1.0 2010-04-08 22:12:04 UTC 2019-11-26 03:12:15 UTC FDB015816 Ginkgolide A Bitter principle from Ginkgo biloba (ginkgo). Ginkgolide A is found in ginkgo nuts and fats and oils. Ginkgolide A C20H24O9 408.3992 408.142032366 (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-trione 15291-75-5 C[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@@]12O 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 FPUXKXIZEIDQKW-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 bilobalides Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aliphatic heteropolycyclic compounds Acetals Carbonyl compounds Carboxylic acid esters Cyclic alcohols and derivatives Diterpenoids Furofurans Gamma butyrolactones Hydrocarbon derivatives Organic oxides Oxacyclic compounds Secondary alcohols Tertiary alcohols Tetrahydrofurans Tricarboxylic acids and derivatives Acetal Alcohol Aliphatic heteropolycyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Diterpenoid Furofuran Gamma butyrolactone Ginkgolide-skeleton Hydrocarbon derivative Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Secondary alcohol Tertiary alcohol Tetrahydrofuran Tricarboxylic acid or derivatives logp 1.21 ALOGPS logs -2.13 ALOGPS solubility 3.05e+00 g/l ALOGPS melting_point Mp 280° dec. logp 0.34 ChemAxon pka_strongest_acidic 11.77 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac (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 ChemAxon average_mass 408.3992 ChemAxon mono_mass 408.142032366 ChemAxon smiles C[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@@]12O ChemAxon formula C20H24O9 ChemAxon 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 ChemAxon inchikey FPUXKXIZEIDQKW-VKMVSBOZSA-N ChemAxon polar_surface_area 128.59 ChemAxon refractivity 90.17 ChemAxon polarizability 38.24 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 248916 Specdb::MsMs 248917 Specdb::MsMs 248918 Specdb::MsMs 268857 Specdb::MsMs 268858 Specdb::MsMs 268859 Specdb::MsMs 374137 Specdb::MsMs 374138 HMDB36862 #<Reference:0x000055ce325ce8c8> Fats and oils Unknown generic Ginkgo nuts Type 1 specific Ginkgo biloba 3311 bitter