8-tert-butyl-6,9,12,17-tetrahydroxy-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: 169631
• Molecular Formular: C20H24O11
• Molecular Mass: 440.39796
• Monoisotopic Mass: 440.13186159
• SMILES: C1(C(=O)OC2C1(C13OC4C5(C(C(C(C15C2O)OC3=O)O)C(C)(C)C)C(C(=O)O4)O)O)C
• Canonical SMILES: O=C1OC2C(C1C)(O)C13C4(C2O)C(OC3=O)C(C(C24C(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
• InChIKey: AMOGMTLMADGEOQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-tert-butyl-6,9,12,17-tetrahydroxy-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-6,9,12,17-tetrahydroxy-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: (1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11R,11aR)-3-(1,1-Dimethylethyl)hexahydro-2,4,7b,11-tetrahydroxy-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 52022; Ginkgolide C

Database IDs

• CAS Number: 15291-76-6
• PubChem SID: 162263763
• PubChem CID: 161120

CALCULATED PROPERTIES

• Acid pKa: 11.704632
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.5791627
• LogD (pH = 7.4): -1.5791839
• Log P: -1.5791625
• Molar Refractivity: 92.6665 cm^3
• Polarizability: 39.107513 Å^3
• Polar Surface Area: 169.05 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: >275° (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G387435

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)