1.02010-04-08 22:12:04 UTC2019-11-26 03:12:15 UTCFDB015816Ginkgolide ABitter principle from Ginkgo biloba (ginkgo). Ginkgolide A is found in ginkgo nuts and fats and oils.Ginkgolide AC20H24O9408.3992408.142032366(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(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-trione15291-75-5C[C@@H]1C(=O)O[C@H]2C[C@@]34[C@H]5C[C@@H](C(C)(C)C)[C@@]33[C@@H](O)C(=O)O[C@H]3O[C@@]4(C(=O)O5)[C@@]12OInChI=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/s1FPUXKXIZEIDQKW-VKMVSBOZSA-N belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure.Ginkgolides and bilobalidesOrganic compoundsLipids and lipid-like moleculesPrenol lipidsTerpene lactonesAliphatic heteropolycyclic compoundsAcetalsCarbonyl compoundsCarboxylic acid estersCyclic alcohols and derivativesDiterpenoidsFurofuransGamma butyrolactonesHydrocarbon derivativesOrganic oxidesOxacyclic compoundsSecondary alcoholsTertiary alcoholsTetrahydrofuransTricarboxylic acids and derivativesAcetalAlcoholAliphatic heteropolycyclic compoundCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterCyclic alcoholDiterpenoidFurofuranGamma butyrolactoneGinkgolide-skeletonHydrocarbon derivativeLactoneOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleSecondary alcoholTertiary alcoholTetrahydrofuranTricarboxylic acid or derivativeslogp1.21logs-2.13solubility3.05e+00 g/lmelting_pointMp 280° dec.logp0.34pka_strongest_acidic11.77pka_strongest_basic-4.1iupac(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-trioneaverage_mass408.3992mono_mass408.142032366smilesC[C@@H]1C(=O)O[C@H]2C[C@@]34[C@H]5C[C@@H](C(C)(C)C)[C@@]33[C@@H](O)C(=O)O[C@H]3O[C@@]4(C(=O)O5)[C@@]12OformulaC20H24O9inchiInChI=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/s1inchikeyFPUXKXIZEIDQKW-VKMVSBOZSA-Npolar_surface_area128.59refractivity90.17polarizability38.24rotatable_bond_count1acceptor_count6donor_count2physiological_charge0formal_charge0Specdb::MsMs248916Specdb::MsMs248917Specdb::MsMs248918Specdb::MsMs268857Specdb::MsMs268858Specdb::MsMs268859Specdb::MsMs374137Specdb::MsMs374138HMDB36862#<Reference:0x0000555674587f08>Fats and oilsUnknowngenericGinkgo nutsType 1specificGinkgo biloba3311bitter