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O4511

Okadaic acid from Prorocentrum concavum

≥90% (HPLC), translucent film

Synonym(s):

OA

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About This Item

Empirical Formula (Hill Notation):
C44H68O13
CAS Number:
78111-17-8
Molecular Weight:
805.00
UNSPSC Code:
12352202
PubChem Substance ID:
24897998
MDL number:
MFCD00083455

Key Documents

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storage temp.

−20°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

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 key

QNDVLZJODHBUFM-WFXQOWMNSA-N

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

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.
Okadaic acid is a dinoflagellate toxin and an ionophore-like polyether derivative of a 38 carbon, fatty acid.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Skin Irrit. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBK5786V
SLBK4954V
SLBK6729V
MKBR2410V
MKBQ8271V

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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
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
J J Fernández et al.
Current medicinal chemistry, 9(2), 229-262 (2002-02-28)
One of the most interesting groups of substances of marine origin, from structural and pharmacological points of view are polyether toxins, which generally present a great diversity in size and potent biological activities. The subject of this review is limited
Sherzad K Rashid et al.
PloS one, 9(5), e97458-e97458 (2014-05-17)
Portal hypertension characterized by generalized vasodilatation with endothelial dysfunction affecting nitric oxide (NO) and endothelium-dependent hyperpolarization (EDH) has been suggested to involve bacterial translocation and/or the angiotensin system. The possibility that ingestion of probiotics prevents endothelial dysfunction in rats following
View All Related Papers

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Product Information Sheet - O4511

Product Information Sheet

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