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Calyculin A, a natural product derived from the marine sponge Discodermia calyx, is a potent inhibitor of serine-threonine protein phosphatases 1 and 2A (PP1 and PP2A). With a molecular weight of 1008 Da, it has gained significant attention for its ability to modulate various cellular processes and its potential applications in research and therapeutics.

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  • 101932-71-2 Structure
  • Basic information

    1. Product Name: CALYCULIN A
    2. Synonyms: C05370;N-[(3S)-[4-(1E)-3-[(2R,3R,4R,7S,8S,9R)-2-[(1S,3S,4S,5R,7E,9E,11E,13Z)-14-Cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraenyl]-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propenyl]-2-oxazoly]butyl]-4-deoxy-4-(dimethylamino)-5-O-methyl-L-ribonamide;N-[(3S)-[4-(1E)-3-[(2R,3R,4R,7S,8S,9R)-2-[(1S,3S,4S,5R,7E,9E,11E,13Z)-14-Cyano-3,5-dihydroxy-1-Methoxy-4,6,8,9,13-pentaMethyl-7,9,11,13-tetradecatetraenyl]-9-hydroxy-4,4,8-triMethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propenyl]-2-o;CALYCULIN A;CALYCULIN A, DISCODERMIA CALYX;calyculin A from discodermia calyx;CALYCULIN A FROM DISCODERMIA CALYX, 10 U G;N-[(3S)-[4-(1E)-3-[(2R,3R,4R,7S,8S,9R)-2-[(1S,3S,4S,5R,7E,9E,11E,13Z)-14-Cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentam
    3. CAS NO:101932-71-2
    4. Molecular Formula: C50H81N4O15P
    5. Molecular Weight: 1009.17
    6. EINECS: N/A
    7. Product Categories: Kinase/Phosphatase Biology;Serine/Threonine Kinase Biology;Protein phosphatase-1, Catalytic SubunitCancer Research;Tumor Promotors;Cell Signaling and Neuroscience;P to;Phosphatase InhibitorsSerine/Threonine Kinase Biology;Protein Phosphatase 1 (PP1)Enzyme Inhibitors by Enzyme;Serine/Threonine Phosphatase Inhibitors;Tumor Growth Regulation;Inhibitor;Serine/Threonine Phosphatase Substrates
    8. Mol File: 101932-71-2.mol
  • Chemical Properties

    1. Melting Point: 247-249°
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: white/solid
    5. Density: 1.25g/cm3
    6. Refractive Index: 1.57
    7. Storage Temp.: −20°C
    8. Solubility: DMSO: soluble
    9. PKA: 1.81±0.10(Predicted)
    10. Water Solubility: Soluble in DMSO (50 mM), ethanol (1 mg/ml), methanol, acetone, acetonitrile, chloroform, methylene chloride, and benzene. Insolu
    11. Merck: 13,1731
    12. BRN: 4903216
    13. CAS DataBase Reference: CALYCULIN A(CAS DataBase Reference)
    14. NIST Chemistry Reference: CALYCULIN A(101932-71-2)
    15. EPA Substance Registry System: CALYCULIN A(101932-71-2)
  • Safety Data

    1. Hazard Codes: T
    2. Statements: 23/24/25-38
    3. Safety Statements: 36/37/39-45
    4. RIDADR: UN 3462 6.1/PG 3
    5. WGK Germany: 3
    6. RTECS:
    7. F: 8-10
    8. HazardClass: 6.1(a)
    9. PackingGroup: II
    10. Hazardous Substances Data: 101932-71-2(Hazardous Substances Data)

101932-71-2 Usage

Uses

Used in Research Applications:
Calyculin A is used as a research tool for studying the role of protein phosphatases in cellular processes. Its ability to inhibit PP1 and PP2A makes it a valuable compound for investigating the functions of these enzymes and their involvement in signal transduction pathways, cell cycle regulation, and other biological activities.
Used in Cancer Research:
In the field of cancer research, Calyculin A is used as a tumor inducer to explore the mechanisms of cancer development and progression. Its inhibitory effects on PP1 and PP2A can provide insights into the dysregulation of these phosphatases in cancer cells and their potential as therapeutic targets.
Used in Pharmaceutical Industry:
Calyculin A is used as a lead compound in the development of novel drugs targeting protein phosphatases. Its potent inhibitory activity against PP1 and PP2A suggests that it may have potential as a therapeutic agent for treating various diseases, including cancer, by modulating the activity of these enzymes.
Used in Cell Biology Studies:
In cell biology, Calyculin A is used as an inhibitor of cyclin D1 phosphatase in human breast cancer cells. This application helps researchers understand the role of cyclin D1 and its regulation by protein phosphatases in cell cycle progression and tumor growth.
Used in Mouse Melanoma Cell Line Studies:
Calyculin A is used as an inhibitor of protein phosphatase 2A (PP2A) and PP1 in mouse melanoma cell lines B16-F0 cells. This application aids in studying the role of these phosphatases in melanoma development and identifying potential therapeutic strategies for treating this type of cancer.

Biological Activity

Potent and selective cell-permeable inhibitor of protein phosphatase 1 (IC 50 = 0.3-0.7 nM) and protein phosphatase 2A (IC 50 = 0.5-1 nM). Displays > 10,000,000-fold selectivity over PP2B and PP2C.

Biochem/physiol Actions

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

Check Digit Verification of cas no

The CAS Registry Mumber 101932-71-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,1,9,3 and 2 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 101932-71:
(8*1)+(7*0)+(6*1)+(5*9)+(4*3)+(3*2)+(2*7)+(1*1)=92
92 % 10 = 2
So 101932-71-2 is a valid CAS Registry Number.
InChI:InChI=1/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

101932-71-2 Well-known Company Product Price

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  • Sigma

  • (C5552)  Calyculin A from Discodermia calyx  ≥90% (HPLC), solid

  • 101932-71-2

  • C5552-10UG

  • 1,917.63CNY

  • Detail
  • Sigma

  • (21279)  Calyculin A from Discodermia calyx  ≥90% (HPLC)

  • 101932-71-2

  • 21279-10UG

  • 2,414.88CNY

  • Detail

101932-71-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Calyculin A from Discodermia calyx

1.2 Other means of identification

Product number -
Other names Calyculin A,N-[(3S)-[4-(1E)-3-[(2R,3R,4R,7S,8S,9R)-2-[(1S,3S,4S,5R,7E,9E,11E,13Z)-14-Cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraenyl]-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propenyl]-2-o

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

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