wortmannin   Click here for help

GtoPdb Ligand ID: 6060

Synonyms: antibiotic SL-2052 | KY 12420
PDB Ligand
Comment: Wortmannin is extracted from Penicillium funiculosum. The compound is a specific, covalent inhibitor of phosphoinositide 3-kinases (PI3Ks).
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2D Structure
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Physico-chemical Properties
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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
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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
1. Anastassiadis T, Deacon SW, Devarajan K, Ma H, Peterson JR. (2011)
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
Nat Biotechnol, 29 (11): 1039-45. [PMID:22037377]
2. Brian PW, Curtis PJ, Hemming HG, Norris GLF. (1957)
Wortmannin, an antibiotic produced by Penicillium wortmanni.
Trans. Brit. mycol. Soc., 40 (3): 365-368. DOI: 10.1016/S0007-1536(57)80033-3
3. Castro-Falcón G, Seiler GS, Demir Ö, Rathinaswamy MK, Hamelin D, Hoffmann RM, Makowski SL, Letzel AC, Field SJ, Burke JE et al.. (2018)
Neolymphostin A Is a Covalent Phosphoinositide 3-Kinase (PI3K)/Mammalian Target of Rapamycin (mTOR) Dual Inhibitor That Employs an Unusual Electrophilic Vinylogous Ester.
J Med Chem, 61 (23): 10463-10472. [PMID:30380865]
4. Finlay MR, Griffin RJ. (2012)
Modulation of DNA repair by pharmacological inhibitors of the PIKK protein kinase family.
Bioorg Med Chem Lett, 22 (17): 5352-9. [PMID:22835870]
5. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ. (2013)
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
Biochem J, 451 (2): 313-28. [PMID:23398362]
6. Gehrmann T, Gülkan H, Suer S, Herberg FW, Balla A, Vereb G, Mayr GW, Heilmeyer Jr LM. (1999)
Functional expression and characterisation of a new human phosphatidylinositol 4-kinase PI4K230.
Biochim Biophys Acta, 1437 (3): 341-56. [PMID:10101268]
7. Griffin RJ, Fontana G, Golding BT, Guiard S, Hardcastle IR, Leahy JJ, Martin N, Richardson C, Rigoreau L, Stockley M et al.. (2005)
Selective benzopyranone and pyrimido[2,1-a]isoquinolin-4-one inhibitors of DNA-dependent protein kinase: synthesis, structure-activity studies, and radiosensitization of a human tumor cell line in vitro.
J Med Chem, 48 (2): 569-85. [PMID:15658870]
8. Meyers R, Cantley LC. (1997)
Cloning and characterization of a wortmannin-sensitive human phosphatidylinositol 4-kinase.
J Biol Chem, 272 (7): 4384-90. [PMID:9020160]
9. Singh V, Praveen V, Tripathi D, Haque S, Somvanshi P, Katti SB, Tripathi CK. (2015)
Isolation, characterization and antifungal docking studies of wortmannin isolated from Penicillium radicum.
Sci Rep, 5: 11948. [PMID:26159770]