1.0 2010-04-08 22:11:59 UTC 2019-11-26 03:12:01 UTC FDB015672 Bilobalide A Constituent of leaves of Ginkgo biloba (ginkgo). Bilobalide A is found in ginkgo nuts and fats and oils. Bilobalide C15H18O8 326.2986 326.100167552 (1S,4R,7S,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0¹,¹¹.0⁴,⁸]tetradecane-2,6,13-trione (1S,4R,7S,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0¹,¹¹.0⁴,⁸]tetradecane-2,6,13-trione 33570-04-6 [H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2 InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8+,11-,13-,14+,15+/m0/s1 MOLPUWBMSBJXER-NRSGSQFTSA-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 Acylals Carbonyl compounds Cyclic alcohols and derivatives Diterpenoids Furofurans Gamma butyrolactones Hydrocarbon derivatives Organic oxides Oxacyclic compounds Secondary alcohols Tertiary alcohols Tetrahydrofurans Tricarboxylic acids and derivatives Acetal Acylal Alcohol Aliphatic heteropolycyclic compound Bilobalide Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Diterpenoid Furofuran Gamma butyrolactone Hydrocarbon derivative Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Secondary alcohol Tertiary alcohol Tetrahydrofuran Tricarboxylic acid or derivatives logp 0.16 ALOGPS logs -1.50 ALOGPS solubility 1.03e+01 g/l ALOGPS melting_point Mp 300° logp -0.52 ChemAxon pka_strongest_acidic 11.97 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (1S,4R,7S,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0¹,¹¹.0⁴,⁸]tetradecane-2,6,13-trione ChemAxon average_mass 326.2986 ChemAxon mono_mass 326.100167552 ChemAxon smiles [H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2 ChemAxon formula C15H18O8 ChemAxon inchi InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8+,11-,13-,14+,15+/m0/s1 ChemAxon inchikey MOLPUWBMSBJXER-NRSGSQFTSA-N ChemAxon polar_surface_area 119.36 ChemAxon refractivity 69.99 ChemAxon polarizability 29.39 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20380 Specdb::CMs 45005 Specdb::CMs 158889 Specdb::MsMs 52536 Specdb::MsMs 52537 Specdb::MsMs 52538 Specdb::MsMs 130116 Specdb::MsMs 130117 Specdb::MsMs 130118 Specdb::MsMs 2336902 Specdb::MsMs 2336903 Specdb::MsMs 2336904 Specdb::MsMs 2628788 Specdb::MsMs 2628789 Specdb::MsMs 2628790 Specdb::NmrOneD 136870 Specdb::NmrOneD 136871 Specdb::NmrOneD 136872 Specdb::NmrOneD 136873 Specdb::NmrOneD 136874 Specdb::NmrOneD 136875 Specdb::NmrOneD 136876 Specdb::NmrOneD 136877 Specdb::NmrOneD 136878 Specdb::NmrOneD 136879 Specdb::NmrOneD 136880 Specdb::NmrOneD 136881 Specdb::NmrOneD 136882 Specdb::NmrOneD 136883 Specdb::NmrOneD 136884 Specdb::NmrOneD 136885 Specdb::NmrOneD 136886 Specdb::NmrOneD 136887 Specdb::NmrOneD 136888 Specdb::NmrOneD 136889 HMDB36735 #<Reference:0x000055ce306d8018> Fats and oils Unknown generic Ginkgo nuts Type 1 specific Ginkgo biloba 3311