|
Okadaic Acid
Cayman Chemical Item Number 10011490
Description
Okadaic acid is a marine sponge toxin which potently inhibits certain serine/threonine protein phosphatases. This cell permeable inhibitor targets the multiple isoforms of PP1 (IC50 = 10-50 nM), both isoforms of PP2A (IC50 = 0.5 nM) and PP3 (IC50 = 4 nM).1↗,2↗,3↗ It is a very weak inhibitor of PP2B (IC50 > 2 μM) and does not inhibit PP2C or other phosphatases.1↗,3↗ Presumably through these actions, okadaic acid is a potent carcinogen and induces tau phosphorylation.4↗,5↗ In sponge, okadaic acid plays a role in defense, inducing apoptosis in symbiotic or parasitic annelids.6↗
Synonyms 35-Demethyl-DTX 1,Acanthifolicin,NSC 677083
Formal Name
(6R)-αR,5R-dihydroxy-a,10-dimethyl-8S-[(2E)-1R-methyl-3-[(2R,4'aR,8'aS)-octahydro-8'R-hydroxy-6'S-[1S-hydroxy-3S-[(6S)-3R-methyl-1,7-dioxaspiro[5.5]undec-2S-yl]butyl]-7'-methylenespiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran]-5R-yl]-2S-propen-1-yl]-1,7-dioxaspiro[5.5]undec-10-ene-2S-propanoic acid
CAS Number 78111-17-8
Molecular Formula C44H68O13
Formula Weight 805.0
Formulation A solution in ethanol
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES OC([C@](C)(O)C[C@H]1[C@@H](O)CC[C@@]2(OC([C@H](C)/C=C/[C@@H]3O[C@]4(CCC(O[C@H]([C@@H](O)C[C@H](C)[C@H]5O[C@@]6(CCCCO6)CC[C@H]5C)C([C@H]7O)=C)C7O4)CC3)CC(C)=C2)O1)=O
InCHI Code 1S/C44H68O13/c1-25-21-34(54-44(23-25)18-13-31(45)35(55-44)24-41(6,50)40(48)49)26(2)9-10-30-12-17-43(53-30)19-14-33-39(57-43)36(47)29(5)38(52-33)32(46)22-28(4)37-27(3)11-16-42(56-37)15-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2
InCHI Key MXGNSHJYTLIUNO-VZBWRVJUSA-N |