(1R,3R,6R,7S,8S,10R,11S,13S,16S,17R)-8-tert-butyl-6,17-dihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^{1,11}.0^{3,7}.0^{7,11}.0^{13,17}]nonadecane-5,15,18-trione

• ChemBase ID: 4464
• Molecular Formular: C20H24O9
• Molecular Mass: 408.39916
• Monoisotopic Mass: 408.14203235
• SMILES: C1(=O)O[C@@H]2[C@]([C@@H]1C)([C@@]13[C@]4([C@@]5([C@H](O1)OC(=O)[C@@H]5O)[C@@H](C[C@H]4OC3=O)C(C)(C)C)C2)O
• Canonical SMILES: O=C1O[C@@H]2[C@@]([C@@H]1C)(O)[C@@]13[C@]4(C2)[C@H](OC3=O)C[C@H]([C@@]24[C@H](O1)OC(=O)[C@@H]2O)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/t7-,8+,9-,10+,11+,15+,17-,18+,19-,20-/m1/s1
• InChIKey: FPUXKXIZEIDQKW-VKMVSBOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,6R,7S,8S,10R,11S,13S,16S,17R)-8-tert-butyl-6,17-dihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^{1,11}.0^{3,7}.0^{7,11}.0^{13,17}]nonadecane-5,15,18-trione
• IUPAC Traditional name: (1R,3R,6R,7S,8S,10R,11S,13S,16S,17R)-8-tert-butyl-6,17-dihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^{1,11}.0^{3,7}.0^{7,11}.0^{13,17}]nonadecane-5,15,18-trione
• Synonyms: Ginkgolide a; ginkgolide-A

Database IDs

• CAS Number: 15291-75-5
• PubChem SID: 99443279; 160967896
• PubChem CID: 9909368

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 1.21
• LOG S: -2.13
• Solubility (Water): 3.05e+00 g/l

DETAILS

DrugBank - DB06743

• Drug Groups: nutraceutical
• Description: A highly active PAF antagonist cage molecule that is isolated from the leaves of the Ginkgo biloba tree. Shows potential in a wide variety of inflammatory and immunological disorders.