8-tert-butyl-6,17-dihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione

• ChemBase ID: 169629
• Molecular Formular: C20H24O9
• Molecular Mass: 408.39916
• Monoisotopic Mass: 408.14203235
• SMILES: C1(C(=O)OC2C1(C13OC4C5(C(CC(C15C2)OC3=O)C(C)(C)C)C(C(=O)O4)O)O)C
• Canonical SMILES: O=C1OC2C(C1C)(O)C13C4(C2)C(OC3=O)CC(C24C(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
• InChIKey: FPUXKXIZEIDQKW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-tert-butyl-6,17-dihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^1,^1^1.0^3,^7.0^7,^1^1.0^1^3,^1^7]nonadecane-5,15,18-trione
• IUPAC Traditional name: 8-tert-butyl-6,17-dihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^1,^1^1.0^3,^7.0^7,^1^1.0^1^3,^1^7]nonadecane-5,15,18-trione
• Synonyms: (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS)-3-(1,1-Dimethylethyl)hexahydro-4,7b-dihydroxy-8-methyl-9H-1,7a-(epoxymethano)-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione; BN 52020; Ginkgolide A

Database IDs

• CAS Number: 15291-75-5
• PubChem SID: 162263761
• PubChem CID: 115221

CALCULATED PROPERTIES

• Acid pKa: 11.767949
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.33678335
• LogD (pH = 7.4): 0.336765
• Log P: 0.3367836
• Molar Refractivity: 90.1745 cm^3
• Polarizability: 37.710293 Å^3
• Polar Surface Area: 128.59 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dioxane; Ethanol; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: >300° (dec)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G387425

Family of bioactive terpenes treating cardiovascular and cerebrovascular diseases. Specific platelet activating factor (PAF) antagonists.

REFERENCES

• Korth, R., et al.: Eur. J. Pharmacol., 152, 101 (1988)
• Braquet, P., et al.: Med. Res. Rev., 11, 295 (1988)
• van Beek, T.A., et al.: Bioorg. Med. Chem., 13, 5001 (2005)