Identification |
Name: | 1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoicacid, a,5-dihydroxy-a,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4'aR,5R,6'S,8'R,8'aS)-octahydro-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl]-7'-methylenespiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran]-5-yl]-2-propen-1-yl]-,(aR,2S,5R,6R,8S)- |
Synonyms: | 1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoicacid, a,5-dihydroxy-a,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4'aR,5R,6'S,8'R,8'aS)-octahydro-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl]-7'-methylenespiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran]-5-yl]-2-propenyl]-,(aR,2S,5R,6R,8S)- (9CI);Acanthifolicin, 9,10-deepithio-9,10-didehydro-; 1,7-Dioxaspiro[5.5]undecane,acanthifolicin deriv.; Spiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran],acanthifolicin deriv.; 1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoic acid, a,5-dihydroxy-a,10-dimethyl-8-[1-methyl-3-[octahydro-8'-hydroxy-6'-[1-hydroxy-3-(3-methyl-1,7-dioxaspiro[5.5]undec-2-yl)butyl]-7'-methylenespiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran]-5-yl]-2-propenyl]-,[2'R-[2'a[R*[1R*[2S*(R*),5R*,6R*,8S*],2E]],4'ab,6'b[1S*,3S*(2S*,3R*,6S*)],8'a,8'aa]]-; NSC 677083; Okadaic acid |
CAS: | 78111-17-8 |
Molecular Formula: | C44H68 O13 |
Molecular Weight: | 805.00292 |
InChI: | 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 |
Molecular Structure: |
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Properties |
Transport: | UN 3462 6 |
Density: | 1.28 g/cm3 |
Stability: | Stable. Light and heat-sensitive. Combustible. Incompatible with strong oxidizing agents. |
Refractive index: | 1.584 |
Appearance: | white crystals or powder |
Specification: |
Okadaic acid (78111-17-8) is a toxin that accumulates in bivalves and causes diarrhetic shellfish poisoning. It was named from the marine sponge Halichondria okadai, from which okadaic acid was isolated for the first time. It has also been isolated from another marine sponge, H. malanodocia, as a cytotoxin. The real producer of okadaic acid is a marine dinoflagellate.
Administration of okadaic acid has been shown to profoundly increase the secretion of nerve growth factor, and to also promote nerve growth factor gene transcription and the stability of mRNA in primary cultures of cortical astrocytes.
The cytotoxicities of okadaic acid as EC50 against the P388 and L1210 cell lines are 1.7 nanomolar and 17 nanomolar, respectively. Additionally, okadaic acid strongly inhibits protein serine / threonine phosphatase 1, 2A, and 2B. The inhibitory effect of okadaic acid is strongest for 2A, followed by 1, and then 2B. The dissociation constant of the inhibition on protein serine / threonine phosphatase 2A is 30 pico-molar.
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Packinggroup: | II |
Biological Activity: | Potent inhibitor of protein phosphatase 1 (IC 50 = 3 nM) and protein phosphatase 2A (IC 50 = 0.2-1 nM). Displays > 100,000,000-fold selectivity over PP2B and PP2C. Tumor promotor. Shown to activate atypical protein kinase C in adipocytes. |
Storage Temperature: | −20°C |
Color: | translucent |
Safety Data |
Hazard Symbols |
T: Toxic
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