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Sigma-Aldrich

Calyculin A from Discodermia calyx

≥90% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C50H81N4O15P
CAS Number:
101932-71-2
Molecular Weight:
1009.17
Beilstein:
4903216
MDL number:
MFCD06795864
UNSPSC Code:
12352200
PubChem Substance ID:
329752128
NACRES:
NA.77

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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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

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331,H315

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Carole A Farah et al.
Journal of neurochemistry, 123(3), 360-372 (2012-08-24)
Protein kinase Cs (PKCs) are critical signaling molecules controlled by complex regulatory pathways. Herein, we describe an important regulatory role for C2 domain phosphorylation. Novel PKCs (nPKCs) contain an N-terminal C2 domain that cannot bind to calcium. Previously, we described
L.C. Starke et al.
The American Journal of Physiology, 264 (1993)
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
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
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