(1S,4R,7R,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0^{1,11}.0^{4,8}]tetradecane-2,6,13-trione

• ChemBase ID: 72929
• Molecular Formular: C15H18O8
• Molecular Mass: 326.29862
• Monoisotopic Mass: 326.10016754
• SMILES: O1C(=O)[C@@]23C4([C@H]1OC(=O)[C@@H]4O)[C@@](C[C@@H]2OC(=O)C3)(C(C)(C)C)O
• Canonical SMILES: O=C1O[C@@H]2[C@@]3(C1)C(=O)O[C@H]1C3([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
• InChIKey: MOLPUWBMSBJXER-ISSLQHLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R,7R,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0^{1,11}.0^{4,8}]tetradecane-2,6,13-trione
• IUPAC Traditional name: bilobalide
• Synonyms: Bilobalide

Database IDs

• CAS Number: 33570-04-6
• PubChem SID: 162037849
• PubChem CID: 12308750

CALCULATED PROPERTIES

• Acid pKa: 11.97425
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.28442824
• LogD (pH = 7.4): -0.28443965
• Log P: -0.5177614
• Molar Refractivity: 69.9879 cm^3
• Polarizability: 29.278425 Å^3
• Polar Surface Area: 119.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2276

Research Area: Neurological Disease
Biological Activity:
Bilobalide is a biologically active terpenic trilactone present in Ginkgo biloba. It is a main constituent of the terpenoids found in Ginkgo leaves. It also exists in minor amounts in the roots Bilobalide is important for producing several of the effects of Gingko biloba extracts, and it has neuroprotective effects, as well as inducing the liver enzymes CYP3A1 and 1A2, which may be partially responsible for interactions between gingko and other herbal medicines or pharmaceutical drugs. Bilobalide has recently been found to be an antagonist at the GABAA and GABAA-rho receptors. Of GABAA, it may possibly be selective for the subunits predominantly implicated in cognitive and memory functioning such as α1. [1][2]

REFERENCES

• http://en.wikipedia.org/wiki/Bilobalide