regulated by phosphorylation. Okadaic Acid is an activator of PKC.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Rats: Okadaic acid (200 ng) was microinjected bilaterally
into cerebral ventricle (from the bregma: posterior 0.5 mm,
lateral ±1.5 mm and from skull surface 3.6 mm ventrally) in light
of the rat brain in stereotaxic coordinates. For each side a volume of 5.0 l was
injected over a period of 10 min (0.2 l/min) followed by an additional
10 min waiting time before the micro-injection needle was
removed in order to permeate local tissue sufficiently.
Route of Administration:
Other
Mouse oocytes were transiently exposed in vitro to different dosages (0, 0.01, 0.1, or 1.0 ug/ml) of the PP1 and PP2A phosphatase inhibitor okadaic acid (OA) during meiosis I and oocytes were cytogenetically analyzed. Significant (p < 0.05) OA dose-response increases in the frequencies of metaphase I (MI) arrested oocytes, MI oocytes with 80 chromatids instead of the normal 20 tetrads, and anaphase I telophase I (AI-TI) oocytes with two groups of an unequal number of chromatids were found.
SUBSTANCE RECORD
