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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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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
Assay:
≥98% (HPLC and TLC)
Form:
powder
Quality level:
300
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Product Name

Wortmannin, from Penicillium funiculosum, ≥98% (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.

2-8°C

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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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

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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

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
0000091882
0000334570
0000195911
0000232726
0000334570

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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
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Global Trade Item Number

SKUGTIN
W1628-10MG04061833265956
W1628-1MG04061837488665
W1628-5MG04061837488672

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