Compound: wortmannin
SMILES: O=C1O[C@@H]([C@@]2(C3=C([C@H]4[C@](C(=O)CC4)(C)C[C@H]3OC(=O)C)C(c5c2c1co5)=O)C)COC
InChIKey: QDLHCMPXEPAAMD-QAIWCSMKSA-N
Synonyms: wortmannin, 19545-26-7, Wartmannin, Antibiotic SL-2052, SL-2052, XVA4O219QW, NSC221019, DTXSID8040642, NSC-627609, CHEBI:52289, NSC627609, (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, [(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, (1S,6bR,9aS,11R,11bR)-9a,11b-dimethyl-1-[(methyloxy)methyl]-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate, MS54, MS-54, ((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, (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, (1S,6bR,9aS,11R,11bR)-9a,11b-dimethyl-1-((methyloxy)methyl)-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo(4,3,2-de)indeno(4,5-h)isochromen-11-yl acetate, RefChem:389363, DTXCID6020642, (1 Alpha,11 alpha)-11-(acetyloxy)-1-(methoxymethyl)-2-oxaandrosta-5,8-dieno(6,5,4-bc)furan-3,7,17-trione, 2-Oxaandrosta-5,8-dieno(6,5,4-bc)furan-3,7,17-trione, 11-(acetyloxy)-1-(methoxymethyl)-, (1alpha,11alpha)-, 606-337-5, KY 12420, MFCD00133927, MLS002703028, CHEMBL428496, (1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate, 3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione,11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6bR,9aS,11R,11bR)-, KY-12420, (1alpha,11alpha)-11-(Acetyloxy)-1-(methoxymethyl)-2-oxaandrosta-5,8-dieno(6,5,4-bc)furan-3,7,17-trione, (1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),12(19),14-trien-3-yl acetate, UNII-XVA4O219QW, wortmanin, Wortmannin?, Wortmannin, Wm, 3H-FURO(4,3,2-DE)INDENO(4,5-H)-2-BENZOPYRAN-3,6,9-TRIONE, 11-(ACETYLOXY)-1,6B,7,8,9A,10,11,11B-OCTAHYDRO-1-(METHOXYMETHYL)-9A,11B-DIMETHYL-, (1S,6BR,9AS,11R,11BR)-, 3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6bR,9aS,11R,11bR)-, SL-2052;KY-12420, nchembio866-comp1, NSC 627609, BRN 0067676, WORTMANNIN [MI], (+)-WORTMANNIN, SCHEMBL4531, BSPBio_001232, 4-19-00-03134 (Beilstein Handbook Reference), cid_312145, GTPL6060, MEGxm0_000446, orb1300904, orb3024939, Wortmannin,Penicillium wortmannin, ACon0_000951, BDBM15234, GLXC-07906, HMS1792N13, HMS1990N13, HMS3403N13, Wortmannin, Penicillium funiculosum, (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, EX-A1930, MSK001432, ST-415, AKOS027327288, Wortmannin - CAS 19545-26-7, CCG-208290, CS-5073, DB08059, NSC-221019, Wortmannin; SL-2052; KY-12420, NCGC00163485-01, NCGC00163485-02, (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., AC-35862, BS-16306, HY-10197, NCI60_001835, SMR001566836, W0007, CU-00000000011-1, BRD-K87343924-001-02-4, BRD-K87343924-001-12-3, 3,2-DE]INDENO[4,5-H][2]BENZOPYRAN-11-YL ACETATE, Wortmannin, from Penicillium funiculosum, >=98% (HPLC and TLC), 3H-furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 11-(acetyloxy)-1,, (1R,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b- decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate, (1S,6bR,9aS,11R,11bR)-1-(Methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h][2]benzopyran-11-yl acetate, (1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-ylacetate, (1S,6BR,9AS,11R,11BR)-9A,11B-DIMETHYL-1-[(METHYLOXY)METHYL]-3,6,9-TRIOXO-1,6,6B,7,8,9,9A,10,11,11B-DECAHYDRO-3H-FURO[4,, 2-Oxaandrosta-5,5,4-bc]furan-3,7,17-trione, 11-(acetyloxy)-1-(methoxymethyl)-, (1.alpha.,11.alpha.)-, 3H-Furo[4,2-de]indeno[4,5,-h]-2-benzopyran-3,6,9-trione, 11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6br,9aS,11R,11bR), 3H-Furo[4,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6br,9aS,11R,11bR), 3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-, 6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6bR,9aS,11R,11bR)-, octahydro-1-(methoxymethyl)-9a,11b-dimethyl-, [1S-(1alpha,6baalpha,9abeta,11alpha,11bbeta)]-
Theoretical properties:
molecular_formula: C23H24O8
molecular_weight: 428.4 g/mol
exact_mass: 428.14711772 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 4
heavy_atom_count: 31
topological_polar_surface_area: 109 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Wortmannin is a delta-lactone, an organic heteropentacyclic compound, a cyclic ketone and an acetate ester. It has a role as a radiosensitizing agent, an anticoronaviral agent, a geroprotector, an antineoplastic agent, an EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor, a Penicillium metabolite and an autophagy inhibitor.
chembl: WORTMANNIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Wortmannin, a steroid metabolite of the fungi Penicillium funiculosum, Talaromyces wortmannii, is a non-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-PKcs, some phosphatidylinositol 4-kinases, myosin light chain kinase (MLCK) and mitogen-activated protein kinase (MAPK)  at high concentrations Wortmannin has also been reported to inhibit members of the polo-like kinase family with IC50 in the same range as for PI3K.  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.