Okadaic acid

Names

[ Name ]:
Okadaic acid

[Synonym ]:
(2R)-2-hydroxy-3-[(2S,5R,6R,8S)-5-hydroxy-8-{(2R,3E)-4-[(2R,4a'R,5R,6'S,8'R,8a'S)-8'-hydroxy-6'-{(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl}-7'-methylideneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl}-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-methylpropanoic acid
Halochondrine A
Okadic acid
9,10-deepithio-9,10-didehydroacanthifolicin
okadaic acd
MFCD00083455
1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoic acid, α,5-dihydroxy-α,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4a'R,5R,6'S,8'R,8a'S)-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]-, (αR,2S,5R,6R,8S)-
Okadaic acid
OKADAICACID,HIGHPURITY
Ocadaic Acid
(2R)-2-Hydroxy-3-[(2S,5R,6R,8S)-5-hydroxy-8-{(2R,3E)-4-[(2R,4a'R,5R,6'S,8'R,8a'S)-8'-hydroxy-6'-{(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl}-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl]-3-buten-2-yl}-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-methylpropanoic acid
1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoic acid, α,5-dihydroxy-α,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4a'R,5R,6'S,8'R,8a'S)-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]-, (αR,2S,5R,6R,8S)-

Biological Activity

[Description]:

Okadaic acid is extracted from black sponges of the genus Halichondria. Okadaic acid is a non-comepetitive, selective and reversible serine/threonine-specific protein phosphatases 1 (PP1), PP2A and PP3 inhibitor with IC50s of 10-15 nM, 0.5 nM and 4 nM, respectively.[1][2] Okadaic acid eliminate metazoan symbionts/parasites by apoptosis[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphatase

Research Areas >> Infection

[Target]

IC50: 10-15 nM (PP1), 0.5 nM (PP2) and 4 nM (PP3)[1]

[References]

[1]. Bialojan C, et al. Inhibitory effect of a marine-sponge toxin, okadaic acid, on protein phosphatases. Specificity and kinetics. Biochem J. 1988 Nov 15;256(1):283-90.

[2]. McCluskey A, et al. Serine-threonine protein phosphatase inhibitors: development of potential therapeutic strategies. J Med Chem. 2002 Mar 14;45(6):1151-75.

[3]. Schröder HC, et al. Okadaic acid, an apoptogenic toxin for symbiotic/parasitic annelids in the demosponge Suberites domuncula. Appl Environ Microbiol. 2006 Jul;72(7):4907-16.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
921.6±65.0 °C at 760 mmHg

[ Melting Point ]:
164-166ºC

[ Molecular Formula ]:
C₄₄H₆₈O₁₃

[ Molecular Weight ]:
805.003

[ Flash Point ]:
269.4±27.8 °C

[ Exact Mass ]:
804.466003

[ PSA ]:
182.83000

[ LogP ]:
4.21

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.585

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AA8227800

CHEMICAL NAME :: Acanthifolicin, 9,10-deepithio-9,10-didehydro-

CAS REGISTRY NUMBER :: 78111-17-8

LAST UPDATED :: 199403

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C44-H68-O13

MOLECULAR WEIGHT :: 805.12

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 192 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 12 mg/kg/30W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 10 ug/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 250,375,1991

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301 + H311 + H331-H315

[ Precautionary Statements ]:
Missing Phrase - N15.00950417-P261-P280-P302 + P352 + P312-P304 + P340 + P312-P403 + P233

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
S26;S45;S36/S37

[ RIDADR ]:
UN 3462 6.1/PG 1

[ WGK Germany ]:
3

[ RTECS ]:
AA8227800

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
29321900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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