E6201   

GtoPdb Ligand ID: 7836

Synonyms: E 6201 | E-6201
Compound class: Synthetic organic
Comment: The discovery of E6201 is described in [1]. It is a fully synthetic analogue of the naturally occurring fungal resorcylic lactone LL-Z1640-2 (PubChem CID 9863776).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 116.09
Molecular weight 389.18
XLogP 2.69
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCNc1cc2C=CCC(O)C(O)C(=O)C=CC(C(OC(=O)c2c(c1)O)C)C
Isomeric SMILES CCNc1cc2/C=C/C[C@H](O)[C@H](O)C(=O)/C=C\[C@H]([C@@H](OC(=O)c2c(c1)O)C)C
InChI InChI=1S/C21H27NO6/c1-4-22-15-10-14-6-5-7-16(23)20(26)17(24)9-8-12(2)13(3)28-21(27)19(14)18(25)11-15/h5-6,8-13,16,20,22-23,25-26H,4,7H2,1-3H3/b6-5+,9-8-/t12-,13+,16+,20+/m1/s1
InChI Key MWUFVYLAWAXDHQ-HMNLTAHHSA-N
Bioactivity Comments
E6201 has significant inhibitory effects on pro-inflammatory cytokine production from various immune cells, and inhibits hyperproliferation of human keratinocytes [1-3], activities which underscore its potential as a drug candidate for the treatment of psoriasis. The compound also has potential antineoplastic activity.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
mitogen-activated protein kinase kinase 1 Hs Inhibitor Inhibition 8.3 pIC50 - 1
pIC50 8.3 (IC50 5.2x10-9 M) [1]
mitogen-activated protein kinase kinase kinase 1 Hs Inhibitor Inhibition 7.5 pIC50 - 1
pIC50 7.5 (IC50 3.1x10-8 M) [1]