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
References
1. Hawthorne R, Cromer BA, Ng HL, Parker MW, Lynch JW. (2006)
Molecular determinants of ginkgolide binding in the glycine receptor pore.
J. Neurochem., 98 (2): 395-407. [PMID:16805834]
2. Thompson AJ, Duke RK, Lummis SC. (2011)
Binding sites for bilobalide, diltiazem, ginkgolide, and picrotoxinin at the 5-HT3 receptor.
Mol. Pharmacol., 80 (1): 183-90. [PMID:21505038]
3. Thompson AJ, Jarvis GE, Duke RK, Johnston GA, Lummis SC. (2011)
Ginkgolide B and bilobalide block the pore of the 5-HT(3) receptor at a location that overlaps the picrotoxin binding site.
Neuropharmacology, 60 (2-3): 488-95. [PMID:21059362]