ginkgolide C   Click here for help

GtoPdb Ligand ID: 1863

Synonyms: BN 52022
Comment: From the plant Ginkgo biloba. There is some ambiguity on online resources as to the exact stereochemistry of ginkgolide C. Other representations on PubChem include CID 9867869 and CID 11826309.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 1
Topological polar surface area 169.05
Molecular weight 440.13
XLogP -1.09
No. Lipinski's rules broken 1
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Canonical SMILES O=C1OC2C(C1C)(O)C13C4(C2O)C(OC3=O)C(C(C24C(O1)OC(=O)C2O)C(C)(C)C)O
Isomeric SMILES O=C1O[C@@H]2[C@@]([C@@H]1C)(O)[C@@]13C4(C2O)[C@H](OC3=O)[C@@H]([C@H](C24[C@H](O1)OC(=O)C2O)C(C)(C)C)O
InChI InChI=1S/C20H24O11/c1-5-12(24)28-11-8(22)18-10-6(21)7(16(2,3)4)17(18)9(23)13(25)30-15(17)31-20(18,14(26)29-10)19(5,11)27/h5-11,15,21-23,27H,1-4H3/t5-,6-,7+,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]