bilobalide   

GtoPdb Ligand ID: 2366

2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 119.36
Molecular weight 326.1
XLogP -0.17
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C1OC2C3(C1)C(=O)OC1C3(C(C2)(O)C(C)(C)C)C(O)C(=O)O1
Isomeric SMILES O=C1O[C@@H]2[C@@]3(C1)C(=O)O[C@H]1[C@]3([C@](C2)(O)C(C)(C)C)[C@@H](O)C(=O)O1
InChI InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8-,11-,13-,14+,15+/m0/s1
InChI Key MOLPUWBMSBJXER-YDGSQGCISA-N
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Glycine Receptor (All subtypes) N/A Subunit-specific Inhibition - - < 1x10-6 1
Conc range: < 1x10-6 M α2 > α1 > α2β > α1β [1]
glycine receptor α2 subunit Hs Antagonist Antagonist 5.1 pIC50 -
pIC50 5.1 (IC50 8x10-6 M)
glycine receptor α1 subunit Hs Antagonist Antagonist 4.7 pIC50 -
pIC50 4.7 (IC50 2x10-5 M)
glycine receptor β subunit Hs Antagonist Antagonist 3.7 – 4.3 pIC50 -
pIC50 4.3 (IC50 5x10-5 M) when co-expressed with the α2 subunit
pIC50 3.7 (IC50 2.04x10-4 M) when co-expressed with the α1 subunit
5-HT3A Hs Channel blocker - 3.3 pIC50 - 2
pIC50 3.3 (IC50 4.7x10-4 M) [2]
5-HT3AB Hs Channel blocker - 2.5 pIC50 - 3
pIC50 2.5 (IC50 3.1x10-3 M) [3]
Ligand mentioned in the following text fields