1.0 2010-04-08 22:12:04 UTC 2019-11-26 03:12:15 UTC FDB015815 Ginkgolide B Isolated from Ginkgo biloba (ginkgo). Ginkgolide B is found in ginkgo nuts and fats and oils. 1-Hydroxy-(1beta)-ginkgolide a BN52021 Gingko lactone Ginkgolide A, 1-hydroxy-, (1beta)- Ginkgolide B Ginkolide b C20H24O10 424.3986 424.136946988 (1R,3R,6R,7S,8S,10R,11R,12R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-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,11R,12R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-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 15291-77-7 C[C@@H]1C(=O)O[C@H]2[C@H](O)[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/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/t6-,7+,8-,9+,10+,11+,15+,17+,18+,19-,20-/m1/s1 SQOJOAFXDQDRGF-MMQTXUMRSA-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 Polyols 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 Polyol Secondary alcohol Tertiary alcohol Tetrahydrofuran Tricarboxylic acid or derivatives logp 0.49 ALOGPS logs -1.91 ALOGPS solubility 5.21e+00 g/l ALOGPS melting_point Mp 280° dec. logp -0.58 ChemAxon pka_strongest_acidic 11.71 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (1R,3R,6R,7S,8S,10R,11R,12R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-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 424.3986 ChemAxon mono_mass 424.136946988 ChemAxon smiles C[C@@H]1C(=O)O[C@H]2[C@H](O)[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 C20H24O10 ChemAxon 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/t6-,7+,8-,9+,10+,11+,15+,17+,18+,19-,20-/m1/s1 ChemAxon inchikey SQOJOAFXDQDRGF-MMQTXUMRSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 91.38 ChemAxon polarizability 39.09 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 249276 Specdb::MsMs 249277 Specdb::MsMs 249278 Specdb::MsMs 269217 Specdb::MsMs 269218 Specdb::MsMs 269219 HMDB36861 #<Reference:0x000055ce31c12708> Fats and oils Unknown generic Ginkgo nuts Type 1 specific Ginkgo biloba 3311 bitter