์ฝ˜ํ…์ธ ๋กœ ๊ฑด๋„ˆ๋›ฐ๊ธฐ
Merck

์ฃผ์š” ๋ฌธ์„œ

๋ชจ๋“  ๋ฌธ์„œ ๋ณด๊ธฐ

W1628

Wortmannin

From Penicillium funiculosum, โ‰ฅ98% (HPLC and TLC), phosphatidylinositol 3-kinase inhibitor, powder

๋™์˜์–ด(๋“ค):

KY 12420

์กฐ์ง ๋ฐ ๊ณ„์•ฝ ๊ฐ€๊ฒฉ์„ ๋ณด๋ ค๋ฉด ๋กœ๊ทธ์ธ๋ฅผ ํด๋ฆญํ•ฉ๋‹ˆ๋‹ค.

ํฌ๊ธฐ ์„ ํƒ

๋ณด๊ธฐ ๋ณ€๊ฒฝ

์ œํ’ˆ์ •๋ณด (DICE ๋ฐฐ์†ก ์‹œ ๋น„์šฉ ๋ณ„๋„)

์‹คํ—˜์‹(Hill ํ‘œ๊ธฐ๋ฒ•):
C23H24O8
CAS ๋ฒˆํ˜ธ:
19545-26-7
Molecular Weight:
428.43
NACRES:
NA.77
PubChem Substance ID:
24278777
UNSPSC Code:
12352207
MDL number:
MFCD00133927
Beilstein/REAXYS Number:
67676
Assay:
≥98% (HPLC and TLC)
Form:
powder
Quality level:
300
๊ธฐ์ˆ  ์„œ๋น„์Šค
๋„์›€์ด ํ•„์š”ํ•˜์‹ ๊ฐ€์š”? ์ €ํฌ ์ˆ™๋ จ๋œ ๊ณผํ•™์ž ํŒ€์ด ๋„์™€๋“œ๋ฆฌ๊ฒ ์Šต๋‹ˆ๋‹ค.
๋„์›€ ๋ฌธ์˜

์ œํ’ˆ ์ด๋ฆ„

Wortmannin, from Penicillium funiculosum, โ‰ฅ98% (HPLC and TLC)

biological source

Penicillium funiculosum

Quality Level

300

assay

≥98% (HPLC and TLC)

form

powder

color

off-white

solubility

DMSO: soluble, H2O: unstable

storage temp.

2-8ยฐC

SMILES string

[H][C@@]12CCC(=O)[C@@]1(C)C[C@@H](OC(C)=O)C3=C2C(=O)c4occ5C(=O)O[C@H](COC)[C@@]3(C)c45

InChI

1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1

InChI key

QDLHCMPXEPAAMD-QAIWCSMKSA-N

Gene Information

human ... PIK3CD(5293), PIK3CG(5294), PIK3R1(5295)

Biochem/physiol Actions

Wortmannin is a potent and specific phosphatidylinositol 3-kinase (PI3-K) inhibitor with an IC50 of 2-4 nM.
Wortmannin is a potent and specific phosphatidylinositol 3-kinase (PI3-K) inhibitor with an IC50 of 2-4 nM. Inhibition of PI3-K/Akt signal transduction cascade enhances the apoptotic effects of radiation or serum withdrawal and blocks the antiapoptotic effect of cytokines. Inhibition of PI3-K by wortmannin also blocks many of the short-term metabolic effects induced by insulin receptor activation.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide and Kinase Phosphatase Biology research. Discover more featured Cyclic Nucleotide and Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the G Proteins (Heterotrimeric) and Phosphoinositide Kinases pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 1 Oral - Acute Tox. 2 Dermal

์ €์žฅ ๋“ฑ๊ธ‰

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

๊ฐ€์žฅ ์ตœ์‹  ๋ฒ„์ „ ์ค‘ ํ•˜๋‚˜๋ฅผ ์„ ํƒํ•˜์„ธ์š”:

์‹œํ—˜ ์„ฑ์ ์„œ(COA)

Lot/Batch Number
0000195911
0000232726
0000091882
0000334570
0000232726

์ ํ•ฉํ•œ ๋ฒ„์ „์„ ์ฐพ์„ ์ˆ˜ ์—†์œผ์‹ ๊ฐ€์š”?

ํŠน์ • ๋ฒ„์ „์ด ํ•„์š”ํ•œ ๊ฒฝ์šฐ ๋กœํŠธ ๋ฒˆํ˜ธ๋‚˜ ๋ฐฐ์น˜ ๋ฒˆํ˜ธ๋กœ ํŠน์ • ์ธ์ฆ์„œ๋ฅผ ์ฐพ์„ ์ˆ˜ ์žˆ์Šต๋‹ˆ๋‹ค.

COA ๊ฒ€์ƒ‰

์ด ์ œํ’ˆ์„ ์ด๋ฏธ ๊ฐ€์ง€๊ณ  ๊ณ„์‹ญ๋‹ˆ๊นŒ?

๋ฌธ์„œ ๋ผ์ด๋ธŒ๋Ÿฌ๋ฆฌ์—์„œ ์ตœ๊ทผ์— ๊ตฌ๋งคํ•œ ์ œํ’ˆ์— ๋Œ€ํ•œ ๋ฌธ์„œ๋ฅผ ์ฐพ์•„๋ณด์„ธ์š”.

๋ฌธ์„œ ๋ผ์ด๋ธŒ๋Ÿฌ๋ฆฌ ๋ฐฉ๋ฌธ

๋ฌธ์„œ

๊ณ ๋ฆฌํ˜• ๋‰ดํด๋ ˆ์˜คํƒ€์ด๋“œ๋ฅผ ์œ„ํ•œ ์ƒ์ฒด ํ™œ์„ฑ ์ €๋ถ„์ž

๊ณ ๋ฆฌํ˜• AMP(cAMP), ๊ณ ๋ฆฌํ˜• GMP(cGMP), ๊ณ ๋ฆฌํ˜• ADP-๋ฆฌ๋ณด์Šค๋ฅผ ํฌํ•จํ•˜์—ฌ ๊ณ ๋ฆฌํ˜• ๋‰ดํด๋ ˆ์˜คํƒ€์ด๋“œ๋Š” GPCR ํ™œ์„ฑํ™”์— ์˜ํ•ด ๊ฐœ์‹œ๋œ ์„ธํฌ๋‚ด ์ด๋ฒคํŠธ์˜ 2์ฐจ ์ „๋‹ฌ์ž๋กœ์„œ ๊ด‘๋ฒ”์œ„ํ•˜๊ฒŒ ์—ฐ๊ตฌ๋˜์—ˆ์Šต๋‹ˆ๋‹ค. cAMP๋Š” ์ฃผ๋กœ cAMP ์˜์กด์„ฑ ๋‹จ๋ฐฑ์งˆ ์ธ์‚ฐํ™”ํšจ์†Œ(PKA)์˜ ํ™œ์„ฑํ™”๋ฅผ ํ†ตํ•ด ๋ชจ๋“  ์ง„ํ•ต์ƒ๋ฌผ ์„ธํฌ์—์„œ ์„ธํฌ ๊ธฐ๋Šฅ์„ ๋ณ€ํ˜•์‹œํ‚ค์ง€๋งŒ cAMP ๊ฐœํ ์ด์˜จ ์ฑ„๋„ ๋ฐ cAMP์— ์˜ํ•ด ์ง์ ‘ ํ™œ์„ฑํ™”๋˜๋Š” ๊ตฌ์•„๋‹Œ ๋‰ดํด๋ ˆ์˜คํƒ€์ด๋“œ ๊ตํ™˜ ์ธ์ž๋ฅผ ํ†ตํ•ด์„œ๋„ ๋ณ€ํ˜•์‹œํ‚ต๋‹ˆ๋‹ค.

์ง€์งˆ ์‹ ํ˜ธ์ „๋‹ฌ ์—ฐ๊ตฌ๋ฅผ ์œ„ํ•œ ์ƒ์ฒด ํ™œ์„ฑ ์ €๋ถ„์ž

์ง€์งˆ ์‹ ํ˜ธ์ „๋‹ฌ ์—ฐ๊ตฌ๋ฅผ ์œ„ํ•œ ์ƒ์ฒด ํ™œ์„ฑ ์ €๋ถ„์ž

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

๋ชจ๋“  ๊ธฐ์‚ฌ ๋ณด๊ธฐ

๊ด€๋ จ ์ฝ˜ํ…์ธ 

S Nakanishi et al.
The Journal of biological chemistry, 267(4), 2157-2163 (1992-02-05)
We have found that a fungal strain, Talaromyces wortmannin KY12420, produces a potent inhibitor of smooth muscle myosin light chain kinase (MLCK). This active product, designated as MS-54, was isolated and purified from the culture broth of the fungus and
Alban R Pereira et al.
Journal of medicinal chemistry, 53(24), 8523-8533 (2010-12-03)
Analogues of the sponge meroterpenoid liphagal have been synthesized and evaluated for inhibition of PI3Kฮฑ and PI3Kฮณ as part of a program aimed at developing new isoform-selective PI3K inhibitors. One of the analogues, compound 24, with ICโ‚…โ‚€ values of 66
Alexander D Crawford et al.
PloS one, 6(2), e14694-e14694 (2011-03-08)
Natural products represent a significant reservoir of unexplored chemical diversity for early-stage drug discovery. The identification of lead compounds of natural origin would benefit from therapeutically relevant bioassays capable of facilitating the isolation of bioactive molecules from multi-constituent extracts. Towards
๋ชจ๋“  ๊ด€๋ จ๋œ ์„œ๋ฅ˜ ๋ณด๊ธฐ