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W1628

Wortmannin

From Penicillium funiculosum, ≥98% (HPLC and TLC), phosphatidylinositol 3-kinase inhibitor, powder

Synonym(s):

KY 12420

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1 MG

CZK 4,560.00

5 MG

CZK 9,410.00

10 MG

CZK 15,980.00

CZK 4,560.00

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About This Item

Empirical Formula (Hill Notation):
C23H24O8
CAS Number:
19545-26-7
Molecular Weight:
428.43
NACRES:
NA.77
PubChem Substance ID:
24278777
UNSPSC Code:
12352207
MDL number:
MFCD00133927
Beilstein/REAXYS Number:
67676

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Product Name

Wortmannin, from Penicillium funiculosum, ≥98% (HPLC and TLC)

InChI key

QDLHCMPXEPAAMD-QAIWCSMKSA-N

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

biological source

Penicillium funiculosum

assay

≥98% (HPLC and TLC)

form

powder

color

off-white

solubility

DMSO: soluble
H2O: unstable

storage temp.

2-8°C

Quality Level

300

Gene Information

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

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1 of 4

This Item
681675M9440C2020
Wortmannin from Penicillium funiculosum, ≥98% (HPLC and TLC)

Sigma-Aldrich

W1628

Wortmannin

Wortmannin Wortmannin, CAS 19545-26-7, is a cell-permeable, potent, selective, and irreversible inhibitor of PI3-Kinase (IC50 = 5 nM). Does not affect any upstream signaling events.

Sigma-Aldrich

681675

Wortmannin

Methyl-3,4-dephostatin >98% (HPLC), powder

Sigma-Aldrich

M9440

Methyl-3,4-dephostatin

α-Cyano-4-hydroxycinnamic acid ≥98% (TLC), powder

Sigma-Aldrich

C2020

α-Cyano-4-hydroxycinnamic acid

form

powder

form

solid

form

powder

form

powder

assay

≥98% (HPLC and TLC)

assay

≥98% (HPLC)

assay

>98% (HPLC)

assay

≥98% (TLC)

Quality Level

300

Quality Level

100

Quality Level

100

Quality Level

300

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: soluble, H2O: unstable

solubility

DMSO: 25 mg/mL

solubility

DMSO: soluble 18 mg/mL, H2O: insoluble

solubility

H2O: slightly soluble, methanol: water: soluble, polar organic solvents: soluble

color

off-white

color

white to off-white

color

red-brown

color

yellow

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.

comparable product

Product No.
Description
Pricing

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

Storage Class

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000462987
0000462987
0000395836
0000334570
0000138034

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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 PI3Kα and PI3Kγ as part of a program aimed at developing new isoform-selective PI3K inhibitors. One of the analogues, compound 24, with IC₅₀ 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
Matthew G K Benesch et al.
Journal of lipid research, 56(6), 1134-1144 (2015-04-22)
Autotaxin (ATX) is a secreted enzyme, which produces extracellular lysophosphatidate (LPA) from lysophosphatidylcholine (LPC). LPA activates six G protein-coupled receptors and this is essential for vasculogenesis during embryonic development. ATX is also involved in wound healing and inflammation, and in
D A Cunha et al.
Cell death and differentiation, 21(8), 1313-1324 (2014-05-03)
Diets rich in saturated fats may contribute to the loss of pancreatic β-cells in type 2 diabetes. JunB, a member of the activating protein 1 (AP-1) transcription factor family, promotes β-cell survival and mediates part of the beneficial effects of
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