ginkgolide C   

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.
2D Structure
Click here for structure editor
Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key AMOGMTLMADGEOQ-WXQWCWKOSA-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. 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]