1.0 2010-04-08 22:06:05 UTC 2019-11-26 02:59:49 UTC FDB004114 Lappaphen A Lappaphen b belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Lappaphen b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Lappaphen b can be found in burdock, which makes lappaphen b a potential biomarker for the consumption of this food product. C27H26O4S2 478.623 478.1272507 3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-yl}ethyl)-dodecahydroazuleno[4,5-b]furan-2-one 3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-yl}ethyl)-octahydroazuleno[4,5-b]furan-2-one CC#CC1=CC=C(S1)C1=CC=C(S1)C(=O)CC1(O)C2CCC(=C)C3CCC(=C)C3C2OC1=O InChI=1S/C27H26O4S2/c1-4-5-17-8-11-22(32-17)23-13-12-21(33-23)20(28)14-27(30)19-10-7-15(2)18-9-6-16(3)24(18)25(19)31-26(27)29/h8,11-13,18-19,24-25,30H,2-3,6-7,9-10,14H2,1H3 WKQBNYGTPIGLMV-UHFFFAOYSA-N belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Guaianolides and derivatives Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aromatic heteropolycyclic compounds 2,5-disubstituted thiophenes Aryl alkyl ketones Beta-hydroxy ketones Bi- and oligothiophenes Carboxylic acid esters Gamma butyrolactones Guaianes Heteroaromatic compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Tertiary alcohols Tetrahydrofurans 2,5-disubstituted thiophene Alcohol Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Beta-hydroxy ketone Bithiophene Carbonyl group Carboxylic acid derivative Carboxylic acid ester Gamma butyrolactone Guaiane sesquiterpenoid Guaianolide-skeleton Heteroaromatic compound Hydrocarbon derivative Ketone Lactone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Sesquiterpenoid Tertiary alcohol Tetrahydrofuran Thiophene logp 4.96 ALOGPS logs -4.62 ALOGPS solubility 1.14e-02 g/l ALOGPS logp 5.56 ChemAxon pka_strongest_acidic 9.99 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac 3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-yl}ethyl)-dodecahydroazuleno[4,5-b]furan-2-one ChemAxon average_mass 478.623 ChemAxon mono_mass 478.1272507 ChemAxon smiles CC#CC1=CC=C(S1)C1=CC=C(S1)C(=O)CC1(O)C2CCC(=C)C3CCC(=C)C3C2OC1=O ChemAxon formula C27H26O4S2 ChemAxon inchi InChI=1S/C27H26O4S2/c1-4-5-17-8-11-22(32-17)23-13-12-21(33-23)20(28)14-27(30)19-10-7-15(2)18-9-6-16(3)24(18)25(19)31-26(27)29/h8,11-13,18-19,24-25,30H,2-3,6-7,9-10,14H2,1H3 ChemAxon inchikey WKQBNYGTPIGLMV-UHFFFAOYSA-N ChemAxon polar_surface_area 63.6 ChemAxon refractivity 126.71 ChemAxon polarizability 52.85 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 54177 Specdb::MsMs 54178 Specdb::MsMs 54179 Specdb::MsMs 127119 Specdb::MsMs 127120 Specdb::MsMs 127121 Specdb::MsMs 3599999 Specdb::MsMs 3600000 Specdb::MsMs 3600001 Specdb::MsMs 3600002 Specdb::MsMs 3600003 Specdb::MsMs 3600004 Burdock Type 1 specific Arctium lappa 4217 0.0 0.0 0.0 mg/100 g