CHEBI:52289 - wortmannin

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ChEBI Name wortmannin
ChEBI ID CHEBI:52289
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sandra Orchard
Supplier Information
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Formula C23H24O8
Net Charge 0
Average Mass 428.43190
Monoisotopic Mass 428.147
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 [H][C@@]12CCC(=O)[C@@]1(C)C[C@@H](OC(C)=O)C1=C2C(=O)c2occ3C(=O)O[C@H](COC)[C@@]1(C)c23
Roles Classification
Biological Role(s): EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
An inhibitor of phosphatidylinositol 3-kinase, EC 2.7.1.137, a family of related enzymes capable of phosphorylating the 3 position hydroxy group of the inositol ring of a phosphatidylinositol.
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ChEBI Ontology
Outgoing wortmannin (CHEBI:52289) has role EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor (CHEBI:50914)
wortmannin (CHEBI:52289) is a δ-lactone (CHEBI:18946)
wortmannin (CHEBI:52289) is a acetate ester (CHEBI:47622)
wortmannin (CHEBI:52289) is a cyclic ketone (CHEBI:3992)
wortmannin (CHEBI:52289) is a organic heteropentacyclic compound (CHEBI:38164)
Incoming PX-866 (CHEBI:65345) has functional parent wortmannin (CHEBI:52289)
IUPAC Name
(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
Synonym Source
Wartmannin ChemIDplus
Manual Xrefs Databases
C00023672 KNApSAcK
C15181 KEGG COMPOUND
KWT PDBeChem
LSM-3947 LINCS
View more database links
Registry Numbers Types Sources
19545-26-7 CAS Registry Number ChemIDplus
67676 Reaxys Registry Number Reaxys
67676 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
22003059 PubMed citation Europe PMC
22056625 PubMed citation Europe PMC
22524784 PubMed citation Europe PMC
Last Modified
25 February 2016
Submitter Remark
2009-04-08 12:17:02.0 Inma Spiteri a fungal metabolite that specifically inhibits phosphatidylinositol 3-kinase (PI-3), mitogen-activated protein kinase (MAPK) and myosin light-chain kinase . (MLCK). Wortmannin is obtained from Penicillium fumiculosum Wortmannin ; CAS [19545-26-7] Wortmannin has M.W. 428.4. Wortmannin is hygroscopic.Structure to be found at http://wortmannin.noneto.com/