ginkgolide J   Click here for help

GtoPdb Ligand ID: 1864

Comment: There is some ambiguity online as to the exact structure and stereochemistry of ginkgolide J. Our structure matches that represented in the PubChem entry linked to above, but PubChem also lists activity data for several other entries. ChEMBL represents the compound with the entry CHEMBL374004.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 1
Topological polar surface area 148.82
Molecular weight 424.14
XLogP -0.07
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C1OC2C(C1C)(O)C13C4(C2)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(C2)[C@H](OC3=O)[C@@H]([C@H](C24[C@H](O1)OC(=O)C2O)C(C)(C)C)O
InChI InChI=1S/C20H24O10/c1-6-12(23)27-7-5-17-11-8(21)9(16(2,3)4)18(17)10(22)13(24)29-15(18)30-20(17,14(25)28-11)19(6,7)26/h6-11,15,21-22,26H,5H2,1-4H3/t6-,7+,8-,9+,10?,11-,15+,17?,18?,19-,20-/m1/s1
InChI Key LMEHVEUFNRJAAV-MHIVRBJNSA-N
References
1. Heads JA, Hawthorne RL, Lynagh T, Lynch JW. (2008)
Structure-activity analysis of ginkgolide binding in the glycine receptor pore.
J. Neurochem., 105 (4): 1418-27. [PMID:18221374]
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]