8-tert-butyl-6,12,17-trihydroxy-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: 169630
• Molecular Formular: C20H24O10
• Molecular Mass: 424.39856
• Monoisotopic Mass: 424.13694697
• SMILES: C1(C(=O)OC2C1(C13OC4C5(C(CC(C15C2O)OC3=O)C(C)(C)C)C(C(=O)O4)O)O)C
• Canonical SMILES: O=C1OC2C(C1C)(O)C13C4(C2O)C(OC3=O)CC(C24C(O1)OC(=O)C2O)C(C)(C)C
• InChI: InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3
• InChIKey: SQOJOAFXDQDRGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-tert-butyl-6,12,17-trihydroxy-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-6,12,17-trihydroxy-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,11R,11aR)-3-(1,1-Dimethylethyl)hexahydro-4,7b,11-trihydroxy-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 52021; Ginkgolide B

Database IDs

• CAS Number: 15291-77-7
• PubChem SID: 162263762
• PubChem CID: 65243

CALCULATED PROPERTIES

• Acid pKa: 11.709941
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.5822128
• LogD (pH = 7.4): -0.5822338
• Log P: -0.58221257
• Molar Refractivity: 91.382 cm^3
• Polarizability: 38.405952 Å^3
• Polar Surface Area: 148.82 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: >300°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G387430

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)