For research use only. Not for therapeutic Use.
Wortmannin（Cat No.:I002494）is a potent, irreversible inhibitor of phosphoinositide 3-kinase (PI3K), originally isolated from the fungus Penicillium funiculosum. It inhibits PI3K by covalently binding to its catalytic domain, effectively blocking the PI3K/Akt signaling pathway, which is critical for cell growth, proliferation, and survival. Wortmannin has been extensively used as a research tool to study PI3K-related cellular processes, including cancer, inflammation, and metabolism. Despite its potency, its toxicity and lack of specificity limit its therapeutic use, but it remains a key compound for elucidating PI3K functions in various biological studies.
| Catalog Number | I002494 |
| CAS Number | 19545-26-7 |
| Synonyms | (1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-3,6,6b,7,8,9,9a,10,11,11b-decahydro-1H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate |
| Molecular Formula | C₂₃H₂₄O₈ |
| Purity | ≥95% |
| Target | Autophagy |
| Solubility | 10 mM in DMSO |
| Storage | 3 years -20C powder |
| IC50 | 3 nM (PI3K) , 16 nM (DNA-PK) , 150 nM (ATM) , 170 nM (MLCK) |
| IUPAC Name | [(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] acetate |
| InChI | 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 |
| InChIKey | QDLHCMPXEPAAMD-QAIWCSMKSA-N |
| SMILES | CC(=O)O[C@@H]1C[C@]2([C@@H](CCC2=O)C3=C1[C@]4([C@H](OC(=O)C5=COC(=C54)C3=O)COC)C)C |
| Reference | </br>1:Enantioselective Total Synthesis of (+)-Wortmannin. Guo Y, Quan T, Lu Y, Luo T.J Am Chem Soc. 2017 May 11. doi: 10.1021/jacs.7b02515. [Epub ahead of print] PMID: 28474885 </br>2:PI3K inhibitor LY294002, as opposed to wortmannin, enhances AKT phosphorylation in gemcitabine-resistant pancreatic cancer cells. Wang Y, Kuramitsu Y, Baron B, Kitagawa T, Tokuda K, Akada J, Maehara SI, Maehara Y, Nakamura K.Int J Oncol. 2017 Feb;50(2):606-612. doi: 10.3892/ijo.2016.3804. Epub 2016 Dec 14. PMID: 28000865 </br>3:AKTs/PKBs: molecular characterization, tissue expression and transcriptional responses to insulin and/or wortmannin in yellow catfish Pelteobagrus fulvidraco. Zhuo MQ, Pan YX, Wu K, Xu YH, Zhang LH, Luo Z.Fish Physiol Biochem. 2017 Jun;43(3):719-730. doi: 10.1007/s10695-016-0327-y. Epub 2016 Dec 20. PMID: 28000079 </br>4:Wortmannin-induced vacuole fusion enhances amyloplast dynamics in Arabidopsis zigzag1 hypocotyls. Alvarez AA, Han SW, Toyota M, Brillada C, Zheng J, Gilroy S, Rojas-Pierce M.J Exp Bot. 2016 Dec;67(22):6459-6472. Epub 2016 Nov 5. PMID: 27816929 Free PMC Article</br>5:Profiling Kinase Activity during Hepatitis C Virus Replication Using a Wortmannin Probe. Desrochers GF, Sherratt AR, Blais DR, Nasheri N, Ning Z, Figeys D, Goto NK, Pezacki JP.ACS Infect Dis. 2015 Sep 11;1(9):443-52. doi: 10.1021/acsinfecdis.5b00083. Epub 2015 Aug 20. PMID: 27617927 </br>6:Is Wortmannin-Induced Reorganization of the trans-Golgi Network the Key to Explain Charasome Formation? Foissner I, Sommer A, Hoeftberger M, Hoepflinger MC, Absolonova M.Front Plant Sci. 2016 Jun 3;7:756. doi: 10.3389/fpls.2016.00756. eCollection 2016. PMID: 27375631 Free PMC Article</br>7:Wortmannin influences hypoxia-inducible factor-1 alpha expression and glycolysis in esophageal carcinoma cells. Zeng L, Zhou HY, Tang NN, Zhang WF, He GJ, Hao B, Feng YD, Zhu H.World J Gastroenterol. 2016 May 28;22(20):4868-80. doi: 10.3748/wjg.v22.i20.4868. PMID: 27239113 Free PMC Article</br>8:CL316243 induces phosphatidylinositol 3,4,5-triphosphate production in rat adipocytes in an adenosine deaminase-, pertussis toxin-, or wortmannin-sensitive manner. Ohsaka Y, Nomura Y.Physiol Res. 2016 Jul 18;65(3):543-6. Epub 2016 Mar 15. PMID: 26988163 Free Article</br>9:Investigating the Inhibitory Effect of Wortmannin in the Hotspot Mutation at Codon 1047 of PIK3CA Kinase Domain: A Molecular Docking and Molecular Dynamics Approach. Kumar DT, Doss CG.Adv Protein Chem Struct Biol. 2016;102:267-97. doi: 10.1016/bs.apcsb.2015.09.008. Epub 2015 Oct 29. Review. PMID: 26827608 </br>10:Wortmannin, PI3K/Akt signaling pathway inhibitor, attenuates thyroid injury associated with severe acute pancreatitis in rats. Abliz A, Deng W, Sun R, Guo W, Zhao L, Wang W.Int J Clin Exp Pathol. 2015 Nov 1;8(11):13821-33. eCollection 2015. PMID: 26823696 Free PMC Article |
