Skip to Content
Merck
CN

Key Documents

View All Documentation

C5552

Calyculin A

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C50H81N4O15P
CAS Number:
101932-71-2
Molecular Weight:
1009.17
UNSPSC Code:
12352200
PubChem Substance ID:
24892795
NACRES:
NA.77
Beilstein/REAXYS Number:
4903216
MDL number:
MFCD06795864
Assay:
≥90% (HPLC)
Form:
solid
Quality level:
200
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

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

biological source

sea sponge (Discodermia calyx)

Quality Level

200

assay

≥90% (HPLC)

form

solid

mol wt

~_1.0 kDa

color

white

mp

247-249  °C

solubility

DMSO: soluble, ethanol: soluble

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

General description

Calyculin A is derived from the marine sponge Discodermia calyx. It corresponds to a molecular weight of 1008 Da.

Application

Calyculin A from Discodermia calyx has been used:
  • as an inhibitor of serine-threonine protein phosphatase 2A
  • as an inhibitor of cyclin D1 phosphatase in human breast cancer cells
  • as an inhibitor of protein phosphatase 2A (PP2A) and PP1 in mouse melanoma cell lines B16-F0 cells

Biochem/physiol Actions

Calyculin A from Discodermia calyx binds to the okadaic acid receptors. In smooth muscles, it activates calcium channel. Calyculin A regulates protein phosphorylation thereby regulating capacitation in sperm. It enhances phosphorylation of nuclear factor κ-light-chain-enhancer of activated B cells (NF-κB) and apoptosis.
Inhibitor of protein phosphatases types 1 and 2A; marine toxin, potent tumor promotor.

Features and Benefits

This compound is featured on the Phosphoprotein Phosphatases (Serine/Threonine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Still not finding the right product?

Explore all of our products under Calyculin A from Discodermia calyx

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

高风险级别生物产品--病毒，疫苗等

This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SLCM5691
SLCH9511
SLCH9512
SLCH7202
SLCH7203

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Articles

ReadyShield Phosphatase and Protease Inhibitor Cocktail FAQ

ReadyShield® phosphatase and protease inhibitor cocktail FAQ for sample protection in a variety of cell types and tissue extracts, including mammalian, plant, and microbial samples. Our ReadyShield® Protease Inhibitor Cocktail is a non-freezing solution that contains inhibitors with a broad specificity for serine, cysteine, acid proteases and aminopeptidases.

Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin
Suganuma M, et al.
Cancer Research, 50(12), 3521-3525 (1990)
Calyculin A, protein phosphatase inhibitor, enhances capacitation of human sperm
Furuya S, et al.
Fertility and Sterility, 59(1), 216-222 (1993)
I Bize et al.
The American journal of physiology, 277(5 Pt 1), C926-C936 (1999-11-24)
Activation of K-Cl cotransport is associated with activation of membrane-bound serine/threonine protein phosphatases (S/T-PPases). We characterize red blood cell S/T-PPases and K-Cl cotransport activity regarding protein phosphatase inhibitors and response to changes in ionic strength and cell size. Protein phosphatase
View All Related Papers

Global Trade Item Number

SKUGTIN
C5552-10UG04061833502303