wortmannin   

GtoPdb Ligand ID: 6060

Synonyms: antibiotic SL-2052 | KY 12420
Comment: Wortmannin is extracted from Penicillium funiculosum. The compound is a specific, covalent inhibitor of phosphoinositide 3-kinases (PI3Ks).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 109.11
Molecular weight 428.15
XLogP 0.71
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COCC1OC(=O)c2c3C1(C)C1=C(C(=O)c3oc2)C2C(CC1OC(=O)C)(C)C(=O)CC2
Isomeric SMILES COC[C@H]1OC(=O)c2c3[C@@]1(C)C1=C(C(=O)c3oc2)[C@H]2[C@@](C[C@H]1OC(=O)C)(C)C(=O)CC2
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
InChI Key QDLHCMPXEPAAMD-QAIWCSMKSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
(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
Synonyms
antibiotic SL-2052 | KY 12420
Database Links
CAS Registry No. 19545-26-7
ChEBI CHEBI:52289
ChEMBL Ligand CHEMBL428496
DrugBank Ligand DB08059
GtoPdb PubChem SID 178102681
PubChem CID 312145
RCSB PDB Ligand KWT
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SynPHARM 80594 (in complex with phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha)
Wikipedia Wortmannin