Wortmannin

Title: Wortmannin
CAS Registry Number: 19545-26-7
CAS Name: (1S,6bR,9aS,11R,11bR)-11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-3H-furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione
Molecular Formula: C23H24O8
Molecular Weight: 428.43
Percent Composition: C 64.48%, H 5.65%, O 29.88%
Literature References: Antifungal antibiotic from Penicillium wortmanni Klocker: Brian et al., Trans. Br. Mycol. Soc. 40, 365 (1957). Similar to viridin, q.v. Structure: MacMillan et al., Chem. Commun. 1968, 613; eidem, J. Chem. Soc. Perkin Trans. 1 1972, 2898. Absolute stereochemistry: Petcher et al., Chem. Commun. 1972, 1061; MacMillan et al., ibid. 1063.
Properties: Neutral solid, mp 240°. Unstable in aq solns pH 3-8.
Melting point: mp 240°
Xamoterol Xanthatin Xanthinol Niacinate Xanthocillin Xanthone

Wortmannin
Wortmannin chemical structure.png
Identifiers
CAS number 19545-26-7 YesY
PubChem 312145
ChemSpider 276037 N
ChEMBL CHEMBL428496 N
Jmol-3D images Image 1
Properties
Molecular formula C23H24O8
Molar mass 428.43186
Melting point 238−242 °C
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Wortmannin, a steroid metabolite of the fungi Penicillium funiculosum, Talaromyces (Penicillium) wortmannii,[1] is a specific, covalent inhibitor of phosphoinositide 3-kinases (PI3Ks). It has an in vitro inhibitory concentration (IC50) of around 5 nM, making it a more potent inhibitor than LY294002, another commonly used PI3K inhibitor. It displays a similar potency in vitro for the class I, II, and III PI3K members although it can also inhibit other PI3K-related enzymes such as mTOR, DNA-PK, some phosphatidylinositol 4-kinases, myosin light chain kinase (MLCK) and mitogen-activated protein kinase (MAPK) at high concentrations [2],[3] Wortmannin has also been reported to inhibit members of the polo-like kinase family with IC50 in the same range as for PI3K.[4] The half-life of wortmannin in tissue culture is about 10 minutes due to the presence of the highly reactive C20 carbon that is also responsible for its ability to covalently inactivate PI3K. Wortmannin is a commonly used cell biology reagent that has been used previously in research to inhibit DNA repair, receptor-mediated endocytosis and cell proliferation[citation needed].