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21279

Calyculin A

Name: Calyculin A
Brand: SIGMA

from Discodermia calyx, ≥90% (HPLC), protein phosphatases types 1 and 2A inhibitor, solid

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About This Item

Empirical Formula (Hill Notation):

C₅₀H₈₁N₄O₁₅P

CAS Number:

101932-71-2

Molecular Weight:

1009.17

UNSPSC Code:

12352200

PubChem Substance ID:

329752128

NACRES:

NA.77

Beilstein/REAXYS Number:

4903216

MDL number:

MFCD06795864

Assay:

≥90% (HPLC)

Form:

solid

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Product Name

Calyculin A from Discodermia calyx, ≥90% (HPLC)

assay

≥90% (HPLC)

form

solid

storage temp.

−20°C

SMILES string

COC[C@@H]([C@H](O)[C@H](O)C(=O)NCC[C@H](C)c1nc(\C=C\C[C@@H]2O[C@]3(C[C@@H](O)[C@@H]2C)OC([C@H](C[C@H](O)[C@H](C)[C@H](O)[C@H](C)\C=C(C)\C(C)=C\C=C\C(C)=C/C#N)OC)[C@H](OP(O)(O)=O)C3(C)C)co1)N(C)C

InChI

1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m0/s1

InChI key

FKAWLXNLHHIHLA-YCBIHMBMSA-N

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Related Categories

Bioactive Small Molecules

Biochem/physiol Actions

Inhibitor of protein phosphatases types 1 and 2A; marine toxin, potent tumor promotor.

Other Notes

Potent inhibitor of protein phosphatases 1 and 2A. More than 10 times more effective for PP1 than okadaic acid

pictograms

GHS06

signalword

Danger

hcodes

H301 + H311 + H331,H315

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

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

高风险级别生物产品--毒素类产品

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L.C. Starke et al.

The American Journal of Physiology, 264 (1993)

Protease activation and the signal transduction pathway regulating motility in sperm from the water strider Aquarius remigis.

Haruhiko Miyata et al.

Cytoskeleton (Hoboken, N.J.), 69(4), 207-220 (2012-01-27)

Many motile processes are regulated such that movement occurs only upon activation of a signaling cascade. Sperm from a variety of species are initially quiescent and must be activated prior to beating. The signaling events leading to the activation and

[The effect of glutoxim on Na+ transport in frog skin: the role of cytoskeleton].

A V Mel'nitskaia et al.

Tsitologiia, 54(2), 143-148 (2012-05-18)

Using voltage-clamp technique, the possible role of the cytoskeleton in the effect of pharmacological analogue of oxidized glutathione (GSSG), drug glutoxim, on Na+ transport in the frog Rana temporaria skin was investigated. It was shown for the first time that

The effect of calyculin A on the dephosphorylation of the histone γ-H2AX after formation of X-ray-induced DNA double-strand breaks in human blood lymphocytes.

Michael A Kuefner et al.

International journal of radiation biology, 89(6), 424-432 (2013-02-01)

The purpose of this study was to investigate the effect of calyculin A on the number of γ-H2AX foci (phosphorylated histone variant 2AX) in lymphocytes after in vitro and in vivo irradiation with rather low doses as they are used

Calyculin A reveals serine/threonine phosphatase protein phosphatase 1 as a regulatory nodal point in canonical signal transducer and activator of transcription 3 signaling of human microvascular endothelial cells.

Carlos Zgheib et al.

Journal of interferon & cytokine research : the official journal of the International Society for Interferon and Cytokine Research, 32(2), 87-94 (2011-12-07)

Vascular inflammation is initiated by stimuli acting on endothelial cells. A clinical feature of vascular inflammation is increased circulating interleukin 6 (IL-6) type cytokines such as leukemia inhibitory factor (LIF), but their role in vascular inflammation is not fully defined.

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Global Trade Item Number

SKU	GTIN
CDS013757-500MG	04061828991358
21279-10UG	04061833216996
21279-1EA	04061833616024

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