ginkgolide A   Click here for help

GtoPdb Ligand ID: 1861

Comment: There is some ambiguity in the exact stereochemistry of ginkgolide A therefore representations on other databases may vary slightly from that shown here.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 128.59
Molecular weight 408.14
XLogP 1.18
No. Lipinski's rules broken 0
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Canonical SMILES O=C1OC2C(C1C)(O)C13C4(C2)C(OC3=O)CC(C24C(O1)OC(=O)C2O)C(C)(C)C
Isomeric SMILES O=C1O[C@@H]2[C@@]([C@@H]1C)(O)[C@@]13C4(C2)[C@H](OC3=O)C[C@H](C24[C@H](O1)OC(=O)C2O)C(C)(C)C
InChI InChI=1S/C20H24O9/c1-7-12(22)26-10-6-17-9-5-8(16(2,3)4)18(17)11(21)13(23)28-15(18)29-20(17,14(24)27-9)19(7,10)25/h7-11,15,21,25H,5-6H2,1-4H3/t7-,8+,9-,10+,11?,15+,17?,18?,19-,20-/m1/s1
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. Strømgaard K, Saito DR, Shindou H, Ishii S, Shimizu T, Nakanishi K. (2002)
Ginkgolide derivatives for photolabeling studies: preparation and pharmacological evaluation.
J Med Chem, 45 (18): 4038-46. [PMID:12190325]