Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H24O8 |
| Molecular Weight | 428.4319 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC[C@H]1OC(=O)C2=COC3=C2[C@@]1(C)C4=C([C@@H]5CCC(=O)[C@@]5(C)C[C@H]4OC(C)=O)C3=O
InChI
InChIKey=QDLHCMPXEPAAMD-QAIWCSMKSA-N
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
| Molecular Formula | C23H24O8 |
| Molecular Weight | 428.4319 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7667888
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7667888
Wortmannin is a fungal metabolite that so far has been shown to act as a selective inhibitor of phosphoinositide 3-kinase. Wortmannin inhibits cancer cell growth and has shown activity against mouse and human tumor xenografts in mice. Wortmannin is the first described PI3K inhibitor with IC50 of 3 nM in a cell-free assay, with little selectivity within the PI3K family. Also blocks autophagosome formation and potently inhibits DNA-PK/ATM with IC50 of 16 nM and 150 nM in cell-free assays.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Phosphatidylinositol 3-kinase, not extracellular signal-regulated kinase, regulates activation of the antioxidant-responsive element in IMR-32 human neuroblastoma cells. | 2001-06-08 |
|
| P2Y(2) nucleotide receptor signaling in human monocytic cells: activation, desensitization and coupling to mitogen-activated protein kinases. | 2001-05 |
|
| Trypanosoma cruzi: phosphatidylinositol 3-kinase and protein kinase B activation is associated with parasite invasion. | 2001-04-01 |
|
| Proinsulin C-peptide rapidly stimulates mitogen-activated protein kinases in Swiss 3T3 fibroblasts: requirement of protein kinase C, phosphoinositide 3-kinase and pertussis toxin-sensitive G-protein. | 2001-04-01 |
|
| Lipopolysaccharide activates Akt in human alveolar macrophages resulting in nuclear accumulation and transcriptional activity of beta-catenin. | 2001-04-01 |
|
| Beta(2)-adrenergic receptors potentiate glucocorticoid receptor transactivation via G protein beta gamma-subunits and the phosphoinositide 3-kinase pathway. | 2001-04 |
|
| Regulatory role of phosphatidylinositol 3-kinase on TNF-alpha-induced cyclooxygenase 2 expression in colonic epithelial cells. | 2001-04 |
|
| Intracellular Angiotensin II and cell growth of vascular smooth muscle cells. | 2001-04 |
|
| p110-related PI 3-kinases regulate phagosome-phagosome fusion and phagosomal pH through a PKB/Akt dependent pathway in Dictyostelium. | 2001-04 |
|
| Insulin increases the turnover rate of Na+-K+-ATPase in human fibroblasts. | 2001-04 |
|
| Mechanism by which wortmannin and LY294002 inhibit catecholamine secretion in the rat adrenal medullary cells. | 2001-04 |
|
| Pleiotrophin induces angiogenesis: involvement of the phosphoinositide-3 kinase but not the nitric oxide synthase pathways. | 2001-04 |
|
| The cell survival signal Akt is differentially activated by PDGF-BB, EGF, and FGF-2 in osteoblastic cells. | 2001-03-26 |
|
| Oxidative stress induced by ascorbate causes neuronal damage in an in vitro system. | 2001-03-23 |
|
| A novel family of phosphatidylinositol 4-kinases conserved from yeast to humans. | 2001-03-16 |
|
| Reduction of potassium currents and phosphatidylinositol 3-kinase-dependent AKT phosphorylation by tumor necrosis factor-(alpha) rescues axotomized retinal ganglion cells from retrograde cell death in vivo. | 2001-03-15 |
|
| A low-pH culture condition enhances the radiosensitizing effect of wortmannin. | 2001-03-15 |
|
| PTEN inhibits insulin-stimulated MEK/MAPK activation and cell growth by blocking IRS-1 phosphorylation and IRS-1/Grb-2/Sos complex formation in a breast cancer model. | 2001-03-15 |
|
| Study of the cytolethal distending toxin (CDT)-activated cell cycle checkpoint. Involvement of the CHK2 kinase. | 2001-03-02 |
|
| Activation of BMK1 via tyrosine 1062 in RET by GDNF and MEN2A mutation. | 2001-03-02 |
|
| TNFalpha elicits association of PI 3-kinase with the p60TNFR and activation of PI 3-kinase in adherent neutrophils. | 2001-03-02 |
|
| Activation of phosphatidylinositol-3 kinase (PI-3K) and extracellular regulated kinases (Erk1/2) is involved in muscarinic receptor-mediated DNA synthesis in neural progenitor cells. | 2001-03-01 |
|
| Induction of the monocytic differentiation of myeloid leukaemia cells by cotylenin A, a plant growth regulator. | 2001-03 |
|
| Biosynthesis and processing of cathepsin K in cultured human osteoclasts. | 2001-03 |
|
| Human rad21 gene, hHR21(SP), is downregulated by hypoxia in human tumor cells. | 2001-03 |
|
| Integrin signaling via the PI3-kinase-Akt pathway increases neuronal resistance to glutamate-induced apoptosis. | 2001-03 |
|
| Rac recruits high-affinity integrin alphavbeta3 to lamellipodia in endothelial cell migration. | 2001-03 |
|
| Insulin regulation of protein translation repressor 4E-BP1, an eIF4E-binding protein, in renal epithelial cells. | 2001-03 |
|
| Resistance to induced apoptosis in the human neuroblastoma cell line SK-N-SH in relation to neuronal differentiation. Role of Bcl-2 protein family. | 2001-03 |
|
| Phosphoinositide 3-kinase, but not mitogen-activated protein kinase, pathway is involved in hepatocyte growth factor-mediated protection against bile acid-induced apoptosis in cultured rat hepatocytes. | 2001-03 |
|
| Roles of phosphatidylinositol 3-kinase and phospholipase D in temporal activation of superoxide production in FMLP-stimulated human neutrophils. | 2001-03 |
|
| Regulation of p42/p44 MAPK and p38 MAPK by the adenosine A(1) receptor in DDT(1)MF-2 cells. | 2001-02-16 |
|
| Up-regulation of vascular endothelial growth factor in breast cancer cells by the heregulin-beta1-activated p38 signaling pathway enhances endothelial cell migration. | 2001-02-15 |
|
| Nitric oxide increases glucose uptake through a mechanism that is distinct from the insulin and contraction pathways in rat skeletal muscle. | 2001-02 |
|
| Mitogenic and antiapoptotic actions of hepatocyte growth factor through ERK, STAT3, and AKT in endothelial cells. | 2001-02 |
|
| Signaling events mediating the additive effects of oleic acid and angiotensin II on vascular smooth muscle cell migration. | 2001-02 |
|
| Molecular mechanisms for the antiapoptotic action of gastrin. | 2001-02 |
|
| Insulin signal transduction in rat small intestine: role of MAP kinases in expression of mucosal hydrolases. | 2001-02 |
|
| Involvement of PI 3-kinase in IGF-I stimulation of jejunal Na+-K+-ATPase activity and nutrient absorption. | 2001-02 |
|
| Insulin-like growth factor-I is a potential trophic factor for amacrine cells. | 2001-02 |
|
| Nonhomologous end-joining of ionizing radiation-induced DNA double-stranded breaks in human tumor cells deficient in BRCA1 or BRCA2. | 2001-01-01 |
|
| Beta1 integrin activation on human neutrophils promotes beta2 integrin-mediated adhesion to fibronectin. | 2001-01 |
|
| Hypoxia activates Akt and induces phosphorylation of GSK-3 in PC12 cells. | 2001-01 |
|
| Regulation of intracellular trafficking of the EGF receptor by Rab5 in the absence of phosphatidylinositol 3-kinase activity. | 2001-01 |
|
| Evidence that phosphorylation of human Upfl protein varies with intracellular location and is mediated by a wortmannin-sensitive and rapamycin-sensitive PI 3-kinase-related kinase signaling pathway. | 2001-01 |
|
| Phosphatidylinositol 3-kinase activity is required for the expression of glial fibrillary acidic protein upon cAMP-dependent induction of differentiation in rat C6 glioma. | 2001-01 |
|
| Survival activity of troglitazone in rat motoneurones. | 2001-01 |
|
| Early growth response factor-1 mediates insulin-inducible vascular endothelial cell proliferation and regrowth after injury. | 2001 |
|
| Involvement of p70 S6 kinase in bone morphogenetic protein signaling: vascular endothelial growth factor synthesis by bone morphogenetic protein-4 in osteoblasts. | 2001 |
|
| 17 beta-estradiol-BSA conjugates and 17 beta-estradiol regulate growth plate chondrocytes by common membrane associated mechanisms involving PKC dependent and independent signal transduction. | 2001 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:28:12 GMT 2025
by
admin
on
Mon Mar 31 22:28:12 GMT 2025
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| Record UNII |
XVA4O219QW
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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NCI_THESAURUS |
C2152
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admin on Mon Mar 31 22:28:12 GMT 2025 , Edited by admin on Mon Mar 31 22:28:12 GMT 2025
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| Code System | Code | Type | Description | ||
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m11521
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312145
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DTXSID8040642
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19545-26-7
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627609
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DB08059
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Wortmannin
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C1277
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XVA4O219QW
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